2025 IRA Contributions for Beginners

There are only three types of annual contributions to individual retirement accounts (“IRAs”). They are:

  • Traditional, nondeductible contributions
  • Traditional, deductible contributions
  • Roth contributions

This post discusses when a taxpayer can make one or more of these types of annual contributions.

Let’s dispense with what we are not talking about. This post has nothing to do with annual contributions to employer retirement plans (401(k)s and the like) and self-employed retirement plans. We’re only talking about IRAs. The Individual in “IRA” is the key – anyone can set up their own IRA. IRAs are not pegged to any particular job or self-employment.

The above list is the exhaustive list of the possible types of annual contributions you can make to an IRA. But there is plenty of confusion about when you are eligible to make each of the three types of annual contributions.

Maximum IRA Contributions

The maximum amount anyone can contribute to an IRA (traditional and/or Roth) for 2025 is $7,000. For those age 50 or older by the end of 2025, the limit is $8,000.

Two notes on this. First the limit is shared between traditional IRAs and Roth IRAs. In theory, someone under age 50 could contribute $4,000 to a traditional IRA and $3,000 to a Roth IRA. In practice, contributions are rarely divided between the traditional and the Roth, but it does occasionally happen.

Second, the limits have an additional limit: the contribution cannot exceed earned income. This means that those fully retired cannot contribute to an IRA unless they have a spouse who has earned income. A fully retired person (or a homemaker) can use their spouse’s earned income as their earned income and contribute to what is often referred to as a Spousal IRA. 

Why Contribute to an IRA?

Why you would consider contributing to an IRA? The main reason is to build up tax-deferred wealth (traditional IRAs) and/or tax-free wealth (Roth IRAs) for your future, however you define it: financial independence, retirement, etc. A second potential benefit is the ability to deduct some annual contributions to traditional IRAs. A third benefit is some degree of creditor protection. States offer varying levels of creditor protection to traditional IRAs and Roth IRAs, while the federal government provides significant bankruptcy protection for traditional IRAs and Roth IRAs. 

Traditional Nondeductible IRA Annual Contributions

There’s are only one requirement to contribute to a traditional, nondeductible IRA for a taxable year:

  • You and/or your spouse have earned income during that taxable year.

That’s it! As long as you satisfy that requirement, you can contribute to a traditional nondeductible IRA, no further questions asked.

Example: Teve Torbes is the publisher of a successful magazine. He is paid a salary of $1,000,000 in 2025 and is covered by the magazine’s 401(k) plan. Teve can make up to a $7,000 nondeductible contribution to a traditional IRA, and Teve’s wife can also make up to a $7,000 nondeductible contribution to a traditional IRA.

There is no tax deduction for contributing to a traditional nondeductible IRA. The amount of your nondeductible contribution creates “basis” in the traditional IRA. When you withdraw money from the traditional IRA in retirement, a ratable portion of the withdrawal is treated as a return of basis and thus not taxable (the “Pro-Rata Rule”).

Example: Ted makes a $6,000 nondeductible traditional IRA contribution for each of 10 years ($60,000 total). When he retires, the traditional IRA is worth $100,000, and he takes a $5,000 distribution from the traditional IRA. Ted is over 59 ½ when he makes the withdrawal. Of the $5,000 withdrawal, Ted will include $2,000 in his taxable income, because 60 percent ($3,000 — $60,000 basis divided by $100,000 fair market value times the $5,000 withdrawn) will be treated as a withdrawal of basis and thus tax free.

Traditional nondeductible IRA contributions generally give taxpayers a rather limited tax benefit. However, since 2010 traditional nondeductible IRA contributions have become an important tax planning tool because of the availability of the Backdoor Roth IRA.

Making a nondeductible IRA contribution requires the filing of a Form 8606 with your federal income tax return.

Traditional Deductible IRA Annual Contributions

In order to make a deductible contribution to a traditional IRA, three sets of qualification rules apply.

ONE: No Workplace Retirement Plan

Here are the qualification rules if neither you nor your spouse is covered by an employer retirement plan (401(k)s and the like and self-employment retirement plans):

  • You and/or your spouse have earned income during that taxable year.

That’s it! As long as you satisfy that requirement and you and your spouse are not covered by an employer retirement plan, you can make a deductible contribution to a traditional IRA, no further questions asked.

Coverage by an employer retirement plan means either you or your employer contributed any amount to an employer retirement plan (on your behalf) during the taxable year. Coverage by an employer retirement plan includes coverage under a self-employment retirement plan.

Example: Teve Torbes is the publisher of a successful magazine. He and his wife are 45 years old. He is paid a salary of $1,000,000 in 2025. Neither he nor his wife is covered by an employer retirement plan. Teve can make up to a $7,000 deductible contribution to a traditional IRA, and Teve’s wife can also make up to a $7,000 deductible contribution to a traditional IRA.

TWO: You Are Covered by a Workplace Retirement Plan

Here are the deductible traditional IRA qualification rules if you are covered by an employer retirement plan:

  • You and/or your spouse have earned income during that taxable year.
  • Your modified adjusted gross income (“MAGI”) for 2025 is less than $89,000 (if single), $146,000 (if married filing joint, “MFJ”), or $10,000 (if married filing separate, “MFS”). 

Note that in between $79,000 and $89,000 (single), $126,000 and $146,000 (MFJ) and $0 and $10,000 (MFS), your ability to make a deductible contribution to a traditional IRA phases out ratably. Here is an illustrative example.

Example: Mike is 30 years old, single, and is covered by a 401(k) plan at work. Mike has a MAGI of $84,000 in 2025, most of which is W-2 income. Based on a MAGI in the middle of the phaseout range, Mike is limited to a maximum $3,500 deductible contribution to a traditional IRA.

Assuming he makes a $3,500 deductible IRA contribution, Mike has $3,500 worth of IRA contributions left. He can either, or a combination of both (up to $3,500) (a) make a contribution to a nondeductible traditional IRA, since he meets the qualification requirement to contribute to a nondeductible traditional IRA or (b) make a contribution to a Roth IRA, since he meets the qualification requirements (discussed below) to contribute to a Roth IRA.

THREE: Only Your Spouse is Covered by a Workplace Retirement Plan

Here are the deductible traditional IRA qualification rules if you are not covered by an employer retirement plan but your spouse is covered by an employer retirement plan:

  • You and/or your spouse have earned income during that taxable year.
  • Your MAGI for 2025 is less than $246,000 (MFJ) or $10,000 (MFS). 

Note that in between $236,000 and $246,000 (MFJ) and $0 and $10,000 (MFS), your ability to make a deductible contribution to a traditional IRA phases out ratably. 

Roth IRA Annual Contributions

Here are the Roth IRA annual contribution qualification rules.

  • You and/or your spouse have earned income during that taxable year.
  • Your MAGI for 2025 is less than $165,000 (single), $246,000 (MFJ), or $10,000 (MFS). 

Note that in between $150,000 and $165,000 (single), $236,000 and $246,000 (MFJ), and $0 and $10,000 (MFS), your ability to make a Roth IRA contribution phases out ratably. 

Notice that whether you and/or your spouse are covered by an employer retirement plan (including a self-employment retirement plan) is irrelevant. You and your spouse can be covered by an employer retirement plan and you can still contribute to a Roth IRA (so long as you meet the other qualification requirements).

Here is an example illustrating your options in the Roth IRA MAGI phaseout range.

Example: Mike is 30 years old, single, and covered by a workplace retirement plan. Mike has a MAGI of $159,000 for 2025, most of which is W-2 income. Based on a MAGI 60 percent through the phaseout range, Mike is limited to a maximum $2,800 contribution to a Roth IRA.

Assuming he makes a $2,800 annual Roth IRA contribution, Mike has $4,200 worth of IRA contributions left. He can make up to $4,200 in annual contributions to a nondeductible traditional IRA, since he meets the qualification requirement to contribute to a nondeductible traditional IRA.

Deadlines

The deadline to make an IRA contribution for a particular year is April 15th of the year following the taxable year (thus, the deadline to make a 2025 IRA contribution is April 15, 2026). The deadline to make earned income for a taxable year is December 31st of that year.

Rollover Contributions

There’s a separate category of contributions to IRAs: rollover contributions. These can be from other accounts of the same type (traditional IRA to traditional IRA, Roth IRA to Roth IRA) or from a workplace retirement plan (for example, traditional 401(k) to traditional IRA, Roth 401(k) to Roth IRA). 

Rollover contributions do not require having earned income and have no income limits and should be generally tax-free. For a myriad of reasons, it is usually best to effectuate rollovers as direct trustee-to-trustee transfers. 

As a practical matter, it is often the case that IRAs serve at the retirement home for workplace retirement plans such as 401(k)s. 

Further Reading

Deductible traditional IRA or Roth IRA? If you qualify for both, it can be difficult to determine which is better. I’ve written here about some of the factors to consider in determining whether a deductible traditional contribution or a Roth contribution is better for you.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on X at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Constitution or Delayed RMDs?

The Constitution or delayed RMDs?

Incredibly, Donald Trump has signed up to make that choice, starting January 20th.

How can that be? It relates to SECURE 2.0. SECURE 2.0 made dozens of additions to the already complicated retirement account rules. Many like its delaying retirement account required minimum distributions (“RMDs”) for many Americans from age 72 to age 73 (and eventually to age 75). 

But there is a big time issue few have commented on. 

It has to do with the Omnibus Bill’s purported passage in December 2022. If the Omnibus, which contained SECURE 2.0, was not passed in a Constitutionally qualified manner, any Administration enforcing it would be acting counter to the Constitution and contrary to the rule of law. 

The Constitutional Problem with SECURE 2.0

A federal judge, in a very well written and reasoned opinion, determined that the 2022 Omnibus Bill, was passed by the House of Representatives at a time the House did not have a required quorum to enact legislation. In Texas v. Garland (accessible here and here), Judge James W. Hendrix ruled for the State of Texas that the House of Representatives impermissibly used proxies to establish a quorum. The House did not have a majority of members physically present, and thus did not have a sufficient quorum to enact legislation at the time of Omnibus’s purported passage. 

The quorum rule isn’t contained in the back of a House of Representatives parliamentary procedure manual. Rather, it is contained in the Quorum Clause of the United States Constitution, making it the highest level of legal authority. 

This ruling has broad implications for SECURE 2.0. If the Omnibus was not enacted in a Constitutionally qualified manner, SECURE 2.0 is not the law of the land. Any Administration enforcing it would be enforcing a law that is simply not the law of the land.

I encourage the reader to read the Texas v. Garland opinion. I find it convincing, but you get to be the judge and jury in your own mind. 

Assuming the new Administration agrees with Judge Hendrix’s reasoning, they should announce they will not enforce SECURE 2.0 in order to avoid acting contrary to the law.

Proposed Action

I recommend that shortly after President Trump’s inauguration the IRS and Treasury issue a Notice announcing the following:

  • In order to uphold the Constitution and the rule of law, the IRS and Treasury will not enforce SECURE 2.0.
  • Considering the equities involved, the uniqueness of taxpayers having acted under an announced law that was not, in fact, the law, and the limited enforcement resources available, the IRS will not challenge any acts made, plan/account qualification, and tax return positions taken based on SECURE 2.0 prior to the issuance of the Notice. Plans and financial institutions will be allowed a reasonable amount of time to adequately account for the Notice.
  • In order to eliminate harm from detrimental reliance on SECURE 2.0, appropriate equitable remedies will be applied to prior acts taken under SECURE 2.0 with relevance going forward. For example, any Roth SEP IRAs and Roth SIMPLE IRAs properly created and funded under SECURE 2.0 will be deemed to be Roth IRAs with respect to which valid contributions were previously made.
  • The IRS and Treasury will exercise their authority under Sections 402(c)(3)(B) and 408(d)(3)(I) and waive the 60-day requirement with respect to rollovers for any SECURE 2.0 qualified distributions followed by three year repayments so long as the distribution occurred prior to the issuance of the Notice and repayment is made back to the retirement account no later than December 31, 2025. 
  • The IRS will not require RMDs and not enforce the failure to withdraw penalty for those who turned age 73 in 2023 and for those who turned age 73 in 2024.
  • The IRS will require RMDs and enforce the failure to withdraw penalty for those who turn age 73 starting in 2025. 
  • Relevant 2025 limits will be applied not factoring in provisions from SECURE 2.0. Thus, guidance such as Notice 2024-80 is modified accordingly. For example, the 2025 qualified charitable distribution limit is $100,000 and for those age 60-63 the catch-up contribution limit is $7,500.

I recommend the new Administration issue that notice shortly after Inauguration Day to uphold the Constitution regardless of whether the new Congress chooses to take additional action with respect to SECURE 2.0.

The question then becomes what to do in Congress, if anything, with respect to SECURE 2.0. Since it is likely Congress will enact significant tax legislation, there will be one or more opportunities to address the issue.

I propose that as part of the 2025 tax changes Congress passes, Congress include a provision repealing SECURE 2.0 for the avoidance of doubt. That will end any possible litigation around SECURE 2.0, since the IRS will have waived any challenges resulting from acts occurring prior to the Trump Administration, and Congress will have repealed it (in case it is the law, counter to my opinion) going forward. 

SECURE 2.0 had more to do with 401(k) plan administrators and lawyers securing full employment than securing retirement for working Americans. SECURE 2.0 being pushed to the side would be no tragedy. Perhaps Congress should salvage a few good provisions, but most of it should be left on the scrap heap while Congress focuses on more important tax reforms and extending Tax Cuts and Jobs Act individual tax cuts.

I am more ambivalent about the delays in RMDs. Congress could simply enact SECURE 2.0’s RMD delays as part of its 2025 tax reforms. That said, I believe that tax cuts such as eliminating the taxes on tips and overtime are much better tax policy and should be prioritized. 

Further, the tax benefit of eliminating the tax on Social Security potentially dwarfs the tax benefit of a one or three year delay in RMDs. There’s a very valid argument that eliminating taxes on Social Security and having RMDs start at age 72 is appropriate and will leave many seniors in a vastly improved tax position when compared to where they stood prior to 2025. 

Conclusion

I would pick the Constitution over delayed RMDs any day of the week. The Constitution is far more important than any retirement account tax rule. While it is not good to say dozens of rules that Americans have planned around are invalid, it is far worse to disregard the Constitution. 

My hope is that the new Administration’s tax policy staff, including the new Assistant Secretary for Tax Policy, work to uphold the Constitution.

The new Administration, consistent with Judge Hendrix’s ruling, should acknowledge the Constitutional problem with SECURE 2.0 and addresses it head on. Doing so will demonstrate President Trump’s commitment to honor the Constitution and the rule of law. 

Follow me on X at @SeanMoneyandTax

This post is for educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Note that a version of this proposal has been posted to the crowd sourced policy website PoliciesforPeople.com. The views reflected in this post are only those of the author, Sean Mullaney, and are not the views of anyone else.

2025 Solo 401(k) Update

Before we explore new developments for 2025, 2024 was so chock full of Solo 401(k) developments that it deserves its own rundown. Then we will move onto 2025 Solo 401(k) changes. 

Vanguard Out!

Vanguard transferred all of their Solo 401(k) accounts to Ascensus in 2024. Vanguard is now entirely out of the Solo 401(k) business.

The good news for those fond of Vanguard is that the Ascensus Solo 401(k) offers Vanguard mutual funds. 

The transition was not entirely smooth. Notably, beneficiary designation forms did not transfer from Vanguard to Ascensus. The Ascensus Solo 401(k) contribution portal is quite different from Vanguard’s and is not intuitive, in my opinion. I did a YouTube video about making contributions to a Solo 401(k) at Ascensus. 

I’m not in the business of making generic recommendations about which Solo 401(k) plan provider to use. In my book, I advocate strongly for considering a pre-approved plan (sometimes referred to as a prototype plan). Schwab, Fidelity, and Ascensus are now among the larger providers of pre-approved plans. While I will not provide any plan provider recommendation, I believe Ascensus, Fidelity, and Schwab are all reasonable options to consider.

Solo 401(k)s at Retirement

During 2024 I did a deep-dive on some Solo 401(k) history. The results of that research is a 27 page self-published article concluding that for Schedule C solopreneurs, a Solo 401(k) should survive the solopreneur’s retirement. 

One of the implications of that finding is that Solo 401(k)s should qualify for the Rule of 55. However, one must always consult with their own individual plan, as the plan itself must have rules facilitating Rule of 55 distributions. 

Doubts About SECURE 2.0

SECURE 2.0 made dozens of changes to retirement account rules. It made what I believe to be rather inconsequential changes to Solo 401(k) planning. Nevertheless, it did change some Solo 401(k) rules.

Based on a court case in federal district court in Texas, the legal foundation of SECURE 2.0 is now shaky. I discussed the situation on YouTube. It will be very interesting to see what the new Administration does with SECURE 2.0 considering that a federal district court judge made a very convincing argument that the passage of the Omnibus bill (which included SECURE 2.0) in December 2022 was not valid. 

New Solo 401(k) Employee Contributions Limit for 2025

The IRS announced that for 2025, the employee deferral limit for all 401(k)s, including Solo 401(k)s, will be $23,500. 

Solo 401(k) Catch-Up Contributions Limit for 2025

The IRS also announced that for 2025, the normal employee deferrals catch-up contribution limit remains $7,500. As a result, those aged 50 or older can contribute, in employee contributions, a maximum of the lesser of $31,000 ($23,500 plus $7,500) or earned income. 

New Solo 401(k) All Additions Limit for 2025

The new all-additions limit for Solo 401(k)s is $70,000 (or earned income, whichever is less). For those aged 50 or older during 2025, the $70,000 number is $77,500 ($70,000 plus $7,500). 

New Additional Catch-Up Contributions for Those Aged 60 Through 63

SECURE 2.0 increased the catch-up contribution for those aged 60 through 63 (see page 2087 of this file). In 2025, the catch-up contribution for these people is $11,250, not $7,500. As this is a SECURE 2.0 rule, I believe that Solo 401(k) users should (1) proceed with caution and (2) stay tuned. 

Traditional Solo 401(k) Contributions More Attractive Than Ever

I believe traditional Solo 401(k) contributions are now more attractive than ever. Why? The change in tax policy coming with the 2024 Election results.

There’s been plenty of debate: traditional versus Roth. The way to resolve that is to compare today’s marginal tax rate with the tax rate on the income in retirement. Today’s rate is pretty knowable, but tomorrow’s rate isn’t. 

That said, we do know that America has a history of standard deductions and graduated progressive tax rates. That, combined with Congress’s political incentives (retirees tend to vote), suggests that retirees will be relatively low taxed in retirement. 

Social Security has been a fly in the ointment to that view. Up to 85 percent of Social Security income fills up the standard deduction and lower tax brackets with income. Doesn’t that mean that traditional retirement account withdrawals will be taxed against higher tax brackets?

Starting in 2025, that issue may go away. Eliminating income tax on Social Security was a major promise of the Trump campaign. Considering the GOP majorities in both houses of Congress, the tax on Social Security should be repealed. Stay tuned! 

Removing Social Security from taxable income means significant amounts of traditional retirement account withdrawals should be tax free (offset by the standard deduction) or subject to the lower 10 percent and 12 income tax brackets. The possibility of even lighter taxation on traditional retirement account withdrawals makes traditional Solo 401(k) contributions more attractive than ever. 

2025 Update to Solo 401(k): The Solopreneur’s Retirement Account

Solo 401(k): The Solopreneur’s Retirement Account explores the nooks and crannies of Solo 401(k)s. On page 16 of the paperback edition, I provide an example of the Solo 401(k) limits for 2022 if a solopreneur makes $100,000 of Schedule C income. Here is a revised version (in italics) of the example (with the footnote omitted) applying the new 2025 employee contribution limit:

Lionel, age 35, is self-employed. His self-employment income (as reported on the Schedule C he files with his tax return) is $100,000. Lionel works with a financial institution to establish his own Solo 401(k) plan and choose investments for the plan. Lionel can contribute $23,500 to his Solo 401(k) as an employee deferral (2025 limit) and can choose to contribute, as an employer contribution, anywhere from 0-20% of his self-employment income.

Lionel’s maximum potential tax-advantaged Solo 401(k) contribution for 2025 is $42,087! That is a $23,500 employee contribution and a $18,587 employer contribution. Note there’s no change in the computation of the employer contribution for 2025 in this example. 

On page 18 I provide an example of the Solo 401(k) contribution limits factoring in catch-up contributions. Here’s the example revised for 2025:

If Lionel turned 50 during the year, his limits are as follows:

  • Employee contribution: lesser of self-employment income ($92,935) or $31,000: $31,000
  • Employer contribution: 20% of net self-employment income (20% X $92,935): $18,587
  • Overall contribution limit: lesser of net self-employment income ($92,935) or $77,500: $77,500

Amazon Reviews

If you have read Solo 401(k): The Solopreneur’s Retirement Account, you can help more solopreneurs find the book! How? By writing an honest, objective review of the book on Amazon.com. Reviews help other readers find the book!

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on X at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2024 Year-End Tax Planning

It’s that time of year again. The air is cool and the Election is in the rear-view mirror. That can only mean one thing when it comes to personal finance: time to start thinking about year-end tax planning.

I’ll provide some commentary about year-end tax planning to consider, with headings corresponding to the timeframe required to execute. 

As always, none of this is advice for your particular situation but rather it is educational information. 

Urgent

By urgent, I mean those items that (i) need to happen before year-end and (ii) may not happen if taxpayers delay and try to accomplish them late in the year. 

Donor Advised Fund Contributions

The donor advised fund is a great way to contribute to charity and accelerate a tax deduction. My favorite way to use the donor advised fund is to contribute appreciated stock directly to the donor advised fund. This gets the donor three tax benefits: 1) a potential upfront itemized tax deduction, 2) removing the unrealized capital gain from future income tax, and 3) removing the income produced by the assets inside the donor advised fund from the donor’s tax return. 

In order to get the first benefit in 2024, the appreciated stock must be received by the donor advised fund prior to January 1, 2025. This deadline is no different than the normal charitable contribution deadline.

However, due to much year end interest in donor advised fund contributions and processing time, different financial institutions will have different deadlines on when transfers must be initiated in order to count for 2024. Donor advised fund planning should be attended to sooner rather than later. 

Taxable Roth Conversions

For a Roth conversion to count as being for 2024, it must be done before January 1, 2025. That means New Year’s Eve is the deadline. However, taxable Roth conversions should be done well before New Year’s Eve because 

  1. It requires analysis to determine if a taxable Roth conversion is advantageous, 
  2. If advantageous, the proper amount to convert must be estimated, and 
  3. The financial institution needs time to execute the Roth conversion so it counts as having occurred in 2024. 

Remember, generally speaking it is not good to have federal and/or state income taxes withheld when doing Roth conversions!

Gotta Happen Before 2026!!!

Before the Election, many commentators said “you’ve gotta get your Roth conversions done before tax rates go up in 2026!” If this were X (the artist formerly known as Twitter), the assertion would likely be accompanied by a hair-on-fire GIF. 😉

I have disagreed with the assertion. As I have stated before, there’s nothing more permanent than a temporary tax cut! Now with a second Trump presidency and a Republican Congress, it is likely that the higher standard deduction and rate cuts of the Tax Cuts and Jobs Act will be extended. 

Regardless of the particulars of 2025 tax changes, I recommend that you make your own personal taxable Roth conversion decisions based on your own personal situation and analysis of the landscape and not a fear of future tax hikes.

Adjust Withholding

This varies, but it is a good idea to look at how much tax you owed last year. If you are on pace to get 100% (110% if 2023 AGI is $150K or greater) or slightly more of that amount paid into Uncle Sam by the end of the year (take a look at your most recent pay stub), there’s likely no need for action. But what if you are likely to have much more or much less than 100%/110%? It may be that you want to reduce or increase your workplace withholdings for the rest of 2024. If you do, don’t forget to reassess your workplace withholdings for 2024 early in the year.

One great way to make up for underwithholding is through an IRA withdrawal mostly directed to the IRS and/or a state taxing agency. Just note that for those under age 59 ½, this tactic may require special planning.  

Backdoor Roth IRA Diligence

The deadline for the Backdoor Roth IRA for 2024 is not December 31st, as I will discuss below. But if you have already completed a Backdoor Roth IRA for 2023, the deadline to get to a zero balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs is December 31, 2024. 

Solo 401(k) Planning

There’s plenty of planning that needs to be done for solopreneurs in terms of retirement account contributions. 

The Solo 401(k) can get complicated. That’s why I wrote a book about them and post an annual update on Solo 401(k)s here on the blog. 

Year-End Deadline

These items can wait till close to year-end, though you don’t want to find yourself doing them on New Year’s Eve.

Tax Gain Harvesting

For those finding themselves in the 12% or lower federal marginal income tax bracket and with an asset in a taxable account with a built-in gain, tax gain harvesting prior to December 31, 2024 may be a good tax tactic to increase basis without incurring additional federal income tax. Remember, though, the gain itself increases one’s taxable income, making it harder to stay within the 12% or lower marginal income tax bracket. 

I’m also quite fond of tax gain harvesting that reallocates one’s portfolio in a tax efficient manner. 

Tax Loss Harvesting

The deadline for tax loss harvesting for 2024 is December 31, 2024. Just remember to navigate the wash sale rule. 

RMDs from Your Own Retirement Account

The deadline to take any required minimum distributions from one’s own retirement account is December 31, 2024. Remember, the rules can get a bit confusing. Generally, IRAs can be aggregated for RMD purposes, but 401(k)s cannot. 

RMDs from Inherited Accounts

The deadline to take any RMDs from inherited retirement accounts is December 31st. For some beneficiaries of retirement accounts inherited during 2020, 2021, 2022, and 2023, the IRS has waived 2024 RMDs. That said, all beneficiaries of inherited retirement accounts may want to consider affirmatively taking distributions (in addition to RMDs, if any) before the end of 2024 to put the income into a lower tax year, if 2024 happens to be a lower taxable income year vis-a-vis future tax years. 

Can Wait Till Next Year

Traditional IRA and Roth IRA Contribution Deadline

The deadline for funding either or both a traditional IRA and a Roth IRA for 2024 is April 15, 2025. 

Backdoor Roth IRA Deadline

There’s no law saying “the deadline for the Backdoor Roth IRA is DATE X.” However, the deadline to make a nondeductible traditional IRA contribution for the 2024 tax year is April 15, 2025. Those doing the Backdoor Roth IRA for 2024 and doing the Roth conversion step in 2025 may want to consider the unique tax filing when that happens (what I refer to as a “Split-Year Backdoor Roth IRA”). 

HSA Funding Deadline

The deadline to fund an HSA for 2024 is April 15, 2025. Those who have not maximized their HSA through payroll deductions during the year may want to look into establishing payroll withholding for their HSA so as to take advantage of the payroll tax break available when HSAs are funded through payroll. 

The deadline for those age 55 and older to fund a Baby HSA for 2024 is April 15, 2025. 

2025 Tax Planning at the End of 2024

HDHP and HSA Open Enrollment

It’s open enrollment season. Now is a great time to assess whether a high deductible health plan (a HDHP) is a good medical insurance plan for you. One of the benefits of the HDHP is the health savings account (an HSA).

For those who already have a HDHP, now is a good time to review payroll withholding into the HSA. Many HSA owners will want to max this out through payroll deductions so as to qualify to reduce both income taxes and payroll taxes.

Self-Employment Tax Planning

Year-end is a great time for solopreneurs, particularly newer solopreneurs, to assess their business structure and retirement plans. Perhaps 2024 is the year to open a Solo 401(k). Often this type of analysis benefits from professional consultations.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

SECURE 2.0 and Section 72(t) Comment Letter

Recently, the IRS and Treasury issued Notice 2024-55. This notice provided initial rules for SECURE 2.0 emergency personal expense distributions (“EPEDs”), domestic abuse victim distributions, and repayments into retirement accounts. The Notice also asked for comments on the above and on Section 72(t) in general.

I wrote a comment letter (which you can read here) to the IRS and Treasury obliging that request. The letter addresses EPEDs, repayments into retirement accounts, and the impact of Texas v. Garland on SECURE 2.0. Further, the comment letter requests clarification that Solo 401(k)s of retired solopreneurs qualify for the Rule of 55 exception to the Section 72(t) ten percent early withdrawal penalty.

Follow me on X: @SeanMoneyandTax

This post (and the linked-to comment letter) is for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice for you or any other individual. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Roth 401(k)s and the Rule of 55

We live in a world where two things are true. First, more investors are using the Roth 401(k) to save and invest for retirement. Second, as demonstrated by the strength of the financial independence movement, many are interested in retiring early by conventional standards. 

Some potential “early” retirees are thinking about the so-called “Rule of 55” and many of them have Roth 401(k)s.

How does the Roth 401(k) work with the Rule of 55? Is there a better option than the Rule of 55 for those looking to retire using in part or in whole a Roth 401(k) prior to turning age 59 ½?

We will explore both the Roth 401(k) and the Rule of 55, then we will discuss planning involving the potential combination of the Roth 401(k) and the Rule of 55. We will also discuss a planning alternative to combining the Roth 401(k) with the Rule of 55.

Roth 401(k)

The Roth 401(k) is a 401(k) that is taxed as a Roth. Employers offering a 401(k) are not required to offer a Roth 401(k) option, but many do.

Roth 401(k) Contributions

There are now three main potential sources of “Roth contributions” to a Roth 401(k).

  1. Employee Deferrals: In 2024, these are limited to the lesser of earned income or $23,000 ($30,000 if age 50 or older). These are done through W-2 withholding into the Roth 401(k).
  2. Mega Backdoor Roth: These are after-tax contributions by the employee (also through W-2 withholding) to the traditional 401(k) followed by a soon-in-time Roth conversion of the after-tax 401(k) amount to the Roth 401(k). 
  3. Employer Contributions: Employers contribute to 401(k)s. SECURE 2.0 allows for employers to contribute to Roth 401(k)s. Traditionally, employer contributions had always been to the traditional 401(k), but SECURE 2.0 established the possibility of Roth 401(k) employer contributions. Note that a February 2024 federal court decision has called SECURE 2.0 into question. 

There’s a limit on the combination of 1 plus 2 plus 3. I refer to this limit as the “all additions limit” and some refer to it as the “415(c)” limit, as that’s where the limit lives in the Internal Revenue Code. For 2024, the all additions limit is $69,000. For those aged 50 or older, it is $76,500. 

Note that Roth IRAs cannot be rolled over to a Roth 401(k). 

There’s a fourth potential source of Roth 401(k) funds: Taxable conversions from traditional 401(k)s. Taxable Roth conversions (traditional 401(k) to Roth 401(k)) have no limit. These are usually not done during one’s working years.

Roth 401(k) Withdrawals

If “done right” a Roth 401(k) withdrawal in retirement is fully tax and penalty free. 

However, if a distribution from a Roth 401(k) occurs before either (or both) the account owner is 59 ½ years old or the owner has owned that particular Roth 401(k) for five years, the “earnings” portion of the distribution is subject to ordinary income tax and the potential 10 percent early withdrawal penalty. 

Here’s a quick example illustrating that rule: 

Ken is age 53. He’s early retired. At a time when his Roth 401(k) is worth $200,000 and he’s previously contributed $100,000 to it, Ken takes a $50,000 distribution from the Roth 401(k) to help fund his retirement. Fifty percent of the distribution ($25,000) is a return of Ken’s previous contributions and fully tax and penalty free. The other fifty percent of the distribution ($25,000) is earnings and since Ken is under age 59 ½ will be taxable to Ken and subject to the 10 percent early withdrawal penalty. 

Rule of 55

The Rule of 55 is an exception to the 10 percent early withdrawal penalty. It applies to a specific employer’s qualified plan, such as a 401(k). It applies distributions from an employer’s qualified plan if

  1. The qualified plan account owner separated from service from the employer no earlier than the beginning of his or her age 55 birthday year, and 
  2. The distribution occurs after the separation from service.

Here is an example:

Rob was born on June 7, 1969. On January 16, 2024, Rob retired from Acme Industries. 2024 is Rob’s 55th birthday year. Any distribution occurring after January 16, 2024 from the Acme Industries 401(k) to Rob qualifies for the Rule of 55 exception to the 10 percent early withdrawal penalty. 

Note that a transfer from the former employer’s qualified plan to an IRA blows qualification for the Rule of 55. Distributions from an IRA are not distributions from the employer’s qualified plan. Further, the Rule of 55 applies only to the particular employer’s plan. If Rob had separated from Consolidated Industries at age 52 and still had a 401(k) there, distributions from that 401(k) would not qualify for the Rule of 55.

Read more about the legislative history of the Rule of 55 on page 18 of my article Solo 401(k)s and the Rule of 55: Does the Answer Lie in 1962?

Planning

Perhaps you’re sitting at home saying “Roth 401(k)s are great. The Rule of 55 is great. Why not combine them?”

I have four reasons not to combine them.

Taxing Roth 401(k) Earnings

Paying tax on a Roth distribution is the planning equivalent of breaking into jail. Combining the Roth 401(k) with the Rule of 55 means taxing Roth earnings as ordinary income. That isn’t a great outcome, particularly when there was no tax deduction on the way into the Roth 401(k).

Here is an example:

Ted leaves Maple Industries at age 56. He withdraws $60,000 from his Maple Industries Roth 401(k) at a time it was worth $300,000 and had $120,000 of previous contributions. Forty percent of the withdrawal ($24,000) is a tax and penalty free return of contributions. Sixty percent of the withdrawal ($36,000) is penalty free under the Rule of 55 but is subject to income taxation. 

Perhaps a significant portion of the taxable withdrawal is protected by the standard deduction (what I refer to as the Hidden Roth IRA in the context of traditional retirement account withdrawals). But even at a 10 or 12 percent marginal federal income tax rate, from a planning perspective having any sort of taxable distribution from a Roth account is a bad outcome.

Further, taking money out of a Roth in our 50s means foregoing additional years or decades of tax free growth on that money. 

A Great, Easily Accessible Alternative Exists

Before age 59 ½, a Roth 401(k) represents a challenge and an opportunity for an early retiree. 

First, the challenge. The challenge is the “cream-in-the-coffee” rule I previously discussed in this post. Distributions before age 59 ½ attract both old contributions and earnings. Earnings are subject to both ordinary income tax and the 10 percent early withdrawal penalty. 

Here’s an example: 

Moe is age 53. He has a $500,000 Roth 401(k). $200,000 is old contributions and $300,000 is growth on those contributions (earnings). If Moe takes a distribution of $10,000 from the Roth 401(k), $4,000 (40%) will be a tax and penalty free return of contributions and $6,000 (60%) will be a distribution of earnings, subject to both income taxation and a 10 percent early withdrawal penalty (add 2.5% if Moe lives in California). 

Here’s the opportunity: Someone like Moe can “isolate” his $200,000 of Roth 401(k) basis and avoid taxation on his Roth withdrawals.

It’s pretty easy. Moe can simply transfer his entire Roth 401(k) to a Roth IRA. That will immediately give Moe $200,000 of “basis” in his Roth IRA (old annual contributions which can be removed at any time for any reason tax and penalty free). Once the Roth 401(k) is in a Roth IRA, Moe has $200,000 (plus any other Roth basis he has separately built up) he can withdraw entirely tax and penalty free for early retirement.

A Good, Not Too Difficult Alternative Exists

There’s another path to basis isolation and avoiding taxation on a Roth 401(k) distribution, but it will be more complicated. This path involves Moe keeping most of the money inside the Roth 401(k).

Returning to the facts of Moe’s example: Say Moe is 53 years old and early retired. If the Roth 401(k) plan allows partial pre-age 59 ½ withdrawals, and Moe wants $10,000 tax and penalty free, he could withdraw $25,000 from the Roth 401(k) and (i) keep $10,000 (40%) and (ii) transfer $15,000 (60%) to a Roth IRA. The transaction will be entirely tax and penalty free as Moe is deemed to get the basis ($10,000) distributed to him and to have transferred the earnings ($15,000) to his Roth IRA. See Exception 3: Roth 401(k) Withdrawal then Rollover in this post for more details. 

Why Not Use Taxable Accounts, if Possible?

I’ve said it before and I’ll say it again: I prefer using taxable accounts, if possible, to fund retirement prior to using retirement accounts. While that will not be possible for everyone, why not save before retirement in a manner that facilitates (1) living off taxable accounts prior to age 59 ½ (and pay very low capital gains taxes) while (2) doing very low tax rate Roth conversions in retirement. 

Obviously, there’s only so much tax planning anyone can do if they are in their mid-to-late 50s and a couple of months away from retirement. But for those in their 30s, 40s, and even early 50s, now is the time to plan to set up a retirement that is as tax advantageous as possible. 

For anyone with a decent amount of time between now and retirement, I would not recommend planning into relying on using the Rule of 55 for a Roth 401(k). 

ACA Premium Tax Credit Considerations

I’m concerned that some people take the Roth too far. If you get to retirement prior to age 65 and need to go on an ACA medical insurance plan, having every last penny in Roth accounts is not a good place to be. It can mean that you’re not able to generate taxable income in retirement, meaning you can’t qualify for a significant Premium Tax Credit against hefty ACA insurance premiums.

In theory, the Rule of 55 could be a workaround to that problem. Imagine Jane retires at age 56, and other than a paid off house and $50,000 in a savings account she has a $2,000,000 Roth 401(k) and a $500,000 Roth IRA. How is she going to create any taxable income to qualify for the Premium Tax Credit? 

The answer, for a few years, can be the Rule of 55. Jane could take from her Roth 401(k) (assuming it allows partial pre-age 59 ½ distributions), create taxable income on the “earnings” portion of the distribution as discussed above, and avoid the 10 percent early withdrawal penalty under the Rule of 55.

This is still not something that should be planned into. Why not? At age 59 ½, assuming Jane has had the Roth 401(k) for 5 or more years, she will qualify for a “qualified distribution” from the Roth 401(k), meaning that all distributions from it will be entirely tax free. 

That’s bad news from a Premium Tax Credit perspective: at that point Jane will have hardly any taxable income (just some interest income from the small savings account) and thus will not generate sufficient income to qualify for the Premium Tax Credit!

Conclusion

It is good that the Roth 401(k) and the Rule of 55 are available options for retirement. Absent unique and extreme circumstances, they generally should not be combined when it comes to retirement planning. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

New to Financial Independence? Start Here!

Financial independence is great. But sometimes it can be daunting. Personal finance itself can be daunting, and now we’re adding something called financial independence or “FIRE” to it?

I decided it was time to come up with an approachable, understandable, and cost free entry point into financial independence. With the four resources listed below, I believe one can rather quickly get up to speed without needing any sort of advanced knowledge or education. The four resources, including one podcast episode, one very short academic article, and two blog posts, are free and easy to digest.

ChooseFI Episode 100: Welcome to the FI Community

This podcast episode goes over the basics of financial independence. 

The Shockingly Simple Math Behind Early Retirement by Mr. Money Mustache

This blog post discusses the math behind early retirement.

The Arithmetic of Active Management by William F. Sharpe

This very brief academic article compares active investing versus passive investing (generally speaking, index funds).

FI Tax Strategies for Beginners by Sean Mullaney

My blog post goes over the basic tactics of tax planning for FI beginners.


Obviously there are plenty more FI resources, and I encourage you to explore them. But my hope is that these four resources comprise a relatively easy on-ramp into financial independence and personal finance for those starting out.

Subscribe to my YouTube Channel: @SeanMullaneyVideos

Follow me on X: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, medical, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, medical, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

FI Tax Strategies For Beginners

New to financial independence (FI or FIRE)? Are you steeped in financial independence, but confused about tax optimization?

If so, this is the post for you. It’s not “comprehensive tax planning for FI” but rather an initial primer on some basic financial independence tax planning tactics. 

But first, a caveat: none of this is advice for your specific situation, but rather, this comprises a list of the top four moves I believe those pursuing financial independence should consider. No blog post (this one included) is a substitute for your own and your advisors’ analysis and judgment of your own situation.

ONE: Contribute Ten Percent to Your Workplace Retirement Plan

To start, your top retirement savings priority in retirement should be to contribute at least 10 percent of your salary to your workplace retirement plan (401(k), 403(b), 457, etc.). I say this for several reasons.

  • It starts a great savings habit.
  • Subject to vesting requirements, it practically guarantees that you will get the employer match your 401(k) has, if any.
  • Assuming a traditional retirement account contribution, it gets you a valuable tax deduction at your marginal tax rate.
  • It will be incredibly difficult to get to financial independence without saving at least 10 percent of your salary. 

Here are some additional considerations.

Traditional or Roth 

In some plans, the employee does not have a choice – employee contributions are “traditional” deductible contributions. Increasingly, plans are offering the Roth option where the contribution is not deductible today, but the contribution and its growth/earnings are tax-free in the future.

This post addresses the traditional versus Roth issue. I strongly favor traditional 401(k) contributions over Roth 401(k) contributions for most people. The “secret” is that most people pay much more in tax during their working years than they do during their retired years (even if they have significant balances in their traditional retirement accounts). Thus, it makes more sense to take the tax deduction when taxes are highest and pay the tax when taxes tend to be much lower (retirement).

Bad Investments

I’d argue that most people with bad investments and/or high fees in their 401(k) should still contribute to it. Why? First, consider the incredible benefits discussed above. Second, you’re probably not going to be at that job too long anyway. In this video, I discuss that the average/median employee tenure is under 5 years. When one leaves a job, they can roll a 401(k) out of the 401(k) to the new employer’s 401(k) or a traditional IRA and get access to better investment choices and lower fees. 

Resource

Your workplace retirement plan should have a PDF document called a “Summary Plan Description” available in your workplace benefits online portal. Reviewing that document will help you figure out the contours of your 401(k) or other workplace retirement plan.

TWO: Establish a Roth IRA

For a primer on Roth IRAs, please read my Ode to the Roth IRA. Roth IRAs, like traditional IRAs, are “individual.” You establish one with a financial institution separate from your employer. 

Generally speaking, a Roth IRA gives you tax-free growth, and if done correctly, money withdrawn from a Roth IRA is both tax and penalty free. 

Roth IRA contributions can be withdrawn tax and penalty free at any time for any reason! The Roth IRA is the only retirement account that offers unfettered, tax-free access to prior contributions. Note, however, in most cases the best Roth IRA strategy is to keep money in the Roth IRA for as long as possible (so it continues to grow tax free!). 

Find out why the Roth IRA might be much better than a Roth 401(k). 

THREE: Contribute to an HSA 

A health savings account is a very powerful saving vehicle. You have access to it if you have a high deductible health plan. To have an HDHP through your employer, you need to determine (i) if your employer offers a HDHP and (ii) whether the HDHP is appropriate medical insurance for you. 

If you do not have employer provided insurance, you may be able to obtain an HDHP in the individual marketplace.

HSA contributions have several benefits. You receive an upfront income tax deduction for the money you contribute. If the funds in your HSA are used to pay qualified medical expenses, or are used to reimburse you for qualified medical expenses, the contributions and the earnings/growth are tax-free when paid out of the HSA. This tax-friendly combination means the HSA should be a high priority. 

Here are a few additional considerations:

HDHP Benefit

I believe the HDHP is itself a great benefit in addition to the HSA. Why? One reason is that the HDHP reduces a known expense: medical insurance premiums! Why pay significant premiums for a low deductible plan when the point of medical insurance is not “coverage” but rather to avoid financial calamity in the event of injury or illness?

Dr. Suneel Dhand has a great YouTube channel. He has stated that as a doctor he is quite leery about getting treated for disease by Western medicine. I believe that is a very fair critique.

We over-medicalize our problems. Too often we run to the doctor looking for a solution when the answer lies in what we’re eating and/or our environment. We should work to avoid disease and doctor visits by taking control of our own health. That is very much in line with both the high deductible model of medical insurance and financial independence. 

Part of “independence” (including financial independence) is questioning established systems. I am glad Dr. Dhand and others are starting to do just that when it comes to medicine. HDHPs help us do that while providing financial protection in the event of significant injury or illness.  

Thinking about a future mini-retirement? One great way to lay the foundation today for tomorrow’s mini-retirement is to increase one’s financial independence from the medical system and decrease dependence on any one employer’s medical insurance.

State Income Taxes

In California and New Jersey, HSAs are treated as taxable accounts. Thus, in these states there are no state income tax deductions for contributions to an HSA. Furthermore, dividends, interest and other realized income and gains generated by HSA assets are subject to state income taxes. While detrimental, the federal income tax benefits are so powerful that even residents of these states should prioritize HSA contributions.

Employer Contributions

Check to see if your employer offers an employer contribution to your HSA. Many do. When the employer does, the employee leaves free money on the table if they do not enroll in the HDHP.

Reimbursements

In most cases, it is advisable to (i) pay current medical costs out of your own pocket (your checking account and other taxable accounts) and (ii) record and track these medical expenses. Leaving the money in the HSA during our working years allows it to grow tax-free!

Years later when the money has grown, you can reimburse yourself tax-free from your HSA for the Previously Unreimbursed Qualified Medical Expenses (PUQME), as there is no time limit on reimbursements. Note that only qualified medical expenses incurred after you first open the HSA are eligible for tax-free reimbursement.

FOUR: Save, Save, Save!!!

My last recommendation is simple: save, save, save! Are there ways to do it in a tax-efficient manner? Absolutely! But the absolute most important consideration is the act of saving and investing itself. Between retirement plans, lack of a payroll tax, and favored dividend and capital gain tax rates, saving and investing are often tax efficient without trying to be. 

If in doubt, traditional 401(k) contributions are often fantastic.

Conclusion

Here are the top four tax moves I believe FI beginners should consider:

First, contribute 10 percent to your 401(k) or other workplace retirement plan

Second, establish a Roth IRA

Third, establish an HSA

Fourth, Save, Save, Save

Of course, this post is not tailored for any particular taxpayer. Please consult with your own tax advisor(s) regarding your own tax matters.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Subscribe to my YouTube Channel: @SeanMullaneyVideos

Follow me on X: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, medical, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, medical, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Revisiting Solo 401(k)s and the Rule of 55

On a recent episode of ChooseFI, I stated my then-held view that it is unlikely a distribution from a Solo 401(k) qualifies for the Rule of 55. My concern was this: once the Schedule C solopreneur retires, there does not appear to be an “employer” remaining in the picture to sponsor the Solo 401(k).

If that is the case, the Solo 401(k) should be rolled over to an IRA and there’s no ability to use the Rule of 55.

Until now, I’m not aware that anyone has done a deep dive to validate or disprove that concern. So I decided to do it myself. My research took me as close to the year 1962 as one can get without a flux capacitor, a DeLorean, and 1.21 gigawatts of electricity. 

I’ve now changed my view on the Solo 401(k) Rule of 55 issue. The analysis is too complicated to write adequately in a blog post. Thus, I’m self-publishing an article, Solo 401(k)s and the Rule of 55: Does the Answer Lie in 1962? (accessible here), on the topic.

Of course, the article is not legal or tax advice for you, any other individual, and any plan. 

For those of you who read my book, Solo 401(k): The Solopreneur’s Retirement Account (thank you!), please know the article is written differently. The book is a “101” and “201” level discussion of tax planning for the self-employed with some beginning and intermediate tax rule analysis. The article is much more akin to a “501” level discussion of a complex and somewhat uncertain tax issue emerging from ambiguities in the Internal Revenue Code

Enjoy the article and let me know what you think in the comments below. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post and the linked-to article are for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Five Reasons to Avoid the 529

Happy National 529 College Savings Day! Let’s celebrate with five reasons to avoid 529s.

Cart Before the Horse

I’ve said it before and I’ll say it again: far too often new parents have relatives extolling the virtues of a 529 at the reception after the Baptism.

Those relatives rarely step back and ask “how are Mom and Dad’s finances?”

Picture a typical late-20s / early 30s Mom and Dad of a newborn. What are their financial pain points? What’s needed in their financial lives? 

I can tell you what is not their financial pain point: taxes on investment income. Yet this is what the 529 solves for. The 529 for a newborn’s parents is often the equivalent of a cast for someone with a paper cut! 

What do Mom and Dad need in their financial lives? If they are anything like the typical American adult, they probably need more in the way of retirement savings. Shouldn’t Mom and Dad prioritize their own compelling retirement needs over saving for a speculative potential future expense of their newborn baby, college education? 

Listen to me discuss the 529 on The Personal Finance Podcast. 

The Tax Benefits Aren’t That Great

In 2024 we’re in a great time to own taxable investments. Long term capital gains and qualified dividend income are taxed at 0%, 15%, 18.8%, and 23.8% (when factoring in the potential net investment income tax). Having equities inside a 529 avoids that tax, which is quite modest by historical standards. That tax is particularly small considering the low dividend yield environment we currently have. 

Further, the state tax benefits are usually modest. In our three largest states, California, Texas, and Florida, there’s no immediate state benefit for a 529 contribution.

Flexibility

As much as possible, a dollar ought to be able to serve multiple masters and multiple purposes.

Inside a taxable brokerage account, a dollar can efficiently support (i) Mom and Dad during their working years, (ii) Mom and Dad during their retirement, (iii) a new roof for the house, (iv) a family vacation to Yellowstone, and/or (v) Junior’s college education. 

Inside a 529, a dollar can efficiently support (i) Junior’s college education.

Why should the parents of a newborn handcuff their money when the tax benefits are quite modest? Why shouldn’t Mom and Dad remain flexible for their own financial future and decide what to do with that dollar later on, when they have more knowledge and information?

Many things can happen in the future that could make having a large sum in a 529 a bad thing: maybe Junior went to trade school, Junior got a scholarship, and/or Mom and Dad had financial struggles and now need that dollar to support their own retirement. 

The 529 Overfunding Problem

Scholarships happen. Some newborns don’t end up going to college. These are just two of the reasons that 529s get overfunded.

Taken for non-educational purposes, 529 distributions that represent earnings are subject to ordinary income tax rates and a 10 percent penalty. Ouch!

There are bailout techniques available to avoid negative tax consequences, but they are all limited to various degrees. The SECURE 2.0 529-to-Roth IRA rollover is very limited and, in my opinion, not something to be planned into. 

Feeding the Beast

What grade would you give American higher education in 2024?

American higher education often produces graduates who are ill-equipped for the modern economy and/or have staggering student debt loads. Many colleges and universities have administrative bloat that has gotten wildly out of hand.

Why should newborns’ parents handcuff their money such that they can only avoid a penalty by paying it over to American higher education? How does that make sense? Very modest tax benefits are nowhere near sufficient to make that make sense. 

Conclusion

I’m not here to say funding a 529 never makes sense. But I am here to say (1) I believe that 529s are wildly overhyped and (2) 529s rarely make sense for the financial profile and needs of the parents of newborns. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Accumulators Should Ignore the Conventional Wisdom

The conventional wisdom says to accumulators “Save through a Roth 401(k)! Don’t you dare contribute to traditional 401(k)s. Those things are infested with taxes!!!”

Doubt that prioritizing Roth 401(k) contributions over traditional deductible 401(k) contributions is the conventional wisdom? Let’s hear from some very prominent personal finance commentators:

These commentators have much bigger platforms than I have, and they are to be commended for their many solid contributions to the personal finance discourse. On this particular issue, however, I believe their conventional wisdom misses the mark. I believe most of those saving for retirement during their working years should prioritize traditional deductible 401(k) contributions. 

Here are the eight reasons why I believe the conventional wisdom on the traditional 401(k) versus Roth 401(k) debate is wrong.

Traditional Retirement Account Distributions are Very Lightly Taxed

Those 401(k)s and traditional IRAs are infested with taxes, right!

Wrong!!!

I have run the numbers in several blog posts and YouTube videos. Long story short, while working contributions into traditional 401(k)s generally enjoy a tax benefit at the taxpayer’s highest marginal tax rate while traditional retirement account distributions are taxed going up the progressive tax brackets in retirement (including the 10% and 12% brackets). This results in surprisingly low effective tax rates on traditional 401(k) and traditional IRA withdrawals in retirement.

The Tax Hikes Aren’t Coming

If “experts” keep predicting A and the exact opposite of A, B, keeps occurring and A never occurs, then the experts constantly predicting A aren’t good at predicting the future!

That’s where we are when it comes to predicting future tax hikes on retirees. Experts keep predicting that taxes are going through the roof on retirees. Experts use those predictions to justify the Roth 401(k) contribution push. 

There’s a problem with those predictions: they have been dead wrong!

I did a video on this. Not only does Congress avoid tax hikes on retirees, recent history indicates Washington is addicted to tax cuts on retirees. To wit:

  • December 2017: TCJA increases the standard deduction and reduces the 15% bracket to 12%. There are few better ways to cut retiree taxes!
  • December 2019: The SECURE Act delays required minimum distributions (“RMDs”) from age 70 ½ to age 72.
  • March 2020: The CARES Act cancels 2020 RMDs and allows those already taken to be rolled back into retirement accounts in a very liberal fashion.
  • November 2020: The Treasury gets into the act by publishing new RMD tables that reduce annual RMDs.
  • December 2022: SECURE 2.0 purports to delay RMDs from age 72 to ages 73 or 75 (for those born in 1960 or later). Congress was in such a rush to cut taxes on retirees the House didn’t dot the Is and cross the Ts from a Constitutional perspective!

Sure, the federal government has too much debt. Does that mean that taxes must necessarily rise on retirees? Absolutely not! 

There are many solutions that can leave retirees unscathed, including:

  1. Raising tariffs.
  2. Raising taxes on college endowments, private foundations, high income investors’ dividends and capital gains, and hedge fund managers.
  3. Eliminating electric vehicle tax credits.
  4. Spending cuts, particularly to military spending and foreign spending. These are becoming more likely as American politics continue to change. 

Conventional Wisdom Misses the Sufficiency Problem

How much tax do you pay on an empty 401(k)? How much tax do you pay on a nearly empty 401(k)?

Those crying wolf over taxes in retirement miss the real issue: sufficiency! According to this report, the median American adult wealth is about $108,000 as of 2022 (see page 16). 

Let’s imagine all that $108K is in a traditional retirement account. Few will take it all out at once. The rather annual modest withdrawals will hardly be taxed at all due to the standard deduction and/or the 10% tax bracket.

If people are behind in their retirement savings, what’s the best way to catch up? Deduct, deduct, deduct! Those deductions save taxes now, opening the door for more savings. For those behind in retirement savings, sacrificing the valuable tax deduction to make Roth contributions makes little sense in my opinion. Why? Because those behind in retirement savings will face very low taxes in retirement. 

Sadly, the median American adult has a sufficiency problem and would be fortunate to one day have an (overblown) tax problem instead!

Missing Out on the Hidden Roth IRA

Q: What’s it called when I take money out of a retirement account and don’t pay tax on it?

A: A Roth IRA!!!

Well, many Americans have a Roth IRA that lives inside their traditional 401(k). I call this the Hidden Roth IRA. 

Prior to collecting Social Security, many Americans will have the opportunity to take tax free distributions from their traditional IRA or 401(k) because they will be offset by the standard deduction. 

If all your 401(k) contributions (and possible employer contributions) are Roth, you miss out on the Hidden Roth IRA. 

I break down the phenomenon of the Hidden Roth IRA in this video. 

Missing Out on Incredible Roth Conversions

Did you know that you might be able to do Roth conversions in retirement and pay federal income tax at a 6% or lower federal tax rate? It’s true! I break that opportunity down in this video.

If you’re telling a 22 year old college graduate that all of their 401(k) contributions should be Roth you’re foreclosing many or all future Roth conversions! Why? Shouldn’t younger workers be setting up low tax Roth conversions in retirement while they are working?

“Roth, Roth, Roth!!!” sounds great and makes for a fun slogan. But it precludes incredibly valuable future tax planning!

The Widow’s Tax Trap and IRMAA are Overblown

The Widow’s Tax Trap is a phenomenon in American income taxation where surviving spouses pay more tax on less income. It’s real. But just how bad is it?

In one example, I found that an incredibly affluent 75 year-old married couple would be subject to a combined effective federal income tax/IRMAA rate of 15.44%. The surviving spouse would then be subject to a combined 19.87% effective rate after the first spouse’s death. 

That’s the Widow’s Tax Trap. Real? Yes. Terrifying? No.

Few things are as overblown in American personal finance as IRMAA. IRMAA, income-related monthly adjustment amounts, are technically increases in Medicare premiums as one’s income exceeds certain thresholds. In practice, it is a nuisance tax on showing high income in retirement.

In one extreme example, I discussed a 90 year old widow with $304,000 of RMDs and Social Security income. Her IRMAA was about $5,500, a nuisance tax of about 1.8% on that income. Annoying? Sure. Something to factor into planning during the accumulation phase? Absolutely not.

Missing Out on Premium Tax Credits

Mark, age 22, graduates from college and buys into “Roth, Roth, Roth!!!” Every dollar he contributes to his 401(k) is in the Roth 401(k), and he elects to have all his employer 401(k) contributions put into the Roth 401(k) as well. At age 55, Mark decides to retire. He has a paid off house, $200,000 in a savings account, and $2.5 million in his Roth 401(k).

Mark will be on an ACA medical insurance plan from retirement (or the end of COBRA 18 months later) until the month he turns 65. There’s just one big snag: he has no income! Because of that he will not qualify for the combination of an ACA plan and a Premium Tax Credit, since, based on income, he’s eligible for Medicaid. Ouch!

Mark falls into this trap because he has no ability to create taxable income in retirement. Had he simply put some of his 401(k) into the traditional 401(k), he could have “turned on” taxable income by doing Roth conversions (mostly against the standard deduction!). Doing so would qualify Mark for hundreds of dollars in monthly Premium Tax Credits, greatly offsetting the significant cost of ACA medical insurance. Note Mark could turn on income by claiming Social Security at age 62, permanently reducing his annual Social Security income. 

Retirement Isn’t the Only Priority

The tax savings from a traditional 401(k) contribution can go to tremendously important things before retirement. Perhaps a Mom wants to step back from the workforce to spend valuable time with her infant son or daughter. Maybe Mom & Dad want to pay for a weeklong vacation with their children. Maybe a single Mom wants to qualify her son for scholarship money. 

There are pressing priorities for retirement savers prior to retirement. You know what can help pay for them? The tax deduction offered by a traditional 401(k) contribution. 

Conclusion

The Conventional Wisdom is wrong!

Traditional deductible contributions to 401(k)s and other workplace retirement plans are a great way to save and invest for the future. Future taxes are a drawback to that tactic. But they have to be assessed keeping in mind the eight reasons I raise above. To my mind, it’s more important to build up wealth than to be tax efficient. As discussed above, those aren’t mutually exclusive, including for those using traditional deductible 401(k) contributions for the majority of their retirement savings.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Vanguard Exits the Solo 401(k) Business

Big news in the Solo 401(k) world! Vanguard is closing their Solo 401(k) and will exit the Solo 401(k) business in July.

On April 19th I recorded a YouTube video with my initial reaction.

On April 20th I posted a lengthy X thread and a LinkedIn post with additional thoughts.

UPDATE July 22, 2024: The Vanguard to Ascensus transfer is now complete. For those with a new Ascensus account, it’s vitally important to file a new beneficiary designation form!

UPDATE October 12, 2024 The Ascensus Solo 401(k) contribution portal is not intuitive. I walk through tips for new Ascensus Solo 401(k) owners in this YouTube video.

My Solo 401(k) Book

If you’re interested in the Solo 401(k), I wrote a book about it.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Accessing Retirement Accounts Prior to Age 59 ½

One thing I like about the Financial Independence community is that members are not beholden to Conventional Wisdom.

Many in the Establishment believe retirement is for 65 year olds (and some basically think it’s not for anyone). 

My response: Oh, heck no! 

Sure, some people have jobs they very much enjoy. If that’s the case, then perhaps retirement isn’t your thing in your 50s. But many in the FI movement have accumulated assets such that they no longer have a financial need to work. Perhaps their job is not all that enjoyable – it happens. Or perhaps their job won’t exist in a year or two – that happens too.

The tax rules require some planning if one retires prior to turning age 59 ½. Age 59 ½ is the age at which the pesky 10 percent early withdrawal penalty no longer applies to tax-advantaged retirement account distributions.

Thus, there’s a need to consider what to live off of once one is age 59 ½. Below I list the possibilities in a general order of preference and availability. Several of these options (perhaps many of them) will simply not apply to many 50-something retirees. Further, some retirees may use a combination of the below discussed options. 

Listen to Sean discuss accessing money in retirement prior to age 59 ½ on a recent ChooseFI episode! Part Two on the ChooseFI podcast is coming soon. 

Taxable Accounts

The best retirement account to access if you retire before age 59 ½ isn’t even a “retirement” account: it’s a taxable account. I’m so fond of using taxable accounts first in retirement I wrote a post about the concept in 2022.

The idea is to use some combination of cash in taxable accounts (not at all taxable – it’s just going to the ATM!) and sales of brokerage assets (subject to low long term capital gains federal income tax rates) to fund your pre-59 ½ retirement. This keeps taxable income low and sets up potential additional tax planning. 

Pros: Because of tax basis, living off $100,000 of taxable brokerage accounts doesn’t cause $100,000 of taxable income. Further, long term capital gains receive very favorable federal income tax treatment. Some may even qualify for the 0% long term capital gains tax rate!

But that’s not all. There are significant creditor protection benefits to living off taxable assets first. As we spend down taxable assets, we are reducing those assets that are most vulnerable to potential creditors. By not spending down tax-advantaged retirement accounts, we are generally letting them grow, thus growing the part of our balance sheet that tends to enjoy significant creditor protection. Note that personal liability umbrella insurance is usually a good thing to consider in the creditor protection context regardless of tax strategy. 

Spending taxable assets first tends to limit taxable income, which can open the door to (1)  a significant Premium Tax Credit in retirement (if covered by an Affordable Care Act medical insurance plan) and (2) very tax advantageous Roth conversions in early retirement. 

There’s also a big benefit for those years after we turn 59 ½. By spending down taxable assets, we reduce future “uncontrolled income.” Taxable accounts are great. But they kick off interest, dividends, and capital gains income, even if we don’t spend them. By reducing taxable account balances, we reduce the future income that would otherwise show up on our tax return in an uncontrolled fashion. 

Cons: To my mind, there are few cons to this strategy in retirement. 

The one con in the accumulation phase is that when we choose to invest in taxable accounts instead of in traditional deductible retirement accounts we forego a significant tax arbitrage opportunity. That said, these are not mutually exclusive. Members of the FI community can max out deductible retirement account contributions and also build up taxable accounts.

Ideal For: Someone who is able to save beyond tax-advantaged retirement accounts during their working years. This is the “ideal” for financial independence in my opinion, though it may be challenging for some. 

Inherited Retirement Accounts

Withdrawals from inherited retirement accounts (other than those the spouse treats as their own) are never subject to the 10% early withdrawal penalty. Often they are subject to a 10-year drawdown rule, so usually they should be accessed prior to using many other draw down techniques.

Pros: If it’s a traditional retirement account inherited from a parent or anyone else more than 10 years older than you are, you generally have to take the money out within 10 years. Why not just live on that money? Simply living on that money, instead of letting the traditional inherited retirement grow for ten years, avoids a “Year 10 Time Bomb.” The time bomb possibility is that the inherited traditional retirement account grows to a huge balance that needs to come out in the tenth full year following death. Such a large distribution could subject the recipient subject to an abnormally high marginal federal income tax rate. 

Cons: Not very many other than if the account is a Roth IRA, using the money for living expenses instead of letting it grow for 10 years sacrifices several years of tax free growth. 

Ideal For: Someone who has inherited a retirement account prior to turning age 59 ½.

Rule of 55 Distributions

Rule of 55 distributions are only available from a qualified retirement plan such as a 401(k) from an employer the employee separates from service no sooner than the beginning of the year they turn age 55. 

This is a great way to avoid the early withdrawal penalty. But remember, the money must stay in the workplace retirement account (and not be rolled over to a traditional IRA) to get the benefit. 

Pros: Funds retirement prior to age 59 ½ without having to incur the 10 percent early withdrawal penalty. 

Whittles down traditional retirement accounts in a manner that can help reduce future required minimum distributions (“RMDs”).

Cons: You’re handcuffed to the particular employer’s 401(k) (investments, fees, etc.) prior to age 59 ½. Review the plan’s Summary Plan Description prior to relying on this path to ensure flexible, periodic distributions are easily done after separation from service and prior to turning age 59 ½. 

Limited availability as one must separate from service no sooner than the year they turn age 55. 

Creates taxable income (assuming a traditional account is used), which is less than optimal from a Premium Tax Credit and Roth conversion perspective.

Ideal For: Those with (1) large balances in their current employer 401(k) (or other plan), (2) a quality current 401(k) or other plan in terms of investment selection and fees, (3) a plan with easily implemented Rule of 55 distributions, and (4) plans to retire in their mid-to-late 50s.

Governmental 457(b) Plans

Withdrawals from governmental 457(b) plans are generally not subject to the 10% early withdrawal penalty. This is the Rule of 55 exception but they deleted the “55” 😉

Like the Rule of 55, this is only available so long as the governmental 457(b) is not rolled to a traditional IRA.

Pros: Funds retirement prior to age 59 ½ without having to incur the 10 percent early withdrawal penalty. If you have a governmental 457(b), it’s better than the Rule of 55 because you don’t have to worry about your separation from service date. 

Whittles down traditional retirement accounts in a manner that can help reduce future RMDs.

Cons: You’re handcuffed to the particular employer’s 457 (investments, fees, etc.) prior to age 59 ½. Review the plan’s Summary Plan Description prior to relying on this path to ensure flexible, periodic distributions are easily done after separation from service and prior to turning age 59 ½. 

Creates taxable income (assuming a traditional account is used), which is less than optimal from a Premium Tax Credit and Roth conversion perspective.

Ideal For: Those (1) with large balances in their current employer governmental 457(b) and (2) a quality current governmental 457(b) in terms of investment selection and fees.

Roth Basis

Old annual contributions and conversions that are at least 5 years old can be withdrawn from Roth IRAs tax and penalty free at any time for any reason. This can be part of the so-called Roth Conversion Ladder strategy, though it does not have to be, since many will have Roth Basis going into retirement. 

Pros: Roth Basis creates a tax free pool of money to access prior to turning age 59 ½. 

Cons: We like to let Roth accounts bake for years, if not decades, of tax free growth. Using Roth Basis in one’s 50s significantly reduces that opportunity. 

Some may need taxable income in early retirement to qualify for Premium Tax Credits. Relying solely on Roth Basis can be much less than optimal if Premium Tax Credits are a significant part of one’s early retirement plan. 

Roth 401(k) contributions, for many workers, are disadvantageous in my opinion. Many Americans will forego a significant tax rate arbitrage opportunity if they prioritize Roth 401(k) contributions over traditional 401(k) contributions. 

Creates income for purposes of the FAFSA. 

Ideal For: Those with significant previous contributions and conversions to Roth accounts. 

72(t) Payments

I did a lengthy post on this concept. The idea is to create an annual taxable distribution from a traditional IRA and avoid the 10 percent early withdrawal penalty.

Pros: Avoids the early withdrawal prior to turning age 59 ½. 

Whittles down traditional retirement accounts in a manner that can help reduce future RMDs.

Inside a traditional IRA, the investor controls the selection of financial institutions and investments and has great control on investment expenses. 

Cons: This opportunity may require professional assistance to a degree that many of the other concepts discussed do not.

There is a risk that if not done properly, previous years’ distributions may become subject to the 10 percent early withdrawal penalty and related interest charges. 

They are somewhat inflexible. That said, if properly done they can be either increased (by creating a second 72(t) payment plan) or decreased (via a one-time switch in method). 

Creates taxable income, which is less than optimal from a Premium Tax Credit and Roth conversion perspective.

Ideal For: Those with most of their financial wealth in traditional deferred retirement accounts prior to age 59 ½ and without easy access to other alternatives (such as the Rule of 55 and/or governmental 457(b) plans. 

HSA PUQME

Withdrawals of Previously Unreimbursed Qualified Medical Expenses (“PUQME”) from a health savings account are tax and penalty free at any time for any reason. Thanks to ChooseFI listener and correspondent Kristin Smith for suggesting the idea to use PUQME to help fund retirement in one’s 50s. 

Pros: Withdrawals of PUQME creates a tax free pool of money to access prior to turning age 59 ½. 

Does not create income for purposes of the FAFSA.

Reduces HSA balances in a way that can help to avoid the hidden HSA death tax in the future.

Cons: This is generally a limited opportunity. The amount of PUQME that can be used prior to age 59 ½ is limited to the smaller of one’s (1) PUQME and (2) HSA size. Because HSAs have relatively modest contribution limits, in many cases HSA PUQME withdrawals would need to be combined with one or more of the other planning concepts to fund retirement prior to age 59 ½.

We like to let HSAs bake for years, if not decades, of tax free growth. Using HSA PUQME in one’s 50s significantly reduces that opportunity. 

Some may need taxable income in early retirement to qualify for Premium Tax Credits. Relying on PUQME can be less than optimal if Premium Tax Credits are a significant part of one’s early retirement plan. 

Ideal For: Those with significant HSAs and significant PUQME. 

Net Unrealized Appreciation

Applies only to those with significantly appreciated employer stock in a 401(k), ESOP, or other workplace retirement plan. I’ve written about this opportunity before. That employer stock with the large capital gains can serve as a “Capital Gains IRA” in retirement. Retirees can possibly live off sales of employer stock subject to the 0% long term capital gains rate. 

This opportunity usually requires professional assistance, in my opinion. 

The move of the employer stock out of the retirement plan into a taxable brokerage account (which sets up what I colloquially refer to as the “Capital Gains IRA” may need to be paired with the Rule of 55 (or another penalty exception) to avoid the 10 percent early withdrawal penalty on the “basis” of the employer stock. 

Pros: Moves income from “ordinary” income to “long term capital gains” income, which can be very advantageous, particularly if one can keep their income entirely or mostly in the 0% long term capital gains marginal bracket. 

Cons: Remember Enron? NUA is essentially Enron if it goes fabulously well instead of failing spectacularly. 

Employer stock is problematic during the accumulation phase since your finances are heavily dependent on your employer without a single share of employer stock. People make their finances more risky by having both their income statement and their balance sheet highly dependent on a single corporation.

It keeps the retiree heavily invested in the stock of their former employer, which is much less than optimal from an investment diversification perspective.  

Another con is that this usually requires professional assistance (and fees) to a much greater degree than several of the other withdrawal options discussed on this post. 

Ideal For: Those with large balances of significantly appreciated employer stock in a workplace 401(k), ESOP, or other retirement plan. 

Pay the Penalty

The federal early withdrawal penalty is 10 percent. For those in California, add a 2.5 percent state penalty. For some, perhaps the best idea is to simply bite-the-bullet and pay the early withdrawal penalty. That said, anyone accessing a tax-advantaged retirement account in a way not covered above should always consult the IRS list to see if perhaps they qualify for one of the myriad penalty exceptions.  

Pros: Why let a 10 percent penalty prevent you from retiring at age 58 if you have sufficient assets to do so and you might be looking at a year or two of the penalty, tops? 

Whittles down traditional retirement accounts in a manner that can help reduce future RMDs.

Cons: Who wants to pay ordinary income tax and the early withdrawal penalty? Even for those close to the 59 ½ finish line, a 72(t) payment plan for five years might be a better option and would avoid the penalty if properly done. 

Ideal For: Those very close to age 59 ½ who don’t have a more readily available drawdown tactic to use. That said, even these retirees should consider a 72(t) payment plan, in my opinion. 

Combining Methods to Access Funds Prior to Age 59 1/2

For some, perhaps many, no single one of the above methods will be the optimal path. It may be that the optimal path will involve combining two or more of the above methods.

Here’s an example: Rob retires at age 56. He uses the Rule of 55 to fund most of his living expenses prior to turning age 59 ½. Late in the year, he finds that a distribution from his traditional 401(k) would push him up into the 22% federal income tax bracket for the year. Thus, for this last distribution he instead elects to take a recovery of Roth Basis from his Roth IRA. This allows him to stay in the 12% marginal federal income tax bracket for the year. 

Conclusion

Don’t let anyone tell you you can’t retire in your 50s. If you have reached financial independence, why not? Of course, you will need to be very intentional about drawing down your assets and funding your living expenses. This is particularly important prior to your 59 1/2th birthday.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Tax Basketing for a 72(t) Payment Plan

Some retiring in their 50s will need to use a 72(t) payment plan. This often involves establishing a “72(t) IRA” and a “non-72(t) IRA.”

People wonder “how do you allocate your portfolio when you have a 72(t) payment plan?”

Below we tackle 72(t) IRAs from a tax basketing perspective. Most investors in the financial independence community want some allocation to bonds and some to equities.* Thus, questions emerge for those employing a 72(t) payment plan: what should be in my 72(t) IRA? What should be in my non-72(t) IRA?

* This post simply takes that as an assumption and is not investment advice for you or anyone else. 

Watch me discuss portfolio allocation for 72(t) payments plans on YouTube.

72(t) Example

Monty, age 53, has a $2M traditional 401(k), $10,000 in a savings account, and a paid off house. He wants to retire and take his first annual $80,000 72(t) payment in February 2023. Monty also wants to have a 75/25 equity/bond allocation. 

First, Monty would need to transfer his 401(k) to a traditional IRA (preferably through a direct trustee-to-trustee transfer).

Once the 401(k) is in the traditional IRA, Monty needs to split his traditional IRA into two traditional IRAs, one being the 72(t) IRA (out of which he takes the annual 72(t) payment) and one being the non-72(t) IRA. 

To determine the size of the 72(t) IRA, Monty uses the commonly used fixed amortization method and decides to pick the following numbers: 

  • Maximum allowable interest rate, 5.79%, 
  • The Single Life Table factor for age 53 (33.4), and 
  • The annual payment he’s selected, $80,000. 

With those three numbers, Monty can do a calculation (see IRS Q&A 7 and my YouTube video on the calculation) and determine that the 72(t) IRA should be $1,170,848.59. Thus, the non-72(t) IRA should be $829,151.41.

72(t) Portfolio Allocation

How does Monty allocate the 72(t) IRA and the non-72(t) IRA such that (1) his overall financial asset portfolio ties out to the desired 75/25 allocation and (2) he is as tax optimized as possible. 

I believe that Monty should aim to keep his 72(t) IRA as small as possible. Why? Because it is possible that Monty will not need his 72(t) payment at some point prior to turning age 59 ½. 

Perhaps Monty inherits $300,000 when he is age 57. At that point, he can use that money to fund his lifestyle until age 59 ½. Why does he want to keep paying taxes on the $80,000 annual 72(t) payment?

Monty has an option available: a one-time change of the 72(t) payment to the RMD method. If Monty switches to the RMD method, he’s likely to dramatically reduce the annual amount of the required 72(t) payment. The RMD method keys off the account balance at the end of the prior year. The lower the balance, the lower the required annual payment under the RMD method. 

Since Monty has decided to invest in equities and bonds, I believe that Monty should house his bonds inside his 72(t) IRA. While there are absolutely no guarantees when it comes to investment returns, equities tend to grow more than bonds. Since bonds tend to be lower growth, they are a great candidate for the 72(t) IRA.

It would stink if Monty wanted to reduce his annual 72(t) payment only to find that a 72(t) IRA composed entirely of equities had skyrocketed in value, increasing the amount of his revised annual payment under the RMD method. 

Thus, I believe that Monty should put his entire bond allocation, $500,000, inside his 72(t) IRA. That makes the rest of the tax basketing easy: have the entire non 72(t) IRA be invested in equities, and have the remainder of his 72(t) IRA, $670,849, be invested in equities.

72(t), Sequence of Returns Risk, and Safe Withdrawal Rate

One must remember that 72(t) is entirely a tax concept. At least in theory, it has nothing to do with sequence of returns risk and safe withdrawal rate. 

Some might look at the 72(t) IRA, $1,170,848.59, and say “Wait a minute: an $80K withdrawal is way more than 4% or 5% of that 72(t) IRA! Isn’t this a dangerous withdrawal rate? Doesn’t this amplify the sequence of returns risk?”

Remember, Monty’s withdrawal rate is $80,000 divided by the entire $2M portfolio (4%), not $80,000 divided by the $1,170,848.59 72(t) IRA. Further, Monty’s sequence of returns risk on this withdrawal rate exists regardless of the 72(t) plan. The greater the overall withdrawal rate, the greater the sequence of returns risk.

Lastly, the 5.79% interest rate Monty chooses has nothing to do with the withdrawal rate. It has everything to do with keeping the size of the 72(t) IRA as small as possible. The chosen interest rate doesn’t change the amount of the annual withdrawal ($80,000) but rather changes the size of the 72(t) IRA.

Conclusion

Tax basketing should be considered when crafting a 72(t) payment plan. I generally believe that investments that are less likely to have substantial gains sit better inside an investor’s 72(t) IRA rather than their non-72(t) IRA. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters.Please also refer to the Disclaimer & Warning section found here.

San Diego Tax Delay

It’s deja vu all over again – Yogi Berra

Last year, most of California received several deadline delays when it came to 2022 tax returns, tax payments, and IRA and HSA contributions.

Sure enough, San Diego County now has a deadline delay for their 2023 tax returns, tax payments, and IRA and HSA contributions. Hat tip to Jennifer Mah’s Instagram for alerting me to this development. 

San Diego County Tax Deadline Delay

The IRS announced that because of early 2024 flooding in San Diego, San Diegons have an extended deadline, June 17, 2024, to perform most 2023 tax acts that otherwise would have been due early in 2024. The Franchise Tax Board has followed suit and also issued their own delay announcement. 

2023 Traditional and Roth IRA Contributions

The deadline for San Diegons to make 2023 contributions to traditional and/or Roth IRAs has been extended to June 17, 2024. As a practical matter, I wouldn’t encourage reliance on this particular deadline delay. Financial institutions may find it difficult to allow “late but timely” 2023 IRA contributions on their platform when it is available only to residents of a single county. 

If you are a San Diegon reading this in May 2024 and want to make an IRA contribution for 2023, I recommend initiating the process by calling the financial institution using a seldom used app on your phone, the phone.  

2023 Backdoor Roth IRAs

San Diegons now have until June 17, 2024 to execute the first step of a 2023 Backdoor Roth IRA, the nondeductible contribution to a traditional IRA for 2023. This would be a Split-Year Backdoor Roth IRA. 

2023 HSA Contributions

San Diegons now have until June 17, 2024 to contribute to a 2023 health savings account. The same comments that apply to traditional IRA and Roth IRA contributions made using the deadline extension apply to 2023 HSA contributions made using the deadline extension. 

2023 Tax Returns and Payments and 2024 Q1 Estimated Tax Payments

San Diegons now have until June 17, 2024 to (i) file their 2023 federal and California income tax returns, (ii) pay the amount due with their 2023 federal and California income tax returns, and (iii) make 2024 first quarter estimated payments. 

Who Benefits?

Residents of San Diego County qualify for the extended deadline. Taxpayers with records in San Diego County can also benefit. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Tax Return Reporting for Net Unrealized Appreciation

By Sean Mullaney and Andrea MacDonald

Net Unrealized Appreciation Planning

Net unrealized appreciation is a tax planning opportunity that applies to the gain attributable to employer stock inside an employer retirement plan. Plans that can have employer stock in them include 401(k) plans and employee stock ownership plans (ESOPs).

Growth in tax deferred retirement accounts is great. But it comes with a cost: ordinary income tax on that growth. The tax code has one major exception: Net Unrealized Appreciation! The idea is this: an employee can transfer, in-kind, any employer stock from the employer retirement account to a taxable brokerage account. 

Instead of the entire amount being subject to ordinary income tax, only the “basis,” i.e., the historic cost, of the stock is subject to ordinary income tax. The growth is only subject to capital gains tax when the stock is later sold. Obviously, if there has been a significant gain in the stock, NUA treatment, instead of ordinary income tax treatment on that growth, will be advantageous.

“In-kind” Transfer: An “in-kind” transfer is a transfer of the exact same thing. In this case, it is a transfer of the exact employer stock owned within the employer plan. Selling that stock and repurchasing it shortly thereafter blows the NUA planning opportunity. 

NUA Planning Example

Mark works at Acme Corporation. Inside his Acme retirement account he has $1M worth of Acme stock. He and Acme paid $100,000 for that stock.

Mark is 53 years old and leaves employment at Acme. His NUA opportunity is as follows: he can transfer all his Acme retirement accounts invested in assets other than Acme stock to IRAs (or a new employer’s retirement account) and transfer, in-kind, the Acme stock to a taxable brokerage account (the “NUA distribution”). 

Mark creates a $100,000 income hit on this year’s tax return and will owe the 10% early withdrawal penalty (unless he qualifies for an exception) if he does this. However, the $900K of capital gains in that Acme stock gets two big tax benefits. First, it will never be subject to RMDs. Second, when the Acme stock is sold that gain will be taxed at capital gains rates instead of ordinary income tax rates. That is a tremendous advantage to using the NUA strategy. 

Does NUA Treatment Make Sense?

NUA does not always make sense when it comes to employer stock in retirement accounts. In fact, in most cases it is likely not to make sense. You saw in Mark’s example there was a real price to pay: ordinary income tax and the possible 10 percent early withdrawal penalty. 

What if, instead of paying $100K for the Acme stock over the years, Mark and Acme had paid $700K? There’s no way Mark should use NUA treatment to get $300K of gain into capital gains tax when it would trigger immediate taxation on $700,000 and a $70,000 penalty!

But if the “basis” number is low, being subject to the 0%, 15%, and 20% marginal capital gains tax on the employer stock gain inside the plan can be a great outcome. 

NUA treatment has requirements, such as emptying all retirement accounts from the employer in the same year. Thus, oftentimes those with significant amounts of employer stock in a retirement plan should work with professional advisors. For more information on the planning surrounding NUA treatment, read Michael Kitces’ great blog post on the subject. 

Tax Return Reporting

Transfer of Employer Stock to Taxable Account

Information Reporting to the Taxpayer and the IRS

First up is the transfer of the employer stock from the workplace retirement plan to a taxable brokerage account (the NUA distribution). This must be an in-kind transfer by the employer plan of the employer  stock to the taxable brokerage account.. The NUA distribution results in some amount of taxable income. The employer plan issues a Form 1099-R to report the NUA distribution. The Form 1099-R reports the gross distribution amount in Box 1. The taxable amount reported in Box 2a. The Box 2a amount is the amount that the employee and employer contributed to buy the employer stock and is taxable in the year of the NUA distribution. The Net Unrealized Appreciation, the difference between Box 1 and Box 2a, is reported in Box 6. The Net Unrealized Appreciation is the gain that will be subject to long-term capital gains rates in any post-NUA distribution sale of the employer stock. 

Reporting on the Taxpayer’s Form 1040

On the individual’s Form 1040 tax return, the gross distribution will be reported on the line for pensions & annuities (line 5a for the tax year 2023 Form 1040), with the taxable amount showing on line 5b.

Now, what about that 10% early withdrawal penalty? There are several exceptions, all of which are reported on Form 5329, Part 1. If, for example, Mark was 55 years old when he left his employment at Acme, qualifies for exception 01 – separation from service distribution in or after the year of reaching 55 (age 50 for qualified public safety employees). 

Disposition of Employer Stock

Information Reporting to the Taxpayer and the IRS

These transactions are reported on Form 1099-B. This form will include the number of shares sold, the date they were sold, and the proceeds from the sale. 

Reporting on the Taxpayer’s Form 1040

When the employer stock is actually sold, two gains on the sale of that stock must be recognized. The first is the net unrealized appreciation in the employer stock. That amount is crystalized at the time of the NUA distribution from the plan to the taxable account. This gain is always a long-term capital gain, regardless of when the post-distribution sale occurs. The gain is reported by the taxpayer on Form 8949 and Schedule D.

There is a second potential gain. It could be a gain or a loss. It is the amount of the increase (or decrease) in value the stock has experienced since the NUA distribution into the taxable account. 

Continuing with Mark’s example, assume the NUA distribution occurred on January 16, 2024. At that time, Mark owned 1,000 Acme shares, each worth $1,000 and each with Net Unrealized Appreciation of $900. On February 20, 2024, Mark sells 40 Acme shares for $1,040 each. This triggers two gains: $36,000 of Net Unrealized Appreciation ($900 NUA times 40), which is taxed as long term capital gain, and $1,600 of short term capital gain ($40 times 40), which is taxed as ordinary income. 

Post-NUA Distribution Losses

What if, instead of a post-NUA distribution gain, there’s a loss? The loss simply reduces the NUA recognized on each sale. For example, if Mark’s sale of 40 shares on February 16, 2024 was for $960 per share, the NUA triggered on each share is $860 per share instead of $900 per share. 

NUA and the Net Investment Income Tax (Form 8960)

One more form may be required: Form 8960. If the seller’s modified adjusted gross income (“MAGI”) is above $200K (single) or $250K (married filing joint), the gain on top of the NUA ($40 per share in Mark’s example) is subject to the 3.8% net investment income tax. However, the NUA gain itself is not subject to the net investment income tax. See Treas. Reg. Sec. 1.1411-8(b)(4)(ii). 

Transfer of Other Employer Plan Assets to IRAs

Information Reporting to the Taxpayer and the IRS

As part of the NUA process, all the other qualified plan assets need to be transferred to a traditional IRA (or Roth IRA if there are Roth qualified plan assets). Assuming this occurs via a direct trustee-to-trustee transfer, it is reported on Form 1099-R with a box 7 code “G” (direct rollover). Box 1 of the 1099-R will indicate the gross distribution, and box 2a, Taxable amount, will be $0, since it’s a direct rollover. 

Reporting on the Taxpayer’s Form 1040

On the individual’s tax return, the gross distribution should show up on the line for pensions and annuities (line 5a for the tax year 2023 Form 1040), with $0 showing on line 5b for taxable amount.

Conclusion

For the right situation, NUA is a potentially great tax planning opportunity. For those taking advantage of the opportunity, it is important to get the tax return reporting correct. We leave with one parting thought: those considering NUA are usually well advised to consider working with professional advisors, and those who have implemented an NUA planning process often benefit from working with a professional tax return preparer. 

This post is a collaboration by Sean Mullaney, CPA and Andrea MacDonald, CPA. It is posted on fitaxguy.com and on Steadfast Bookkeeping’s blog.

Follow Sean on X at @SeanMoneyandTax

Follow Andrea on X at @Andreamacdcpa

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Spousal IRA

Is earned income required to contribute to an individual retirement account (an “IRA”)? If you’re married, it may not be, thanks to the Spousal IRA. 

The Spousal IRA is a great opportunity for families to build financial stability, and perhaps get a juicy tax deduction, even if only one of the spouses work outside of the home. It can help families save for the future and prioritize other important goals such as raising children.

IRA Basics

There are two types of IRAs that most working Americans can consider. I did a primer about them here.

A traditional IRA offers tax-deferred growth and the possibility of a tax deduction for contributions. While distributions from a traditional IRA in retirement are taxable, many will find that traditional IRA distributions in retirement are only lightly taxed. 

A Roth IRA offers no tax deduction on the way in, but features tax-free growth and tax-free withdrawals in retirement. 

Both can be a great way to build up tax-advantaged wealth for retirement.

IRA Contribution Limits

The limit on IRA contributions for 2023 is the lesser of $6,500 or earned income ($7,500 or earned income if you are age 50 or older in 2023). The limit on IRA contributions for 2024 is the lesser of $7,000 or earned income ($8,000 or earned income if you are age 50 or older in 2024). Remember that traditional IRAs and Roth IRAs share that contribution limit, so a dollar contributed to a traditional IRA is a dollar that cannot be contributed to a Roth IRA and vice-versa. 

IRA Contribution Deadlines

Generally speaking, the deadline to contribute to either a traditional IRA or a Roth IRA is April 15th of the following year. The deadline cannot be extended even if the taxpayer files for an extension to file their own tax return. On rare occasions the IRS may provide a very limited exception to the April 15th IRA contribution deadline. 

The Spousal IRA

For purposes of having earned income allowing one to make an IRA contribution (tradition and/or Roth), a non-working spouse can use their spouse’s earned income for purposes of making either (or both) a traditional IRA or a Roth IRA contribution.

Here is an example:

Joe and Mary are married. Joe has a W-2 job and Mary does not. Mary can make an IRA contribution (a Spousal IRA) based on Joe’s W-2 earned income. 

The Spousal IRA can be used to increase tax-advantaged retirement savings. It can also be used to strategically optimize tax deductions. Many W-2 workers are covered by a workplace 401(k) plan. Thus, based on low income limits, it is difficult for them to deduct a traditional IRA contribution. 

However, when one is not covered by a workplace retirement plan, it is much easier to qualify to deduct a traditional IRA contribution. It is often the case that a Spousal IRA will offer a potential tax deduction when the working spouse is not able to deduct a traditional IRA contribution. 

Split-Year Spousal IRA Contribution Example

As I write this, the 2024 tax return season (for 2023 tax returns) is about to get started. Now’s the time to be thinking about 2023 IRA contributions if you have not yet made one!

There’s still plenty of time to contribute to an IRA (traditional or Roth) for the year 2023. Some of that planning might involve strategically employing a Spousal IRA. Here’s an example:

Mark and Theresa, both age 41, are married and have three children. They live in California. Mark works a W-2 job and Theresa does not have earned income. Mark is covered by a 401(k) at work. Their modified adjusted gross income (“MAGI”) for 2023 is $190,000. This puts them in the 22% marginal federal income tax bracket and the 9.3% marginal California income tax bracket. They have made no IRA contributions for either of them for 2023 going into tax season. 

It is early April 2024 and Mark and Theresa are about to file their tax returns. They see they have $8,500 in cash available to use to make 2023 IRA contributions. What they might want to do is contribute $6,500 to a 2023 deductible traditional IRA for Theresa (a Spousal IRA) and the remaining $2,000 to a 2023 Roth IRA for Mark, since he cannot deduct a traditional IRA contribution. By prioritizing a tax deduction, Mark and Theresa save $2,034.50 on their 2023 income taxes. 

The Spousal IRA as a Backdoor Roth IRA

The Spousal IRA can be executed as a Backdoor Roth IRA. Here is an example:

Jack and Betty, both age 42, are married. Jack works a W-2 job and Betty does not have earned income. Jack is covered by a 401(k) at work. Their MAGI for 2024 is $260,000 and thus neither of them qualify to make a regular annual contribution to a Roth IRA. 

Assuming Betty has no balances in traditional IRAs, SEP IRAs, and SIMPLE IRAs (and thus does not have a Pro-Rata Rule problem), Betty can contribute $7,000 to a nondeductible traditional IRA and then convert that amount (plus any growth) to a Roth IRA. Doing so uses a Spousal IRA to implement a Backdoor Roth IRA. 

Spousal IRA Tax Return Reporting

To report a deductible traditional Spousal IRA contribution, the amount of the contribution must be reported on Schedule 1, line 20, filed with the couple’s annual federal income tax return. 

To report a nondeductible traditional Spousal IRA contribution, the amount of the contribution must be reported on Part I of the Form 8606.

There is no required federal income tax return reporting for a Roth Spousal IRA contribution. However, such contributions should be entered into the tax return software to help determine the potential eligibility for a retirement savers’ credit. 

Conclusion

The Spousal IRA creates a great opportunity for married couples to save for retirement and possibly gain access to valuable tax deductions. It can help married couples focus on important priorities such as child rearing and still make significant contributions to retirement accounts.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

SECURE 2.0 Comment Letter

SECURE 2.0, passed in December 2022, made dozens of changes to the rules governing tax-advantaged retirement accounts.

When Congress passes a major tax law change, the IRS and Treasury issue regulations and other guidance regarding the change. Practitioners and taxpayers often provide the IRS and Treasury comment letters bringing issues and concerns to the government’s attention.

I wrote a comment letter (which you can read here) to the IRS and Treasury addressing facets of the following provisions:

SECURE 2.0 Section 115

SECURE 2.0 Section 314

SECURE 2.0 Section 317

SECURE 2.0 Section 326

SECURE 2.0 Section 331

SECURE 2.0 Section 603

SECURE 1.0 Section 113

Follow me on Twitter: @SeanMoneyandTax

This post (and the linked-to comment letter) is for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Retire on 72(t) Payments

Want to retire before age 59 ½? Have most of your wealth in traditional tax-deferred retirement accounts? Worried about the 10 percent early withdrawal penalty? 

This post is for you!

Picture it: You’re age 53, have $50,000 in a savings account, a paid-off home, and $2.5M in a 401(k). Including income taxes, you spend about $80,000 a year. You want to retire, but you’re worried about paying the early withdrawal penalty, which would be about $8,000 a year (not factoring in the penalty on the penalty!). 

What to do, what to do? The tax law allows someone in this situation to take a “series of substantially equal periodic payments” to avoid the 10 percent penalty. The payments must occur annually for the longer of 5 years or until the taxpayer turns 59 ½. 

72(t) payments can make retirement possible prior to age 59 ½ when one has most of their assets in traditional deferred retirement accounts. Done properly, these payments avoid the 10 percent early withdrawal penalty. 

Below I explore some of the rules of 72(t) payments (sometimes referred to as a “72(t) SEPP” or “SEPP”) and lay out what I hope will be an informative case study. 

** As always, none of this is personalized advice for you, but rather educational information for your consideration. Consult with your own advisors regarding your own situation. 

72(t) Substantially Equal Periodic Payments

Methods

The IRS and Treasury provide three methods for computing a 72(t) payment. As a practical matter, the third one I discuss, the fixed amortization method, tends to be the most commonly used and most user friendly in my opinion.

The required minimum distribution method allows taxpayers to take a 72(t) payment just like an RMD. Take the prior year end-of-year balance and divide it by the factor off the IRS table. The biggest problems with this method are it tends to produce a smaller payment the younger you are and the payment changes every year and can decrease if the IRA portfolio declines in value. The fixed annuitization method usually requires actuarial assistance, making it more complicated and less desirable. See Choate, referenced below, at page 587. 

We will focus the rest of the post on the fixed amortization method of computing 72(t) payments (other than a brief foray into the RMD method to account for changing circumstances)). 

Computing Fixed Amortization 72(t) Payments

To compute a 72(t) payment and the size of the 72(t) IRA using the fixed amortization method, we will need to run through some math. Four numbers are required: the interest rate, the life expectancy, the annual payment, and the size of the 72(t) IRA. 

Usually the IRS gives us the interest rate and the life expectancy and we need to solve for the 72(t) IRA size. 

Interest Rate: In a very positive development, the IRS and Treasury issued Notice 2022-6 early in 2022. This notice allows taxpayers to always use an interest rate anywhere from just above 0% to 5%. There is a second, older rule: the taxpayer can use any interest rate that is not more than 120% of the mid-term federal rate for either of the previous two months. The IRS publishes that rate on a monthly basis.  

As a general rule, taxpayers will usually want to use the greatest interest rate permitted to as to decrease the size of the 72(t) IRA. Decreasing the size of the 72(t) IRA will usually be advantageous, for the reasons discussed below. 

Life Expectancy: The life expectancy comes to us from an IRS table. While we have three possible choices to use, generally speaking taxpayers will want to use the Single Life Table found at Treas. Reg. Section 1.401(a)(9)-9(b). See Choate, referenced below, at page 587. The taxpayer takes their age on their birthday of the year of the first 72(t) payment and uses the factor from the Single Life Table as the life expectancy. 

Payment: Finally, we, not the IRS, get to determine a number! The payment is simply the annual payment we want to receive as a 72(t) payment every year. While this amount is rather inflexible, as discussed below it will be possible to establish additional 72(t) IRAs and payments to increase the amount received if desired. 

Size of the 72(t) IRA: This is what we’re solving for to establish a “right-sized” IRA to produce the desired 72(t) payment. In Google Sheets, we do a present value calculation to solve for the size of the 72(t) IRA that generates the desired payment amount. The formula is rather simple: =-PV(Interest Rate Cell, Life Expectancy Cell, Annual Payment Cell). I put a negative sign in front of the PV to have the size of the 72(t) IRA appear as a positive number. It’s important that the formula be entered in that order and that the formatting be correct in each cell.

Note on 72(t) Payments with non-IRA Accounts: Setting up a 72(t) from a non-IRA is possible but not frequent in practice. It is not possible to divide up a 401(k) account in a manner conducive to establishing a “right-sized” 72(t) payment account. See Choate, referenced below, at page 595. 

Annual Equal 72(t) Fixed Amortization Payments

The computed payments must be made annually and equally. This means that no more and no less than the computed payment comes out every year. I believe that taking an annual flat payment on or around the first payment anniversary date is a best practice. However, this best practice is not required. See also Choate, referenced below, at page 600. For example, monthly payments of the computed amount are allowable. See Choate, referenced below, at page 600. 

Annual payments must be made for the longer of five years or until the taxpayer reaches age 59 ½. 

72(t) Payments Case Study

Let’s return to the example discussed above: it is early November 2023 and you (let’s call you Pat) are 53 years old (your birthday was June 8th) and you want to retire, spending $80K a year from your $2.5M 401(k). Let’s solve for the size of the 72(t) IRA:

Interest Rate: 5.33% (the highest 120% of federal mid-term rate of the previous two months per the IRS)

Life Expectancy: 33.4

Payment: $80,000

The size of the 72(t) IRA is $1,236,012.95. See IRS FAQ Q&A 7.

Pat would first transfer (preferably through a direct trustee-to-trustee transfer) the 401(k) to a traditional IRA worth $2.5M. Once in the traditional IRA, Pat would call their financial institution and ask them to divide the traditional IRA into two IRAs: one with exactly $1,236,012.95 (the “72(t) IRA”) and one with the reminder of the traditional IRA (the “non-72(t) IRA”). I recommend initially investing the 72(t) IRA in a money market fund so that it can be clearly established that the beginning account balance was exactly the $1,236,012.95 computed to yield the correct payment. Pat takes the first payment of $80,000 on November 29th from the 72(t) IRA in this hypothetical scenario.

Let’s keep going. Assume that in 2027, when Pat turns age 57 and interest rates are well below 5%, Pat wants to increase their November withdrawal from $80K to $90K. As discussed below, Pat can’t simply increase the withdrawal from the 72(t) IRA. But since Pat kept a non-72(t) IRA, Pat can slice that one up to create a second 72(t) IRA. That second 72(t) IRA can give Pat the extra $10,000 Pat wants to spend.

Here’s what that looks like.  

Interest Rate: 5.00% 

Life Expectancy: 30.6

Payment: $10,000

The size of the second 72(t) IRA is $155,059.55.

Pat would call their financial institution and ask them to divide the non-72(t) IRA into two IRAs: one with exactly $155,059.55 (the “Second 72(t) IRA”) and one with the remainder of the traditional IRA (the surviving non-72(t) IRA). Pat takes the additional payment of $10,000 also on November 29th from the Second 72(t) in this hypothetical scenario.

Here is what Pat’s withdrawals would look like:

YearBirthday AgeRequired First 72(t) November 29 WithdrawalRequired Second 72(t) November 29 WithdrawalTotal Annual Withdrawal
202353$80,000$0$80,000
202454$80,000$0$80,000
202555$80,000$0$80,000
202656$80,000$0$80,000
202757$80,000$10,000$90,000
202858$80,000$10,000$90,000
202959$80,000$10,000$90,000
203060$0$10,000$10,000
203161$0$10,000$10,000

Remember that the First 72(t) IRA and the Second 72(t) are locked up for a period of time. See Locking the Cage below. The First 72(t) IRA is locked up until and through December 7, 2029, the day before Pat’s 59 ½ birthday. The Second 72(t) IRA is locked up until and through November 28, 2032, the day before the fifth anniversary of the first $10,000 payment from the Second 72(t) IRA. See IRS FAQ 13 on this point. Generally speaking, no amount other than the annual payment should go into, or out of, a 72(t) IRA until the end of the lock-up period.

Maintain Flexibility

I strongly recommend maintaining as much flexibility as possible. One way to do that is to have the 72(t) IRA be as small as possible, leaving as much as possible in a non-72(t) IRA or IRAs. Why? 

First, the non-72(t) can be, in a flexible manner, sliced and diced to create a second 72(t) IRA if wanted or needed. Second, it is not abundantly clear what happens when a 72(t) IRA is used for partial Roth conversions. See Choate, referenced below, at page 384. As Ms. Choate discusses, the only clarity we have is that if the entire 72(t) IRA is Roth converted, the taxpayer must continue to take withdrawals from the Roth IRA for the remainder of the 72(t) term. Doing so limits the benefit of doing Roth conversions in the first place, since we usually want Roth converted amounts to stay in a Roth IRA to facilitate many years of tax-free growth. 

Imagine if Pat did not divide the $2.5M traditional IRA into two IRAs. Pat could have simply used a smaller interest rate on the entire $2.5M traditional IRA to get the $80,000 annual payment out. However, then Pat would not have had the flexibility to create a second 72(t) payment stream. This is an important reason that it is usually best to use the highest possible interest rate to lower the 72(t) IRA size and maintain the most flexibility.

72(t) Payment Plan Disqualification

A “modification” to the 72(t) payment plan blows up the plan with unfavorable consequences. In the year of the modification the taxpayer owes the 10 percent early withdrawal penalty plus interest on the penalty on all the previously taken 72(t) payments. See Choate, referenced below, at page 596. 

A blow up after age 59 ½, for those on the five year rule, is bad but tends to be less deleterious than a blow up occurring with respect to a SEPP ending at age 59 1/2. The early withdrawal penalty and related interest are not assessed on 72(t) payments taken after one’s 59 ½ birthday. See Choate, referenced below, at page 596. 

There are a few modifications to a 72(t) payment plan that do not blow it up (i.e., they are permissible and don’t trigger the penalty and interest). See Choate, referenced below, at pages 597-601. Those looking to change the payment amount are often well advised to set up a second 72(t) payment plan (as Pat did) rather than seeking a modification to the existing 72(t) payment plan. 

72(t) Payment Reduction

Imagine that instead of wanting an additional 72(t) payment amount, Pat wanted to reduce the 72(t) payment. This is not uncommon. Perhaps Pat has a significant inheritance in 2027 and thus no longer needs to take an $80,000 annual payment and pay tax on it.

Unfortunately, Pat is not allowed to simply discontinue or reduce the 72(t) payment without triggering the early withdrawal penalty (and interest charges) on the previously taken 72(t) payments.

But, the rules allow a one-time switch to the RMD method. Making the switch is likely to significantly reduce the annual 72(t) payment. For example, if Pat wants a smaller payment starting in 2027, Pat could take the 72(t) IRA balance on December 31, 2026 (imagine it is exactly $1M) and divide it by the age 57 factor off the Single Life Table (29.8) and get a 2027 72(t) payment of $33,557.05. Alternatively, Pat could use the age 57 factor off the Notice 2022-6 Uniform Life Table (41.6) and get a 2027 72(t) payment of $24,038.46.

If Pat makes this one-time switch, Pat will annually compute the 72(t) payment for the remainder of the 72(t) term using the table used in 2027 (see Notice 2022-6 page 6) and the prior-year end-of-year 72(t) IRA balance.

The one-time switch to the RMD method is helpful if the taxpayer wants to significantly reduce their 72(t) annual payment, perhaps because of an inheritance, marriage, YouTube channel blowing up, or returning to work. The availability of this method to reduce required 72(t) payments (if desired) is another reason to keep 72(t) IRAs as small as possible.

72(t) Locking The Cage

The 72(t) IRA should be thought of as a locked cage. No one goes in, and only the 72(t) payment comes out annually. The rigidity with which the IRS treats the 72(t) IRA gives early retirees incentive to use as high an interest rate as possible to get the highest annual payment out of the smallest 72(t) IRA possible.

Just how rigid is the IRS? In one case, the IRS disqualified a 72(t) SEPP because a taxpayer transferred a workplace retirement plan into the 72(t) IRA during the 72(t) payment period. See page 4 of this newsletter (page 4 is behind a paywall). Imagine paying penalties and interest on old 72(t) payments for what is seemingly an unrelated rollover!

Remember, the “series of substantially equal periodic payments” requires not just an annual payment. It requires that the 72(t) IRA be locked up. Assuming one is using the fixed amortization method for their 72(t) payments, not a dollar more than the 72(t) SEPP should come out each year. It appears the IRS expects the amount to be equal each tax year, see page 5 of this PLR. 

Further, the 72(t) lockup does not end with the taking of the last payment. Rather, as described in IRS FAQ 13, it ends at the end of the lock up period. So if Sean, age 57 in 2023, takes his first 72(t) SEPP of $10,000 from IRA 1 on July 15, 2023, his taking of payment number 5 ($10,000) on July 15, 2027 does not end the lock up. Sean can’t take any additional money out of IRA 1 until July 1, 2028 (the fifth anniversary of his first $10,000 72(t) payment). 

Practice Point: Never add money to a 72(t) IRA during the lockup period. This includes never making an annual contribution to a 72(t) IRA and never rolling an IRA, 401(k), or other qualified plan into a 72(t) IRA. 

IRS FAQ 13 is instructive in terms of when the lock up ends. The IRS is clear that the lock up ends on the date of the 59 ½ birthday, not on January 1st of that year. Say Rob, born January 14, 1971, takes his first SEPP of $40,000 on August 16, 2023. His 72(t) IRA is free on his 59 ½ birthday, which is July 14, 2030. Presumably, Rob takes his last $40,000 SEPP on or around August 16, 2029. Nevertheless, he can’t add to or withdraw from his 72(t) IRA prior to July 14, 2030 without blowing up his 72(t) payment plan and incurring significant penalties and interest. 

As discussed above, the one-time switch to the RMD method is a permissible modification to the 72(t) payment terms that does not trigger the early withdrawal penalty and related interest on previously taken 72(t) payments.

A Note on the 72(t) Risk Profile

The earlier in life the 72(t) payment plan starts, the greater the risk profile on the 72(t) payment plan. The opposite is also true: the later in life a 72(t) payment plan starts, the lower the risk profile.

Why?

Because the sooner the 72(t) payment plan starts, the more years (and more interest) that can be blown up by a future modification requiring the payment of the 10 percent early withdrawal penalty and interest. 

Consider Pat’s example. If Pat blows up the First 72(t) payment plan in early 2028, Pat owes the 10% early withdrawal penalty and interest on five previously taken 72(t) payments from the First 72(t) IRA (2023 through 2027). If Pat blows up the Second 72(t) payment plan in 2032, Pat only owes the early withdrawal penalty and interest on the three 72(t) payments received before Pat turned age 59 ½. 

72(t) Payment Tax Return Reporting

Taxpayers should keep the computations they and/or their advisors have done to document the 72(t) payment plan. Distributions should be reported as taxable income and on Form 5329. Code 02 should be entered on Line 2 of Form 5329. 

72(t) Is An Exception to More Than One Rule

72(t) payment plans are an exception to the 10 percent early withdrawal penalty. They are also an exception to the general rule that the IRS views all of your IRAs as a single IRA. The 72(t) IRA is the 72(t) IRA. If you have a separate IRA and take ten dollars out of it prior to age 59 ½, you trigger ordinary income tax and a $1 penalty. If you take an additional ten dollars out of the 72(t) IRA prior to the end of the 72(t) lock up, you blow up the 72(t) payment plan and owe the 10 percent early withdrawal penalty and interest on all the pre-59 ½ 72(t) payments. 

Other Penalty Free Sources of Early Retirement Funding

Let’s remember that 72(t) payments are a tool. In many cases they are not a “go-to” strategy. I’ve written this post not because 72(t) payments are a go-to strategy but rather because I know there are many in their 50s thinking about retirement but daunted by the prospect of accessing traditional retirement accounts prior to age 59 ½.

Generally speaking, I encourage using resources other than 72(t) payments if you are able to. They include:

Taxable Accounts: I’m so fond of using taxable accounts first in retirement I wrote a post about the concept in 2022.

Inherited Retirement Accounts: Withdrawals from inherited retirement accounts (other than those the spouse treats as their own) are never subject to the 10% early withdrawal penalty. Often they are subject to a 10-year draw down rule, so usually they should be accessed prior to implementing a 72(t) payment plan from one’s own accounts.

Rule of 55 Distributions: Only available from a qualified retirement plan such as a 401(k) from an employer the employee separates from service no sooner than the beginning of the year they turn age 55. This is a great workaround from the early withdrawal penalty, and much more flexible than a 72(t) payment plan. But remember, the money must stay in the workplace retirement account (and not be rolled over to a traditional IRA) to get the benefit. 

Governmental 457(b) Plans: Withdrawals from governmental 457(b) plans are generally not subject to the 10% early withdrawal penalty. 

Roth Basis: Old annual contributions and conversions that are at least 5 years old can be withdrawn from Roth IRAs tax and penalty free at any time for any reason.

I previously discussed using a 72(t) payment plan to bail out Roth IRA earnings penalty-free prior to age 59 ½. This is a tactic that I would not recommend unless absolutely necessary (which I believe is a very rare situation). 

72(t) Landscape Change

It should be noted that the issuance of Notice 2022-6 in early 2022 changed the landscape when it comes to 72(t) payments. Before the 5 percent safe harbor, it was possible that taxpayers could be subject to sub-0.5 percent interest rates, meaning that it would take almost $1M in a retirement account to generate just $30,000 in an annual payment in one’s mid-50s. Now with the availability of the 5 percent interest rate much more modest account balances can be used to generate significant 72(t) payments in one’s mid-50s. 

I Tweeted some additional thoughts on what the changing landscape means for how we should approach 72(t) payments.

72(t) and Employer Stock

What if Pat’s 401(k) contained significant amounts of employer stock? What if that employer stock had significantly appreciated in value since the time Pat and/or Pat’s employer contributed that stock? If so, a 72(t) payment plan may not be ideal. Rather, Pat may want to work with Pat’s advisor(s) to look into a separate and distinct tax planning opportunity, net unrealized appreciation (“NUA”). 

I collaborated with Andrea MacDonald to discuss the tax return reporting requirements for NUA here.

Resource

Natalie B. Choate’s treatise Life and Death Benefits for Retirement Planning (8th Ed. 2019), frequently referenced above, is an absolutely invaluable resource regarding retirement account withdrawals.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters.Please also refer to the Disclaimer & Warning section found here.

The Basis Isolation Backdoor Roth IRA

If you have basis in an IRA, you will want to read this post. Basis in an IRA creates all sorts of confusion, but it also presents a great planning opportunity for many of those still working. I refer to this opportunity as the Basis Isolation Backdoor Roth IRA. 

Where Does IRA Basis Come From?

Basis in a traditional IRA generally emerges from two sources. The first source is old nondeductible traditional IRA contributions that have not been Roth converted or withdrawn. Nondeductible traditional IRA contributions should be reported on a Form 8606 filed with one’s annual federal income tax return. 

Many times this basis is simply exhausted annually by Backdoor Roth IRAs. Here’s a quick example:

Example 1: Becky contributed $6,500 to a traditional, nondeductible IRA on January 2, 2023. On February 1, 2023, when the traditional IRA was worth $6,504, she converted the entire traditional IRA balance to a Roth IRA. On December 31, 2023, she had $0 in all traditional IRAs, SEP IRAs, and SIMPLE IRAs. She successfully completed the Backdoor Roth IRA, which created $6,500 of IRA basis on January 2nd and exhausted all $6,500 of that basis on February 1st.

However, there are plenty of Americans who have existing and remaining IRA basis because they can’t do the Backdoor Roth IRA efficiently, or they never did the Backdoor Roth IRA. 

To sum up, those doing annual tax-efficient Backdoor Roth IRAs tend not to have any IRA basis at year-end. But some Americans do have existing and remaining IRA basis.

The second source of IRA basis is from after-tax 401(k) contributions that have been transferred to a traditional IRA (see Natalie B. Choate’s treatise Life and Death Benefits for Retirement Planning (8th Ed. 2019), page 150). 

There are Americans with existing IRA basis through transfers from a 401(k) (or other qualified plan) to a traditional IRA. However, going forward this should generally not occur. The IRS and Treasury issued Notice 2014-54, which provides that after-tax 401(k) contribution amounts can be rolled directly to a Roth IRA. From a planning perspective, after-tax 401(k) contributions (and other qualified plan after-tax contributions) should generally be directed into Roth IRAs if the plan participant prefers to exit the plan for IRAs (at retirement or a job change, for example). 

Example 2: Chris is age 53. He leaves employment at Consolidated Industries, Inc. on November 1, 2023. At that time, he had a traditional 401(k) at Consolidated worth $500,000. During his time at Consolidated, Chris made $75,000 of after-tax contributions to the traditional 401(k) which remain in the traditional 401(k). Chris prefers to manage the money himself in an IRA or IRAs. Thus, he has two options:

Option One: Transfer the money (preferably through a direct trustee-to-trustee transfer) to a single traditional IRA. Chris now has $75,000 of traditional IRA basis. 

Option Two: Transfer (preferably through direct trustee-to-trustee transfers) the after-tax money $75,000 to a Roth IRA and $425,000 to a traditional IRA. The $75,000 goes into the Roth IRA as a nontaxable conversion contribution (see also Notice 2014-54 Example 4). Chris receives no basis in his traditional IRA.

Which option is better for Chris? Clearly it is Option Two, which gives Chris tax-free growth on his $75,000. Further, Chris can withdraw the $75,000 from the Roth IRA tax and penalty free at any time while Chris would be subject to the hard bite of the Pro-Rata Rule if he used Option 1 and later withdrew $75,000 from the traditional IRA. Thus, while Chris is allowed to roll his $75K 401(k) basis into a traditional IRA, he would be much better served to roll the basis tax-free into a Roth IRA. 

A Current Employer Qualified Plan That Accepts Rollovers

In order to have an IRA basis isolation opportunity, one must be currently employed by an employer with a qualified plan (often a 401(k)) that accepts IRA roll-ins. Many qualified plans accept IRA roll-ins but not all do. 

Former employees generally are not able to contribute to 401(k)s and other qualified plans, so having a 401(k) plan at a former employer is generally not sufficient for this planning opportunity. 

One should generally employ the Basis Isolation Backdoor Roth IRA if they have a 401(k) or other qualified plan at work they are satisfied with from both an investment choice standpoint and a fee standpoint. If one isn’t satisfied with their workplace retirement plan the Basis Isolation Backdoor Roth IRA may not be a good tactic to employ. 

Comprehensive Basis Isolation Backdoor Roth IRA Case Study

Having addressed the two prerequisites to do a Basis Isolation Backdoor Roth IRA, let’s dive in with a comprehensive case study. 

Imagine Ray has two (and only two) traditional IRAs. IRA 1 is a $100K traditional IRA rollover from an old 401(k). No basis came along in the rollover into IRA 1. IRA 2 is a traditional IRA worth $25K. It was established with three $6K nondeductible traditional IRA contributions for 2020 through 2022. He filed Forms 8606 reporting those contributions. 

Ray’s current employer (Acme) has a great 401(k) that accepts roll-ins of traditional IRAs. What could Ray do to take advantage of his traditional IRA basis? He will need to isolate that basis, and that’s where the Basis Isolation Backdoor Roth IRA comes in. 

Step 1

Ray transfers IRA 1 to the Acme 401(k), preferably through a direct trustee-to-trustee transfer. 

Step 2

Ray invests about $18,010 of IRA 2 in a money market account and invests the remainder of IRA 2 in any investment of his choice (Mutual Fund A).* 

By putting that $18,000 and a bit of change in a money market, Ray makes sure he “leaves behind” the IRA basis in the IRA! We will come back to why this “leave behind” asset is so critically important in the Step 3 discussion and analysis. 

* As a practical matter, it may be easier to split IRA 2 into IRA 2 and IRA 3, with the $18,010 in IRA 2 and Mutual Fund A in IRA 3. Either path can work, but splitting into IRA 2 and IRA 3 may be the easier path. That split should be done internally at the IRA 2 institution without any check coming out of IRA 2 to the owner.  

Step 3

Ray transfers the entire value of Mutual Fund A to the Acme 401(k), preferably through a direct trustee-to-trustee transfer. 

The money market account is crucial. The Internal Revenue Code provides that IRA basis cannot be transferred to a 401(k) (see also Natalie B. Choate’s treatise Life and Death Benefits for Retirement Planning (8th Ed. 2019), page 158). By establishing that IRA 2 will have at least $18K that will not be moved into the 401(k), Ray ensures that he “leaves behind” at least his basis inside the IRA. 

If the $18,010 was invested in an equity mutual fund (call it Mutual Fund B), there’s a risk that when Ray does Step 3 he will leave behind only Mutual Fund B, which could be less than his $18K basis if Mutual Fund B declines in value.

Example 3: Imagine Ray does Step 3 when Mutual Fund A is worth $10K and Mutual Fund B, originally worth $18K is now only worth $14K based on market declines. In such a case, $4K of basis would (theoretically) move into the Acme 401(k) with the $10K going from IRA 2 to the Acme 401(k). That would be a prohibited transfer of basis. 

IRA Aggregation: Remember that for tax purposes, the IRS looks at all of Ray’s traditional IRAs (whether he has one or ten) as a single traditional IRA. We can’t say that basis attaches to IRA 2 only, so it is important that Ray leave at least $18K behind in an IRA so that after the transfers from his IRAs to qualified plans he can demonstrate that his basis was left behind in one or more of his traditional IRAs. 

Step 4

Step 4: Ray converts the entire remaining balance in IRA 2 (likely to be $18,010 plus a bit of additional interest) to a Roth IRA. The only taxable amount is the small amount over $18,000.

Step 4 is reported on a Form 8606 (Parts 1 and 2). 

Step 5

Ray ensures that as of December 31st of the year Step 4 occurs, Ray has $0 balances in all traditional IRAs, SEP IRAs, and SIMPLE IRAs. 

The Benefits of the Basis Isolation Backdoor Roth IRA

Ray has moved approximately $107K from traditional IRAs to the Acme 401(k). That is entirely tax free and does not change the future tax treatment of that money. Perfectly fine, but by itself this doesn’t improve Ray’s tax position.

Before this planning, Ray had $18K of IRA basis that was of limited value due to the Pro-Rata Rule. Future taxable distributions or conversions from his traditional IRAs would have picked up only a small portion of that $18K, meaning that it would only protect small portions of future distributions and conversions from current taxation. 

Example 4 The Pro-Rata Rule Bites Ray: If Ray had $18K of basis and $125K of total traditional IRAs and decided to do a $10K Roth conversion (without first doing the Basis Isolation Backdoor Roth IRA), approximately $1,440 of that Roth conversion would have been tax free and approximately $8,560 would have been taxable. See the mock Form 8606 Part I here and Form 8606 Part II here (though note that tax return software programs may use a separate statement instead of actually completing the form). 

But with the Basis Isolation Backdoor Roth IRA Ray puts $18K plus into a Roth IRA and paid almost no tax to do so! Ray successfully isolated all $18,000 of basis to get it all into a Roth IRA without being adversely affected by the Pro-Rata Rule. Further, that $18,000 can now grow tax free for the rest of Ray’s life. Previously, inside a traditional IRA that $18,000 was growing tax-deferred, not tax free. 

The Basis Isolation Backdoor Roth IRA improved Ray’s position by getting around the Pro-Rata Rule to get $18K plus into a Roth IRA for hardly any income tax. The only tax Ray pays is on the small amount the conversion amount in Step 4 exceeds $18,000.

The Basis Isolation Backdoor Roth IRA also opens another future tax planning opportunity. Going forward, Ray can do annual Backdoor Roth IRAs in a tax-efficient manner because he cleaned out his traditional IRAs into his workplace 401(k). 

Practical Considerations

The Basis Isolation Backdoor Roth IRA is not a tactic to be affirmatively planned into. Rather, it is a clean up tactic. It makes the best of a situation where one has both basis and pretax amounts in traditional IRAs. The Backdoor Roth IRA is an affirmative planning technique, though it may require similar clean-up steps prior to implementation. 

This planning is sophisticated and benefits from professional assistance. I recommend that most work with a professional if they are considering this sort of planning. Further, this planning does not occur every day. My experience suggests that most professionals are unfamiliar with this type of planning. Professionals will need to review resources such as this blog post and other sources and measure two or three times to dot I’s and cross T’s on this type of planning. 

Of course, this blog post is not advice for the reader or any particular individual. 

Additional IRA Basis and IRA Basis Isolation Resource

I went into detail on this planning in a June 2023 Measure Twice Planners presentation. While the presentation is mostly geared towards advisors, I hope I presented it in such a way that layman can also understand much of it and get value from it. The presentation and its slides, like this particular post, are for educational purposes only and are not intended as advice for any particular individual. 

Conclusion

Existing basis in IRAs is a planning opportunity if the investor has a good workplace 401(k) or other qualified plan that accepts IRA roll-ins. That planning requires intention and diligence, and measuring two or three times, even if working with a professional. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on X at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2024 Solo 401(k) Update

There are some new developments in the world of the Solo 401(k). Here are the highlights:

New Solo 401(k) Employee Contributions Limit for 2024

The IRS announced that for 2024, the employee deferral limit for all 401(k)s, including Solo 401(k)s, will be $23,000. 

Solo 401(k) Catch-Up Contributions Limit for 2024

The IRS also announced that for 2024, the employee deferrals catch-up contribution limit remains $7,500. As a result, those aged 50 or older can contribute, in employee contributions, a maximum of the lesser of $30,500 ($23,000 plus $7,500) or earned income. 

New Solo 401(k) All Additions Limit for 2024

The new all-additions limit for Solo 401(k)s is $69,000 (or earned income, whichever is less). For those aged 50 or older during 2024, the $66,000 number is $76,500 ($69,000 plus $7,500). 

Wither Roth Employer Contributions?

One of the changes SECURE 2.0 ushered in was allowing Roth employer contributions to 401(k) plans, including Solo 401(k)s. Interestingly enough, three of the largest institutions offering Solo 401(k)s, Fidelity, Schwab, and Vanguard, have not added that feature to their Solo 401(k)s. Vanguard’s website goes so far as to affirmatively state it will not add the Roth employer contribution feature to their Solo 401(k) at this time. 

I mention this development to inform the reader, not to criticize Solo 401(k) providers. If you’ve read some of my other work, you may know I don’t think a lack of Roth employer contributions in Solo 401(k)s is a problem.

UPDATE March 2, 2024: Today I learned that Schwab now offers Roth employee contributions (a change) and Roth employer contributions (also a change). Based on this January 21, 2024 post, I suspect this change occurred prior to the federal district court’s publishing of its decision in Texas v. Garland on February 27, 2024.

Ambiguity on New Schedule C Solo 401(k) Funding Deadline

UPDATE December 14, 2023: I Tweeted a thread about the provision that allows Schedule C solopreneurs to establish and fund a new Solo 401(k) with an employee deferral contribution after year-end. There is at least some concern that if one is diligent enough to establish a new Solo 401(k) prior to year-end they might not get the benefit of Section 401(b)(2)‘s funding deadline extension. If that is true (and to my mind this is an ambiguous issue), then the solopreneur establishing the new Solo 401(k) prior to year-end would need to either fund the employee contribution prior to year-end or elect to make an employee deferral contribution prior to year-end.

UPDATE March 2, 2024: There’s new uncertainty when it comes to the new Solo 401(k) establishment deadline for Schedule C solopreneurs looking to make a first-time employee contribution. A federal district court in Texas held on February 27, 2024, in Texas v. Garland, that the House of Representatives did not have a sufficient Quorum when it passed the Omnibus, which includes SECURE 2.0 and the Solo 401(k) deadline extension in SECURE 2.0 Section 317. Here’s my X/Twitter thread on the case and here’s my YouTube video on the case. Stay tuned to my YouTube channel for future updates!

2024 Update to Solo 401(k): The Solopreneur’s Retirement Account

Solo 401(k): The Solopreneur’s Retirement Account explores the nooks and crannies of Solo 401(k)s. On page 16 of the paperback edition, I provide an example of the Solo 401(k) limits for 2022 if a solopreneur makes $100,000 of Schedule C income. Here is a revised version (in italics) of the example (with the footnote omitted) applying the new 2024 employee contribution limit:

Lionel, age 35, is self-employed. His self-employment income (as reported on the Schedule C he files with his tax return) is $100,000. Lionel works with a financial institution to establish his own Solo 401(k) plan and choose investments for the plan. Lionel can contribute $23,000 to his Solo 401(k) as an employee deferral (2024 limit) and can choose to contribute, as an employer contribution, anywhere from 0-20% of his self-employment income.

Lionel’s maximum potential tax-advantaged Solo 401(k) contribution for 2024 is $41,587! That is a $23,000 employee contribution and a $18,587 employer contribution. Note there’s no change in the computation of the employer contribution for 2024 in this example. 

On page 18 I provide an example of the Solo 401(k) contribution limits factoring in catch-up contributions. Here’s the example revised for 2024:

If Lionel turned 50 during the year, his limits are as follows:

  • Employee contribution: lesser of self-employment income ($92,935) or $30,500: $30,500
  • Employer contribution: 20% of net self-employment income (20% X $92,935): $18,587
  • Overall contribution limit: lesser of net self-employment income ($92,935) or $76,500: $76,500

Amazon Reviews

If you have read Solo 401(k): The Solopreneur’s Retirement Account, you can help more solopreneurs find the book! How? By writing an honest, objective review of the book on Amazon.com. Reviews help other readers find the book!

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2024 IRA Contributions for Beginners

There are only three types of annual contributions to individual retirement accounts (“IRAs”). They are:

  • Traditional, nondeductible contributions
  • Traditional, deductible contributions
  • Roth contributions

This post discusses when a taxpayer can make one or more of these types of annual contributions.

Let’s dispense with what we are not talking about. This post has nothing to do with annual contributions to employer retirement plans (401(k)s and the like) and self-employed retirement plans. We’re only talking about IRAs. The Individual in “IRA” is the key – anyone can set up their own IRA. IRAs are not pegged to any particular job or self-employment.

The above list is the exhaustive list of the possible types of annual contributions you can make to an IRA. But there is plenty of confusion about when you are eligible to make each of the three types of annual contributions.

Why Contribute to an IRA?

Before we dive into annual contributions to IRAs, let’s discuss why you would consider contributing to an IRA. The main reason is to build up tax-deferred wealth (traditional IRAs) and/or tax-free wealth (Roth IRAs) for your future, however you define it: financial independence, retirement, etc. A second potential benefit is the ability to deduct some annual contributions to traditional IRAs. A third benefit is some degree of creditor protection. States offer varying levels of creditor protection to traditional IRAs and Roth IRAs, while the federal government provides significant bankruptcy protection for traditional IRAs and Roth IRAs. 

IRA Annual Contribution Requirement: Earned Income

In order to make any of the three types of IRA annual contributions for any particular year, you or your spouse must have earned income during that year. Earned income is generally that income that is reported to you on your Form W-2, or is reported by you on your tax return on Schedule C (self-employment income). It also includes self-employment income reported to you on a Form K-1 (because you are a self-employed partner in a partnership). It does not include income reported to you on a Form K-1 from an S corporation.

While wages, nontaxable combat income, and self-employment income qualify as earned income for this purpose, several types of income do not. Social security, pensions, rentals, royalties, interest, and dividends are not earned income. Income excluded from taxable income under the foreign earned income exclusion also does not constitute “earned income” for IRA purposes.

Traditional Nondeductible IRA Annual Contributions

There’s are only one requirement to contribute to a traditional, nondeductible IRA for a taxable year:

  • You and/or your spouse have earned income during that taxable year.

That’s it! As long as you satisfy that requirement, you can contribute to a traditional nondeductible IRA, no further questions asked.

Example: Teve Torbes is the publisher of a successful magazine. He is paid a salary of $1,000,000 in 2024 and is covered by the magazine’s 401(k) plan. Teve can make up to a $7,000 nondeductible contribution to a traditional IRA, and Teve’s wife can also make up to a $7,000 nondeductible contribution to a traditional IRA.

There is no tax deduction for contributing to a traditional nondeductible IRA. The amount of your nondeductible contribution creates “basis” in the traditional IRA. When you withdraw money from the traditional IRA in retirement, a ratable portion of the withdrawal is treated as a return of basis and thus not taxable (the “Pro-Rata Rule”).

Example: Ted makes a $6,000 nondeductible traditional IRA contribution for each of 10 years ($60,000 total). When he retires, the traditional IRA is worth $100,000, and he takes a $5,000 distribution from the traditional IRA. Ted is over 59 ½ when he makes the withdrawal. Of the $5,000 withdrawal, Ted will include $2,000 in his taxable income, because 60 percent ($3,000 — $60,000 basis divided by $100,000 fair market value times the $5,000 withdrawn) will be treated as a withdrawal of basis and thus tax free.

Traditional nondeductible IRA contributions generally give taxpayers a rather limited tax benefit. However, since 2010 traditional nondeductible IRA contributions have become an important tax planning tool because of the availability of the Backdoor Roth IRA.

Making a nondeductible IRA contribution requires the filing of a Form 8606 with your federal income tax return.

Traditional Deductible IRA Annual Contributions

In order to make a deductible contribution to a traditional IRA, three sets of qualification rules apply.

ONE: No Workplace Retirement Plan

Here are the qualification rules if neither you nor your spouse is covered by an employer retirement plan (401(k)s and the like and self-employment retirement plans):

  • You and/or your spouse have earned income during that taxable year.

That’s it! As long as you satisfy that requirement and you and your spouse are not covered by an employer retirement plan, you can make a deductible contribution to a traditional IRA, no further questions asked.

Coverage by an employer retirement plan means either you or your employer contributed any amount to an employer retirement plan (on your behalf) during the taxable year. Coverage by an employer retirement plan includes coverage under a self-employment retirement plan.

Example: Teve Torbes is the publisher of a successful magazine. He and his wife are 45 years old. He is paid a salary of $1,000,000 in 2024. Neither he nor his wife is covered by an employer retirement plan. Teve can make up to a $7,000 deductible contribution to a traditional IRA, and Teve’s wife can also make up to a $7,000 deductible contribution to a traditional IRA.

TWO: You Are Covered by a Workplace Retirement Plan

Here are the deductible traditional IRA qualification rules if you are covered by an employer retirement plan:

  • You and/or your spouse have earned income during that taxable year.
  • Your modified adjusted gross income (“MAGI”) for 2024 is less than $87,000 (if single), $143,000 (if married filing joint, “MFJ”), or $10,000 (if married filing separate, “MFS”). 

Note that in between $77,000 and $87,000 (single), $123,000 and $143,000 (MFJ) and $0 and $10,000 (MFS), your ability to make a deductible contribution to a traditional IRA phases out ratably. Here is an illustrative example.

Example: Mike is 30 years old, single, and is covered by a 401(k) plan at work. Mike has a MAGI of $82,000 in 2024, most of which is W-2 income. Based on a MAGI in the middle of the phaseout range, Mike is limited to a maximum $3,500 deductible contribution to a traditional IRA.

Assuming he makes a $3,500 deductible IRA contribution, Mike has $3,500 worth of IRA contributions left. He can either, or a combination of both (up to $3,500) (a) make a contribution to a nondeductible traditional IRA, since he meets the qualification requirement to contribute to a nondeductible traditional IRA or (b) make a contribution to a Roth IRA, since he meets the qualification requirements (discussed below) to contribute to a Roth IRA. In such a case, Mike would be likely to favor a Roth IRA contribution over a nondeductible traditional IRA contribution.

THREE: Only Your Spouse is Covered by a Workplace Retirement Plan

Here are the deductible traditional IRA qualification rules if you are not covered by an employer retirement plan but your spouse is covered by an employer retirement plan:

  • You and/or your spouse have earned income during that taxable year.
  • Your MAGI for 2024 is less than $240,000 (MFJ) or $10,000 (MFS). 

Note that in between $230,000 and $240,000 (MFJ) and $0 and $10,000 (MFS), your ability to make a deductible contribution to a traditional IRA phases out ratably. 

Roth IRA Annual Contributions

Here are the Roth IRA annual contribution qualification rules.

  • You and/or your spouse have earned income during that taxable year.
  • Your MAGI for 2024 is less than $161,000 (single), $240,000 (MFJ), or $10,000 (MFS). 

Note that in between $146,000 and $161,000 (single), $230,000 and $240,000 (MFJ), and $0 and $10,000 (MFS), your ability to make a Roth IRA contribution phases out ratably. 

Notice that whether you and/or your spouse are covered by an employer retirement plan (including a self-employment retirement plan) is irrelevant. You and your spouse can be covered by an employer retirement plan and you can still contribute to a Roth IRA (so long as you meet the other qualification requirements).

Here is an example illustrating your options in the Roth IRA MAGI phaseout range.

Example: Mike is 30 years old, single, and covered by a workplace retirement plan. Mike has a MAGI of $155,000 for 2024, most of which is W-2 income. Based on a MAGI 60 percent through the phaseout range, Mike is limited to a maximum $2,800 contribution to a Roth IRA.

Assuming he makes a $2,800 annual Roth IRA contribution, Mike has $4,200 worth of IRA contributions left. He can make up to $4,200 in annual contributions to a nondeductible traditional IRA, since he meets the qualification requirement to contribute to a nondeductible traditional IRA.

IRA Annual Contribution Limits

For taxpayers younger than 50 years old during the entire year, the maximum (for 2024) that can be contributed to the combination of all three types of IRAs is the lesser of:

  • The taxpayer’s and their spouse’s combined earned income, or
  • $7,000.

Thus, if both spouses are younger than 50 years old, the maximum IRA contributions for a married couple is $14,000.

For taxpayers 50 years old or older during any part of the taxable year the maximum (for 2024) that can be contributed to the combination of all three types of IRAs is the lesser of:

  • The taxpayer’s and their spouse’s combined earned income, or
  • $8,000.

Thus, if both spouses are 50 or older, the maximum IRA contributions for a married couple is $16,000.

Deadlines

The deadline to make an IRA contribution for a particular year is April 15th of the year following the taxable year (thus, the deadline to make a 2024 IRA contribution is April 15, 2025). The deadline to make earned income for a taxable year is December 31st of that year.

Rollover Contributions

There’s a separate category of contributions to IRAs: rollover contributions. These can be from other accounts of the same type (traditional IRA to traditional IRA, Roth IRA to Roth IRA) or from a workplace retirement plan (for example, traditional 401(k) to traditional IRA, Roth 401(k) to Roth IRA). 

Rollover contributions do not require having earned income and have no income limits and should be generally tax-free. For a myriad of reasons, it is usually best to effectuate rollovers as direct trustee-to-trustee transfers. 

As a practical matter, it is often the case that IRAs serve at the retirement home for workplace retirement plans such as 401(k)s. 

Correction

A previous version of this blog post, titled “IRA Contributions for Beginners” erroneously stated that one must be a citizen or resident of the United States to make an IRA contribution. I regret the error. 

Further Reading

Deductible traditional IRA or Roth IRA? If you qualify for both, it can be difficult to determine which is better. I’ve written here about some of the factors to consider in determining whether a deductible traditional contribution or a Roth contribution is better for you.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2023 Year-End Tax Planning

It’s that time of year again. The air is crisp and my favorite football team is surging. That can only mean one thing when it comes to personal finance: time to start thinking about year-end tax planning.

I’ll break it down with three categories: Urgent, Year-End Deadline, and Can Wait Till Next Year. I will also provide some thoughts on 2024 tax planning that can/should be done before year-end in 2023.

As always, none of this is advice for your particular situation but rather it is educational information. 

Urgent

By urgent, I mean those items that (i) need to happen before year-end and (ii) may not happen if taxpayers delay and try to accomplish them late in the year. 

Donor Advised Fund Contributions

The donor advised fund is a great way to contribute to charity and accelerate a tax deduction. My favorite way to use the donor advised fund is to contribute appreciated stock directly to the donor advised fund. This gets the donor three tax benefits:

  1. A tax deduction for the fair market value of the contributed appreciated stock,
  2. Elimination of the built-in capital gain on the contributed appreciated stock, and
  3. Tax-free treatment of the income earned inside the donor advised fund.

In order to get the first benefit in 2023, the appreciated stock must be received by the donor advised fund prior to January 1, 2024. This deadline is no different than the normal charitable contribution deadline.

However, due to much year end interest in donor advised fund contributions and processing time, different financial institutions will have different deadlines on when transfers must be initiated in order to count for 2023. Donor advised fund planning should be attended to sooner rather than later. 

Taxable Roth Conversions

For a Roth conversion to count as being for 2023, it must be done before January 1, 2024. That means New Year’s Eve is the deadline. However, taxable Roth conversions should be done well before New Year’s Eve because 

  1. It requires analysis to determine if a taxable Roth conversion is advantageous, 
  2. If advantageous, the proper amount to convert must be estimated, and 
  3. The financial institution needs time to execute the Roth conversion so it counts as having occurred in 2023. 

Remember, generally speaking it is not good to have federal and/or state income taxes withheld when doing Roth conversions!

Roth Conversion Example: See slides 8 through 10 of this slide deck for an example of a Roth conversion in retirement. You might be surprised by just how little federal income tax is owed on a $23,000 Roth conversion.

Example Where I Disfavor Roth Conversions: I present an example of a 73-year old married couple with $400K in deferred retirement accounts and $87K in 2023 gross income. I would not recommend they do end-of-year Roth conversions. This spreadsheet computes the taxable Social Security with and without a $10K Roth conversion.

Gotta Happen Before 2026!!!

You will hear many commentators say “do more Roth conversions before tax rates go up in 2026!” If this were X (the artist formerly known as Twitter), the assertion would likely be accompanied by a hair-on-fire GIF. 😉

I disagree with the assertion. As I have stated before, there’s nothing more permanent than a temporary tax cut. You do your own risk assessment, but mine is this: members of Congress like to win reelection, and they are not going to want to face voters without having acted to ensure popular tax cuts, such as the reduction of the 15% tax rate down to 12% and the increased standard deduction, are extended. 

I recommend that you make your own personal taxable Roth conversion decisions based on your own personal situation and analysis of the landscape and not a fear of future tax hikes.

Learn all about the Pro-Rata Rule here.

Adjust Withholding

This varies, but it is a good idea to look at how much tax you owed last year (line 24 on the Form 1040). If you are on pace to get 100% (110% if 2022 AGI is $150K or greater) or slightly more of that amount paid into Uncle Sam by the end of the year (take a look at your most recent pay stub), there’s likely no need for action. But what if you are likely to have much more or much less than 100%/110%? It may be that you want to reduce or increase your workplace withholdings for the rest of 2023. If you do, don’t forget to reassess your workplace withholdings for 2024 early in the year. 

Backdoor Roth IRA Diligence

The deadline for the Backdoor Roth IRA for 2023 is not December 31st, as I will discuss below. But if you have already completed a Backdoor Roth IRA for 2023, the deadline to get to a zero balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs is December 31, 2023. 

Solo 401(k) Planning

There’s plenty of planning that needs to be done for solopreneurs in terms of retirement account contributions. Even though Schedule C solopreneurs can now establish a Solo 401(k) after year-end (up to April 15th), it is absolutely the case that it is better to do the planning upfront. For those Schedule C solopreneurs with a Solo 401(k) established, December 31st is the deadline to make 2023 employee deferral contributions or make a 2023 deferral election as an alternative to making the payments in 2023. December 31st is also the 2023 employee deferral contribution for solopreneurs operating out of S corporations.

The Solo 401(k) can get complicated. That’s why I wrote a book about them and post an annual update on Solo 401(k)s here on the blog. 

Year-End Deadline

These items can wait till close to year-end, though you don’t want to find yourself doing them on New Year’s Eve.

Tax Gain Harvesting

For those finding themselves in the 12% or lower federal marginal income tax bracket and with an asset in a taxable account with a built-in gain, tax gain harvesting prior to December 31, 2023 may be a good tax tactic to increase basis without incurring additional federal income tax. Remember, though, the gain itself increases one’s taxable income, making it harder to stay within the 12% or lower marginal income tax bracket. 

I’m also quite fond of tax gain harvesting that reallocates one’s portfolio in a tax efficient manner. 

Tax Gain Harvesting Example: See slide 15 of this slide deck for an example of tax gain harvesting in retirement.

Tax Loss Harvesting

The deadline for tax loss harvesting for 2023 is December 31, 2023. Just remember to navigate the wash sale rule. 

RMDs from Your Own Retirement Account

The deadline to take any required minimum distributions from one’s own retirement account is December 31, 2023. Remember, the rules can get a bit confusing. Generally, IRAs can be aggregated for RMD purposes, but 401(k)s cannot. 

RMDs from Inherited Accounts

The deadline to take any RMDs from inherited retirement accounts is December 31st. For some beneficiaries of retirement accounts inherited during 2020, 2021, and 2022, the IRS has waived 2023 RMDs. That said, all beneficiaries of inherited retirement accounts may want to consider affirmatively taking distributions (in addition to RMDs, if any) before the end of 2023 to put the income into a lower tax year, if 2023 happens to be a lower taxable income year vis-a-vis future tax years. 

Can Wait Till Next Year

Traditional IRA and Roth IRA Contribution Deadline

The deadline for funding either or both a traditional IRA and a Roth IRA for 2023 is April 15, 2024. 

Backdoor Roth IRA Deadline

There’s no law saying “the deadline for the Backdoor Roth IRA is DATE X.” However, the deadline to make a nondeductible traditional IRA contribution for the 2023 tax year is April 15, 2024. Those doing the Backdoor Roth IRA for 2023 and doing the Roth conversion step in 2024 may want to consider the unique tax filing when that happens (what I refer to as a “Split-Year Backdoor Roth IRA”). 

HSA Funding Deadline

The deadline to fund an HSA for 2023 is April 15, 2024. Those who have not maximized their HSA through payroll deductions during the year may want to look into establishing payroll withholding for their HSA so as to take advantage of the payroll tax break available when HSAs are funded through payroll. 

The deadline for those age 55 and older to fund a Baby HSA for 2023 is April 15, 2024. 

2024 Tax Planning at the End of 2023

HDHP and HSA Open Enrollment

It’s open enrollment season. Now is a great time to assess whether a high deductible health plan (a HDHP) is a good medical insurance plan for you. One of the benefits of the HDHP is the health savings account (an HSA).

For those who already have a HDHP, now is a good time to review payroll withholding into the HSA. Many HSA owners will want to max this out through payroll deductions so as to qualify to reduce both income taxes and payroll taxes.

Self-Employment Tax Planning

Year-end is a great time for solopreneurs, particularly newer solopreneurs, to assess their business structure and retirement plans. Perhaps 2024 is the year to open a Solo 401(k). Perhaps their business is growing such that an S corporation election makes sense. The best time to be thinking about these sorts of things for 2024 is late in 2023. Often this analysis benefits from professional consultations.

Additional Resource

Please see my November 11, 2023 ChooseFI Orange County year-end tax planning presentation slide deck.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

CampFI 2023 Presentation

Here are my presentation slides for my presentation delivered October 7, 2023 at CampFI Southwest.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Traditional Versus Roth 2023

The debate continues: what’s preferable, traditional retirement accounts or Roth retirement accounts?

Fortunately, there are plenty of shades of gray in this debate. There’s no “right” answer, but I do believe that there are good insights that can help individuals make the right planning decisions for themselves.

Traditional and Roth Retirement Basics

Before we dive into the traditional versus Roth debate, we should quickly survey the basics of these types of retirement accounts.

Traditional

Traditional retirement accounts feature a tax deduction on the way in (i.e., for contributions) and ordinary income tax on the way out (i.e., for withdrawals). At work these are known as traditional 401(k)s, 403(b), 457s, and occasionally have other names. At home these are known as traditional IRAs.

Additional twist: many working Americans do not qualify to deduct a traditional IRA contribution due to relatively low income limits on claiming a deduction. 

Part of the appeal of traditional retirement accounts includes: (i) the notion that many will have lower taxable income (and thus lower income tax) in retirement than they did during their working years and (ii) the tax saved by contributing to traditional accounts can be invested, potentially creating more wealth for retirement. 

Roth

Roth retirement accounts feature no tax deduction on the way in (i.e., for contributions) and tax free treatment on the way out (i.e., for withdrawals). At work these are known as Roth 401(k)s, 403(b), 457s, and (after SECURE 2.0 implementation) will occasionally have other names. At home these are known as Roth IRAs.

Additional twist: some working Americans do not qualify to make an annual Roth IRA contribution based on income limits, but many can get around this rule by implementing a Backdoor Roth IRA. 

Part of the appeal of contributions to Roth retirement accounts is the notion that it is better for our younger, healthier selves to pay the tax associated with retirement savings when cash flow is good and the investor knows they can bear the cost. 

The basics out of the way, we can get into 2023 insights on the debate between the two types of retirement accounts.

The Risk of Traditional Retirement Accounts is Vastly Overstated

We hear it time and again: be worried about all the tax lurking inside traditional retirement accounts such as 401(k)s and IRAs!

Here’s the thing: rarely do commentators offer any sort of mathematical analysis backing up that contention. I ran the math, and I repeatedly find that many retirees with traditional retirement accounts are likely to pay Uncle Sam a very manageable amount of income taxes in retirement. 

You be the judge and jury. I believe a fair assessment of my posts and videos and the numbers behind them shows that most Americans do not face a high risk of crippling federal income taxes in retirement, even if the vast majority of their portfolio is in traditional 401(k)s and IRAs. 

While I cannot give readers of this blog individualized advice, I can say that if one considers themselves to be an “Average Joe” it is difficult to see how having significant amounts in traditional retirement accounts is a problem. 

The Needle Keeps Moving Towards Traditional

Picture it: United States, September 2017, six short years ago. You’re bright-eyed, bushy-tailed, and fear only one thing: incredibly high taxes on your traditional 401(k) and IRA in retirement.

Then a few things happened.

  • December 2017: TCJA increased the standard deduction and lowered the 15% bracket to 12%
  • December 2019: The SECURE Act (SECURE 1.0) delayed RMDs from age 70 ½ to 72
  • March 2020: CARES Act cancels 2020 RMDs and allows taken RMDs to be rolled back in
  • November 2020: IRS and Treasury issue a new Uniform Life Table, decreasing the amount of annual RMDs beginning in 2022
  • December 2022: SECURE 2.0 delays RMDs from age 72 to 73, and all the way to age 75 for those born in 1960 and later

Tax cut after tax cut for traditional retirement accounts and retirees! In the traditional versus Roth debate, DC keeps putting a thumb on the scale for traditional. 

Watch me assess recent tax law change history as it applies to retirees.

Taxable Roth Conversions Going Away?

One reason I like traditional 401(k) contributions is that they do not close the door on Roths. Rather, traditional retirement account contributions at work are a springboard for years of Roth conversions in retirement for many in the FI community! 

The idea is to take deductions at high marginal tax rates at work into a 401(k) and build up wealth for an early retirement. Then, in retirement, one’s tax rate is artificially low as they no longer have W-2 income to report. This opens up room for potentially very efficient Roth conversions (affirmatively moving money in traditional accounts to Roth accounts) taxed at the 10% or 12% federal income tax rate. 

That’s a great plan, in theory. But couldn’t Congress take it away? Sure, they could, but I seriously doubt they will in an effective way. First, let’s look at recent history. In 2021 the Democratic Congress proposed, but did not pass, a provision to eliminate (starting a decade in the future) taxable Roth conversions for those north of $400K of annual income. Such a rule would have had no effect on most retirees, who will never have anything approaching $400K of income in retirement.

Second, why would Congress eliminate most taxable Roth conversions? They “budget” tax bills in a 10 year window. Taxable Roth conversions create tax revenue inside that budget window, making it that much less likely a Congress would eliminate most of them.

While there is not zero risk taxable Roth conversions will go away, I believe that the risk is negligible. The greater one believes Roth conversion repeal risk is, the more attractive Roth contributions during one’s working years look. 

Special Years Favor Roths

I’ve written before about how workers in the early years of their careers may want to consider Roth 401(k) contributions prior to their income significantly increasing. Those in transition years, such as those starting a job after graduating college and those about to take a mini retirement may want to prioritize Roth 401(k) contributions over traditional 401(k) contributions.

Optimize for Known Trade-Offs

People want to know: what’s the optimal income for switching from traditional to Roth? What’s the optimal percentage to have each of traditional, Roth, and taxable accounts?

Here’s the thing: there are simply too many unknown future variables to come up with any precision in this regard. That said, I don’t believe we have to.

Why? Because in retirement planning, we can optimize for known trade-offs. Let me explain. At work, Americans under age 50 can contribute up to $22,500 (2023 number) to a 401(k). At most employers, that can be any combination of traditional or Roth contributions. Every dollar contributed to a Roth 401(k) is a dollar that cannot be contributed to a traditional deductible 401(k). That’s a known trade-off.

What about at home? For most working Americans covered by a 401(k), a dollar contributed to a Roth IRA is not a dollar that could have been contributed to a deductible traditional IRA. So a Roth IRA contribution is not subject to the trade-off downside that a Roth 401(k) contribution is.

Why not optimize for known trade-offs? Contribute to a traditional 401(k) at work and a Roth IRA (or Backdoor Roth IRA) at home. This approach optimizes for the known trade-offs and sets one up with both traditional and Roth assets heading into retirement. 

Further, Roth IRA contributions and Backdoor Roth IRAs can serve as emergency funds, while traditional IRAs, traditional 401(k)s, and Roth 401(k)s do not serve well as emergency funds. Roth IRA contributions do not suffer from an adverse trade-off when it comes to emergency withdrawals, unlike Roth 401(k) contributions. 

Roth Contributions End the Planning

Traditional retirement account contributions set up great optionality. A retiree may have years or decades of opportunity to strategically convert traditional accounts to Roth accounts. Or, a retiree might say, “thanks, but no thanks, on those Roth conversions, I’ll simply wait to withdraw for RMDs or living expenses later in retirement at a low tax rate.” Traditional retirement account contributions open the doors to several planning options.

Roth contributions end the planning. That’s it, the money is inside a Roth account. Considering the potential to have low tax years after the end of one’s working years, is that always a good thing?

Rothification Risks

Having all one’s retirement eggs in the Roth basket can create significant problems. This is an issue I do not believe receives sufficient attention. Previously I posited an example where an early retiree had almost all his wealth in Roth accounts (what I refer to as the Rothification Trap). 

Risks of having all of one’s eggs inside the Roth basket going into retirement include:

  • Missing out on standard deductions
  • Inability to qualify for ACA premium tax credits
  • Missing out on benefits of qualified charitable distributions (QCDs)
  • Missing out on tax efficient Roth conversions in retirement

Sufficiency

Much of the traditional versus Roth debate misses the forest for the trees. Rarely do commentators state that long before one worries about taxation in retirement they have to worry about sufficiency in retirement!

Recent reports indicate that many if not most Americans struggle to afford a comfortable retirement. A quick review of average retirement account balances indicates that many Americans are not set up for what I’d call a comfortable retirement. Further, according to a recent report, the median American adult has a wealth around $108,000. That means the median adult has a significant sufficiency concern when it comes to retirement planning. 

Most Americans will be lucky to have a tax problem in retirement! Most Americans need to build up retirement savings. The quickest, easiest way to do that is by making deductible traditional 401(k) contributions. That deduction makes the upfront sacrifice involved in retirement saving easier to stomach. Further, if one is not likely to have substantial retirement savings, they are not likely to be in a high marginal tax bracket in retirement. 

If all the above is true, what is the problem with having taxable retirement accounts? The tax savings in retirement from having Roth accounts is not likely to be very high for many Americans. 

Conclusion

Both traditional retirement accounts and Roth retirement accounts have significant benefits. When viewed over the spectrum of most Americans’ lifetimes, I believe that workplace retirement plan contributions should be biased toward traditional retirement accounts. For many Americans, either or both of the following will be true. First, there will be low tax years in retirement during which retirees can take advantage of low tax Roth conversions. Second, many Americans will be in a low tax bracket when taking retirement account withdrawals for living expenses and/or RMDs.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

It’s Not Too Late, California!

HUGE UPDATE: On October 16, 2023, the IRS issued this, extending the October 16, 2023 deadline for 2022 tax acts and filings to November 2023. The IRS announcement allows (most) Californians to make Roth IRA, traditional IRA, and HSA contributions for 2022 up to November 16, 2023 and delays the deadline for many 2022 federal income tax returns and income tax payments to November 16, 2023. Hat tip to Justin Miller on X for the news.

ADDITIONAL UPDATE 10/16/2023 7:06PM: California has also extended the 2022 filing and payment deadline to November 16, 2023. Hat tip to Kelly Phillips Erb.

Please enjoy below the rest of my post, as originally authored in August 2023, understanding that now you can replace “October 16” with “November 16” for most Californians.

I’m glad that title intrigued you enough to stop on by. It’s not too late for most Californians to make a 2022 IRA contribution, a 2022 Roth IRA contribution, a 2022 HSA contribution, and/or do a 2022 Backdoor Roth IRA contribution. 

You’re probably thinking “What the heck are you talking about? It’s the late summer 2023. Time to be thinking about football, not funding 2022 IRAs and HSAs.”

Your thoughts are correct as applied to most Americans. However, most Californians are the beneficiaries of a special situation. The IRS announced that because of early 2023 flooding in many areas of California, most Californians have an extended deadline, October 16, 2023, to perform most 2022 tax acts that otherwise would have been due early in 2023.

This extension opens the door for millions of Californians to consider 2022 contributions to tax-advantaged accounts. Of course, nothing increases the amount Californians can contribute. Thus, those who have already maxed out for 2022 do not benefit from this deadline extension. 

2022 Traditional IRA Contributions

Most working Californians can still make 2022 contributions to a traditional IRA. If the taxpayer has not yet filed their 2022 Form 1040, the deduction or the Form 8606 (for a nondeductible contribution) can simply be included with the to-be filed Form 1040.

But what if the taxpayer has already filed their Form 1040 for 2022? Then the question becomes: are they deducting their 2022 traditional IRA contribution? If no, then the taxpayer can simply file a Form 8606 as a standalone tax return to report the 2022 nondeductible contribution. 

However, if the contribution is tax deductible, then the taxpayer would need to file amended Forms 1040 and 540 (for California) to report the deductible IRA contribution and claim refunds from both the IRS and the Franchise Tax Board for the tax reduced because of the deductible traditional IRA deduction. 

2022 Roth IRA Contributions

Many working Californians can still make 2022 contributions to a Roth IRA. Since Roth IRA contributions are not deductible, and do not require a separate form to report them, the contribution likely would not require any amending of already-filed 2022 tax returns. One exception would be the case of a taxpayer with a low income in 2022. He or she could make a 2022 Roth IRA contribution and possibly qualify for the Saver’s Credit. In order to claim the credit, they would need to amend their Form 1040 if they already filed it for 2022. 

2022 Backdoor Roth IRAs

It’s not too late for a 2022 Backdoor Roth IRA for some Californians! This would be a Split-Year Backdoor Roth IRA. The pressing deadline as of late August 2023 is that the 2022 nondeductible traditional IRA contribution needs to be made by October 16, 2023. 

Anyone pursuing a Split-Year Backdoor Roth IRA for 2022 in 2023 should ensure they have no balances in traditional IRAs, SEP IRAs, and/or SIMPLE IRAs as of December 31, 2023. 

2022 HSA Contributions

Some Californians can still make 2022 contributions to a health savings account. If the taxpayer has not yet filed their 2022 Form 1040, the tax deduction can simply be added to the to-be filed Form 1040.

But what if the taxpayer has already filed their Form 1040 for 2022? Then the taxpayer would need to file amended Form 1040 to claim the tax deduction and the resulting tax refund from the IRS. Since California does not recognize HSAs, there’s no California tax deduction and no need to amend the California Form 540. 

Of course, the taxpayer must meet the eligibility requirements (generally, having had a high deductible health plan as their only medical insurance) in 2022 in order to contribute to a HSA for 2022. 

Practical Considerations

First, contributions to IRAs, Roth IRAs, and HSAs made in 2023 that are to count for 2022 must be specifically designated as being for 2022. 

Second, I believe that in many cases, in order for qualifying Californians to do this, it will be necessary to use the phone, not internet portals. I suspect most financial institutions’ internet portals will not accommodate a 2022 IRA/Roth IRA/HSA contribution this late. Remember, financial institutions would not want to encourage the vast majority of Americans who do not currently qualify to make 2022 contributions to make 2022 contributions.

Thus, I believe as a practical matter using the phone is a best practice in terms of making any 2022 contributions at this late date. 

Who Benefits?

Residents of all California counties except three qualify for the extended deadline. The vast majority of the population of the state qualifies for the extended deadline, but residents of Lassen, Modoc, and Shasta do not appear to qualify (don’t blame me, I don’t make the rules!). 

Note that some taxpayers in parts of Alabama and Georgia qualify for this opportunity, but I personally have not explored this in any detail. 

Conclusion

Many California residents should consider whether there is some extended last minute 2022 tax planning they can implement by October 16, 2023. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

FI Tax Guy Nominated for a Plutus Award

I’m pleased to announce that FI Tax Guy has been nominated for the Best Tax-Focused Content Plutus Award at the upcoming 14th Annual Plutus Awards.

The Plutus Awards honor personal finance independent media content creators.

The award winners will be announced on September 22nd.

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Traditional 401(k) Contributions Are Fine for Most Americans (Really!)

Yesterday I posted Time to Stop 401(k) Contributions?, arguing that as applied to many in the FI community, traditional deductible 401(k) contributions are fine.

Today two very interesting pieces of content hit my radar. First, one of my favorite personal finance content creators, Clark Howard, is advocating for Roth contributions instead of traditional contributions for most Americans.

Second, UBS and Credit Suisse issued their Global Wealth Report for 2023. Allow me to call your attention to page 16. The median American adult has personal wealth just a bit under $108,000. This means almost half of American adults have less than $100K of wealth, and the majority of American adults do not have $200K of wealth. For most Americans, deferred taxation is not the problem! Sufficiency is the problem!

For me this report cracks the case. If the median American adult does not have close to sufficient wealth to comfortably retire, why are they worried about taxes in retirement?

Assuming this report is anywhere near close to a correct measure of adult American wealth, I believe I am correct and personal finance legends Ed Slott and Clark Howard are wrong when it comes to the traditional 401(k) versus Roth 401(k) debate.

The best way for working Americans to address sufficiency problems is by contributing to traditional, deductible retirement accounts. As demonstrated below, one employing this sort of deduct, deduct, deduct strategy would need to be successful well beyond what most Americans accomplish in order to create a tax problem.

When one has insufficient resources for retirement, the traditional, deductible 401(k) makes the most sense. He or she needs to build up assets, not worry about future taxes! With relatively little in the way of resources, future taxes are not likely to be a problem (especially in retirement when compared to one’s working years). Further, by contributing to a traditional, deductible 401(k) instead of a Roth 401(k), one behind in retirement saving takes home more money to invest in additional saving mechanisms such as Roth IRAs and taxable brokerage accounts.

Let’s Break Down Some Retirement Numbers

I believe we need some numbers to figure out who’s right.

Example 1: I start with Single Sally, who is 75 years old. Since she is somewhat like the median American, but older, let’s assume she has $250,000 of wealth and receives $30,000 a year in Social Security. Assume further that all $250K is in a traditional IRA and Sally, age 75, wants to live for today: she isn’t constrained by the 4% rule but rather decides to withdraw 10 percent per year ($25,000). On that $55,000 annual gross income, Single Sally pays just over $2,000 in federal income taxes (an effective rate less than 4%).

Why would Sally pass on a 10%, 12%, or 22% deduction from a traditional 401(k) contribution during her working years? Why would Single Sally put the money in a Roth 401(k) so as to avoid a less than 4% federal income tax in retirement? And how different is Sally’s situation from that of many Americans?

Update 8/17/2023: Single Sally is in the Tax Torpedo, an interesting tax phenomenon with a modest impact on her total tax liability. I added a spreadsheet to look at this in more detail.

Example 2: But Sean, I’m reading your blog. I’m not shooting for just $250K in retirement wealth! Okay, let’s start testing it by considering wealth significantly above the mean and median adult Americans. Single Sarah is 75 years old. She receives $30,000 a year in Social Security. But now she also has a $1M traditional IRA and takes an RMD ($40,650) based on her age. Single Sarah also has some taxable accounts and thus has $4,000 of qualified dividend income and $1,000 of interest income. On that approximate $76,000 annual gross income, Single Sarah pays just over $7,200 in federal income taxes (an effective rate of a bit more than 9.5%).

In order to grow a $1M traditional IRA (likely rolled over from workplace 401(k)s), she almost certainly was in the 22% or greater federal marginal tax bracket while working. Why would Single Sarah switch from taking a 22% tax deduction (the traditional 401(k) contribution) to a Roth 401(k) contribution to avoid a 9.5% effective federal tax rate in retirement?

Example 3: Example 3 is Single Sarah at age 80. Her investments are doing so well her traditional IRA is still worth $1M, causing her to be required to take a $49,505 RMD. This causes her federal income tax to increase to $9,175, for an effective federal income tax rate of almost 11%.

How many Americans will get to age 80 with $1M or more in tax deferred accounts? Even if they do, how bad is the tax problem? If Single Sarah’s effective tax rate is 11%, a 50% tax hike gets her to about 16.5%. Will she enjoy paying that tax? No. Is it crippling? Hardly!

Still worried about contributing to a traditional 401(k)? I’ve got a video for you!

Conclusion

The next time you hear “30 or 40% of your 401(k) belongs to the government” you should consider my examples. For many Americans, “10%” will be much closer to the mark than 30% or 40%.

It’s time to step back and ask whether prioritizing Roth 401(k) contributions during one’s working career is the best advice for the majority of Americans. As demonstrated above, a tax increase of 50 percent (highly unlikely) would result in most Americans having an effective tax rate below 20% in retirement.

I believe for many Americans, the optimal retirement savings path combines deductible workplace 401(k) contributions with Roth IRA contributions at home.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Time to Stop 401(k) Contributions?

Ed Slott believes most Americans should not contribute to traditional 401(k)s. His recent essay on the subject is a great opportunity for the FI community to reassess its love for the traditional 401(k).

My conclusion is that for many in the FI community, traditional deductible 401(k) contributions are still the most logical path when it comes to workplace retirement saving. Below I explain my thinking. 

It is important to note it is impossible to make a blanket statement as applied to the entire FI community. 

Why the Traditional 401(k) Is Good for the FI Community

Many in the FI community have the very reasonable hope that in retirement they will have years, possibly decades, where their effective tax rate will be lower than their marginal tax rate in their working years. 

The above is true of many Americans, but it is particularly true if one retires early by conventional standards. The idea is deduct, deduct, deduct into the 401(k) during one’s working years (particularly the high earning years) and then retire early by conventional standards. Prior to collecting Social Security and/or required minimum distributions (“RMDs”), most retirees look artificially poor on their tax return. This opens up the door to affirmatively convert money from traditional retirement accounts to Roth accounts and pay tax at the lowest federal income tax brackets (currently 10% and 12%). For those who deducted contributions into the 401(k) at a 24% or greater marginal federal tax rate, this is great tax rate arbitrage planning.

Minor litigation risks aside, this strategy just got even easier for those born in 1960 and later, who don’t have to take RMDs under SECURE 2.0 until age 75. With the new delayed RMD beginning date, even those retiring as late as age 65 will have a full decade prior to being required to take RMDs to do tax-efficient Roth conversions at low marginal tax rates. For some in the FI community, this opportunity window might not be a decade long but rather a quarter-century long (if they retire at age 50). 

How Bad is the Retiree Tax Problem?

As wonderful as FI tax rate arbitrate planning might be, Ed Slott’s concern that retiree taxes will increase is not entirely unwarranted. It is obvious that the government is not fiscally responsible, and it is obvious that tax increases could be coming in the future. 

Let’s assess the situation by looking at just how bad the problem of taxes is in retirement.

We begin with a baseline case. David and Hannah are in their 70s. They never did Roth conversions in early retirement and have the bulk of their financial assets in traditional IRAs and traditional 401(k)s. During most of their working years, David and Hannah maxed out 401(k)s and got deductions in the 24% bracket or greater. For 2023, they have taxable RMDs of $160,000, Social Security of $40,000, $4,000 of qualified dividends and $1,000 of interest income. How bad is their federal income tax situation?

Federal Income Tax Return
RMDs$ 160,000
Social Security$ 40,000
15% Social Security Exclusion$ (6,000)
Interest$ 1,000
Qualified Dividends$ 4,000
Adjusted Gross Income (“AGI”)$ 199,000
Standard Deduction$ (27,700)
Additional SD Age 65+$ (3,000)
Federal Taxable Income$ 168,300
Federal Income Tax (Estimated)$ 27,361
Effective Tax Rate on AGI13.75%
Marginal Federal Income Tax Rate22%

Under today’s rules, David and Hannah, who did no tax planning other than “deduct, deduct, deduct” are doing great. Their federal effective tax rate, even with $200K of RMDs and Social Security, is just 13.75%. They incur such a low effective tax rate because their RMDs go against the 10% tax bracket, the 12% bracket, and the 22% bracket. 

While I do think David and Hannah would be in a better position had they done some tax efficient Roth conversion planning earlier in retirement, their unbridled enthusiasm for traditional retirement accounts served them well. 

Note: David and Hannah are borderline IRMAA candidates: a $199K 2023 AGI might cost them approximately $2,000 in IRMAA surcharges in 2025 (but it is possible that inflation adjustments for 2025 will prevent that from happening). This is another reason to consider pre-RMD Roth conversions at lower marginal tax rates. 

Update 8/19/2023: But what about the widow’s tax trap? If David or Hannah die, won’t the survivor get crushed by tax increases? Check out this estimate. Assuming the survivor loses the lower-earning spouse’s Social Security benefits of at least $10,000, the survivor’s marginal federal income tax rate would climb from 22% all the way up to . . . 24%!

But what about future tax increases? Okay, let’s add four tax increases to the picture and see just how bad it looks:

  1. Eliminate the TCJA increase to the standard deduction (the law reverts to pre-2018 lower standard deduction and personal exemptions). This would reduce David and Hannah’s deductions by roughly $2,740, costing them approximately $602.80 in additional federal income tax (at today’s 22% marginal tax rate).
  2. Eliminate the TCJA decrease in the 15% tax bracket to 12%. This would cost David and Hannah $2,023.50 in additional federal income tax. I’m highly skeptical that either of these two tax increases will actually occur, but as written in today’s laws they are scheduled to happen in 2026. 
  3. Increase the 15% long term capital gains and qualified dividend income rate to 25%. While I believe that the real risk is an increase in the 20% long term capital gains and qualified dividend income rate, let’s stress test things and consider a large increase in the 15% rate. In David and Hannah’s case, this costs them $400 in additional federal income tax.
  4. Increase the 22% tax rate to 33%. Ed Slott is worried about large tax rate increases, so let’s consider one that I believe is politically infeasible, a 50% increase in the 22% tax bracket. This type of tax rate increase would hit millions of voters in a major way. But it’s helpful to consider what could be a worst case scenario. In this case, this tax rate increase costs David and Hannah an additional $8,233.50 in federal income tax.
  5. There’s one more tax hike to consider: the combination of tax increases numbers 1 and 4. If both occurred together, combined they would cost David and Hannah an additional $301.40 in federal income tax. 

Here’s what David and Hannah’s federal tax picture looks like if all of the above tax increases occur:

Federal Income Tax Return
RMDs$ 160,000
Social Security$ 40,000
15% Social Security Exclusion$ (6,000)
Interest$ 1,000
Qualified Dividends$ 4,000
Adjusted Gross Income (“AGI”)$ 199,000
Standard Deduction$ (15,240)
Additional SD Age 65+$ (3,000)
Personal Exemptions$ (9,720)
Federal Taxable Income$ 171,040
Federal Income Tax (Estimated)$ 38,922
Effective Tax Rate on AGI19.56%
Marginal Federal Income Tax Rate33%

Significant tax increases hurt David and Hannah, but how much? By my math, very significant tax increases, including a 50% increase in the 22% bracket, cost them about 6% of their income. Not nothing, but wow, they’re still doing very well. 

Yes, on the margin, the last dollars David and Hannah contributed to the traditional 401(k) were not ideal since they faced a 33% marginal federal tax rate in retirement. But let’s remember (i) their overall effective rate is still more than 4 percentage points lower than their working years’ marginal rate (at which they deducted their 401(k) contributions), (ii) they have income significantly above what most Americans will have in their 70s, and (iii) in my scenario they face four separate tax hikes and still pay a federal effective tax rate less than 20 percent.

Future Retirees’ Tax Risk

Do future tax hikes pose no threat to future retirees? Absolutely not! But my stress test shows that many Americans with substantial RMDs will not get walloped even if Congress enacts unpopular tax increases. Considering many in the FI community will have modest RMDs due to pre-RMD Roth conversions, the threat of future tax hikes is even less perilous for the FI community.

Further, many Americans, particularly those in the FI community, have a great tool that can mitigate this risk: Roth conversions during retirement! With RMDs now delayed to age 75 for those born in 1960 and later, many Americans will have years if not decades where money can be moved in a tax-efficient manner from old traditional accounts to Roth accounts. 

Further, many Americans can claim deductions at work and then at home contribute to a regular Roth IRA or a Backdoor Roth IRA. This too mitigates the risk of having all of one’s retirement eggs in the traditional basket. 

Last, do we really believe that Congress is just itching to raise taxes on future retirees? Sure, it’s possible. But to my mind taxes are more likely to be raised on (i) those in higher ordinary income tax brackets and/or (ii) long term capital gains and/or qualified dividends (particularly the current 20% bracket). If anything, the most Congress is likely to do to retirees is slightly increase their taxes so as to mitigate the political risk involved in raising taxes on retirees who tend to vote. 

The Risks of Not Having Money in Traditional Retirement Accounts

Risk isn’t a one-way street. There are some risks to not having money in traditional retirement accounts. I identify three below.

Qualification for Premium Tax Credits

Picture it: Joe, age 55, retires with the following assets: (i) a paid off car, (ii) a paid off house, (iii) a $40,000 emergency fund in an on-line savings account, and (iv), $2 million in Roth 401(k)s and Roth IRAs. He heard that Roth is the best, so he only ever contributed to Roth IRAs and Roth 401(k)s, including having all employer contributions directed to a Roth 401(k). Having fallen into the Rothification Trap, in retirement Joe must work in order to generate sufficient taxable income to qualify for any ACA Premium Tax Credit. 

For at least some early retirees, the ability to create modified adjusted gross income by doing Roth conversions will be the way they guarantee qualifying for significant Premium Tax Credits to offset ACA medical insurance premiums. 

Charitable Contributions

Many Americans are at least somewhat charitably inclined. Starting at age 70 ½, Americans can transfer money directly from a traditional IRA to a charity, exclude the distribution from taxable income, and still claim the standard deduction. Essentially, if you’re charitably inclined, at a minimum you would want to go into age 70 ½ with enough in your traditional IRAs (likely through contributions to traditional 401(k)s that are later transferred to an IRA) to fund your charitable contributions from 70 ½ until death. 

Why ever pay tax on that money (i.e., by making contributions to a Roth 401(k) that are later withdrawn to be donated) if the money is ultimately going to charity anyway?

Unused Standard Deductions

Currently, the government tells married couples, hey, you get to make $27,700 a year income tax free! Why not take advantage of that exclusion every year, especially prior to collecting Social Security (which, in many cases will eat up most, if not all, of the standard deduction). 

Why be retired at age 55 with only Roth accounts? By having at least some money in traditional retirement accounts going into retirement, you ensure you can turn traditional money into Roth money tax-free simply by converting (at any time) or even distributing (usually after age 59 1/2) the traditional retirement account against the standard deduction. 

Deduct at Work, Roth at Home

I think for many it makes sense to max out traditional 401(k)s at work and contribute to Roth IRAs or Backdoor Roth IRAs at home. Why? As discussed above, traditional 401(k)s can set up tax rate arbitrage in retirement, help early retirees qualify for Premium Tax Credits, and make charitable giving after age 70 ½ very tax efficient. At home, many working Americans do not qualify to deduct IRA contributions, so why not contribute to a Roth IRA or Backdoor Roth IRA, since (i) you aren’t giving up a tax deduction in order to do so and (ii) you establish assets growing tax free for the future. 

In this post I discuss why deduct at work, Roth at home can often make sense and I provide examples where Roth 401(k) contributions are likely to be better than traditional 401(k) contributions. 

Conclusion

I believe that for many in the FI community, a retirement savings plan that combines (i) traditional deductible 401(k) contributions during one’s working years and (ii) Roth conversions prior to collecting RMDs is likely to be a better path than simply making all workplace retirement contributions Roth contributions.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Taxation of Roth IRA Distributions

Roth IRAs allow tax-free distributions to fund retirement. However, to help secure retirement savings and avoid premature raiding of Roth IRAs, Congress did not give them blanket exemption from taxes and penalties. Thus, there are times where distributions from Roth IRAs are subject to either or both ordinary income tax and/or the 10% early withdrawal penalty. The IRS and Treasury have issued regulations governing the rules of the road for Roth IRAs, which interpret the rules Congress wrote in IRC Section 408A. 

A Few Introductory Notes Before We Get Started

The below post is different from many posts on FITaxGuy.com in two respects. First, my posts tend to be planning focused, though they often dive into tax rules, as a good understanding of the rules helps with planning. This post is almost entirely rules focused rather than planning focused.

Second, the primary audience for this post is tax and financial advisors (though I welcome both laymen and professionals reading and questioning the post). I have recently observed that professionals seem to be confused about the Roth IRA distribution rules. It’s time to lay out the rules with citations to the relevant governing regulations!

Below I lay out my breakdown of the rules with extensive citation to the regulations so you can see where I’m getting my assertions from. You get to be the judge and jury as to whether I have properly presented the relevant rule. 

Now, back to the show. Per Treas. Reg. Section 1.408A-6 Q&A 1(a) “[t]he taxability of a distribution from a Roth IRA generally depends on whether or not the distribution is a qualified distribution.” 

Roth IRA Qualified Distributions

A qualified distribution is not included in the Roth IRA’s owner’s gross income (Treas. Reg. Section 1.408A-6 Q&A 1(b)) and is thus tax free and penalty free (see Treas. Reg. Section 1.408A-6 Q&A 5(a)). 

The way most distributions from a Roth IRA qualify as a “qualified distribution” is by satisfying the requirements that the owner (1) is age 59 ½ or older (see Treas. Reg. Section 1.408A-6 Q&A 1(b)(2)) and (2) has owned a Roth IRA for at least 5 years (see Treas. Reg. Section 1.408A-6 Q&A 1(b)(1)).

Once one qualifies for a qualified distribution by satisfying both the age 59 ½ requirement and the 5 year requirement, he or she no longer has any need to consider either of the two Roth IRA 5-year rules (the so-called 5-Year Conversion Clock and the so-called 5-Year Earnings Clock). 

Roth IRA Nonqualified Distributions

Now we turn to the taxation of distributions that do not qualify as qualified distributions (what I colloquially refer to as “nonqualified distributions”). As a very general matter, the taxation of these distributions is mostly governed by Treas. Reg. Section 1.408A-6 Q&As 1, 4, 5, 8, and 9. 

Ordering Rule

Treas. Reg. Section 1.408A-6 Q&A 8 provides an ordering rule for distributions from a Roth IRA. This creates three layers. Each layer must be fully withdrawn prior to a subsequent layer being accessed. See Treas. Reg. Section 1.408A-6 Q&A 8(a).

First, all annual contributions are withdrawn. Second, all previous Roth conversions are withdrawn (first in, first out). Third, earnings (growth) in the Roth IRA are withdrawn.

Tax Free Withdrawal of Owner Contributions (Both Annual Contributions and Roth Conversions)

Annual contributions and Roth conversions are “contributions” that are always withdrawn income tax free. See Treas. Reg. Section 1.408A-6 Q&A 1(b) (contributions always are withdrawn tax free), Q&A 8(a) (annual contributions and Roth conversions are both “contributions”).

Roth IRA annual contributions can be withdrawn at any time for any reason tax and penalty free! See Treas. Reg. Section 1.408A-6 Q&A 1(b) and Q&A 5(a).

5 Year Clock on Roth Conversions

However, the withdrawal of taxable Roth conversions can be subject to the 10% early withdrawal penalty. See Treas. Reg. Section 1.408A-6 Q&A 5(b) (see also IRC Section 408A(d)(3)(F)). This is only true if the Roth conversion is withdrawn within 5 years. See Treas. Reg. Section 1.408A-6 Q&A 5(b) (the 5-Year Conversion Clock). 

Per Treas. Reg. Section 1.408A-6 Q&A 5(b), the exceptions to the 10% early withdrawal penalty also apply. The most prominent such exception is having attained the age of 59 ½. Thus, a distribution from a Roth IRA received by an owner at least 59 ½ years old will never be subject to the 10% early withdrawal penalty.

Roth Earnings

Nonqualified distributions of earnings are subject to ordinary income tax (see Treas. Reg. Section 1.408A-6 Q&A 4) and potentially the 10% early withdrawal penalty (see Treas. Reg. Section 1.408A-6 Q&A 5(a)). Generally speaking, if one is either under age 59 ½ years old (see Treas. Reg. Section 1.408A-6 Q&A 1(b)(2)) or if the owner has not owned a Roth IRA for at least 5 years (see Treas. Reg. Section 1.408A-6 Q&A 1(b)(1), the 5-Year Earnings Clock), any withdrawal of earnings will be subject to ordinary income tax. Further, if one receives a distribution of earnings prior to age 59 ½, they are generally subject to the 10% early withdrawal penalty, unless they qualify for another exception. 

Note that as a practical matter, distributions of earnings received prior to turning age 59 ½ are rare since all previous annual contributions and Roth conversions must be withdrawn prior to a distribution being considered a distribution of earnings. 

A Quick Note on Roth IRA Aggregation

For purposes of assessing the taxation of a distribution from a Roth IRA, one aggregates all of their Roth IRAs and treats them together as a single Roth IRA. See IRC Section 408A(d)(4), Treas. Reg. Section 1.408A-6 Q&A 9(a) and (b), and my YouTube video on the subject.  

UPDATE October 30, 2023: I appreciate Andy Ives’s post on IRAHelp.com. He lays out very simply the Roth IRA Distribution rules at the end of this short post. His analysis agrees with mine.

Application to Fact Patterns

Having now covered the universe of the taxation of Roth IRA distributions (both qualified distributions and nonqualified distributions), let’s apply the rules to four examples. 

Example 1: Jorge celebrates his 65th birthday in the year 2023. After his birthday party, he converted $40,000 of his traditional 401(k) to a Roth IRA. The conversion is fully taxable. This is the first time Jorge has owned any Roth IRA. On January 1, 2024, Jorge withdrew $25,000 from his Roth IRA. On January 1, 2025, Jorge withdrew $25,000 from his Roth IRA.

What results in 2024 and 2025?

Jorge, as of both 2024 and 2025, does not meet the criteria for taking a qualified distribution because he has not owned a Roth IRA for at least 5 years. Thus, he has a nonqualified distribution in both years. 

In 2024, the $25,000 withdrawal of Roth conversions is income tax free (see Treas. Reg. Section 1.408A-6 Q&A 1(b)) and is penalty free because Jorge is older than age 59 ½. This demonstrates that the 5-Year Conversion Clock is irrelevant once one turns age 59 ½.  Check out Jorge’s 2024 Form 8606 Part III here (pardon the use of the 2022 version, it’s the latest one available as of this writing).

In 2025, the first $15,000 of Jorge’s withdrawal is a return of Roth conversions and thus not subject to ordinary income tax. Further, this withdrawal is not subject to the 10% early withdrawal penalty. The second $10,000 Jorge withdrew is a nonqualified distribution of earnings. Jorge must pay ordinary income tax on those $10,000 (see Treas. Reg. Section 1.408A-6 Q&A 4). This withdrawal of earnings violates the 5-Year Earnings Clock and is thus subject to ordinary income tax. However, this withdrawal of earnings is not subject to the 10% early withdrawal penalty as Jorge is older than age 59 ½. Check out Jorge’s 2025 Form 8606 Part III here.

Example 2: Samantha celebrates her 45th birthday in the year 2023. After her birthday party, she converted $60,000 of her old traditional 401(k) to a Roth IRA. The conversion is fully taxable. This is the first time Samantha has owned any Roth IRA. On January 1, 2024, Samantha withdrew $25,000 from her Roth IRA. On January 1, 2025, Samantha withdrew $40,000 from her Roth IRA.

What results in 2024 and 2025?

Samantha, as of both 2024 and 2025, does not meet the criteria for taking a qualified distribution because she has not owned a Roth IRA for at least 5 years. Thus, she has a nonqualified distribution in both years.

In 2024, Samantha’s withdrawal is a return of Roth conversions and thus not subject to ordinary income tax. However, because the withdrawal is from Roth conversions younger than 5 years old, and Samantha is under age 59 ½, Samantha must pay the 10% early withdrawal penalty ($2,500) on the distribution (she violates the 5-Year Conversion Clock), unless an exception applies.

In 2025, the first $35,000 of Samantha’s withdrawal is a return of Roth conversions and thus not subject to ordinary income tax. However, because the withdrawal is from Roth conversions younger than 5 years old, Samantha must pay the 10% early withdrawal penalty ($3,500) on the distribution (she violates the 5-Year Conversion Clock), unless an exception applies. 

The second $5,000 Samantha withdrew in 2025 is a nonqualified distribution of earnings. Samantha must pay ordinary income tax on those $5,000 (see Treas. Reg. Section 1.408A-6 Q&A 4) and generally must pay the 10% early withdrawal penalty ($500) on that $5,000 distribution of earnings, unless an exception applies. 

Example 3: Ed celebrates his 65th birthday in the year 2023. After his birthday party, he converted $40,000 of his old traditional 401(k) to a Roth IRA. The conversion is fully taxable. Ed has owned a Roth IRA since 1998. On January 1, 2024, Ed withdrew $25,000 from his Roth IRA. On January 1, 2025, Ed withdrew $25,000 from his Roth IRA.

What results in 2024 and 2025?

Unlike Examples 1 & 2, we finally have a qualified distribution! Why? Ed has (i) owned a Roth IRA since 1998 (more than 5 years) and (ii) is over age 59 ½. Thus, the only type of distribution Ed can take from his Roth IRA is a qualified distribution. Per Treas. Reg. Section 1.408A-6 Q&A 1(b), a qualified distribution is tax free. Further, Ed cannot pay the early withdrawal penalty on a distribution from his Roth IRA as he is in his 60s (see also Treas. Reg. Section 1.408A-6 Q&A 5(a)). Thus, there is no tax and no penalty on either the 2024 distribution or the 2025 distribution. 

Example 4: This example is based on my conversation with Brad Barrett on a recent episode of the ChooseFI podcast. Jonathan turns age 57 on July 1, 2023. He’s never had a Roth IRA. On July 1, 2023, he converted $50,000 from a traditional IRA to a Roth IRA. The conversion is fully taxable.

What withdrawal constraints does Jonathan have on his Roth IRA?

If Jonathan withdraws up to $50,000 from his Roth IRA prior to turning age 59 ½ on January 1, 2026, Jonathan will have to pay the 10% early withdrawal penalty as he violates the 5-Year Conversion Clock (unless an exception applies). 

If Jonathan cumulatively withdraws amounts in excess of $50,000 from his Roth IRA prior to turning age 59 ½, he will pay ordinary income tax on the withdrawal of those earnings (as he violates the 5-Year Earnings Clock) and he will pay the 10% early withdrawal penalty (unless an exception applies).

From January 1, 2026 through December 31, 2027, if Jonathan cumulatively withdraws amounts in excess of $50,000 from his Roth IRA, he will pay ordinary income tax on the withdrawal of those earnings (as he violates the 5-Year Earnings Clock). However, Jonathan will not pay the 10% early withdrawal penalty. Starting on January 1, 2028, Jonathan satisfies the 5-Year Earnings Clock (see Treas. Reg. Section 1.408A-6 Q&A 2) and is now permanently able to take a qualified distribution from his Roth IRA going forward.

Example 5: Denzel celebrates his 35th birthday in the year 2023. After his birthday party, he contributed $6,500 to a traditional IRA on July 1, 2023. He cannot deduct the contribution based on his income level. On August 2, 2023, at a time the traditional IRA was worth $6,502, he converted the entire traditional IRA to a Roth IRA, completing a Backdoor Roth IRA. This is the first time Denzel has owned any Roth IRA. He owned no traditional IRAs, SEP IRAs, and/or SIMPLE IRAs on December 31, 2023. Denzel reported $2 of taxable income on his 2023 tax return due to the Backdoor Roth IRA. 

On January 16, 2024, Denzel withdrew $3,000 from his Roth IRA and made no contributions to his Roth IRA during 2024.

What results in 2024?

Denzel, as of 2024, does not meet the criteria for taking a qualified distribution because he has not owned a Roth IRA for at least 5 years. Thus, he has a nonqualified distribution in 2024.

Pursuant to Treas. Reg. Section 1.408A-6 Q&A 8(b), the taxable portion of the Roth conversion ($2 out of $6,502) comes out first. That $2 is subject to the 10% early withdrawal penalty (a $0.20 penalty which rounds down to $0) since he violates the 5-Year Conversion Clock, unless an exception applies. This $2 constitutes what I colloquially refer to as a micro layer inside the Roth IRA: for 5 years it is subject to the 10% early withdrawal penalty if withdrawn (unless an exception applies). 

However, the $2 recovery of the taxable Roth conversion is not subject to ordinary income tax. See Treas. Reg. Section 1.408A-6 Q&A 1(b).

Second, the $2,998 nontaxable portion of the Roth conversion is distributed out. This nonqualified distribution is subject to neither ordinary income tax nor the 10% early withdrawal penalty. See Treas. Reg. Section 1.408A-6 Q&A 1(b), 5(a), and 5(b). Check out Denzel’s 2024 Form 8606 Part III here.

There is some confusion on this latter result. Treas. Reg. Section 1.408A-6 Q&A 4 provides that only once all of the owner’s previous “contributions” have been withdrawn are nonqualified Roth IRA distributions subject to ordinary income tax. For this purpose, it is clear from reading Treas. Reg. Section 1.408A-6 Q&A 8(a) that “contributions” include both “annual contributions” and “Roth conversions.” See also Treas. Reg. Section 1.408A-6 Q&A 5(b) providing that the 10% early withdrawal penalty does not hit withdrawals of nontaxable converted amounts (“For purposes of applying the tax, only the amount of the conversion contribution includible in gross income as a result of the conversion is taken into account.”). Thus, the nontaxable portion of a Backdoor Roth IRA can be recovered tax and penalty free at any time for any reason. 

Other than the minor potential Backdoor Roth IRA micro layer issue, a Backdoor Roth IRA could, in theory, serve as an emergency fund (though generally we want to plan for long term Roth IRA tax-free growth).

Roth IRA Distributions Summary Chart

Type of DistributionOrdinary Income Tax10% Early Withdrawal PenaltyNotes
Qualified DistributionNeverNeverMain way to qualify: attain age 59 ½ and own Roth IRA for 5 years.
NQ Return of Annual ContributionsNeverNeverComes out prior to returns of conversions and earnings.
NQ Return of Roth ConversionsNeverCan apply. Applies if the taxable conversion is less than 5 years old and the owner is under age 59 ½ (though exceptions can apply).Come out “FIFO” (first-in, first out).
NQ Distribution of EarningsAlwaysYes, if the owner is under age 59 ½ (though exceptions can apply).Come out only if all prior annual contributions and conversions have been withdrawn.
NQ stands for nonqualified

Exceptions to the 59 ½ Year Age Requirement

It is possible to qualify for a qualified distribution if one is younger than 59 ½ years of age. It happens if (1) the 5-Year Earnings Clock is satisfied and (2) the Roth IRA owner (i) is using the money for a first-time home purchase (limit of $10,000), or (ii) is disabled, or (iii) has died. See Treas. Reg. Section 1.408A-6 Q&A 1(b)(2). Outside of the owner’s death, these situations are rare. 

Resources

Notice this post cites the to regulation and occasionally the Internal Revenue Code. That’s because they are the law of land! The Code is the primary law of the land, but it tends to be written in a manner inaccessible to most laymen and difficult for many professionals to understand. The regulations interpret the Code. While not an elementary school level read, Treas. Reg. Section 1.408A-6 is much more comprehensible than the Code. The regulation’s question and answer format makes it much easier to digest.

IRS Publication 590-B, Distributions from Individual Retirement Arrangements (IRAs), is an IRS publication. As such it is (i) informative and (ii) not binding authority on either the IRS or on taxpayers. Please understand both when using an IRS publication. I will note that Publication 590-B has an excellent flowchart (Figure 2-1) which can be used to help determine if a distribution from a Roth IRA is a qualified distribution. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

How I Learned to Stop Worrying About the Roth IRA 5 Year Rules

You know what gets too much attention in the personal finance space? The two five-year Roth IRA rules. 

Why do I say that? Because the odds are extremely low that either rule will ever impact most Roth IRA owners. While the rules theoretically have wide effect, in practice, discussed further below, they rarely impact the taxation of Roth IRA distributions.

Before I get started, below is a summary table of the two five-year rules (or five-year clocks, use whichever terminology you prefer). The table is not comprehensive, but rather intended to cover the vast majority of situations. I hope you find this table to be a useful reference regarding the two five-year rules. 

RuleTax BiteAgeCode SectionRegulation
First Five-Year RuleOrdinary income tax on withdrawal of earnings from Roth IRA onlyGenerally bites only if owner is over 59 ½ years old408A(d)(2)(B)1.408A-6 Q&A 2
Second Five-Year Rule10% early withdrawal penalty on withdrawal of taxable converted amounts from Roth IRA onlyOnly bites if owner is under age 59 ½ 408A(d)(3)(F)1.408A-6 Q&A 5(b)

First Five-Year Rule: Earnings Cannot Be Withdrawn Income Tax Free From a Roth IRA Unless the Account Holder has Owned a Roth IRA for Five Full Tax Years

At first, this rule seems daunting. As written, it applies to anyone owning a Roth IRA. But in practice, it rarely has any bite. First, the rule only serves to disqualify a distribution from being a “qualified distribution.” 

Here’s the thing: outside of rare circumstances (see “Two Uncommon Situations” below), anyone under age 59 ½ cannot receive a “qualified distribution” from their own Roth IRA regardless of the first five-year rule.

Thus, as a general matter, the first five-year rule is a rule that only applies to those age 59 ½ and older. 

For those doubting me, I’ll prove it with two examples:

Example 1: Ernestine turns age 25 in the year 2023. In March, she made a $6,500 annual contribution to a Roth IRA for the year 2023. This is her only ever Roth IRA contribution. In 2026, when the Roth IRA is worth $8,000 and Ernestine turns age 28, Ernestine withdraws all $8,000 from the Roth IRA. The first $6,500 is a nontaxable return of the $6,500 contribution, and the remaining $1,500 is a taxable distribution of earnings subject to both ordinary income tax and the 10 percent early withdrawal penalty. 

Example 2: Hortense turns age 25 in the year 2023. In March, she made a $6,500 annual contribution to a Roth IRA for the year 2023. This is her only ever Roth IRA contribution. In 2030, when the Roth IRA is worth $8,000 and Hortense turns age 32, Hortense withdraws all $8,000 from the Roth IRA. The first $6,500 is a nontaxable return of the $6,500 contribution, and the remaining $1,500 is a taxable distribution of earnings subject to both ordinary income tax and the 10 percent early withdrawal penalty. 

Ernestine did not satisfy the first five-year rule, Hortense did. Notice that it did not matter! Both must pay ordinary income tax and the 10% early withdrawal penalty on the $1,500 of earnings they each received from their Roth IRA. The first five-year rule had absolutely no impact on the taxation of the withdrawal because both Roth IRA owners are under age 59 ½. This proves that outside unusual circumstances, the first five-year rule has no impact on those under age 59 ½.

I’ve said it before and I’ll say it again: Previous annual contributions to a Roth IRA can be withdrawn from a Roth IRA tax and penalty free at any time for any reason! The first five-year rule has nothing to do with withdrawals of previously made contributions. See Treas. Reg. Sec. 1.408A-6 Q&A 1(b) (previous contributions are withdrawn tax free) and Q&A 5(a) (tax free withdrawals of previous regular annual contributions are not subject to the 10% early withdrawal penalty).

So when the heck does the first five-year rule matter? Here are two examples to help us figure it out.

Example 3: Ernie turns age 58 in the year 2023. In March, he made a $7,500 annual contribution to a Roth IRA for the year 2023. This is his only ever Roth IRA contribution. In 2026, when the Roth IRA is worth $10,000 and Ernie turns age 61, Ernie withdraws all $10,000 from the Roth IRA. The first $7,500 is a nontaxable return of the $7,500 contribution, and the remaining $2,500 is a taxable distribution of earnings subject to ordinary income tax. Ernie does not pay the 10 percent early withdrawal penalty because he is over age 59 ½ when he receives the earnings. 

Example 4: Harry turns age 58 in the year 2023. In March, he made a $7,500 annual contribution to a Roth IRA for the year 2023. This is his only ever Roth IRA contribution. In 2030, when the Roth IRA is worth $10,000 and Harry turns age 65, Harry withdraws all $10,000 from the Roth IRA. As Harry satisfies both the first five-year rule and is over age 59 ½, the entire $10,000 distribution is a qualified distribution and thus entirely tax and penalty free.

We’ve found where the first five-year rule matters! Generally speaking, the first-five year rule only bites when applied to a distribution of earnings if the recipient is over the age of 59 ½. Further, it only applies to subject the earnings to ordinary income tax, not the 10% early withdrawal penalty (as being age 59 ½ or older is always a valid exception to the early withdrawal penalty). 

Remember, though, in most cases it is difficult to access Roth IRA earnings. Why? Because earnings come out of a Roth IRA last. Ernie’s fact pattern is rare. Many Roth IRA owners will have years of contributions and/or conversions inside their Roth IRA. As I have previously discussed, nonqualified distributions from Roth IRAs first access Roth IRA contributions and then access Roth IRA conversions before they can access a penny of earnings. See also Treas. Reg. Sec. 1.408A-6 Q&A 8 and Natalie B. Choate’s Life and Death Benefits for Retirement Planning (8th Ed. 2019), page 328. 

Further, in today’s world, most (though not all) 59 ½ year old Roth IRA owners will satisfy the five-year rule. All Roth IRAs are aggregated for this purpose, so the funding (through a contribution or conversion) of any Roth IRA starts the five-year clock as of January 1st of the year for which the contribution was made. See Treas. Reg. Sec. 1.408A-6 Q&A 2. 

Two Uncommon Situations: There are two uncommon situations in which a Roth IRA owner under age 59 ½ receiving a Roth IRA distribution could save the ordinary income tax by satisfying the first five-year rule. The first is the taking of an up-to $10,000 first-time home buyer distribution. See Choate, previously referenced, at page 612. The second is if the owner is disabled as defined by Section 72(m)(7). Both are rare situations. Further, in both such cases, satisfying the first five-year rule would be irrelevant if the distribution would have been a return of contributions, nontaxable conversions, and/or taxable conversions at least 5 years old. 

Inherited Roth IRA Twist: The first five-year rule can affect distributions from an inherited Roth IRA. I’ve heard this referred to as the third Roth IRA five-year rule, but I view it as simply a continuation of the first five-year rule. A withdrawal of earnings by a beneficiary from an inherited Roth IRA made less than five tax years after the owner originally funded the Roth IRA is subject to ordinary income tax. See Treas. Reg. Sec. 1.408A-6 Q&A 7.  These situations are quite rare. 

If Anyone on Capitol Hill is Reading This . . .

The first five-year rule serves no compelling purpose, and is superfluous as applied to most taxpayers under the age of 59 ½.

Perhaps in 1997 Congress worried about quick withdrawals from Roth IRAs. Now that we fully understand that contributions and conversions come out of Roth IRAs first, and that being under age 59 ½ prevents a tax-free distribution of earnings in most cases, there’s no reason for the first five-year rule. Being age 59 ½ or older (or death, disability, or first-time home buyer) should be sufficient to receive a qualified distribution. 

I recommend that Congress repeal the first five-year rule by removing Section 408A(d)(2)(B) from the Internal Revenue Code as part of retirement tax simplification.

Second Five-Year Rule: Taxable Conversions Are Subject to the Ten Percent Early Withdrawal Penalty if Withdrawn from the Roth IRA Within Five Taxable Years

This rule is much more logical than the first five-year rule. The reason has nothing to do with Roth IRAs. Rather, the reason is to protect the 10% early withdrawal penalty as applied to traditional IRAs and traditional workplace plans such as 401(k)s and 403(b)s. Without the second five-year rule, taxpayers would never pay the 10% early withdrawal penalty. 

Rather, taxpayers under age 59 1/2 would simply convert any money they want to withdraw from a traditional retirement account to a Roth IRA, and then shortly thereafter withdraw the amount from the Roth IRA tax-free as a return of old contributions or of the conversion itself. 

The second five-year rule prevents the total evisceration of the 10% early withdrawal penalty. 

The second five-year rule applies separately to each taxable Roth conversion. Each Roth conversion that occurs during a year is deemed to occur January 1st of that year for purposes of the second five-year rule. See Treas. Reg. Sec. 1.408A-6 Q&A 5(c).

Note further that the second five-year rule has nothing to do with income tax: its bite only triggers the distribution being subject to the 10% early withdrawal penalty. 

When Might the Second Roth IRA Five-Year Rule Apply

I am not too worried about the application of the second five-year rule. Here’s why.

First, the second five-year rule is not likely to apply while one is working. During the accumulation phase, many are looking to contribute to, not withdraw from, Roth IRAs.

Second, for those retiring after age 59 ½, the second five-year rule will have practically no impact, as (i) they are not likely to take pre-retirement distributions from their Roth IRA, and (ii) distributions taken from the Roth IRA by the owner after turning age 59 ½ are never subject to the 10% early withdrawal penalty. 

Third, many early retirees will choose to live off taxable assets first in early retirement. As a result, many will not access Roth accounts until age 59 ½ or later, and thus the second five-year rule will not be relevant. 

However, some will choose to employ a Roth Conversion Ladder strategy with respect to an early retirement. Here the second five-year rule might bite. Let’s consider a quick example:

Example 5: Josh is considering retiring in 2024 when he turns age 50. In his 30s, he qualified to make an annual Roth IRA contribution and maxed out his Roth IRA each year. In his 40s, he made income in excess of the annual MAGI limits on Roth IRA contributions, so he maxed out the Backdoor Roth IRA for each year. He plans on living on taxable assets for the first five years of retirement and then living off Roth conversion ladders from age 55 through age 59 ½. Josh has never previously taken a distribution from a Roth IRA.

Here is Josh’s Roth IRA history in table form. Thanks to Investopedia for the historic annual contribution maximums. 

YearAgeRoth IRA ContributionBackdoor Roth IRATaxable Amount
200430$3,000
200531$4,000
200632$4,000
200733$4,000
200834$5,000
200935$5,000
201036$5,000
201137$5,000
201238$5,000
201339$5,500
201440$5,502$2
201541$5,503$3
201642$5,501$1
201743$5,502$2
201844$5,501$1
201945$6,001$1
202046$6,002$2
202147$6,002$2
202248$6,001$1
202349$6,004$4

If Josh started withdrawing from his Roth IRA in 2024, he would first withdraw all $45,500 of previous annual contributions (all tax and penalty free) and then withdraw all $33,510 of his 2014 through 2019 Backdoor Roth IRAs (all tax and penalty free) before he could take a distribution with respect to which the second five-year rule could bite. 

Note that for withdrawals of up to $79,010, it is irrelevant that Josh does not satisfy the second five-year rule with respect to the 2020 through 2023 Backdoor Roth IRAs. Josh can withdraw up to $79,010 entirely tax and penalty free in 2024. Perhaps the second five-year rule’s bark is worse than its bite . . .

If, in 2024, Josh withdraws both of the above listed amounts from his Roth IRA, then yes, the next $2 of withdrawals in 2024 would be from the $2 taxable amount of his 2020 Backdoor Roth IRA, which would be subject to the 10% early withdrawal penalty ($0.20) under the second five-year rule. 

In Josh’s extreme example, the second five-year rule bites, but, as you can see, it barely bites!

As an aside, assuming Josh continues to withdraw money from his Roth IRA in 2024, the next $6,000 is a tax and penalty free return of the non-taxable portion of his 2020 Backdoor Roth IRA! See Treas. Reg. Sec. 1.408A-6 Q&A 8. The generosity of the Roth IRA nonqualified distribution rules is, by itself, a reason not to sweat the two Roth IRA five-year clocks too much. 

Assuming Josh follows through with his plan and waits until age 55 (the year 2029) to start withdrawing from his Roth IRA, he can access all of his 30s Roth IRA annual contributions ($45,500), all of his 40s Backdoor Roth IRAs ($57,519), and whatever amount he converted to his Roth IRA in 2024 tax and penalty free in 2029! After that, however, the second five-year rule will bite ten cents on the dollar for amounts additionally distributed in 2029, since amounts converted in 2025 or later would still be subject to the second five-year rule if distributed in 2029. 

In Josh’s early retirement example, assuming Josh takes no distributions from his Roth IRA until age 55, the second five-year rule can only possibly bite from age 55 to 59 ½, and even then, the combination of years of built up Roth basis and affirmative planning make that possibility at least somewhat remote. 

Don’t over think it: If the owner of a Roth IRA is 59 1/2 years old or older, and has owned a Roth IRA for at least 5 years, all distributions they receive from a Roth IRA are qualified distributions and thus fully tax and penalty free. In such circumstances, the 5-year clocks are entirely irrelevant.

Conclusion

It’s perfectly cromulent to proceed with financial planning without too much worry about the two Roth IRA five-year rules. For personal finance nerds (myself included), the two Roth IRA five-year clocks can be fun to dive into. But from a practical standpoint, they rarely impact the taxation of distributions from Roth IRAs. The two five-year clocks are best understood as sporadically applicable exceptions to the general rule that most nonqualified distributions from Roth IRAs are tax and penalty free.

Further Reading

For even more on Roth IRA distributions, please read this post, which goes through the details of Roth IRA distributions, including citations to the relevant regulations and links to three example Forms 8606 Part III.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Medicare Resources

You know what doesn’t get enough coverage in the personal finance space: Medicare! It’s complicated, and frankly, I have neither the time nor the mental bandwidth to become a Medicare expert.

However, recently I have seen some excellent YouTube Videos on the topic. I believe all the links provided below are worthy of consideration. That consideration should, of course, include critical analysis: these videos are great, but they didn’t come down the mountain with Moses (neither did any of my blog posts or YouTube videos).

Further, none of the videos should be relied upon as advice for any particular person. They are all educational resources.

Sarasota Tim on Medicare Basics and Enrolling: https://www.youtube.com/watch?v=FNCk7x26i_M

Clark Howard Shares His Concerns with Medicare Advantage (Medicare Part C): https://youtu.be/QUSdn7nGXvQ?t=192

Danielle Kunkle Roberts on Medigap Part G: https://www.youtube.com/watch?v=XtqfO22-Tss

Danielle Kunkle Roberts on Medigap High Deductible Part G: https://www.youtube.com/watch?v=s2aRGN7pR1Q

MedicareSchool on Medigap Part G Versus Medigap Part N: https://www.youtube.com/watch?v=tYXvKvMPbpI

MedicareSchool on Medicare Part D (Prescription Drugs): https://www.youtube.com/watch?v=rSLx-lFr-DM

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Saving Social Security and Medicare

America has a retirement savings problem. To varying degrees, Social Security and Medicare support retirees. Other than for the very wealthy, a significant diminution in either program would materially hurt retirees. 

Most can agree with a simple proposition: over the long term, there are fiscal holes in Social Security and Medicare. 

I have seven proposals to address the problem. These proposals won’t solve funding problems for all time, but will move the needle significantly towards securing Social Security and Medicare. All the tax related proposals tax those who have benefited the most from the American economy and a very favorable investment tax climate. 

Before I get started, I would like to encourage the reader to endeavor to reduce his or her dependence on these programs by building up their own retirement assets and/or income streams. That said, as a practical matter both Social Security and Medicare are very important to the retirements of the vast majority of Americans. 

Who Pays to Save Social Security and Medicare?

PROPOSAL ONE: No changes to the Social Security and Medicare eligibility ages.

Some propose to increase the eligibility age for Medicare and/or Social Security full retirement age.

I believe that to be a horrible idea, for a myriad of reasons. Over the long term, there are fiscal holes in Social Security and Medicare. By definition, someone in the world must pay for those holes. If we eliminate more outlandish possibilities such as billing invading extraterrestrials and foreign plunder, most of the cost must be made up by some cohort or cohorts of Americans. Raising the eligibility ages to fix the holes simply decides that Americans in their mid-to-late 60s of all income and wealth levels are the cohort of Americans who must pay for those holes.

But why? Are 60-somethings particularly well off compared to other cohorts? I don’t believe they are, and many in their mid-to-late 60s are far worse off than the average American citizen. 

I’m not the only commentator to oppose increasing Social Security eligibility ages.

My three tax proposals below are hardly perfect. But at least they put the onus on filling the holes on those who (i) have benefited most from the recent American economy and (ii) have most benefited from America’s very favorable investment and endowment tax environment. Why shouldn’t the people who have benefited the most, and would be harmed by tax increases the least, fix the Social Security and Medicare holes?

Further, my three tax proposals have a significant advantage over delaying eligibility ages. Delaying eligibility ages is a delayed fix! If enacted in 2023, my three proposals go to work (in full!) on January 1, 2024. 

Any delay of the eligibility age will likely be at least somewhat delayed. No politician is going to vote to raise a 66 year old’s Social Security full retirement age overnight from age 67 to age 70. There’s zero chance of that. That’s demonstrated by this proposal, which proposes to increase Social Security eligibility ages by 3 years and admits that the proposal would not save money for at least 10 years! 

Would you be happy if you called a plumber to fix a leak in your sink and he responded, “Sure, happy to help, I’ll swing on by in 10 years.” No!

Further, I am not going to advocate for a politically untenable solution, and I wouldn’t recommend any politician do so either. There are plenty of solutions that can be implemented short of solutions that are guaranteed to be wildly unpopular with the electorate. 

One piece of evidence demonstrates just how unpopular cutting Social Security and Medicare are. A recent Axios-Ipsos poll (see the bottom of page 9) found that Americans generally oppose Social Security and Medicare cuts by a 7 to 2 margin. Any highly unpopular solution will ultimately be counterproductive. 

A group of Republican Congressmen argue Social Security eligibility ages should be increased in the future to account for increased life expectancy (see the bottom of page 88 of this file). I believe their argument is mistaken for two reasons. First, some increases in life expectancy are attributable to diminished infant mortality instead of increased lifespan in old age. Second, in 2020 and 2021, American life expectancy decreased.

PROPOSAL TWO: No Increase to the FICA Tax Rates (Employee and Employer)

Historically, there have been many payroll tax increases to fund Social Security and Medicare. I believe, in today’s economy, a simple payroll tax rate increase would be unfair and would hurt many Americans who have not benefited from the surge in financial markets the way the affluent have. In a world where working class workers have not experienced real significant salary increases in decades, while the stock market has soared over several decades, we can’t simply increase payroll taxes on everyone and call it fair.

Further, it might be tempting to only increase the payroll tax rates paid by employers. But this runs into two big problems. First, it’s a tax on job creation. I, for one, want employers of all sizes creating more jobs in the United States. Increasing the tax rates employers pay for Social Security and Medicare increases incentives to offshore jobs and shifts towards automation. Count me against that.

Second, increasing employer tax rates is a tax hike on the self-employed. The self-employed face many challenges. They are not a cohort that should shoulder the burden of closing the fiscal holes in Social Security and Medicare.

Tax Increases to Save Social Security and Medicare

PROPOSAL THREE: Increase the additional Medicare tax on earned income from 0.9% to 2.0% Use half the tax (1.0%) fund Medicare and half the tax (1.0%) fund Social Security.

PROPOSAL FOUR: Increase the Medicare surtax on net investment income from 3.8% to 5.0%. Use the increase (1.2%) to fund Social Security. 

These two proposals have several advantages. They incrementally increase taxes on the most successful in America in order to close the shortfalls in Social Security and Medicare. They are not taxes on employers hiring more employees, so they do not discourage hiring. Further, these two tax proposals leverage off existing taxes such that implementation of the proposals should be relatively easy. 

PROPOSAL FIVE: Impose a new 25% excise tax on net investment income of college endowments with $1 billion or more in assets as of year end.

This new tax would replace the tiny 1.4% excise tax on some college endowments enacted as part of the Tax Cuts and Jobs Act (TCJA) in 2018. 

Congress can allocate tax collections between Social Security and Medicare as they best see fit. 

Once subject to the tax, a college endowment would be subject to it going forward until the endowment can demonstrate its year-end assets have been under $750 million for three consecutive years. 

Net investment income for this purpose would be the endowment’s Section 1411(c)(1)(A) income, less the following limited expenses: salaries and benefits for employees primarily working for the endowment (limited to $20,000 per month per employee), endowment tax return preparation fees, endowment legal fees, office supplies and equipment (printers, copiers, scanners, etc.) for the endowment, and computer software for the endowment (limited to $1 million per year). Capital gains and capital losses would be netted and no net capital loss could be taken, though any net capital loss would carry forward without limit to subsequent years. 

As the excise tax taxes endowments of financial assets, dorms, classrooms, and other buildings used by the university in their educational mission would not be endowment assets for purposes of the new excise tax. 

Estimated payments would be due the same dates as individual estimates are due (and the same underpayment penalties would apply), and the net investment income of any controlled endowment entity (domestic or foreign) would also be included in the endowment’s net investment income. 

These tax-free hoards have enjoyed incredibly favored treatment long enough. Some of these endowments now exceed $1 million per student, more than enough to fund many students without collecting a dollar of tuition. 

Most colleges do not pay income tax on tuition and donations received. I don’t propose to change that, but it’s time these colleges, which mostly serve a select privileged few, pay a significant tax on their investment income. Considering these endowments are worth vast sums of money, that tax should be equal to the rate paid by highest income individuals on long term capital gains, 25% (20% long term capital gain rate plus 5% net investment income tax under my proposal).

You might think this is unfair to colleges. But let’s imagine we were tasked with creating the entire U.S. federal tax system from scratch. If I proposed to subject waiters and factory workers to both income taxes and payroll taxes on their entire salary, while exempting colleges from taxation on tuition collected and donations received, and then added a 25% net investment income tax on large endowments, you’d probably say “Wow, you’re being unfair to waiters and factory workers and too generous to colleges.” 

I don’t propose a revolution in tax policy, but rather a fair, equitable, and incremental tax change that increases the tax burden on those most able to bear it in order to combat funding shortfalls in Social Security and Medicare. 

Stabilizing The Federal Government’s Finances

PROPOSAL SIX: Significant reductions in military and foreign spending

Practically all Americans reading this are owed Social Security and/or Medicare benefits! That makes you a creditor of the U.S. government. 

Your creditor’s financial health matters to you. It’s time your creditor got its house in order. Your creditor’s house is not in order for many reasons, including spending that is consistent with neither the founding nor the history of our great republic.

Incredibly enough, the United States has nearly three times as many foreign military bases as it has embassies. It’s time to ditch the bases and bring the troops home for many reasons. Having so many military and other government personnel overseas is contrary to the great history of our republic. As John Quincy Adams said, “America does not go abroad in search of monsters to destroy.” Today’s historically out-of-whack military and foreign spending is destabilizing the government’s finances. It’s time to cut military and foreign spending significantly and redeploy that money to reduce the deficit and secure the financial stability of the federal government. 

A financially stable government is much more likely to be able to successfully meet its Social Security and Medicare obligations. 

Some might argue that neither our current level of military spending nor Social Security and Medicare are consistent with the founding and history of our country, so shouldn’t both be cut? Jeffrey Sachs has observed that there is some popular support for cutting America’s foreign military involvement. On the other hand, there is very little appetite among the electorate for reductions to Social Security and Medicare. There’s no reason to consider wildly unpopular options when there are much more popular options on the table. 

Self-Help

PROPOSAL SEVEN: Change Your Health

Not every change to improve the Social Security and Medicare system needs to come from Congress.

Over the years I have become more and more convinced that almost everything we learned about health and nutrition is wrong. It is time for each of us to radically take charge of our own healthcare. We need to do this regardless of the fiscal state of Social Security and Medicare. But my hope is this shift will reduce spending on Medicare. 

I have seen my health improve by focusing on eating high quality animal fats and proteins, avoiding seed oils (which are very new in human history), and dramatically reducing sugar consumption. One reason I continue with that focus is that, as discussed by Doctors Ken Berry and Lisa Wiedeman, sugar feeds cancer! See also Dr. Ken Berry discussing this further. Avoiding certain foods can dramatically improve health outcomes and reduce medical spending (including Medicare spending). 

My hope is that more and more Americans will become aware of the role of diet in health, and that will, over time, reduce long term medical expenses, including the expenses paid for by Medicare. Eventually, this renewed health will hopefully lead to longer life spans and increase future Social Security payments. If this happens, it hurts Social Security many years in the future. That much delayed good problem to have will hopefully be more than compensated for by earlier (and hopefully permanent) reductions in Medicare costs. 

Conclusion

As the federal government racks up more and more debt, and the clock ticks towards financial peril for both Social Security and Medicare, it’s time to take action to preserve and protect these programs. 

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute medical, accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal medical, accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The above does not represent the opinion of anyone other than the author, Sean W. Mullaney. The author was not compensated by any individual or entity for writing this blog post, and this blog post does not necessarily reflect the views of any current or former employer of Sean W. Mullaney.

Sean on the Catching Up to FI Podcast

Listen as I talk tax with Becky Heptig and Bill Yount on the Catching Up to FI podcast.

You can access the podcast on Apple Podcasts.

We discuss tax planning for financial independence, particularly planning for those catching up later in their careers.

The show notes include references to the following FI Tax Guy blog posts.

The Advantages of Living on Taxable Assets First in Early Retirement

TikTok Tax Advice

Early Retirement and Social Security

HSAs and Las Vegas

This post, and the above mentioned podcast episode, are for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Inherited Health Savings Accounts

Folks love health savings accounts, and why not? A tax deduction or exclusion on the way in, tax-free growth, and then tax-free withdrawals when used for qualified medical expenses or reimbursements of qualified medical expenses. 

Tastes great and less filling! 

Considering the HSA is less than 20 years old (as of this writing) and contribution limits are relatively modest, inherited HSAs have not been much of an issue in the personal finance world. I suspect that will soon change, as HSAs and their account owners age and HSA balances grow. 

HSA Planning

There is something very fundamental one must keep in mind: planning for traditional retirement accounts and Roth retirement accounts is two sided. There is planning that owners should do for those retirement accounts prior to death and there is planning that inheriting beneficiaries should do after the owner’s death.

HSA planning, as you will see below, is mostly prior to the owner’s death. Other than a spouse, anyone else inheriting an HSA has relatively few planning opportunities.

Spousal Beneficiaries

The tax rules generally favor spousal beneficiaries, and the world of HSAs is no different. Section 223(f)(8)(A) has a very specific rule that changes the HSA account owner to the spouse as of death. This means the continuation of HSA account status, and thus continued tax free growth and future tax free withdrawals for payments of qualified medical expenses and for payments of previously unreimbursed qualified medical expenses (what I refer to as PUQME, pronounced “puck-me”). 

As Notice 2004-50 Q&A 39 makes clear, there is no time limit on PUQME reimbursement. Thus, inheriting spouses should, generally speaking, be able to reimburse themselves for built up PUQME unaffected by their spouse’s death. For example, the surviving spouse should be able to reimburse him/herself tax and penalty free from the HSA for medical expenses of the decedent spouse incurred on their deathbed.

Obviously, HSA tax-free carryover treatment is very favorable. It is difficult to imagine circumstances where a married HSA owner would want to name anyone other than their spouse as the 100 percent primary beneficiary of their HSA. In theory, leaving an HSA to a charity at the first spouse’s death could be neutral when compared to leaving to the surviving spouse, if the couple is both very affluent and charitably inclined. Even then, it’s hard to see much of a drawback to naming the spouse as the primary beneficiary. 

Other Individuals

Section 223(f)(8)(B) has some bad news for an individual, other than the surviving spouse, inheriting an HSA. Sure, they get the assets in the HSA. But, (i) the account loses its status as an HSA, and (ii) even worse, the entire amount of the HSA is included in the recipient’s taxable income in the year of the original owner’s death. 

This is the hidden HSA death tax. As the HSA is under 20 years old, and frequently owed by younger people, the issue of the hidden HSA death tax has not come to the forefront of the personal finance space. To my mind, this is a lurking issue that many aren’t aware of.

The tax hit from an HSA inheritance could be quite significant. Here is one theoretical example. 

Jack and Meghan are married, both age 51 in 2023, file joint, and claim the standard deduction.  Planning on having an AGI of approximately $155K for 2023, they each contributed $7,500 to a Roth IRA for 2023 on January 2, 2023. They have one child in college and thus plan on getting a $2,500 AOTC tax credit for tuition paid. 

On September 2, 2023, Meghan’s widowed father died and left his HSA, worth $75K, to Meghan. As a result, their AGI increases by $75K. On March 1, 2024, informed by their tax return preparer they did not qualify to make the Roth IRA contributions, they withdrew the contributions and the earnings attributable to the contributions ($750 each based on 10 percent growth). They also lose the ability to claim a credit for the college tuition they paid.

Here’s the tax consequences of Meghan inheriting the HSA.

ItemW/o HSA InheritanceWith HSA Inheritance
Ordinary Income (Initial)$153,000$153,000
Qualified Dividend Income$2,000$2,000
AGI (Initial)$155,000$155,000
HSA Inheritance$0$75,000
Roth IRA Earnings$0$1,500
AGI$155,000$231,500
Standard Deduction$27,700$27,700
Taxable Income$127,300$203,800
Tentative Tax$18,481$35,572
AOTC$2,500$0
Federal Income Tax$15,981$35,572
Federal Tax Increase$0$19,591
Effective Rate on AGI10.31%15.37%

The tax hit on inheriting the HSA is almost $20,000! Jack and Meghan pay more federal income tax on inheriting the HSA than they do on the rest of their income! Further, because tax benefits such as being able to contribute to a Roth IRA and AOTC qualification are based on MAGI, and inherited HSA income increases MAGI, Jack and Meghan (i) lost their 2023 AOTC and (ii) had to withdraw $15,000 in 2023 Roth IRA contributions and the related earnings. 

Deduction Planning: Yes, Jack and Meghan could potentially tax loss harvest (getting a current deduction of up to $3,000) and/or increase contributions to charities and/or donor advised funds to itemize their deductions in a year they are now in the 24% bracket. This planning is only marginally helpful (particularly in a high standard deduction world) and does not lower their MAGI sufficient to still qualify for the AOTC and to make most of the annual Roth IRA contributions. Further, if Meghan inherited the HSA late in the year, there may not be enough time to execute such planning.

Inherited HSA Tax Exception

There is a narrow exception to full income inclusion. The inheriting non-spouse beneficiary can reduce the inherited HSA income inclusion by the amount of medical expenses incurred by the original owner prior to death and paid by the inheriting beneficiary in the year after the death. 

The Estate

In theory, an HSA could be left to the estate of the HSA owner if (i) the owner elected such treatment on the beneficiary designation form or (ii) they failed to file a beneficiary designation form with the HSA provider. 

The original owner’s final income tax return must include the fair market value of the HSA in taxable income if the HSA is left to the estate. See IRS Publication 969, page 10.

Obviously, this is not a great result. In theory, if the owner is low income and the ultimate intended beneficiary is high income, one might want to name their estate as the beneficiary of the HSA. Considering that the are planning alternatives that can avoid anyone paying income tax on an HSA, this is not likely to be a good “go-to” planning option.

Charitable Beneficiaries

Many HSA owners are at least somewhat charitably inclined. The inherited HSA rules present a planning opportunity: leave HSA balances to charity if the HSA owner is not married. Charities pay no income tax when inheriting an HSA.

As discussed above, the optimal planning for a charitably inclined married couple is likely to be to name the spouse as the primary beneficiary. Only after the death of the first spouse would the primary beneficiary be changed to the charity.

Note that HSA owners should discuss naming a charity or charities as a primary or secondary beneficiary with their HSA account provider. 

Later In Life HSA Planning

What could Meghan’s widowed father have done to avoid costing his daughter and son-in-law almost $20,000 in federal income taxes?

First, strong consideration should be given to bailing out HSAs during old age, particularly if the HSA owner is not married. HSAs will not be too difficult to deplete tax and penalty free. Reimbursements of PUQME can access thousands of dollars of old qualified medical expenses, and the elderly will have plenty of new qualified medical expenses, including final medical expenses of deceased spouses. Further, Medicare Parts B and D premiums qualify as qualified medical expenses, so even the healthy elderly should be able to reimburse themselves tax-free from their HSA annually for some qualified medical expenses. 

Had Meghan’s father reimbursed himself tax-free for PUQME instead of leaving the money inside the HSA, Meghan could have inherited the money (now in a taxable account) income tax free.

Second, Meghan’s widowed father could have named a charity as the primary beneficiary on the HSA, and left taxable brokerage accounts, Roth retirement accounts, and even traditional retirement accounts to Meghan. Even the traditional retirement accounts would not have either created no taxable income to Meghan in 2023, or, at worst, would have required Meghan to take the RMD her father was required to take in 2023 (if her father died before taking it). 

I recently wrote about strategic planning in this regard. If one is not married, accounts such as Roth IRAs and taxable brokerage accounts are great to leave to individual beneficiaries. HSAs are great for unmarried people to leave to a charity if one is charitably inclined.

Conclusion

HSAs are arguably the most tax favored accounts during one’s lifetime. This remains true when passing an HSA to a spouse. However, the tax advantage of an HSA can turn into a tax bomb if left to a non-spouse. I refer to this as the hidden HSA death tax.

Planning to avoid the hidden HSA death tax includes taking reimbursements of PUQME from the HSA later in life and/or naming a charity as the primary beneficiary on an HSA if the owner is not married.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Inherited Roth IRAs

Inherit a Roth IRA in 2023 or later? Thinking about leaving a Roth IRA to heirs at your death? Then this article is for you. Note that it is an educational resource. It is not advice for any individual’s particular situation. Further, this article does not address situations where a person inherited a Roth IRA prior to the year 2023. 

Inheriting a Roth IRA is great, since distributions are always penalty free and tax-free 99.99% of the time. The only time a distribution from a non-spousal inherited Roth IRA could be subject to income tax is if the distribution is a distribution earnings from the Roth IRA prior to the passage of 5 years from January 1st of the year the original owner first contributed to a Roth IRA. See Treas. Reg. Section 1.408A-6 Q&A 1(b). As a practical matter, few distributions from inherited Roth IRAs will be both (i) earnings of the inherited Roth IRA and (ii) made prior to the end of the five year clock. 

Said differently, both the original owner and the beneficiary would have to be incredibly unlucky in order for a beneficiary to pay federal income tax on an inherited Roth IRA distribution. 

In theory, a spouse inheriting a Roth IRA could pay tax and/or a penalty on distributions from an inherited Roth IRA the spouse treated as their own, but even that occurrence is likely to be rare, as discussed in more detail below. 

Terminology and Titling

One inheriting a Roth IRA is a beneficiary. Yes, that inherited Roth IRA is now your property, but you are not the “owner” from a tax perspective. The original owner is the owner. You, the inheritor, are the beneficiary. If you die, the person inheriting the Roth IRA you inherited is a successor beneficiary.

Upon the owner’s death, the beneficiary should work with the Roth IRA’s financial institution to retitle the Roth IRA. The titling should indicate that the beneficiary is a beneficiary and should reference the owner. 

The above two paragraphs are not the case as applied to spouses who choose to treat an inherited Roth IRA as their own. In that case, the inheriting spouse becomes the owner, not the beneficiary. 

Types of Beneficiaries

To my mind, there are generally seven types of Roth IRA beneficiaries. Below, I use my own colloquialisms for each. You will not find the term “10-year beneficiary” in the Internal Revenue Code or the IRS website, for example. Rather, it is simply a term I colloquially use to refer to a particular type of inherited Roth IRA beneficiary. 

To understand what happens when one inherits a Roth IRA, one must first understand what type of beneficiary they are among the below seven categories. 

Watch me discuss Inherited Roth IRAs on YouTube.

Spouses

Spouses are generally favored inherited Roth IRA beneficiaries from a tax planning perspective. Married individuals should think long and hard prior to naming someone other than their spouse as their Roth IRA primary beneficiary for many reasons, including tax planning.

There are three options a spouse has when inheriting a Roth IRA. Two of those options entail the inherited IRA being treated as the inheriting spouse’s own Roth IRA. This is usually advantageous for several reasons, including the fact that an owner is never subject to required minimum distributions (“RMDs”) with respect to their own Roth IRA. Practically speaking, this is how most inherited Roth IRAs are handled by spouses.

SECURE 2.0 added a new fourth option for spouses to be treated as the deceased spouse when inheriting a retirement account. This change appears to matter as applied to RMDs, which the Roth IRA never has for an owner. Thus, I do not believe this change impacts spouses inheriting Roth IRAs to any significant degree.

The inheriting spouse could treat the inherited Roth IRA as an inherited account (i.e., become a beneficiary instead of being the owner). Practically speaking, an inheriting spouse would only consider this if they are under 59 ½ years old and they believe it is likely they would need to access earnings in their Roth IRAs (including the inherited accounts) prior to age 59 ½. 

Considering a spouse treating an inherited Roth IRA as their own can recover their own and their decedent spouse’s Roth IRA contributions and 5 year-old conversions tax and penalty free at any time and recovers these amounts before Roth earnings are ever accessed, most inheriting spouses will not need to elect inherited Roth IRA (i.e., beneficiary) treatment. This may be true even in situations where the inheriting spouse is under 59 ½ years old and needs access to some of the inherited Roth IRA funds prior to age 59 ½. Further, treating the inherited Roth IRA as one’s own Roth IRA instead of keeping it as an inherited IRA will generally be advantageous from a creditor protection standpoint.

One potential planning option for the spouse is to roll the decedent spouse’s Roth IRA to an inherited Roth IRA and later (presumably at age 59 ½) roll it into their own Roth IRA. See Choate, referenced below, page 225. This offers the inheriting spouse protection as it allows him or her to access Roth earnings tax-free prior to the spouse turning age 59 ½ and then later avoids RMDs to the spouse (see discussion of that possibility below). 

In Proposal 10 of my retirement tax reform proposal, I offer suggestions to simplify the treatment when spouses inherit retirement accounts. 

RMD Beneficiaries

The SECURE Act set up a new standard to be an RMD beneficiary (what the SECURE Act termed an “eligible designated beneficiary”). Some practitioners use the term “EDB” for these beneficiaries, but I prefer the term “RMD beneficiary” because these are the beneficiaries that are allowed to (i) avoid the new 10-year rule discussed below and (ii) withdraw from the inherited Roth IRA RMDs based on their own remaining life expectancy. 

Who qualifies as an RMD beneficiary? These include:

  • A spouse electing to treat the inherited Roth IRA as an inherited Roth IRA
  • Any individual not more than 10 years younger than the owner (think parents and adult siblings, but it can be others)
  • Anyone chronically ill or disabled

An RMD beneficiary must start taking RMDs from the inherited IRA in the year after the owner died. He or she goes to the IRS Single Life Table and finds the factor for their age in the year following the owner’s death. The RMD for that first year is the prior-year end-of-year account balance divided by that factor. The following year’s RMD is the prior-year end-of-year account balance divided by the first year’s factor minus one. See Choate, referenced below, at pages 67-68 and 73-74. Here’s an example of how it works. 

Jack died on December 1, 2023. He was 65 at his passing. He leaves his Roth IRA to his brother Jim. In 2024, Jim turns 62. Jim is an RMD beneficiary and should* take an RMD based on his IRS Single Life Table factor at age 62, 25.4. If the inherited Roth IRA balance on December 31, 2023 is $500,000, Jim’s 2024 inherited Roth IRA RMD is $19,685.04 ($500,000 divided by 25.4). If the balance in the inherited Roth IRA is $510,000 on December 31, 2024, Jim’s 2025 RMD is $20,901.65 ($510,000 divided by 24.4). Jim takes annual RMDs in a similar fashion in subsequent years. 

As Natalie Choate notes in her treatise referenced below (see page 74), Jim only looks at the IRS Single Life Table once: for the first RMD year. After that, he simply subtracts 1 from the factor every year. Thus, those using the Single Life Table only look at it a single time.

*Note that an RMD beneficiary can, instead of taking RMDs, elect the 10-year rule discussed below. See Choate supplement, page 12, Andy Ives at IRAHelp.com, and Ian Berger at IRAHelp.com. In many cases, I suspect taking relatively modest tax-free RMDs will facilitate more tax-free growth than avoiding RMDs and emptying the inherited Roth IRA within 10 years. This is because taking RMDs allows a large portion of the inherited Roth IRA to survive well beyond 10 years in cases where the beneficiary is not themselves rather elderly. That said, the older the beneficiary is, the more likely electing into the 10-year rule is to be advantageous. It is not clear how the beneficiary makes the election (see Choate supplement, page 50), though presumably failing to take RMDs would do it.

Spouses electing beneficiary treatment (which is RMD beneficiary treatment in their case) are generally not required to take the annual RMD until the later of (i) the year after the decedent spouse’s death or (ii) the year the decedent spouse would have reached age 72. See Choate, referenced below, page 97, Prop. Reg. Section 1.401(a)(9)-3(d) on page 109 of this PDF file (also see Prop. Reg. Section 1.408-8(b)(2)(ii) on page 253 of the PDF file). 

Successor Beneficiaries

Successor beneficiaries of RMD beneficiaries must, in most cases, empty the inherited Roth IRA by the end of the 10th calendar year following the RMD beneficiary’s death. See Natalie Choate supplement page 43 and Prop. Reg. Section 1.401(a)(9)-5(e)(3) on page 142 of this PDF file. Update August 4, 2023: In addition to being subject to the 10-year rule, the successor beneficiary must continue to take the annual RMDs the RMD beneficiary would have been required to take had they lived. See Natalie Choate supplement page 51.

Update July 10, 2023: Sarah Brenner of IRAHelp.com raises an interesting possibility. What if the RMD beneficiary elects the 10-year rule? If that happens, the successor beneficiary must empty the inherited Roth IRA by the end of the 10th year after the original owner’s death!

Minor Children of the Owner

If a minor child of the owner inherits a Roth IRA, he or she gets to take RMDs for all the years through the year he or she turns 21. Then the inherited Roth IRA must be emptied by the end of the 10th calendar year following the beneficiary turning age 21. See Prop. Reg. Section 1.401(a)(9)-5(e)(4) on pages 142-43 of this PDF file. Update September 11, 2023: the minor child starting the RMDs prior to turning age 21 triggers RMDs during the later 10-year period.

This treatment is quite favorable considering the relatively low RMDs during one’s youth, as the RMD is based on their relatively long life expectancy. 

The only children qualifying for this treatment are the children of the owner. Grandchildren, nieces, nephews, etc. will not qualify, and in most cases will be 10-year beneficiaries. These children could qualify for RMD beneficiary treatment if they are chronically ill or disabled. 

Note that technically minor children of the owner qualify as “eligible designated beneficiaries” but since the treatment they receive is, to my mind, quite different from the treatment RMD beneficiaries receive, I mentally carve them out as their own distinct category. 

Successor Beneficiaries

Natalie Choate observes on page 43 of her supplement that in the case of a minor-child RMD beneficiary, the successor beneficiary must empty the account by the earlier of (i) the end of the 10th full year following the minor-child’s death or (ii) the end of the 10th full year following the former minor child turning age 21. Update August 4, 2023: If the minor-child beneficiary dies while collecting RMDs, it appears the successor beneficiary would also be subject to annual RMDs using the decedent minor-child’s life expectancy during the 10-year time frame.

10-year Beneficiaries

10-year beneficiaries are those individuals who are not spouses, minor children of the owner, and RMD beneficiaries. They are everyone else. From a practical perspective, most 10-year beneficiaries are the adult children of the owner. 

10-year beneficiaries are not subject to RMDs. However, they must empty the inherited Roth IRA by the end of the 10th year following death. From a purely tax planning perspective, the beneficiary will want to leave the money inside the inherited Roth IRA and withdraw the money in December of the 10th full year following the owner’s death to get as much tax-free growth out of the inherited Roth IRA as possible. Of course, distributions prior to the end of the 10th year are permitted, and, as discussed above, should be tax-free in practically all cases. 

Successor Beneficiaries 

Successor beneficiaries of 10-year beneficiaries must empty the inherited Roth IRA by the end of the 10th calendar year following the owner’s death. See Prop. Reg. Section 1.401(a)(9)-5(e)(2) on page 142 of this PDF file. Thus, the death of a 10-year beneficiary does not extend the time to empty an inherited Roth IRA. 

Estates

A pulse is worth at least 5 years of tax-free growth! 

Roth IRAs can be left to one’s own estate, but generally speaking, they should not be. In order to qualify for the 10-year rule or better treatment (see the first four categories of beneficiaries), the beneficiary designation form must leave the Roth IRA to a human being. Estates can become the Roth IRA beneficiary if no beneficiary designation form is filed, or if the filed beneficiary designation form names the estate as the beneficiary. When an estate inherits a Roth IRA, the inherited Roth IRA is subject to a 5-year payout rule. See Choate, referenced below, pages 77 and 104. 

If left to one’s estate, the Roth IRA must be paid out by the end of the fifth full calendar year following death. See Choate supplement page 100. This is true even if the estate will ultimately pay the money out to actual humans who could have, on their own, qualified as 10-year beneficiaries, RMD beneficiaries, and/or spousal beneficiaries. 

Trusts

If you want to see some tax complexity, look at inherited retirement accounts and trusts. Trusts themselves often have human beneficiaries, but the trust mechanism is used to protect the beneficiary and/or the assets inside the trust. There are valid reasons to name a trust as a retirement account beneficiary (usually surrounding the nature of the potential beneficiaries), but naming a trust should not be done lightly. 

The tax risk is that the inherited Roth IRA will be subject to the 5-year rule. Properly structured (including the provisions required by Treas. Reg. Sec. 1.401(a)(9)-4 Q&A 5(b)), the human beneficiaries of the trust can qualify for the applicable treatment offered by one of the first four categories of beneficiary. However, if the trust is not properly structured, the trust and the human beneficiaries of the trust will be subject to the 5-year rule and lose out on 5 or more years of tax-free growth. 

Charities

A charity must take an inherited Roth IRA in 5 years, but it does not care, as it is not generally subject to income tax. From a planning perspective, Roth IRAs are the assets that are least advantageous to leave to charity. Your human heirs like to inherit Roth accounts and generally would prefer to inherit a Roth over an account such as a traditional IRA or a HSA. Here’s an example of how that could play out.

Walter, age 80, is a widow and has one adult son, Paul, age 50. Walter has the following assets:

Asset LocationAmount
Roth IRA$100,000
Taxable Brokerage$100,000
Traditional IRA$50,000
HSA$50,000
Total$300,000

Walter intends on leaving two-thirds of his assets to Paul and one-third of his assets to his Catholic parish, a 501(c)(3) charitable organization. From Paul’s perspective, he’d prefer to inherit the $100,000 Roth IRA (10 more years of tax-free growth, no income tax and full step up in basis when the assets are distributed to him) and $100,000 taxable brokerage (no income tax and full step up in basis). Paul would prefer that the $100,000 left to the parish be the $50,000 traditional IRA (which would be taxable to Paul through RMDs and the 10-year rule) and the $50,000 HSA (which is immediately fully taxable to Paul in the year of Walter’s death if Paul inherits). 

Why waste the Roth’s step-up in basis, tax-free treatment, and 10 years of additional tax-free growth on a charity when you can give the charity assets that are otherwise less favorable to the human beneficiary (the traditional IRA and the HSA)?

Planning

For Owners

Retirement account owners may want to think about inter-generational planning, for two reasons. First, if the owner is in a relatively low marginal tax bracket, and their beneficiaries (perhaps successful adult children) are in relatively high marginal tax brackets, they may want to think about Roth conversions during their lifetimes to move money from traditional retirement accounts to Roth IRAs. This can reduce the income tax paid with respect to the traditional retirement accounts. Second, it eliminates the chance that adult children could be subject to both the 10-year rule and to RMDs (see this article for more details). 

Any planning in this regard should consider that tax planning for one’s adult children is a second order planning priority. The first planning priority should be the financial success of the retirement account owner. His or her financial success should be prioritized ahead of tax planning geared toward a better result for one’s adult children. 

For Beneficiaries

Generally speaking, beneficiaries and successor beneficiaries will want to leave funds inside an inherited Roth IRA for as long as possible. For many in a SECURE Act world, that will be 10 years following the end of the year of death. Here’s a quick example of how that works: Joe dies on August 1, 2023. His 10-year beneficiary has until the end of the 10th year following his death, December 31, 2033, to empty the Roth IRA he inherits from Joe.

Of course, tax is just one consideration. If the money is needed sooner than that, at least the beneficiary knows that the distribution is tax-free in all but the rarest of situations.

As discussed above, beneficiaries should understand how long the owner had any Roth IRA. Once the beneficiary is sure 5 years have passed since January 1st of the year of the original owner’s first contribution, he or she can take Roth earnings out of the inherited Roth IRA and know that it is tax free. Even if the Roth IRA is less than 5 years old, the beneficiary can take old contributions and conversions tax free. Such amounts come out first under the ordering rules prior to the removal of any earnings. 

Further Reading

Natalie B. Choate’s treatise Life and Death Benefits for Retirement Planning (8th Ed. 2019), frequently referenced above, is an absolutely invaluable resource regarding retirement account withdrawals, including inherited Roth IRA withdrawals.

The IRS and Treasury issued controversial proposed regulations on the SECURE Act in 2022. Fortunately, those proposed regulations do not require RMDs with respect to 10-year beneficiaries of inherited Roth IRAs. Jeffrey Levine wrote a great blog post on the proposed regulations here. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

A Critical Look at the 529

Thanks to the SECURE 2.0 bill, it’s time for the FI community to reexamine 529 plans. This post shares my two cents on 529s in general, and specifically as applied to the FI community. The next post, dropping February 15, 2023, addresses in detail the new 529-to-Roth IRA rollover enacted in SECURE 2.0.

Financial Independence

Before we talk about 529s, we have to talk about the primary goal of financial independence. For young parents, the primary goal is to secure Mom & Dad’s financial independence. 

Achieving the parents’ primary goal has an incredible secondary effect. Mom and Dad buy Junior an incredible gift by securing their own financial independence. That gift is that Junior will never have to worry about Mom and Dad’s financial security as an adult. The greatest financial gift parents can ever give their children is the parents’ own financial stability. 

Second, where possible, money and financial assets should be able to support multiple financial goals. We should be at least somewhat hesitant before locking up money such that it can only support one highly specific goal without incurring a penalty. 

529s

529s are tax-advantaged savings accounts generally run by states to facilitate college savings. 529s are best understood as a Roth IRA for college education with far greater contribution limits. Sure, that is an overstatement of how they work, but that gives us a good conceptual framework from which to start the analysis. 

A quick note on terminology: The IRS often refers to 529 plans as “Qualified Tuition Programs” or “QTPs.” I will use the more commonly used colloquialisms, 529 and 529s. 

Contributions to a 529 are not tax deductible for federal income tax purposes. At least initially, there’s no federal income tax benefit to making a 529 contribution. However, money inside a 529 grows federal and state tax-free and can be withdrawn tax-free for qualified education expenses (such as college tuition). 

Contributions are generally not limited by federal tax law, though contributions above the annual exclusion gift tax limit ($17,000 per donor per beneficiary per year in 2023) generally trigger Form 709 reporting requirements (though in 99.99% of cases there should not be a gift tax liability). States generally have lifetime contribution limits per beneficiary. Usually these limits are far in excess of what one would normally need for undergraduate college tuition. 

Very generally speaking, qualified education expenses can be directly paid from the 529 to the educational institution or such expenses can be reimbursed from a 529 in the year the expenses are incurred. Payments for qualified educational expenses are generally tax and penalty free. 529s do not enjoy the rather unlimited reimbursement deadline that HSAs enjoy. 

529s get similar tax treatment to the federal income tax treatment in most states. However, there can be an additional benefit: an annual state tax deduction or credit for some 529 contributions to the state’s own 529 plan (note 8 states allow a 529 tax deduction or credit for contributions to other states’ 529 plans). However, for many readers this will either be irrelevant or only of minor importance. Of the four most populous states (CA, TX, FL, NY), only residents of New York can obtain an up-to $5,000 per person per year state tax deduction for contributions to a home-state 529. California has no 529 tax deduction and Texas and Florida do not have an income tax.  

Okay, sounds great! Clearly there are tax benefits for 529 money used for qualified education expenses. But what about distributions that are used for anything other than qualified education expenses? Well, they are going to be subject to an income tax and likely a 10 percent penalty, in the following manner. A non-qualified distribution is deemed to come ratably out of the contributions to the 529 (tax and penalty free) and earnings of the 529 (subject to income tax and the 10 percent penalty, some penalty exceptions may apply). 

Here’s an example illustrating the application of the nonqualified distribution rules:

Hal, the owner of a 529 account, takes $1,000 out of the 529 to help pay for vacation expenses. Previously, he had made $60,000 of contributions to the 529, and it had grown to $100,000 ($40,000 of earnings) prior to making the $1,000 non qualified distribution. Sixty percent of the distribution ($600) is a nontaxable return of contributions and 40 percent ($400) is subject to both income tax and a 10 percent penalty.

The taxation of non-qualified distributions is a significant drawback of using 529s. 

529s and the FI Community

Let’s remember what is going on with a 529. It is a gift to the next generation. It comes with very modest tax benefits. 

My thesis on the 529 is this: for most parents, including most of those in the FI community, the tax benefits offered by 529s are not sufficient to compensate for the use restrictions on 529s. Thus, my view is that 529s should generally be deployed once Mom and Dad are financially independent (or close to it), not when they are on the path to financial independence. 

The idea behind the 529 is to provide tax-free growth for college savings. It solves for something that, frankly, isn’t much of a problem. Taxes are not why college is unaffordable for many Americans. College tends to be unaffordable not because investment taxes are high, but because tuition and fees are out of control. 

One thing in parents’ favor when thinking about funding college educations is that income taxes on investments are relatively modest over a child’s childhood due to low long term capital gains rates and qualified dividend income rates. Hopefully, by age 22 or 23, the child’s undergraduate education is completed, providing a relatively modest investment time horizon (i.e., a modest tax exposure horizon), even if the parents start saving for college at birth. 

Contrast that to the retirement time horizon of a 20-, 30- or 40-something parent saving for his or her own retirement. The money invested for retirement at age 25 might be accessed at age 60, 70, 80, or 90. Compared to educational savings, retirement savings (which are usually far greater than educational savings) are much more vulnerable to income taxes for a much longer time frame. Even at long term capital gains and qualified dividend income rates, exposing retirement savings to decades of taxation could be very expensive. Retirement savings are also exposed to tax law change risk for a much longer period of time. For example, there’s no guarantee that there will be favored long term capital gains and qualified dividend tax rates 30 years from now.

The tax risk profiles on educational savings and retirement savings are much different. Based on those risk profiles, for most I believe aggressive retirement tax planning makes sense. But I don’t see educational tax planning making as much sense, for the reasons discussed below. 

Of course, tax-advantaged retirement savings can come with a juicy up-front federal income tax deduction. 529s do not offer the possibility of a federal income tax deduction, making them less impactful than tax-advantaged retirement savings regardless of the time frame involved. 

Young Parents and 529s

Let’s consider young parents. Say Junior is born when Mom & Dad are age 30 and have saved 10 times their annual expenses in financial assets. Many, myself included, would say Mom and Dad are doing well with their finances. Here’s where I diverge from some others in the personal finance space: I would not recommend Mom & Dad save in a 529 shortly after Junior’s birth.

Notice I’m not saying Mom & Dad should not pay for Junior’s college. What I’m saying is Mom and Dad should stay flexible for their own financial future. 

What’s so horrible about Mom & Dad starting to save for Junior’s college in a taxable brokerage account under their own names? At birth, they have no idea if Junior will get a scholarship, go to trade school, how Mom & Dad’s finances will be when Junior is ready to go to college, etc. By saving in financial assets that are in their own names–perhaps mentally segregated as potentially being for Junior’s college–Mom & Dad maintain great flexibility without sacrificing too much tax benefit. 

If Junior gets a scholarship, great, the financial assets stay with Mom & Dad. If Mom & Dad are not financially successful when Junior goes to college, great, the financial assets can support Mom & Dad and Junior can figure out other ways to pay for college. 

The Value of the 529’s Tax Benefits

How bad is the tax hit on holding investments for a child’s college education? Imagine owning a 60 / 40 equity to bond portfolio of $100,000 for a child’s college education. If held in the parents’ taxable brokerage account, how much taxable income might that generate annually? Very roughly, if dividend yields are 2 percent, the $60,000 in equities would produce $1,200 of dividend income, most of which is likely to qualify for qualified dividend income tax rates. The $40,000 of bonds would produce $1,800 of ordinary income at a 4.5 percent yield. 

Is it desirable to add $3,000 of income to Mom and Dad’s tax return? Surely not. Cataclysmic? Also surely not. 

Consider what a small amount of additional taxable income buys. If the money is held in the parents’ names, it can be used for anything without penalty. Perhaps Mom and Dad have not been financially successful. That $100,000 could help the parents achieve their own financial goals and retirement. What if the child gets a scholarship and does not need much in the way of tuition assistance from his or her parents? What if the child doesn’t go to college? 

In exchange for paying tax on $3,000 of income annually (some of it at tax-favored QDI rates), and some long term capital gains when used to pay tuition, Mom and Dad have incredible flexibility with the $100,000. Maybe $50,000 goes for Junior’s college tuition, and $50,000 goes for Mom and Dad’s retirement. Further, for many it won’t be $3,000 of income annually. It will take most parents years before they could accumulate the sort of balance that would generate $3,000 of taxable income from educational savings. Thus, the tax hit for not using the 529 is likely to be that much less in the years well before the child is close to college age. 

Outside of the handcuffs of the 529, assets can support multiple financial goals. Even better, as one financial goal is met, the money can be shifted to support another financial goal. Perhaps Mom and Dad are behind in their own savings when Junior is age 10. But things go well, and when Junior turns 16 Mom and Dad have wealth in excess of their FI number. In that case, money that might have been needed for the parents’ retirement now can be used for college tuition.

Use Restrictions

We need to consider the use restrictions on 529s. If not used for qualified education expenses, the growth is subject to both ordinary income tax and usually the 10 percent penalty.

Compare the tight use restrictions on 529s to the use restrictions on the other most prevalent tax baskets: taxable accounts, traditional retirement accounts, Roth accounts, and health savings accounts. Generally speaking, all of them (even HSAs) are not use-restricted or only partially use-restricted. All four of those tax baskets have a significant advantage over 529s in terms of use restrictions.

In many cases, I believe that the 529’s significant use restrictions are not adequately compensated by its tax advantages. 

The 529 has rather onerous time restrictions, as distributions of earnings are generally subject to tax and the 10 percent penalty in those years there are no qualified education expenses.

Feeding the Beast

As much as we might want to, we can’t turn a blind eye towards hyperinflation in college tuition. With that in mind, shouldn’t we ask: Isn’t a hyperfocus on college savings feeding the beast? 

It’s time to scrutinize American higher education. It’s not good for the country to have students graduating with mountains of debt. This is happening for many reasons, including significant administrative bloat in higher education. Clearly, American higher education is failing too many of its students. Is now the time to set aside money to pay American colleges and universities?

I get it: no one reader funding a 529 is the cause of the problems of American higher education. 

But, if I’m a university used to collecting soaring tuition and fees, I’m all for 529s. 529s subsidize what has become bad behavior by university administrators. Less focus on 529s helps move the needle towards universities needing to act responsibly in order to attract students. 

Camilla Jeffs raises an interesting point on her LinkedIn page: Part of the reason college is so expensive is because in many cases the customer (the student) does not bear the cost. 529s feed into that problem. Camilla’s recent podcast episode on 529s is also full of good food for thought. 

529 Use Cases

The above limitations of the 529 noted, I do believe there are good use cases for the 529. These cases assume that the parents have decided to pay for their child’s college education.

Financially Independent Parents

Joe and Sally are married and 45 years old. They have saved 30 times their annual expenses in retirement accounts and taxable brokerage accounts. They have a 10 year old daughter they are reasonably sure will go to college, and they would like to pay for her college education.

This is a great use case for the 529. Mom and Dad’s financial future largely secured (generally speaking), it’s time to focus on (i) college savings, since they want to pay for college, and (ii) tax planning. Joe and Sally, already holding substantial taxable brokerage accounts, benefit from saving through the 529 so they avoid adding more dividend, interest, and capital gains income to their annual tax return. 

Capturing State Tax Benefits

Aaron and Amanda are married and are 50 years old. They have saved 20 times their annual expenses in retirement accounts and taxable brokerage accounts. They have stable jobs. They have a 16 year old son who is very likely to go to college. Aaron and Amanda want to pay for their son’s college education. Since they live in New York State, if they contribute $10,000 annually to the New York 529 for his benefit ($5K each), they get an annual $10,000 state tax deduction on their New York state income tax return.

Aaron and Amanda are not financially independent by many metrics, but they are doing pretty well, and are likely (though not guaranteed) to be financially successful. In their case, paying for college is not financially ruinous. If Aaron and Amanda are going to pay for college, they might as well utilize the 529 annually to scoop up state tax deductions, particularly in a higher income tax state like New York. Further, beginning the 529 much closer to the start of college decreases the odds that the 529 will become over funded.  

Contrast Aaron and Amanda to parents of newborns. Newborns’ parents are closer to the beginning of their financial journey. In most such cases, state tax benefits would not, in my opinion, be valuable enough to justify the use restrictions on 529 contributions. 

Conclusion

My view is that the detriments of the use restrictions on 529s are not adequately compensated by the federal and state tax advantages offered by 529s in most cases. That’s certainly not to say there are not good use cases for the 529, but my view is that most parents should prioritize saving in their own names (even in taxable accounts) before making contributions to 529 accounts. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Health Savings Accounts and Las Vegas

Want to make a bad financial decision? I’ve got an account that can help you do that tax and penalty free!

Of course, I do not recommend making bad financial decisions. However, at times it is useful to look at extremes to help us better understand and analyze financial planning alternatives. 

Health Savings Accounts

If you’ve spent any time on my blog or YouTube channel, you’re probably aware that I’m fond of HSAs. Contributions are tax deductible (or excludable if made through payroll withholding). Amounts inside the HSA grow tax free. Withdrawals for qualified medical expenses, or reimbursements of qualified medical expenses, are tax and penalty free. 

As long as the HSA owner is alive, he or she can reimburse themselves from the HSA for qualified medical expenses incurred after they first owned an HSA. Generally speaking, there’s no time limit on HSA reimbursements, other than the owner must be alive to receive the tax and penalty free reimbursement. See “Distributions from an HSA” on page 9 of IRS Publication 969 and Notice 2004-50 Q&A 39. 

HSAs are great because they combine the best feature of a traditional retirement account (deduction or exclusion on the way in) with the best feature of a Roth retirement account (tax free treatment on the way out). Further, the lack of a time limit on reimbursements from an HSA provides the owner with tremendous flexibility in terms of deciding when to take tax and penalty free distributions. 

Health Savings Accounts PUQME

Previously Unreimbursed Qualified Medical Expenses (PUQME, pronounced “Puck Me”). HSA owners can reimburse themselves tax and penalty free from their HSA up to their amount of their PUQME. PUQME includes qualified medical expenses of the owner, their spouse, and their dependents incurred after the HSA was first established. Qualified medical expenses deducted as an itemized deduction on a tax return (quite rare) do not qualify to be reimbursed from an HSA and thus are not PUQME. PUQME is a technical term I made up. 😉

Restricted Accounts

When we think about taxable brokerage accounts, traditional retirement accounts, Roth retirement accounts, HSAs, and other available options, we should consider the restrictions in place on the use of the funds. The more restrictions in place, the worse the account.

Time Restrictions

Taxable accounts, traditional retirement accounts, and Roth retirement accounts face various time restrictions on withdrawals. For example, taxable accounts qualify for favored long-term capital gains rates if held for a year. Of course, that restriction is academic if there’s a loss or no gain in the account.

Traditional retirement accounts suffer the most stringent time restrictions. Withdrawals occurring prior to the owner turning age 59 ½ are usually subject to the 10 percent early withdrawal penalty. Roth IRAs are not all that time restricted, as amounts withdrawn prior to age 59 ½ are deemed to first be nontaxable withdrawals of prior contributions. Roth 401(k)s can be somewhat time restricted, as amounts withdrawn prior to age 59 ½ are partially deemed to be withdrawals of taxable earnings (usually subject to the 10 percent early withdrawal penalty). 

HSAs are somewhat time restricted, though like Roth IRAs, they are not severely so. Once one has PUQME after having opened an HSA, he or she can withdraw money (up to their PUQME amount) from the HSA tax and penalty free. 

Use Restrictions

Taxable accounts, traditional retirement accounts, and Roth retirement accounts are great in that they have absolutely no use restrictions. The government does not care what you spend the money on. The tax result is, at least generally speaking, unaffected by use. 

There are some exceptions, such as the exceptions to the 10 percent early withdrawal penalty such that early withdrawals from retirement accounts can qualify to avoid the 10 percent penalty. Further, one might say that because of qualified charitable distributions, using traditional IRAs for charitable purposes is use-favored. The above exceptions noted, as a general rule, use does not significantly change the taxation of withdrawals from taxable accounts, traditional retirement accounts, and Roth retirement accounts. 

HSA Use Restrictions

HSA distributions that are not used for qualified medical expenses are subject to both income tax and a 20% penalty if the owner is under age 65. 

However, recall that there is no time limit on the ability to reimburse oneself tax and penalty free for previously incurred qualified medical expenses. As a practical matter, the lack of time limit results in relatively modest use restrictions on an HSA. Below I’ll illustrate that with an extreme example. 

HSAs and Las Vegas

Perhaps you’re yearning for the hot sand, broken dreams, and $5 lobster of Las Vegas. Could an HSA help? Let’s explore that possibility.

Peter, age 70, wants a weekend getaway in Las Vegas. Between a hotel suite, comedy club tickets, airfare, steak dinners, some Texas Hold’em poker, and the breakfast buffet, he estimates it will cost him $10,000. 

Peter was covered by a high deductible health plan from age 55 through age 65. He maxed out his HSA annually during that time, and he has never taken a distribution from his HSA. The HSA is now worth $50,000, and between age 55 and today Peter has $30,000 of PUQME.

Could Peter use his HSA to pay for the weekend? Absolutely! 

Wait a minute, Sean. Vegas isn’t a qualified medical expense! Sure, it isn’t. But Peter has $30,000 of previously unreimbursed qualified medical expenses. He can take out $10,000 from his HSA tax and penalty free and use it to buy poker chips in Las Vegas. Once an HSA owner has previously unreimbursed qualified medical expenses, they generally do not have an HSA use restriction up to the level of that PUQME. 

As a practical matter, even the healthiest Americans are eventually going to have qualified medical expenses. As a result, most HSA owners will have runway, particularly in retirement, to reimburse themselves for previously incurred qualified medical expenses. That reimbursement money is in no way use restricted–it can go for a weekend trip to Vegas if the HSA owner desires. 

HSA Planning Risk

But Sean, there’s no way Congress won’t close the loophole! Surely, at some point in the future, Congress will time-limit tax and penalty free reimbursements from HSAs.

I don’t think so, for three reasons. 

First, the HSA loophole is not that great. Consider the relatively modest HSA contribution limits. Sure, the government loses tax revenue due to HSAs, but it isn’t that much, particularly compared to vehicles such as Roth IRAs. Further, HSAs are, at most, a loophole during the owner’s lifetime and the lifetime of their surviving spouse. That’s it! 

Left to a non-spouse, non-charity beneficiary, the entire HSA is immediately taxable income (typically at the beneficiary’s highest tax rate) in the year of the owner’s death. Death not only ends the loophole, it gives the government a significant revenue raiser by taxing the entire amount at ordinary rates on top of the inheriting beneficiary’s other taxable income. 

Second, I suspect Congress wants taxpayers to bailout HSA money tax and penalty free prior to death. The immediate full taxation of HSA balances in the year of death is going to come as a nasty surprise to many beneficiaries. 

Imagine significant taxes and perhaps dealing with the paperwork and hassle of reversing what becomes an excess contribution to a Roth IRA because of a surprise income hit due to the death of a loved one. Here’s what that could look like.

Mark and Laura are married and both turn age 47 in 2023. They anticipate about $200,000 of MAGI in 2023, in line with their 2022 income. Expecting their 2023 income to fall well within the Roth IRA modified adjusted gross income limits, each contributes $6,500 to a Roth IRA for 2023 on January 2, 2023. In September, Laura’s father passes away and leaves her an HSA worth $50,000. The HSA inheritance increases their 2023 MAGI to $250,000. The federal income tax hit on inheriting the HSA will be over $10,000. 

As a result of their increased income, Mark and Laura are now ineligible to have made the 2023 Roth IRA contributions. The most likely remedial path involves Mark and Laura working with the financial institution to take a corrective distribution of the contributions and the earnings attributable to the contributions. The earnings will be included in Mark and Laura’s MAGI for 2023 as one last insult to inheriting a fully taxable HSA. 

This is a lurking issue. If Congress puts 2 and 2 together, they will hope that HSA balances are small at death so as to avoid their constituents suffering a large, unexpected tax bill related to a loved one’s death. Time-limiting tax and penalty free HSA reimbursements would keep more money inside HSAs during an owner’s lifetime (and thus, at their death). At death, this would set up more beneficiaries to have nasty surprises when inheriting an HSA, a fate Congress most likely wants to avoid. 

Third, time-limiting HSA reimbursements will go counter to the reason HSAs exist in the first place: to encourage the use of high deductible health plans. Time-limiting HSA reimbursements could trap amounts inside HSAs because taxpayers would lose amounts they could withdraw from the HSA without incurring tax (and a 20 percent penalty if under age 65). If taxpayers believe HSA money could become trapped, fewer will opt for a high deductible health plan. This will lead to increased medical costs as more and more Americans have lower deductibles and become sensitive to medical pricing. 

Surviving Spouse’s HSA PUQME

I prepared a short 1-page technical write up providing my views on how previously unreimbursed qualified medical expenses are computed when a spouse inherits a health savings account.

HSA Resource

Kelley C. Long recently authored an excellent article on HSAs in the Journal of Accountancy.

Conclusion

Here’s hoping that you don’t take away the conclusion that HSA owners should spend their HSA money in Las Vegas!

Rather, my primary conclusion is that investments and tax baskets should be assessed considering their time and use restrictions. The fewer the time and use restrictions, the better. Of course, time and use restrictions are not the only factors to consider, but they are significant factors.

Secondary conclusions include (i) the HSA tends to be very flexible and (ii) the tax breaks available to HSA owners are not likely to be repealed or limited by Congress anytime soon.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

SECURE 2.0 and the FI Community

Congress just passed a very long retirement tax bill, colloquially referred to as SECURE 2.0 or the SECURE Act 2.0. The FI community is interested in anything affecting tax-advantaged retirement accounts. This post dives in on the impact of SECURE 2.0 on the FI community. 

SECURE 2.0 Big Picture

SECURE 2.0 tinkers. It contains dozens of new rules. It’s easy to get lost in the weeds of the new rules, but I don’t recommend it. Many new rules have very little impact on financial planning for those in the FI community.

Here’s one example: SECURE 2.0 eliminates (effective 2024) required minimum distributions (“RMDs”) from Roth 401(k)s during the owner’s lifetime. Since Roth IRAs never had RMDs during the owner’s lifetime, and Roth 401(k)s are easily transferable to Roth IRAs at or after retirement, this is a rule change without much practical impact for most from a planning perspective.

However, there are two main takeaways those in the FI community should focus on when it comes to SECURE 2.0. First, SECURE 2.0 makes traditional, deductible retirement account contributions even more attractive. Second, SECURE 2.0 sets what I refer to as the Rothification Trap. Don’t fall into the Rothification Trap!

Traditional Retirement Account Contributions Are Even More Attractive

In the classic traditional versus Roth debate, SECURE 2.0 moves the needle towards traditional deductible retirement account contributions. Why?

SECURE 2.0 delays the required beginning date for RMDs! Starting in 2023, RMDs must begin at age 73, buying those born from 1951 through 1959 one more year to do tax-efficient Roth conversions prior to being required to take RMDs. But for most of the readers of this blog, the news is much better. Those born in 1960 or later now must take RMDs starting at age 75.

This is a big win for the FI community! Why? Many in the FI community will have artificially low taxable income in retirement prior to having to take RMDs at age 75. That increases the window for Roth conversions while a retiree otherwise has low taxable income. 

Delaying RMDs makes traditional FI tax planning even more attractive, particularly for those born after 1959. Retirees will have through the year of their 74th birthday to make Roth conversions to (i) get tax rate arbitrage on traditional retirement accounts and (ii) lower RMDs when they are ultimately required.

The planning runway to do Roth conversions prior to taking RMDs just got three years longer. This gives both early retirees and conventional retirees that much more of an opportunity to do Roth conversions at low income tax rates prior to being required to take RMDs. There are three additional years of progressive tax brackets to absorb efficient Roth conversions and reduce future RMDs. 

Rothification Trap

Be aware of the Rothification Trap!

SECURE 2.0 promotes even more in the way of Roth contributions. It allows employees to elect to have their employer 401(k) and other workplace plan contributions be Roth contributions, effective immediately. See Section 604 of SECURE 2.0. Plans will have to affirmatively add this feature (if they so choose), so it won’t be immediately effective in most cases. I predict that at least some plans will offer this option. I suspect some plans will not offer this option, since Roth employer contributions must be immediately vested. Some employers will be hesitant to eliminate vesting requirements for employer contributions, though it must be remembered that some employers immediately vest all employer contributions.

In addition, effective starting in 2023, SEP IRAs and SIMPLE IRAs can be Roth SEP IRAs and Roth SIMPLE IRAs. See Section 601 of SECURE 2.0. 

Here’s the thing: for those planning an early retirement, Rothification is a trap! The name of the game for those thinking about early retirement is to max out deductions while working and later do Roth conversions in early retirement. This maximizes deductions while one is subject to their highest marginal tax rate (their working years) and moves income to one’s lower taxable income years (the early retirement years). The combination of these opportunities creates tax rate arbitrage. 

I’m worried some in the FI community will say “I really love Roth, so I’ll make all my contributions–IRA, employee 401(k), and employer 401(k))–Roth now!” I believe that path is likely to be a mistake for many in the FI community, for two reasons. First, this foregoes the great tax planning opportunity presented by deducting retirement contributions at one’s highest lifetime marginal tax rates while working and then converting to Roths at low early retirement tax rates. 

Second, it sets one up to have difficulty qualifying for Affordable Care Act Premium Tax Credits. In order to qualify for Premium Tax Credits, which could be worth thousands of dollars in early retirement, one must have income above their state’s applicable Medicaid threshold. For example, in 2023 a family of four in California with a modified adjusted gross income (“MAGI”) of less than $39,750 would qualify for MediCal (California’s Medicaid) and thus get $0 Premium Tax Credits if they choose to use an Affordable Care Act insurance plan. Most early retirees will want to be on an ACA plan instead of their state’s Medicaid insurance for a variety of reasons. 

In a low-yield world, an early retiree with only taxable accounts and Roth accounts may find it difficult to generate sufficient MAGI, even with tax gain harvesting, to avoid Medicaid and qualify for a Premium Tax Credit. The earlier the retirement, the more likely having only taxable accounts and Roth accounts will eventually lead to an inability to generate sufficient MAGI to qualify for Premium Tax Credits. 

Rothification Trap Antidote

How might one qualify for the Premium Tax Credit in early retirement? By doing Roth conversions of traditional retirement accounts! If there’s no money in traditional retirement accounts, there’s nothing to Roth convert. 

I discussed the issue of early retirees not having enough income to qualify for Premium Tax Credits, and the Roth conversion fix, with Brad Barrett on a recent episode of the ChooseFI podcast (recorded before SECURE 2.0 passed). 

Previously, I’ve stated that for many in the FI movement, the “dynamic duo” of tax-advantaged retirement account savings is to max out a traditional deductible 401(k) at work and max out a Roth IRA contribution (regular or Backdoor) at home. Now that SECURE 2.0 has passed, I believe this is still very much the case. 

At the very least, those shooting for an early retirement should strongly consider leaving employer contributions to 401(k)s and other workplace retirement plans as traditional, deductible contributions. This would give them at least some runway to increase MAGI in early retirement sufficient to create enough taxable income to qualify for a Premium Tax Credit. 

401(k), 403(b), and 457 Max Contributions Age 50 and Older

The two most significant takeaways from SECURE 2.0 out of the way, we now get to several other changes members of the FI community should consider. 

First, for those age 50 and older, determining one’s maximum workplace retirement account contributions is about to get complicated. By 2025, there will be up to three questions to ask to determine what one’s maximum retirement contribution, and how it can be allocated (traditional and/or Roth), will look like:

  1. What’s my age?
  2. What was my prior-year wage income from this employer?
  3. Does my employer offer a Roth version of the retirement plan?

Specifically, the changes to 401(k) and other workplace employee contributions are as follows:

Increased Catch-Up Contributions Ages 60, 61, 62, and 63

SECURE 2.0 Section 109 (see page 2087) increases workplace retirement plan catch-up contributions for those aged 60 through 63 to 150% of the regular catch-up contribution limit, starting in 2025.

Catch-Up Contributions Must be Roth if Prior-Year Income Too High

Starting in 2024, 401(k) and other workplace retirement plan catch-up contributions (starting at age 50) must be Roth contributions if the worker made more than $145,000 (indexed for inflation) in wages from the employer during the prior year. Interestingly enough, if the employer plan does not offer a Roth component, then the worker is not able to make a catch-up contribution regardless of whether they made more than $145,000 from the employer during the previous year. Hat tip to Josh Scandlen and Jeffrey Levine for making this latter point, which the flow-chart I featured in the originally published version of this post missed. Sorry for the error as we are all learning about the many intricate contours of SECURE 2.0, myself included!

I do anticipate that many 401(k) plans that do not currently offer a Roth component will start to offer one to allow age 50 and older workers to qualify for catch-up contributions (even if they now must be Roth contributions for those at higher incomes).

From a planning perspective, I still believe that catch-up contributions will make sense for many required to make them as Roth contributions. In such a case, the option is either (i) make the Roth catch-up contribution or (ii) invest the money in a taxable brokerage account. Generally speaking, I believe that it is advantageous to put the money in a Roth account. However, one can easily imagine a situation where someone is thinking about an early retirement and does not have much in taxable accounts such that it might be better to simply invest the money in a taxable account.

Note that the prior-year wage restriction on deducting catch-up contributions does not appear to apply to the Solo 401(k) of a Schedule C solopreneur, but it does appear to apply to the Solo 401(k) of a solopreneur operating out of an S corporation.

No Changes to Backdoor Roths

In another win for the FI community, the Backdoor Roth IRA and the Mega Backdoor Roth are not changed or curtailed by SECURE 2.0.

Rolling 529 Plans to Roth IRAs

SECURE 2.0 has a notable provision allowing up to $35,000 of a 529 plan to be rolled over to the Roth IRA of the beneficiary. I agree with Sarah Brenner that this rule is not one to get too excited about. Why I feel that way is another story for another day. That day is February 15, 2023, when my post on the 529-to-Roth IRA rollover drops on the blog. 

SECURE 2.0 and the FIRE Movement on YouTube

Resources

Sarah Brenner’s helpful summary: https://www.irahelp.com/slottreport/happy-holidays-congress-gifts-secure-20

The Groom Law Group goes through SECURE 2.0 section by section: https://www.jdsupra.com/legalnews/secure-2-0-hitches-a-ride-just-in-the-9280743/

Final Omnibus (which contained SECURE 2.0) text: https://www.appropriations.senate.gov/imo/media/doc/JRQ121922.PDF

Jeffrey Levine’s detailed blog post on SECURE 2.0: https://www.kitces.com/blog/secure-act-2-omnibus-2022-hr-2954-rmd-75-529-roth-rollover-increase-qcd-student-loan-match/

Jeffrey Levine’s detailed Twitter thread on SECURE 2.0: https://twitter.com/CPAPlanner/status/1605609788183924738

My video about the two biggest problems with SECURE 2.0: https://www.youtube.com/watch?v=Zsy1SQXogAg

My December 2022 SECURE 2.0 Resources post: https://fitaxguy.com/secure-2-0-resources/

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

SECURE 2.0 Resources

Here is the bill text for SECURE 2.0.

SECURE 2.0 Big Picture

SECURE 2.0 tinkers, almost in an unprecedented fashion. Instead of repealing obviously bad retirement tax rules, it adds to them! I suspect that for many Americans, SECURE 2.0 will have only a marginal impact on their retirement savings and financial planning. This version of SECURE 2.0 has some aspects of what the House passed much earlier in 2022, but there are many significant additions and changes.

I discuss what I believe to be the two biggest problems with SECURE 2.0

Some Highlights (or Lowlights)

  • Increased catch-up contributions for those aged 60-63, effective starting in 2025
  • Denial of catch-up contribution deduction for those with prior-year income over $145,000, effective starting in 2024
  • Delay RMDs to age 73 for a decade, then delayed to age 75. This change is effective starting in 2023.
  • Increased auto-enrollment for workplace retirement plans
  • Roth options for (i) SIMPLE IRAs, (ii) SEP IRAs, (iii) employer contributions to employer plans such as 401(k)s
  • Minor emergency withdrawals from retirement accounts. Limited to one distribution per year of no more than $1,000, effective starting in 2024
  • $2,500 of contributions to emergency side accounts for workplace retirement plans, effective starting in 2024
  • Elimination of RMDs from Roth 401(k)s during the owner’s lifetime
  • Allowing Schedule C self-employed individuals to adopt a Solo 401(k) after year-end and make employee contributions (first year only), effective starting with the 2023 plan year
  • Indexing for inflation of the $1,000 annual catch-up contribution to traditional IRAs and Roth IRAs
  • Reform to penalties for missed RMDs
  • No change to the Backdoor Roth IRA rules and no change to the Mega Backdoor Roth IRA rules
  • Expansion of the exceptions to the 10% early withdrawal penalty

Resources

Bill text

Jeffrey Levine’s excellent Twitter thread on the particulars of SECURE 2.0: https://twitter.com/CPAPlanner/status/1605609788183924738

Jeffrey Levine’s breakdown of SECURE 2.0 on Kitces.com: https://www.kitces.com/blog/secure-act-2-omnibus-2022-hr-2954-rmd-75-529-roth-rollover-increase-qcd-student-loan-match/

My breakdown of SECURE 2.0 and the FI Community: https://fitaxguy.com/secure-2-0-and-the-fi-community/

My mini Twitter thread on minor emergency withdrawals: https://twitter.com/SeanMoneyandTax/status/1605117417721434113

My mini Twitter thread on new employer plan emergency accounts: https://twitter.com/SeanMoneyandTax/status/1605119482803863552

My Plan

I have a retirement tax reform plan that I believe is better and simpler than SECURE 2.0.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2023 RMDs and Roth Conversions

As I write this, we’re nearing the beginning of 2023. The stock and bond markets are down over the past year. For 2023, that means two things:

  1. 2023 required minimum distributions (“RMDs”) will, in many cases, be lower than they were in 2022, as 2023 RMDs are based on traditional retirement account values on December 31, 2022. 
  2. Roth conversions are now “cheaper” in a sense. 10,000 shares of XYZ mutual fund might have been worth $100,000 on December 31, 2021, but going into 2023 perhaps they are now worth only $90,000. Thus, the tax cost of converting 10,000 shares from a traditional retirement account to a Roth account is lower today than it was a year ago. 

Some retirees may think that they will have lower taxable income in 2023 (due to reduced RMDs). It might occur to them to wake up on New Year’s Day and do a Roth conversion. Is that wise?

Tax Rules: RMDs Come Out First and Cannot be Converted

There are two important tax rules those 73* and older should consider when thinking about 2023 RMDs and Roth conversions. The first rule is that the RMD is the first distribution that comes out of a traditional retirement account during the year. See Choate, referenced below, page 185. All distributions are RMDs until the total RMD has been satisfied. See Choate, page 320.  Further, all of a person’s traditional IRAs are treated as a single IRA for this purpose, so there’s no cherry picking that can solve this issue with respect to IRAs. 

The second rule is that an RMD cannot be converted to a Roth account. See Choate, referenced below, page 320. Anyone doing a Roth conversion prior to taking an RMD generally creates an excess contribution to a Roth IRA, subject to an annual 6% penalty unless properly withdrawn. 

*Note that effective January 1, 2023, SECURE 2.0 changed the age one must begin taking RMDs from age 72 to age 73.

Properly Roth Converting After Taking the RMDs

How does one avoid this fate? By properly taking their total RMD for the year prior to doing any Roth conversions. Sorry, no New Year’s Day Roth conversions.

The RMD can be taken through an actual distribution (or distributions) or through a qualified charitable distribution. 

Income Risk, Reversibility, and Market Risk

In most cases, I prefer taxable Roth conversions to occur in the fourth quarter of the year. There are several reasons for this. By October or November, there is more understanding of the year’s income and deductions. By the fourth quarter there will be fewer surprises in terms of income, bonuses, unexpected gains, etc. that can occur before year-end. The later in the year the Roth conversion occurs, the less likely the risk that there’s an income spike during the year unaccounted for in the planning process prior to executing the Roth conversion. 

Further, Roth conversions are irreversible. The Tax Cuts and Jobs Act eliminated the ability to reverse a Roth conversion. I don’t like the idea of locking into Roth conversions early in the year. If you win the lottery in July, you might not like that January Roth conversion 😉

Of course, there are trade-offs when it comes to delaying Roth conversions to the fourth quarter. There’s always the risk that the stock market and/or the bond market could grow between the early part of the year and later part of the year. While there is a risk the market can go down later in the year (which is favorable from a Roth conversion perspective), in theory over time one expects invested assets to grow (why else invest in them?). Thus, at least theoretically, delaying Roth conversions reduces the amount of shares that can be converted at a specified amount of Roth conversion income. 

Inherited Retirement Accounts

First, one facing an RMD with respect to an inherited retirement account need not worry about taking the inherited account RMD first prior to doing Roth conversions out of their own traditional retirement accounts. Inherited retirement accounts are hermetically sealed off from one’s own retirement accounts when considering the tax ramifications of distributions and conversions from one’s own retirement accounts.

Second, generally speaking, inherited traditional retirement accounts cannot be converted to Roth accounts. There is no opportunity to convert inherited traditional IRAs to Roth IRAs.

There is one major exception to the no conversion of inherited retirement accounts rule: the ability to convert inherited traditional qualified plans (such as 401(k)s) to a Roth IRA. See Choate, referenced below, page 271. Once the inherited 401(k) money is in an inherited traditional IRA, the Roth conversion opportunity is gone. But, the beneficiary can elect to have the 401(k) or other qualified plan transfer the money to an inherited Roth IRA, essentially converting it in a taxable transaction from traditional to Roth. 

Further Reading

Natalie B. Choate’s treatise Life and Death Benefits for Retirement Planning (8th Ed. 2019), frequently referenced above, is an absolutely invaluable resource regarding retirement account withdrawals.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2023 Solo 401(k) Update

There are some new developments in the world of the Solo 401(k). Here are the highlights:

SECURE 2.0 First Year Establishment Deadline for Schedule C Solopreneurs

Section 317 of SECURE 2.0 provides that for the 2023 year and later, a solopreneur reporting their business income and deductions on Schedule C can open a Solo 401(k) after year-end and make employee contributions as long as the Solo 401(k) is established and funded before the tax return filing deadline for the year. See page 2262 of the Omnibus bill.

SECURE 317’s deadline extension does not factor in any extensions.

Thus, for 2023, the deadline to establish and make employee contributions for the first year of a Solo 401(k) is April 15, 2024. However, the deadline to establish and make employer contributions for the first year of a Solo 401(k) is October 15, 2024.

UPDATE December 14, 2023: I Tweeted a thread about the provision that allows Schedule C solopreneurs to establish and fund a new Solo 401(k) with an employee deferral contribution after year-end. There is at least some concern that if one is diligent enough to establish a new Solo 401(k) prior to year-end they might not get the benefit of Section 401(b)(2)‘s funding deadline extension. If that is true (and to my mind this is an ambiguous issue), then the solopreneur establishing the new Solo 401(k) prior to year-end would need to either fund the employee contribution prior to year-end or elect to make an employee deferral contribution prior to year-end.

Note that Section 317 of SECURE 2.0 does not apply for 2022 and does not apply to years beyond the first year of a Solo 401(k).

Based on the wording of SECURE 2.0 Section 317, it is not initially clear if spouses who work in the Schedule C business qualify for the new deadline. I believe the IRS and Treasury may issue regulations clarifying this point.

New Solo 401(k) Employee Contributions Limit for 2023

The IRS announced that for 2023, the employee deferral limit for all 401(k)s, including Solo 401(k)s, will be $22,500. 

New Solo 401(k) Catch-Up Contributions Limit for 2023

The IRS also announced that for 2023, the employee deferrals catch-up contribution limit increased from $6,500 (2022) to $7,500. As a result, those age 50 or older can contribute, in employee contributions, a maximum of the lesser of $30,000 ($22,500 plus $7,500) or earned income. 

New Solo 401(k) All Additions Limit

The new all-additions limit for Solo 401(k)s is $66,000 (or earned income, whichever is less). For those aged 50 or older during 2023, the $66,000 number is $73,500 ($66,000 plus $7,500). 

2023 Update to Solo 401(k): The Solopreneur’s Retirement Account

On sale now, Solo 401(k): The Solopreneur’s Retirement Account explores the nooks and crannies of Solo 401(k)s. On page 16 of the paperback edition, I provide an example of the Solo 401(k) limits for 2022 if a solopreneur makes $100,000 of Schedule C income. Here is a revised version (in italics) of the example (with the footnote omitted) applying the new 2023 employee contribution limit:

Lionel, age 35, is self-employed. His self-employment income (as reported on the Schedule C he files with his tax return) is $100,000. Lionel works with a financial institution to establish his own Solo 401(k) plan and choose investments for the plan. Lionel can contribute $22,500 to his Solo 401(k) as an employee deferral (2023 limit) and can choose to contribute, as an employer contribution, anywhere from 0-20% of his self-employment income.

Lionel’s maximum potential tax-advantaged Solo 401(k) contribution for 2023 is $41,087! That is a $22,500 employee contribution and a $18,587 employer contribution. Note there’s no change in the computation of the employer contribution for 2023 in this example. 

On page 18 I provide an example of the Solo 401(k) contribution limits factoring in catch-up contributions. Here’s the example revised for 2023:

If Lionel turned 50 during the year, his limits are as follows:

  • Employee contribution: lesser of self-employment income ($92,935) or $30,000: $30,000
  • Employer contribution: 20% of net self-employment income (20% X $92,935): $18,587
  • Overall contribution limit: lesser of net self-employment income ($92,935) or $73,500: $73,500

Amazon Reviews

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This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2023 Retirement Tax Reform

An Open Letter to the Members of the 118th Congress

Dear Senators and Congressmen,

Congratulations on your victories in the Senate and House elections. I write with respect to one aspect of your legislative endeavors in the 118th Congress: reforming our tax-advantaged retirement savings system. As you will see, much of it is antiquated and in need of reform.

Before I discuss the problems, allow me to briefly recite my qualifications to write you this letter. My primary qualifications are that I am an American citizen and taxpayer. My secondary qualifications include:

  • I am a financial planner and advise clients on retirement planning and saving.
  • I am the author of a book on one of the tax-advantaged retirement savings accounts, Solo 401(k): The Solopreneur’s Retirement Account.
  • I am a CPA (licensed in California and Virginia) and I have a Juris Doctor degree and a LLM in Taxation degree. My background is on my LinkedIn page.
  • I write a four year-old blog (fitaxguy.com) focused on tax planning for individuals, particularly the use of retirement accounts. 

The views expressed in this open letter are mine only. I have not been compensated for writing this letter and my views are not necessarily the views of any of the clients of my financial planning firm. 

Problems with the Current Retirement Savings System

Limits Are Unequal and Unfair

There’s a myth that Congress and IRS inflation adjustments determine the retirement plan contribution limits every year. If one looks at the Internal Revenue Code and the IRS website, they’d walk away with that belief.

But is that really true? It turns out that one’s employer often defines just how much an employee can get into tax-advantaged retirement accounts every year. In practice, the current system disproportionately benefits a privileged few.

Here are two examples (using 2023 limits) that prove my point in a stark fashion. Josh is a 50 year-old employee of a large Fortune 500 company with a $300,000 salary. Josh maxes out contributions to his traditional 401(k) at work and maxes out his Backdoor Roth IRA and Mega Backdoor Roth (available through his employer’s 401(k)). Further, Josh receives a 3% match in his employer 401(k). Here are what his annual retirement savings contributions look like:

401(k) Employee Deferral: $30,000

401(k) Employer Match: $9,000

401(k) Mega Backdoor Roth: $34,500

Backdoor Roth IRA: $7,500

Total traditional deductible contributions: $39,000. Total Roth contributions: $42,000. Total contributions: $81,000.

Sarah, single, is a 50 year-old non-profit executive director with a $150,000 annual salary and no workplace retirement plan. Under today’s rules, Sarah can only contribute a maximum of $7,500 to a deductible traditional IRA. That’s it! She may be able to make a partial Roth IRA contribution or a Backdoor Roth IRA contribution, but if she does, it reduces her maximum allowed deductible traditional IRA contribution. Thus, her total contributions are, at a maximum, just $7,500 for the year.

Sadly, there are many more workers in the latter situation than in the former situation. 

Because of their choice in employers, Josh gets to put more than 10 times the amount Sarah can into tax-advantaged retirement accounts.

Yes, that is today’s reality. It makes absolutely no sense. Long term, a system that disproportionately rewards workers at some employers and barely covers workers at other employers is not sustainable. 

Where you work should not increase your tax-advantaged retirement account contributions by more than 10 times!

Many retirement provisions benefit a very select few. Most of the time, those select few are among the people who need the least amount of help in achieving a successful retirement. Retirement tax advantages should have broad applicability and should not disproportionately reward any particular subgroup, particularly very small subgroups. 

Other Retirement Account Problems

  • Complexity and confusion (Ever fill out a Form 8606?)
  • Penalties and penalty exceptions that are outdated and not entirely rational
  • Remedies for problems with retirement accounts are neither taxpayer nor IRS friendly

Goals for Retirement Account Reform

Here are the goals I believe the 118th Congress should have in enacting retirement account reform.

  • Reduce complexity and confusion. Simplify the mechanisms of retirement savings. “Backdoors” should be eliminated because retirement savings should occur through direct, simple transactions. 
  • Increase retirement savings, particularly among Americans who have struggled economically over the past three years.
  • Effective yet modest changes. While it is tempting to throw out all the rules, a complete rewrite of the rules would create tremendous confusion and likely reduce, rather than increase, tax-advantaged retirement savings. 
  • Democratize retirement account contributions while acknowledging the role employers can play in offering retirement savings for employees. That said, there should be at least some shift of dollars away from contributions to employer plans towards contributions to individual retirement accounts.
  • Reform cannot simply be a massive tax cut. The federal budget cannot afford a massive tax cut. 
  • Special advantages available to very limited groups should be reduced and eliminated.
  • Remove punitive rules and traps for the unwary. 
  • There are too many penalties in the retirement account system that are too high, too punitive, and too confusing. My proposal attempts to reduce the number of penalties, give the IRS and taxpayers more common sense tools to mitigate them, and make the rules simpler and fairer. 
  • Reduce the competition between funding expenses attendant to having a child and funding retirement savings. 
  • Avoid slogans. Our tax rules are now far too complicated to say “everyone gets a tax cut” or “no one below X income will have a tax increase.” Besides, slogans belong to the politics of the 80s and 90s. 

While my primary audience is the members of the 118th Congress, please allow me to direct a quick word to my fellow American taxpayers who might lose out on an opportunity described below and thus might oppose these proposals. I ask potential opponents of this proposal this question: how sustainable is a retirement system that gives a select few Americans 10 times the tax-advantaged savings capacity as other Americans? 

Why fight to preserve your special tax break when the myriad special tax breaks make the entire system less and less sustainable? Does my proposal make everything entirely fair? Surely not, but, as you will see below, it makes the system much fairer and simpler. I believe that will make the system more sustainable over the long run, which is good for everyone. 

Lastly, retirement savings are far from the only component of the U.S. tax system needing legislative change. But, as you can see from my secondary qualifications above, retirement savings are of particular interest to me, so I’ll mostly limit my commentary here to tax law changes on retirement savings. 

Retirement Tax Reform Proposals

Expanded Universal Roth IRAs and Closing Backdoors

1. Eliminate the MAGI Limitation on annual Roth IRA contributions. Why is there an income limit on contributing to a Roth IRA, which does not produce a tax deduction? Further, removing the income limitation will align the United States Roth account rules with Canadian tax-free savings account rules. Canada does not have an income limit on the ability to contribute. Why should the United States? This proposal also ends the Backdoor Roth IRA. 

2. Increase annual IRA contribution limit (traditional and Roth) to $10,000, then index annually. It is time to shift retirement savings towards individuals. This will help expand individual and spousal contributions to retirement accounts, particularly Roth IRAs, and give individuals more control over their own retirement savings. This proposal makes individuals less reliant on their employer to offer a good retirement savings plan. 

In the 10 year budget window, proposals 1 and 2 will cost some money, but I suspect not a whole lot. In fact, this expansion of Roth IRAs might make Roths more attractive and cause some taxpayers to direct what would have been traditional, deductible 401(k) contributions to their Roth IRA, increasing tax revenue in the early years. 

3. Eliminate nondeductible contributions to IRAs and qualified plans, effective January 1, 2024. This ends Mega Backdoor Roth IRAs as of January 1, 2024. The Mega Backdoor Roth benefits only those few whose employers offer it and can afford to make after-tax contributions. The Mega Backdoor Roth, which only came to prominence starting in 2014, turbocharges the unfair advantages the retirement account system currently confers on a select few Americans (such as Josh in the example above).

As a result of eliminating the Mega Backdoor Roth, most of these contributions will be diverted to taxable accounts, which is not a horrible outcome for those currently taking advantage of the Mega Backdoor Roth. Further, those losing the Mega Backdoor Roth under this proposal gain expanded access to Roth IRAs under proposals 1, 2, and 4. 

4. Increase age 50 or older IRA (traditional and Roth) annual catch-up contribution from $1,000 to $2,000, index for inflation annually. The current $1,000 annual catch-up contribution limit is not enough move the needle in terms of likelihood of financial success in retirement. 

Eliminate Traditional Retirement Account Basis

5. Eliminate IRA Basis / after-tax 401(k) basis, effective January 1, 2027. The Pro-Rata Rule is an unnecessarily complicated rule for retirement account withdrawals. It has even created litigation. Basis record keeping is challenging and creates confusion. Enough already! 

This proposal eliminates retirement account basis recovery as of January 1, 2027. To be fair to those with retirement account basis, this proposal allows elective withdrawal of basis amounts from traditional retirement accounts (including inherited traditional retirement accounts) to taxable accounts during the 2024, 2025, and 2026 tax years. Any elective withdrawals of basis for the year would not count towards RMDs and could not be converted to Roth accounts. Regular withdrawals, RMDs, and Roth conversions in the year of an elective withdrawal of basis could not access existing basis. 

Eliminating basis eliminates page 1 of the Form 8606. This simplifies traditional retirement account withdrawals, inheriting traditional retirement accounts, and Roth conversions. In turn, this makes the retirement account provisions easier for the IRS to administer and easier for taxpayers to understand. 

Simplify and Rationalize Retirement Account Rules

6. Unify Roth account nonqualified withdrawal treatment such that the current Roth IRA nonqualified distribution rules apply to nonqualified Roth 401(k) distributions. The rules for Roth 401(k) nonqualified distributions are confusing, and can be avoided by rolling into a Roth IRA. Why not make them consistent?

7. Change the age for HSA catch-up contributions to age 50. Catch-up contributions to all accounts should kick-in at one, and only one, age. Make it age 50 for all accounts by changing the HSA catch-up contribution kick-in age from 55 to 50. Unifying the HSA/IRA/401(k) catch-up contribution age at age 50 makes the rules simpler. 

8. Unify rules for taking RMDs from traditional retirement accounts. Under this proposal, so long as the total required is taken during the year, it doesn’t matter which account (401(k), 403(b), IRA) or accounts the distributions come from. 

9. Eliminate NUA tax treatment. Net Unrealized Appreciation allows for employer stock in a 401(k) to get preferential tax treatment. As workers are already heavily economically tied to their employer (because of their salary and benefits), NUA treatment encourages something that probably should be discouraged (investing significantly in the stock of one’s own employer). Further, the NUA rules are complex. Removing them simplifies the tax code. 

10. Simplify treatment when spouses inherit a retirement account. Currently, there are three options and planning choices to be made when a spouse inherits a retirement account. The death of a spouse is challenging enough without having to make a complicated tax planning decision. New rule to simplify this: all retirement accounts inherited by spouses are deemed to be the inheriting spouse’s own retirement account as of the first spouse’s death. To prevent any early withdrawal penalties to surviving spouses under age 59 ½ due to this change, add a new 10% early withdrawal penalty exception: being widowed prior to age 59 ½. This new penalty exception applies to all widows and widowers for all pre-age 59 ½ retirement account distributions regardless of whether the widow/widower inherited a retirement account.  

11. Clarify the SECURE Act to provide that if the 10 year rule applies to an inherited account, RMDs do not apply to the account, other than in the final year of the 10 year window. The IRS came out with overly complicated proposed regulations requiring RMDs for many inherited accounts even though the 10 year rule applies to them. This clarification repeals the needlessly complicated proposed regulations, and the government’s interests are already adequately protected by the 10 year rule. 

12. Adopt a supercharged version of SECURE 2.0 Section 321. Allow the self-employed (generally those reporting self-employment income on Schedule C or through partnerships) to both establish a Solo 401(k) after year-end and make employee contributions to their Solo 401(k) before the tax return deadline for the taxable year. This eliminates the election required under Treas. Reg. Sec. 1.401(k)-1(a)(6)(iii). There’s no reason for a self-employed individual to have to make an election with themselves to make a retirement account contribution. This change would make the contribution deadline rules for self-employed employee contributions the exact same as the contribution deadline rules for self-employed employer contributions for every year (not just for the first year as Section 321 proposed to do). 

Combat Mega Retirement Accounts and Limit Benefits for the Very Rich

13. Eliminate (as of enactment) new tax-advantaged retirement account investments in private equity, venture capital, and companies 10% or more owned (by vote or value) by the account owner. These investments have allowed a very select few to accumulate hundreds of millions of dollars in IRAs. IRAs and qualified plans are best when they provide growth and capital preservation from diversified assets to fund retirement. They were never intended to create 9 figure-plus hoards of wealth sheltered from taxation. 

14. Required Accumulation Distribution (RAD) of 20 percent of the amount over $5M anytime all traditional accounts (IRAs and qualified plans) exceed $5M (indexed for inflation) at year-end for the following year prior to age 72. RAD of 20 percent of the amount over $5M anytime all Roth accounts (IRAs and qualified plans) exceed $5M (indexed for inflation) at year-end for the following year. Under this proposal, there would be no penalty on any RAD. RADs from Roths are treated as qualified distributions. This is much simpler than the Build Back Better proposals on mega retirement accounts. RADs from traditional accounts cannot be converted to Roth accounts. 

The hope is that after a while, there will be few, if any RADs. In a world without private equity and venture capital type investments in retirement accounts it will be quite difficult to accumulate in excess of $5M (adjusted for inflation) in either type of retirement account. The RAD rules do not need to apply to traditional retirement accounts at 72 and beyond, since the owner is already subject to the RMD rules. Inherited retirement accounts would be exempt from the RAD rules.  

Examples: Joe, age 65 in 2024, has $4.9 million in all traditional retirement accounts (401(k)s, IRAs, etc.) on December 31, 2023. He also has $4.9 million in all Roth retirement accounts (401(k)s, IRAs, etc.) on December 31, 2023. His 2024 RAD from traditional retirement accounts is $0, and his 2024 RAD from Roth retirement accounts is $0.

Sally, age 65 in 2024, has $7 million in all traditional retirement accounts (401(k)s, IRAs, etc.) on December 31, 2023. She also has $4 million in all Roth retirement accounts (401(k)s, IRAs, etc.) on December 31, 2023. Her 2024 RAD from traditional retirement accounts is $400,000 ($7M minus $5M times 20%), and her 2024 RAD from Roth retirement accounts is $0.

John, age 75 in 2024, has $7 million in all traditional retirement accounts (401(k)s, IRAs, etc.) on December 31, 2023. He also has $7 million in all Roth retirement accounts (401(k)s, IRAs, etc.) on December 31, 2023. His 2024 RAD from traditional retirement accounts is $0 (since he is 72 or older), and his 2024 RAD from Roth retirement accounts is $400,000. Under the existing rules (unchanged by this proposal), John is subject to RMDs in 2024 totalling $284,553 ($7M divided by 24.6) from his traditional retirement accounts (though see proposal 8 giving John more flexibility in terms of which account(s) he can take the RMDs from).

15. Cap at $25,000 the maximum annual amount that can be deferred by those with salaries (W-2, self-employment income) of $400K or more per year (indexed for inflation) under a Section 409A nonqualified deferred compensation plan. This rule change is logical considering (i) the tax law’s benefits for retirement saving have been too skewed towards helping a very affluent few who need the least amount of saving help, (ii) most of the beneficiaries of nonqualified deferred compensation plans are the ones doing best economically, and (iii) the need to provide more benefits of tax-advantaged retirement savings to a larger swath of Americans. Further, those losing a tax benefit because of this rule gain a significant benefit in the removal of income limits on Roth IRA contributions and the increased contribution limits. 

For administrative convenience, the new rule would not apply to any amount deferred at any time during one year and paid out at any time during the immediately following tax year.

Proposals 13, 14, and 15 raise revenue to expand the amounts that every worker can save in Roth IRAs, and some Americans will get increased deductible traditional IRA contributions because of proposals 2 and 4. 

Penalty Reform

16. New 20% penalty on all missed RADs and reduce the missed RMD penalty to 20%. The current 50% penalty on missed RMDs is unnecessarily punitive. 

17. Unify the exceptions to the 10 percent early withdrawal penalty so there is no difference between qualified plans and IRAs. It makes no sense that under current law there are some penalty exceptions only applicable to IRAs and some penalty exceptions applicable only to qualified plans. After this change, the only “plan only” exception would be the exception applicable to nonqualified 457(b) plans.

18. Change the Rule of 55 “separation from service” qualified plan penalty exception to be a broader, fairer age 55 need-based exception. Currently a 56 year-old CEO can leave their job and qualify for the penalty exception from their 401(k) but a 57 year-old teacher cannot qualify for the exception from an IRA. How does that make sense? 

New exception: Starting in the year one turns age 55, if AGI other than the taxpayer’s and/or their spouse’s potential Rule of 55 distribution(s) is less than $70K single, $110K MFJ (indexed for inflation), then the distribution (a “Rule of 55 distribution”) from the qualified plan or IRA is penalty free. Each person would have a $70K annual maximum (indexed for inflation) that could be accessed penalty free under this new, more rational Rule of 55 exception. In between $70K and $90K ($110K to $145K MFJ) of AGI (other than the potential Rule of 55 distributions), the $70K limitation per person is ratably reduced. 

The new Rule of 55 exception would be a Rule of 50 exception for public safety employees subject to the AGI limits described immediately above.

Eliminate Loopholes Benefitting Very Few

19. Age 15 requirement for IRA (traditional and Roth) contributions. Today a very few advantaged families can fund a retirement account for young children. Sometimes this takes the form of paying an infant a salary, which is at best questionable. Even with the elimination of this loophole, the family’s total annual Roth IRA contributions may be greater under this proposal. Instead of $6,500 per person ($19,500 total for family of 3), each parent can contribute $10,000 into a Roth IRA ($20,000 total). Of note, Canada requires being at least age 18 to make contributions to a tax-free savings account.

20. Eliminate the “super HSA” by deeming all persons covered by a HDHP other than the policyholder and their spouse to be a dependent of the policyholder for purposes of determining HSA contribution limits. The super HSA allows young adults covered by their parents’ high deductible health plans to put more into an HSA than most single HSA owners can. That’s not fair and illogical, and the super HSA is a loophole created not by Congressional intent but rather by the drafting technicalities used to create HSAs in IRC Section 223. 

Reform, Expand, and Simplify Qualified Birth Distributions

21. Reform, expand, and simplify SECURE Act Qualified Birth Distributions. Repeal as written in the SECURE Act. Capped at only $5,000 and confusing in their details, the current qualified birth distribution rules are not effective for parents. The new qualified birth distribution and recontributions rules would be as follows: 

For those under age 59 ½, up to $30,000 of distributions from qualified plans, SEP IRAs, SIMPLE IRAs, traditional IRAs, and Roth IRAs per parent distributed within 18 months (9 months before and 9 months after) surrounding a birth and/or an adoption are presumed to be a qualified birth distribution (QBD) and as such (i) are not treated as distributions in the year of the distribution (and not subject to tax withholding) and (ii) can be rolled back into the account by the end of the third year following the distribution. Amounts not repaid to the account are treated as distributions from the account at the end of that third year (including for estimated tax purposes), and are excused from the 10% early withdrawal penalty (if the penalty would otherwise apply to the deemed distribution). No mandatory reporting requirements for the parents (other than for any deemed distribution at the end of the third year), but the IRS is authorized to provide a voluntary reporting form reporting qualified birth distributions and qualified birth recontributions. The new law would authorize financial institutions and plan providers to rely on taxpayer representations for both distributions and recontributions in issuing Forms 1099-R and 5498 and accepting recontributions. 

This is a good idea for several reasons. It means saving for retirement is not a hindrance to financial security when adults are considering whether to have children. Our country is facing a decline in births. This proposal helps parents use retirement accounts to help during pregnancy and after childbirth while not handicapping their retirement. People can invest in Roth IRAs, for example, knowing that the money can be available for both the initial expenses of childbirth and their future retirement. 

Unfortunately, saving for birth and saving for retirement can compete. New, more robust and parent-friendly qualified birth distributions can reduce this competition and allow retirement savings to help during pregnancy and the first nine months after birth. 

Here is an example of how it could work: Robert, age 30, is the father of Mark, born February 2, 2024. On December 1, 2023, Robert withdrew $30,000 from his Roth IRA. At the time of the distribution, Robert had previously made $23,000 of annual contributions to his Roth IRA. Robert’s recontribution deadline is December 31, 2026. On April 2, 2026, Robert recontributes $20,000 to the Roth IRA, and makes no other qualified birth recontributions. On December 31, 2026, the $10,000 Robert did not recontribute to the Roth IRA is deemed to be a distribution from the Roth IRA to Robert. Robert took no other distributions from his Roth IRA prior to December 31, 2026. Since Robert had $23,000 of previous Roth IRA contributions to his Roth IRA as of the end of 2023 and may have made further annual contributions to his Roth IRA after 2023, the deemed distribution of $10,000 is deemed to be return of old annual contributions (under the nonqualified distribution rules) on December 31, 2026 and thus not taxable to Robert. The deemed distribution reduces Robert’s previous annual Roth IRA contributions by $10,000 for purposes of the nonqualified distribution rules as applied to any future nonqualified distributions. 

As a practical matter, the combination of this proposal and proposals 1 and 2 are likely to result in most QBDs coming from Roth IRAs. Thus, most QBDs not recontributed to the Roth IRA will simply be nontaxable deemed distributions of previous Roth IRA annual contributions. 

The new QBD rules would include rules providing that retirement account direct trustee-to-trustee transfers, rollovers, and Roth conversions occurring during the QBD 18 month window are not considered QBDs so as to preserve each parent’s $30K limitation. For simplicity’s sake, each birth and adoption will be treated as a distinct event for QBD purposes. Under this simplicity convention, parents of twins can each take up to $60K of QBDs. In addition, the QBD rules will have no adverse effect on the adoption tax credit. Funds sourced from a QBD for qualified adoption expenses will remain fully eligible for adoption tax credits based on the existing adoption tax credit rules. Lastly, a birth for QBD purposes will include the birth of a baby the parents give up for adoption. 

Expand and Rationalize Remedial Measures for Retirement Accounts

22. Adopt a supercharged version of SECURE 2.0 Section 308. Enact section 308 (expanding the IRS Employee Plans Compliance Resolution System) and add a self-correction safe-harbor (available both before an IRS exam and during IRS examination activity) whereby all individual traditional IRAs and Roth IRAs, and SEP IRAs, SIMPLE IRAs, 401(k)s, and qualified plans involving 10 or fewer individuals/employees (including Solo 401(k)s) automatically qualify for self-correction and forgiveness of all penalties so long as (i) the account owner/plan sponsor implements reasonable corrections (such as refunding excess contributions and attributable earnings penalty free, subject to ordinary taxable income inclusion — in the year of the corrective distribution — for earnings and any returned contributions actually deducted on a tax return or previously excluded from taxable income), and (ii) the total amount in the plan or IRA has never exceeded $500,000 as of any year-end. For this purpose, accounts would only be aggregated for a person or plan sponsor at the same financial institution. The new rules would provide that financial institutions can rely on taxpayer representations in issuing Forms 1099-R to report corrective distributions. Financial institutions will continue to compute attributable earnings as they do under current regulations.

This proposal reduces penalties (such as excess contribution penalties) and helps ensure plans and IRAs remain qualified. Self-correction is much better for taxpayers and the IRS, particularly when accounts are relatively modest in size. Currently, the IRS offers the Voluntary Compliance Program for qualified plans. Since VCP covers very large employer plans, it is a very odd fit for Solo 401(k)s and would be an odd fit for traditional IRAs and Roth IRAs. It is much better to encourage the use of self-correction. This encourages compliance, makes correcting mistakes easier, reduces penalties, and makes the IRS’s oversight of modest sized retirement accounts easier and more effective. 

23. Repeal and reform section 403 of the SECURE Act as applied to Form 5500-EZ filings. The SECURE Act increased penalties for late filed Form 5500 Series filings by tenfold. While this may make sense for large employer plans, the increase in penalties drastically overshot the mark when it comes to small businesses filing the Form 5500-EZ. Under the new law, a self-employed Solo 401(k) owner could (theoretically) be liable for a $150,000 penalty for failing to file a two page informational tax return (the Form 5500-EZ). Such a penalty is excessive and obscene. While relief procedures are available, it is ridiculous that the penalty could be, at least in theory, so onerous. Replace the current $250 per day penalty with a flat $500 per late Form 5500-EZ penalty (capped at $2,000 per plan sponsor) that can be excused for either reasonable cause or a first time abatement distinct to the Form 5500-EZ return. Cap the IRS period to assess the penalty at four years from the original filing deadline. Further, make the new rules effective to all missed Form 5500-EZ filings regardless of when they occurred. In addition, increase the asset threshold whereby a Form 5500-EZ is required from $250,000 to $500,000 to account for the passage of time and inflation. The Form 5500-EZ would still be required at the closing of the plan under this proposal, regardless of account size. 

Repeal Traps for the Unwary

24. Eliminate the once-a-year IRA to IRA 60-day rollover limit. It’s a trap for the unwary and by eliminating it, the rules would be synchronized for all rollovers. The once-a-year limit makes no sense (as the 60-day time limit is sufficient to police money coming out of retirement accounts) and is punitive and unnecessary. 

25. Repeal the SIMPLE IRA 25% penalty for early distributions within the first two years of establishing the SIMPLE IRA. Under this rule, the 25% penalty even applies to rollovers to traditional IRAs within the first two years. It’s a trap for the unwary and should be fully repealed. 

Miscellaneous

26. Do not pass (or repeal if passed) the rest of SECURE 2.0, the EARN Act, and other related proposals, other than as discussed above. My opinion is that SECURE 2.0/EARN Act introduced changes that were at best marginally beneficial for Americans saving for retirement. Unfortunately, SECURE 2.0 has counterproductive provisions (such as eliminating the tax deduction for 401(k) catch-up contributions) and increases the complexity of the retirement account system. 

Revenue Raisers (If Needed)

My hope is that my proposals would reduce federal revenue over the 10 year budget window by only a fairly modest amount, as there are provisions that would cost the government money and proposals that would increase revenue. If this nets out to costing too much money in Congress’s judgment, I recommend the following tax increase: an increase (starting in 2024) of the top capital gain/qualified dividend income rate (currently 20%) by the amount needed to close the gap. Considering that the highest earners have done the best in recent years, and do receive benefits under the overall proposal (see proposals 1, 2, and 4), this tax increase is fair and helps many Americans save for retirement by funding expansion of Roth IRAs and reduction of penalties.

If any other tax increases are deemed necessary, I recommend that Congress consider an increase to the rate of the corporate book minimum tax and/or a tax on investment income of college endowments comprised of $1 billion or more of assets. These two proposals shift the tax burden to those who have benefited the most from the American economy in recent years. 

Landscape After Retirement Account Reform

Let’s return to Josh and Sarah. What might their tax-advantaged retirement account contributions look like after my proposed reform. Here’s Josh’s contributions:

401(k) Employee Deferral: $30,000

401(k) Employer Match: $9,000

Roth IRA: $12,000

Total traditional deductible contributions: $39,000, total Roth contributions: $12,000, total contributions: $51,000. Yes, Josh lost his Mega Backdoor Roth IRA. But, now instead of a gimmicky $7,500 Backdoor Roth IRA, he gets to simply make a $12,000 annual contribution to a Roth IRA. Further, Josh did not lose any tax deductions under my proposal. Josh can invest the difference between $81,000 (his old tax-advantaged contribution total) and $51,000 (his new tax-advantaged contribution total), $30,000, in a taxable account.

Sarah has significantly increased the amount of her contributions. She goes from a $7,500 annual contribution to a traditional deductible IRA or Roth IRA to a $12,000 traditional deductible or Roth IRA contribution. 

Perfect? No. But instead of a 10.8 to 1 ratio we have moved the needle significantly such that the ratio is now 4.25 to 1. Further, many of the retirement account rules are simpler and fairer. If Josh, Sarah, or other Americans run into problems with their retirement accounts, their remedial paths are likely to be easier to navigate and they are more likely to avoid onerous and unfair penalties. 

I believe that our retirement system would be significantly better if Congress passes and the President signs the 26 proposals I outlined above in 2023. If any of you have questions about the above, I would be happy to communicate with you and/or your staff about these proposals.

To my fellow Americans reading this letter, I’d be honored to read your comments in the comments section below. I’m sure there are other ideas that could simplify and improve retirement accounts. 

Sincerely,

Sean Mullaney

This post does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

2022 Year-End Tax Planning

Below are the main tax planning items for the year 2022 as I see them. Of course, this is educational information for the reader, and not tax advice directed toward any particular individual. 

The first two tax loss harvesting items are particularly unique to 2022 vis-a-vis recent years. 

Tax Loss Harvesting

2022 has given us plenty of lemons. For some Americans, it’s time to make some lemonade through tax loss harvesting. The deadline to do this and obtain a benefit on one’s 2022 tax return is December 31, 2022. 

Tax Loss Harvesting and Bonds

There is a tax loss harvesting opportunity in 2022 that has not existed in recent years to the scope and scale it exists today: tax loss harvesting with bonds and bond funds. In a recent post I went into that opportunity in detail and how it might create both a great tax loss harvesting opportunity and a great tax basketing opportunity. 

Tax Loss Harvesting Crypto

Many cryptocurrencies have declined in value. This can create a tax loss harvesting opportunity, regardless of whether the taxpayer wants to remain invested in crypto. To harvest the loss if one wants to get out of crypto, it’s easy: just sell the asset. For those wanting to stay in crypto, it’s not that much harder: sell the crypto (by December 31, 2022 if wanting the loss on their 2022 tax return) and they rebuy the crypto shortly thereafter. Crypto is not a “security” for wash sale purposes, and thus, repurchases of crypto are not subject to the wash sale rule, regardless of when they occur. 

Solo 401(k) Establishment

Quick Update 12/23/2022: My initial reading of SECURE 2.0 is that it does not change any 2022 Solo 401(k) deadlines. The one deadline it appears to change is effective starting for plan years beginning in 2023.

For Schedule C solopreneurs looking to make a 2022 employee contribution to a Solo 401(k), the Solo 401(k) must be established by December 31, 2022. This is NOT the sort of thing you want to try to do on December 30th. Almost certainly those trying to establish a Solo 401(k) will want to act well before the end of December, as it takes time to get the Solo 401(k) established prior to year-end. 

The deadline to establish a Solo 401(k) for an employer contribution is the tax return filing deadline. For individuals, this is April 18, 2023, but can be extended to October 15, 2023. For S corporations, this is March 15, 2023, but can be extended to September 15, 2023. 

Solo 401(k) Funding for Schedule C Solopreneurs

Employee elective deferral contributions (traditional and/or Roth) must meet one of two standards. Either (i) they must be made by December 31st or (ii) they are elected by December 31st and made by the tax return filing deadline, including any filed extensions. 

Employer contributions must be made by the tax return filing deadline, including any filed extensions. 

Roth Conversions 

Taxpayers with lower income (relative to the rest of their lives) may want to consider taxable conversions of traditional retirement accounts to Roth accounts. The deadline to get the Roth conversion on one’s 2022 tax return is December 31st, though it is not wise to wait until the last minute.

For the self-employed, there may be a unique opportunity to use Roth conversions to optimize the qualified business income deduction. 

Tax Gain Harvesting

For those finding themselves in the 12% or lower federal marginal income tax bracket and with an asset in a taxable account with a built-in gain, tax gain harvesting prior to December 31, 2022 may be a good tax tactic to increase basis without incurring additional federal income tax. Remember, though, the gain itself increases one’s taxable income, making it harder to stay within the 12% or lower marginal income tax bracket. 

HSA Funding Deadline

The deadline to fund an HSA for 2022 is April 18, 2023. Those who have not maximized their HSA through payroll deductions during the year may want to look into establishing payroll withholding for their HSA so as to take advantage of the payroll tax break available when HSAs are funded through payroll. 

The deadline for those age 55 and older to fund a Baby HSA for 2022 is April 18, 2023. 

Roth IRA Contribution Deadline

The deadline for funding a Roth IRA for 2022 is April 18, 2023. 

Backdoor Roth IRA

There’s no law saying “the deadline for the Backdoor Roth IRA is DATE X.” However, the deadline to make a nondeductible traditional IRA contribution for the 2022 tax year is April 18, 2023. Those doing the Backdoor Roth IRA for 2022 and doing the Roth conversion step in 2023 may want to consider the unique tax filing when that happens (what I refer to as a “Split-Year Backdoor Roth IRA”). 

Anyone who has already completed a Backdoor Roth IRA for 2022 should consider New Year’s Eve. December 31st is the deadline to be “clean” for 2022. Anyone who has done the Roth conversion step of a Backdoor Roth IRA during 2022 will want to consider (to the extent possible and desirable)  “cleaning up” all traditional IRAs, SEP IRAs, and SIMPLE IRAs as of December 31, 2022. 

Charitable Contributions

The deadline to make charitable contributions that can potentially be deducted on one’s 2022 tax return is December 31, 2022. Planning in this regard could include contributions to donor advised funds. If one is considering establishing a donor advised fund to get a deduction in 2022, I recommend moving well before December 31st, since it takes time for financial institutions to process donations and establish donor advised funds. 

RMDs from Your Own Retirement Account

The deadline to take any required minimum distributions from one’s own retirement account is December 31, 2022. Remember, the rules can get a bit confusing. Generally, IRAs can be aggregated for RMD purposes, but 401(k)s cannot. 

RMDs from Inherited Accounts

The deadline to take any RMDs from inherited retirement accounts is December 31st. For some beneficiaries of retirement accounts inherited during 2020 and 2021, the IRS has waived 2022 RMDs. That said, all beneficiaries of inherited retirement accounts may want to consider affirmatively taking distributions (in addition to RMDs, if any) before the end of 2022 to put the income into a lower tax year, if 2022 happens to be a lower taxable income year vis-a-vis future tax years. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The MAGI Limitation on Roth IRA Contributions

During a recent Econome Encore presentation, a questioner asked a question that caused me to do a double take: Do Roth conversions create MAGI (modified adjusted gross income) for purposes of determining whether someone exceeds the MAGI thresholds to make an annual contribution to a Roth IRA?

I did a double take for several reasons. First, the presentation was early on a Sunday morning 😉 . Second, in practice, the issue rarely comes up, for reasons we will discuss later. Third, why wouldn’t income created by a Roth conversion count as MAGI for this purpose? It is taxable income, after all. Fourth, I was pretty sure the rule states that no, Roth conversions do not create MAGI for this purpose. 

I quickly stated that I thought the rule does not consider Roth conversions to be included in MAGI, but I looked it up to be sure. My initial take was correct. Roth conversions are not included in MAGI for purposes of determining whether one can make an annual contribution to a Roth IRA. See IRC Section 408A(c)(3)(B)(i). 

The Creation of the Roth IRA in 1997

It’s a bit of an odd rule, though. Why carve out Roth conversion income from the Roth IRA MAGI test? It’s especially odd considering that actual taxable withdrawals from a traditional IRA or 401(k) create MAGI for this purpose. Why carve out income from Roth conversions of traditional IRAs and 401(k)s? 

It has to do with how Roth IRAs were created. In 1997, Congress created the Roth IRA to be effective starting in 1998. Roths were new. There was likely a concern along the lines of “a vehicle with tax-free growth could be abused.” Thus, there were two features of the Roth IRA subject to a MAGI limitation. Both the ability to make a direct annual contribution to a Roth IRA and the ability to convert amounts from a traditional retirement account to a Roth IRA were subject to a MAGI limitation. See page 40 of the 1997 Taxpayer Relief Act text. 

The MAGI limitations begged the question: how to define MAGI for this purpose? The bill drafters started with a common technique: they found another relevant definition of MAGI already existing in the Internal Revenue Code. Why reinvent the wheel? They started with the MAGI definition used to determine the ability to make a deductible traditional IRA contribution. 

By itself, however, this definition would create a circular definition problem with respect to Roth conversions, as the IRA deduction MAGI definition used starts with AGI and then kicks out certain items. Roth conversions are included in AGI, so to avoid a circular calculation, the bill drafters had to kick Roth conversion income out of the Roth MAGI definition. 

If Roth conversion income was included in the MAGI definition, then the taxpayer would have to test Roth conversions against themselves to determine if Roth conversions were allowed! For example, if AGI was $90K prior to a $40K Roth conversion, the $40K Roth conversion would disqualify itself, as the MAGI limitation on the ability to convert was $100K of MAGI. 

Further, the bill drafters decided to create one MAGI definition for the two different limitations. They could have created two different MAGI definitions, but this would have made a new Code section even more lengthy and complicated. Remember, none of this existed as of 1997 when the bill was written. So, the final bill only had one MAGI definition for both limits. That one definition kicked out Roth conversion income, which it had to do to avoid the circular definition problem with respect to Roth conversions. 

Changes to Roth IRAs

In 2006, Congress repealed the MAGI limitation on the ability to do Roth conversions, effective 2010. See pages 21 and 22 of this PDF of the Tax Increase Protection and Reconciliation Act of 2005. This is what opened the door to the Backdoor Roth IRA starting in 2010.

Interestingly enough, had there never been a MAGI limitation on the ability to do a Roth conversion, the kick out of Roth conversion income from the MAGI limitation on the ability to make an annual contribution to a Roth IRA might not exist. First, there would have been no circular definition problem to solve. Second, it would have been neater to simply reference the deductible traditional IRA contribution MAGI definition and leave it at that. 

But, that’s not how the history of the Roth IRA transpired. We will never know if there would not have been a kick out of Roth conversion income in defining MAGI for annual Roth contribution purposes had today’s rules been the original Roth IRA rules. 

Roth Conversions and Annual Roth IRA Contributions

For *many* taxpayers, particularly those in the FI community, the time to do Roth conversions is not while one is working. When one is working, he or she is likely to (a) qualify for annual Roth contributions and (b) to be in their highest lifetime marginal tax brackets. Usually, the best time to do a Roth conversion is during early retirement rather than during one’s highest earning years. 

As a practical matter, at the time many Americans qualify to make a Roth contribution, they are not likely to be in an optimal Roth conversion posture. Of course, your circumstances could vary. For example, consider someone taking a 12 month sabbatical from the workforce (starting March 1st) who has 2 months of earned income during the year. Perhaps he or she should (a) make a Roth IRA contribution based on their 2 months of earnings and also (b) do Roth conversions based on having a relatively low income for the year. 

Click here for the IRS website detailing the 2023 MAGI limitations on the ability to contribute to a Roth IRA.

While We’re On the Subject of the Annual MAGI Limit on Roth IRA Contributions . . .

My belief is that one of the next changes Congress should make to Roth IRAs is to remove the MAGI limit on contributions. 

Let’s think about this. A 50+ year old billionaire can contribute up to $30,000 to a workplace traditional or Roth 401(k) regardless of their income level. If this is possible, why is there a MAGI limitation on the ability to contribute $6,500 or $7,500 (age 50 or older, 2023 numbers) to a Roth IRA? It makes absolutely no sense, especially considering that some people, though not all people, can get around the MAGI limitation through the Backdoor Roth IRA.

Further, our neighbors to the north have no income limitation on the ability to contribute to a Tax-Free Savings Account, Canada’s equivalent of the Roth IRA. It’s time for Congress to repeal the MAGI limitation on the ability to make an annual Roth IRA contribution.

Watch me discuss the real answer to the Backdoor Roth IRA gimmick, which is the repeal of the MAGI limitation on the ability to make an annual Roth IRA contribution. 

Conclusion

There’s a bit of an odd rule when it comes to determining MAGI for purposes of determining whether a taxpayer can make a contribution to a Roth IRA. It stems from the creation of the Roth IRA in 1997 and the fact that back then, there was also a MAGI limitation on the ability to convert amounts to a Roth IRA. Today, the kick out of Roth conversion income is a taxpayer favorable rule that is rarely significant in practice. More broadly speaking, I hope Congress repeals the MAGI limitation on the ability to make an annual Roth IRA contribution. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean on New Podcast Episodes

This week I’m on episodes of The Stacking Benjamins Show and the Earn & Invest podcast talking about taxes, retirement savings, and my new book, Solo 401(k): The Solopreneur’s Retirement Account.

I’ve also recently recorded, and will record, several other podcast episodes with some great podcast hosts, so please be on the lookout for those.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post and the podcast episodes referenced in it, are for entertainment and educational purposes only. They do not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Special Tax Loss Harvesting Opportunity for 2022

There is a tax loss harvesting opportunity in 2022 that has not existed in recent years to the scope and scale it exists today: tax loss harvesting with bonds and bond funds. In most recent years, many bonds and bond funds have not had significant built-in-losses. 2022 is different: now there are plenty of bonds and bond funds in taxable accounts with significant built-in-losses. 

Tax Basketing for Bonds and Bond Funds

Bonds tend to be tax inefficient, for two reasons. First, they generate ordinary income, which is taxed at the taxpayer’s highest marginal tax rate. Second, they tend to have higher yields than equity investments. Thus, a dollar of a bond fund often produces more taxable income than a dollar of an equity fund, if they are both owned inside a taxable account.

As a result, holding bonds and bond funds in traditional retirement accounts is often logical from a tax basketing (or tax location) perspective. If they produce ordinary income anyways, why not hold them in a traditional retirement account (IRA, 401(k), etc.) where the owner can defer the timing of the ordinary income taxable event (through later Roth conversions and/or distributions)? 

Tax Basketing for Stocks and Equity Funds

Bonds also don’t suffer from the “transmutation” problem equities have. Stocks and equity funds, in most cases, pay “qualified dividend income” which qualifies for the lower long term capital gains tax rates (including the 0% long term capital gains tax rate). Holding them in a traditional retirement account transmutes that preferred income into ordinary income, subject to the taxpayer’s marginal ordinary tax rate. 

Now, as a practical matter, most Americans have most of their non-real estate financial wealth in traditional retirement accounts. Having some equities in traditional retirement accounts should not in any way cause despair. But, on the margins, it can be beneficial to review the overall portfolio to see if there can be some tax efficiency gains made by some tax rebasketing of assets. 

Rebasketing and Tax Loss Harvesting

The deadline for tax loss harvesting for 2022 is December 31, 2022. 

To my mind, some of the best 2022 tax loss harvesting will be selling bonds and bond funds at a loss in taxable accounts. Why is that? Because this sort of tax loss harvesting enjoys the main benefits of tax loss harvesting and it can achieve a great tax basketing result. 

Bonds create ordinary income and are generally higher yielding than equities, which often produce tax favored qualified dividend income. Thus, from a tax basketing or tax location perspective, it can often make sense to hold bonds and bond funds in a traditional retirement account and hold equities in a taxable account. Today, many investors can do some tax loss harvesting and strategically reconfigure their portfolios to make them much more tax efficient. Here is an example of how this could play out.

Jorge is 30 years old. He currently owns a diversified equity fund (Fund A) inside his workplace traditional 401(k) plan worth $80,000. It has a 2% annual dividend yield, most of which is qualified dividend income (though of course it is tax deferred inside the 401(k) and will later be subject to ordinary income tax when withdrawn or Roth converted). Separately, he owns a diversified bond fund (Fund B) inside his taxable brokerage account. It is worth $20,000, and Jorge has a $24,000 tax basis in the fund. The bond fund has a 3% annual interest yield ($600), all of which is ordinary income. Jorge wants to have an 80% / 20% equity to bond allocation. 

Here’s Jorge’s portfolio today:

AssetAmountAnnual Taxable Income
401(k) Fund A (Equity)$80,000None
Taxable Fund B (Bond)$20,000$600
Total$100,000$600

Jorge, could, in theory, execute two transactions to both tax loss harvest and become more tax efficient from a tax basketing perspective. First, Jorge could exchange his $20K of Fund B for $20K of an equity fund inside his brokerage account with a dividend yield similar to Fund A. Second, inside his 401(k), he could exchange $20K worth of his Fund A holding for a bond fund with an income yield similar to Fund B. If Jorge’s new fund inside the 401(k) is not substantially identical to Fund B, he can claim most, if not all, of the $4,000 loss, though the prior month’s Fund B dividend might slightly reduce the loss under the wash sale rule.

Here’s Jorge’s portfolio after these two transactions:

AssetAmountAnnual Taxable Income
401(k) Fund A (Equity)$60,000None
401(k) Bond Fund$20,000None
Taxable Equity Fund$20,000$400
Total$100,000$400

Jorge may obtain two tax benefits from these transactions. First, assuming he successfully navigates the wash sale rule, he may be able to deduct up to $3,000 against ordinary income by triggering the capital loss on the Fund B sale. 

Second, regardless of whether he successfully navigated the wash sale rule, he has just made his portfolio more tax efficient. It used to be that he reported $600 of ordinary income (from Fund B) on his tax return. Now that sort of interest income is hidden inside the 401(k). If he now receives approximately $400 a year in qualified dividend income from the new equity fund inside the taxable brokerage account, he has (i) reduced his annual taxable income by $200 (and growing through compounding) and (ii) now has mostly qualified dividend income from the taxable account instead of ordinary income, lowering his federal tax rate on his portfolio income. He has done all that without disturbing his overall asset allocation. 

Getting the tax basketing of his investments better without changing his investment allocation is likely to be worth it even if loses the tax loss due to the wash sale rule. He would want to review the options available to him inside his 401(k) to see if there is an acceptable (to him) bond fund that is not “substantially identical” to Fund B so as to avoid the wash sale rule being triggered by the investment in a bond fund inside the 401(k). 

Conclusion

Declines in the stock and bond market are some of the lemons of 2022. But, there’s a chance to make some lemonade. When it comes to bonds held in taxable accounts, there may be an opportunity to obtain two benefits: tax loss harvesting and better tax basketing. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean Presentation at CampFI

These are the slides for my presentation at CampFI in Julian, CA on October 8, 2022.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Three Ways the Solo 401(k) Supports Financial Independence

Financial independence encourages thinking about one’s financial future in a different way. You were told to “build a career and retire at age 65.” Financial independence says you should write your own financial script. The system, your parents, and a large employer should not be the authors of your financial future.

Guess what goes perfectly well with a financial independence mentality? The Solo 401(k)! The Solo 401(k) helps you control today’s tax burden and helps you plan for your retirement your way. 

Here are three ways the Solo 401(k) can support the financial independence journey. 

Choice and Low Fees

One advantage of working for yourself is you gain control over your workplace retirement account. Solopreneurs themselves determine where their Solo 401(k) is established and the investment options available to them. They determine contribution levels and whether or not to contribute to a Roth account.

Solopreneurs are no longer at the mercy of a large employer’s 401(k) plan, which may not have the investments they want, a Roth option, and/or low fees. 

Further, many Solo 401(k) providers offer low or no fees to establish a Solo 401(k) with their institution. For example, today neither Schwab nor Fidelity charges Solo 401(k) fees, other than the fees of the underlying investments (such as mutual fund expenses). Vanguard charges $20 per mutual fund inside a Solo 401(k) (other than the underlying fund fees), though the $20 fee can be waived if the solopreneur has enough qualifying assets invested with Vanguard. 

Tax Rate Arbitrage

The Solo 401(k) supports very significant tax deductions. For those at their peak earning years, contributions to Solo 401(k)s can benefit from high marginal tax rates. Further, in certain circumstances, traditional deductible Solo 401(k) contributions can help solopreneurs qualify for the qualified business income deduction, increasing the marginal tax rate benefit of traditional, deductible Solo 401(k) contributions. 

During early retirement, retired solopreneurs can convert traditional retirement accounts to Roth accounts. Those Roth conversions can be sheltered by the standard deduction, and then taxed at the 10 percent and 12 percent marginal federal income tax rate. This arbitrage opportunity (deduct contributions at high marginal rates, later convert the contributions and earnings to Roth accounts at lower tax rates) can supercharge the journey to financial independence. 

Reducing MAGI for PTC Qualification

Many solopreneurs have their medical insurance through an Affordable Care Act plan. These plans often have hefty annual premiums. However, there is a Premium Tax Credit (“PTC”) that can significantly reduce the cost of those premiums.

PTCs decline as modified adjusted gross income (“MAGI”) increases. Very generally speaking, from a planning perspective, as MAGI increases, PTCs decline by approximately 10 to 15 percent. Solopreneurs can reduce MAGI by contributing to a traditional deductible Solo 401(k). That decrease in MAGI can significantly increase the PTC, defraying their ACA medical insurance premiums. 

Conclusion

The Solo 401(k) can help solopreneurs achieve financial independence. Chapter 13 of my new book, Solo 401(k): The Solopreneur’s Retirement Account, goes into further detail about marrying the Solo 401(k) with one’s own FI journey. The book is available from Amazon, Barnes & Noble, and other outlets. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Advantages of Living On Taxable Assets First in Early Retirement

The FIRE community loves the accumulation phase. Build up assets towards the goal of financial independence.

Questions increasingly creep in when it comes to the distribution phase. Members of the FIRE community wonder: what do I live on when I get to retirement? This is particularly true when one reaches early retirement prior to age 59 ½. 

Below I discuss the options and the reasons I believe that for many, the best assets to live off of first in early retirement are taxable assets. This analysis assumes the early retiree has access to some material amount of assets in each of the three tax baskets discussed below.

Early Retirement Drawdown Options

For most Americans reaching retirement prior to age 59 ½, there are three main tax baskets of assets that can be lived off prior to age 59 ½.

Taxable Assets: This can include cash in bank accounts, brokerage accounts (stocks, bonds, mutual funds, and ETFs), and for some, income from rental properties. For purposes of this blog post, I will assume the early retiree does not own any rental real estate. 

Roth Basis/HSAs: Early retirees can live off of what I colloquially refer to as “Roth Basis.” Generally, Roth Basis is the sum of previous annual contributions to Roth accounts and Roth conversions that are at least five years old. Further, early retirees can harvest amounts in HSAs tax and penalty free to the extent that they have allowable previously unreimbursed qualified medical expenses (what I refer to as PUQME). HSAs can also be used for qualified medical expenses incurred in early retirement. 

Traditional Retirement Assets: Assets such as traditional 401(k)s and traditional IRAs. Generally “inaccessible” prior to turning age 59 ½ due to being subject to both ordinary income tax and the 10% early withdrawal penalty. However, there are exceptions to the early withdrawal penalty. They include:

  • Rule of 55: Separation from service from an employer after turning age 55 (exception available for withdrawals from that workplace retirement plan only).
  • 72(t) Payments: Establishing a series of substantially equal periodic payments.
  • Governmental 457(b) Plans

Drawbacks of Using Roth Basis/HSAs

Some might argue for using tax-free withdrawals of Roth Basis and HSAs to fund early retirement. This allows the early retiree to pay no taxes on funds used for living expenses. 

To my mind, the main drawback of doing so is opportunity cost. Removing assets from Roths and HSAs cuts off the opportunity for future tax free growth. 

As a general planning objective, many will want to let their Roths and HSAs grow as long as possible to maximize tax-free growth. 

Using Roths and HSAs can also have a significant drawback from a creditor protection perspective, as I will discuss below. 

Drawbacks of Using Traditional Retirement Assets

The below analysis assumes that the early retiree qualifies for an exception from the 10% early withdrawal penalty.

The biggest drawback to using traditional retirement accounts to live off of in early retirement is all living expenses become subject to federal and state income taxes. It puts the most important consideration (funding living expenses) in opposition to the secondary (but still important) consideration: tax planning.

Living off traditional retirement accounts in early retirement reduces tax planning flexibility. It reduces the ability to do tax-optimized Roth conversions in early retirement. In addition, living off traditional retirement accounts during early retirement can reduce Premium Tax Credits for those on Affordable Care Act (“ACA”) medical insurance plans.

Premium Tax Credit Planning: Many early retirees will use an Affordable Care Act medical insurance plan. The premiums are subsidized through a tax code mechanism: the Premium Tax Credit (the “PTC”). PTCs are reduced as the taxpayer’s modified adjusted gross income (“MAGI”) increases. Very roughly speaking, for planning purposes, an additional dollar of MAGI often reduces the PTC by 10 to 15 cents, meaning early retirees using traditional retirement accounts to fund living expenses may be subject to a surtax of 10 to 15 percent on retirement account withdrawals due to PTC reduction. Resources for the PTC include this article and this spreadsheet. 

There’s an argument that it is good to live off traditional retirement accounts early because withdrawals used to fund living expenses reduce future required minimum distributions (“RMDs”). But one must consider that there are two types of withdrawals an early retiree can make from a traditional retirement account: an actual withdrawal or a Roth conversion. Both reduce future RMDs, but a Roth conversion is the most tax efficient withdrawal for the early retiree. Why? Because it sets up future tax-free growth! Actual withdrawals used for living expenses do not enhance future tax-free growth. 

Another drawback of using traditional retirement accounts to fund early retirement includes being constrained by the parameters of the applicable penalty exception. For example, needing to keep money inside a former employer’s retirement plan in order to qualify for the Rule of 55, or needing to withdraw precise amounts annually if using a 72(t) payment plan. Further, using traditional retirement accounts in early retirement has creditor protection drawbacks, discussed below. 

Advantages of Using Taxable Assets

Living off drawdowns of taxable assets can be a great way to fund the first expenses of early retirement. Here are some of the advantages. 

Zero Percent Long Term Capital Gains Rate

Early retirees worry: I need $60,000 of income to live my life. Won’t that create $60,000 of taxable income? 

If drawing from a taxable account, almost certainly it will not. Consider Judy, an early retiree needing $60,000 to pay her living expenses. If she sells $60,000 worth of the XYZ Mutual Fund (all of which she has owned for over a year), in which she has $40,000 of basis, her resulting taxable income is only $20,000. Not $60,000!

But it gets even better for Judy. The capital gain can qualify for the 0% federal long term capital gains tax rate. Outstanding! By using taxable assets, Judy may pay $0 federal income tax, and likely only a very small state income tax, on the money she uses to fund her living expenses. Pretty good. 

Even if Judy’s income puts her above the 0% federal capital gains tax bracket, (i) some of her capital gains will likely qualify for the 0% rate, and (ii) the next bracket is only a 15% tax rate.

Basis Recovery While Basis is Valuable

During 2022, we learned an important financial lesson: inflation is a thing. Retirement draw down planning should consider inflation. 

One way to fight inflation is to use tax basis before its value is inflated away. Tax basis is never adjusted for inflation. Thus, failing to harvest tax basis exposes the early retiree to the risk that future capital gains in taxable accounts will be subject to taxation on inflation gains. Early retirees should consider harvesting basis (like Judy in the above example) when the tax basis is its most valuable. 

Using taxable assets as the first assets to fund early retirement takes maximum advantage of tax basis, unless the U.S. dollar begins to deflate (a possible but not very likely long term outcome, in my opinion). 

Opens the Door for Roth Conversions

Now we get to the fun part. Roth conversions! Using taxable assets first for living expenses in early retirement facilitates conversions of amounts in traditional retirement accounts to Roth accounts. The idea is to have artificially low taxable income such that the taxpayer can do Roth conversions taxed at 0% federal (offset by the standard deduction) and then in the 10% or 12% tax bracket. Occasionally, it will be logical for the taxpayer to incur an even greater tax rate on such Roth conversions. 

These Roth conversions move assets to Roth accounts where they enjoy tax free growth. In addition, early retirement Roth conversions reduce future RMDs. 

There is a taxpayer-friendly rule that assists early retirement Roth conversion planning: long-term capital gains income is stacked on top of ordinary income in the tax computation. Thus, Roth conversions can benefit from being sheltered by the standard deduction (or itemized deductions if the taxpayer itemizes). This makes Roth conversion planning in early retirement that much better, as some Roth conversions can benefit from a 0% federal income tax rate. 

Further, this tells us it is generally better from a tax basketing perspective not to have bonds and other assets that generate ordinary income, since that income eats up part of the standard deduction, diminishing the opportunity to 0% taxed Roth conversions. One way to avoid having such ordinary income is to sell bonds, bond mutual funds, and other assets that generate ordinary income and use the proceeds to fund early retirement living expenses. 

Another advantage of early retirement Roth conversions is the reduction of the risk that future tax increases will drive up taxes on future traditional retirement account withdrawals.

Roth Conversions, ACA PTC Eligibility, and Medicaid

Lastly, there can be an ancillary benefit to Roth conversions. Taxpayers lose all ACA subsidies (thus, PTCs) if their MAGI is below certain thresholds. For example, a family of four in California with MAGI less than $41,400 (2023 number) would meet the income threshold for Medi-Cal (Medicaid in California) and thus would get no ACA PTC. 

Roth conversions can keep early retirees’ MAGI sufficiently high such that they do not meet the income threshold for Medicaid. By keeping MAGI above the Medicare threshold, early retirees can qualify for significant PTCs.

Creditor Protection

Financial assets can receive protection from creditors to varying degrees. Taxable brokerage accounts tend to have little, if any, creditor protection. 401(k) and other ERISA government workplace retirement accounts benefit from ERISA’s anti-alienation provisions. Generally speaking, only the IRS and an ex-spouse can get assets out of a 401(k). Traditional IRAs and Roth IRAs enjoy significant protection in bankruptcy. Traditional IRAs have varying degrees of non bankruptcy creditor protection, but in many states are fully protected. Roth IRAs are non bankruptcy protected in most states, but more states protect traditional IRAs than Roth IRAs.

HSAs do not enjoy federal bankruptcy protection, but do enjoy creditor protection in some states (to varying degrees).

By spending down taxable assets in early retirement, the early retiree optimizes for creditor protection in two ways. First, diminishing taxable assets by using them for living expenses reduces creditor vulnerable assets. Second, when an early retiree lives off taxable assets, they leave their more protected assets (traditional and Roth retirement accounts) to grow. Diminishing vulnerable assets while growing protected assets improves the early retiree’s balance sheet from a creditor protection perspective.

Lastly, early retirees should always consider personal umbrella liability insurance and other relevant property and casualty insurance for creditor protection. 

Premium Tax Credit Planning

Living off taxable assets in early retirement limits taxable income. This has a good side effect. It increases the potential PTC available for early retirees using an ACA medical insurance plan. 

Reducing Future Uncontrollable Taxable Income

Roths and HSAs are great because their taxable income is entirely controllable, and generally speaking should be $0. Even traditional retirement accounts have very controllable taxable income. There are no RMDs until age 72, and even then the amount of taxable income is quite modest for the first few years. 

Taxable assets, on the other hand, expose the early retiree to uncontrollable taxable income, in the form of interest, dividends, and capital gain distributions. You never know when a mutual fund or other investment will spit out a taxable dividend or capital gain distribution. Such income reduces the runway for tax planning and can reduce PTCs.

Further, in recent years, we have become accustomed to living in a low-yield world. In the past decade plus a taxable portfolio has kicked off (in many cases) income yields of 3%, 2%, or less. Thus, the tax hit from taxable assets has not been too bad for many. That said, low yields are not guaranteed in the future. It could be that yields will rise, and thus taxable assets will generate increasing amounts of taxable income. 

By living off taxable assets first, early retirees reduce and ultimately eliminate taxable interest, dividends, and capital gain distributions generated by holding assets in taxable accounts. This reduces the tax cost of the overall portfolio, and makes planning MAGI, taxable income, and tax paid annually an easier and potentially more beneficial exercise. 

I discuss the early retirement Roth Conversion Ladder strategy in this video.

Conclusion

In many cases, I believe that the tax optimal path for the early retiree is to live off taxable assets first in early retirement prior to accessing Roth Basis, HSAs, and traditional retirement accounts. Of course, this is not individualized advice for you or any other particular individual. Those considering early retirement are well advised to consider their future drawdown strategy as they are building their assets. Those already retired should consider their own particular circumstances and ways to optimize their drawdown strategy. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Baby HSA

Are you married? Age 55 or older? You might have an opportunity to open up a small health savings account and get a $1,000 annual tax deduction!

HSA Contribution Limits

Health Savings Accounts (“HSAs”) have annual contribution limits. The limits depend on two things: medical insurance coverage through a high deductible health plan (a “HDHP”) and age. Here are the 2024 HSA contribution limits (hat tip to Kay Bell).

AgeHDHP Self CoverageHDHP Family Coverage
Under Age 55$4,150$8,300
Age 55 or Older$5,150$9,300

Family HDHP Coverage

Family HDHP coverage is coverage of an insured plus either or both a spouse or a dependent(s). Coverage must be the only medical insurance coverage the person has. 

HSA Catch-Up Contributions

Those age 55 or older can contribute an extra $1,000 per person to an HSA every year. While the “normal” contribution limits ($4,150 self / $8,300 family) are indexed for inflation, the $1,000 annual catch-up contribution limit is not indexed for inflation.

Two additional notes: First, as a practical matter, at age 65 a taxpayer will no longer qualify for an HSA (and thus, the catch-up contribution). This is because at age 65 most Americans switch from a HDHP to Medicare for their medical insurance. 

Second, for IRAs and qualified plans (such as 401(k)s), the age to be eligible to make “catch-up” contributions is 50. For HSAs, the age is 55, not age 50. 

HSA Contribution Limits for Married Couples

The normal contribution limits are coordinated. Thus, the family contribution maximum for a married couple is normally $8,300, not $8,300 times two. Here’s an example of how that works: 

Example 1: Steven and Holly are married, both age 45, and covered by a family high deductible health plan for all of 2024. Thus, each has an HSA contribution limit of $8,300. However, when looking at Steven’s limit, we must look at what Holly has contributed to her HSA for 2024. If Holly contributes $8,300 to her HSA for 2024, then Steven’s HSA contribution limit is reduced by Holly’s contribution to $0. 

Interestingly enough, catch-up contributions are not coordinated. Let’s change the example to have Steven and Holly be both age 55.

Example 2: Steven and Holly are married, both age 55, and covered by a family high deductible health plan (provided by Holly’s employer) for all of 2024. Thus, each has an HSA contribution limit of $9,300. Holly maxes out her 2024 HSA ($9,300) through payroll withholding (to get the payroll tax exclusion as well as the income tax exclusion). When looking at Steven’s normal contribution limit, we must look at what Holly has contributed to her HSA for 2024. Since Holly maxed out her HSA, Steven’s normal contribution limit is $0. However, Steven’s catch-up contribution limit is still $1,000, since it is not reduced for contributions Holly made to her HSA.

Steven is eligible for what I refer to as a Baby HSA. He will need to find a financial institution which offers HSAs. He can contribute up to $1,000 to his Baby HSA for 2024. Even better, Steven and Holly will get a $1,000 tax deduction on their 2024 tax return which lowers their adjusted gross income. 

Note that Steven’s Baby HSA cannot just be simply added to Holly’s HSA. Each of them have their own limits, and an HSA is an account in the name of a single owner (the same as an IRA). Thus, Steven will need to reach out to a financial institution to establish his own HSA. 

Benefits of the Baby HSA

Yes, a $1,000 tax deduction is nice, but it is not life changing. Let’s not pooh-pooh it too quickly, however. Steven might qualify for 10 years of that $1,000 Baby HSA, which is $10,000 of tax deductions. Second, Steven and Holly get this deduction against adjusted gross income, which means that they won’t have to claim itemized deductions to obtain it. 

Third, most tax deductions require giving up money to get a tax benefit. Often we think about business deductions, charitable contributions, and home mortgage interest. It’s great to take tax deductions for those, but you are giving up the money. The deduction for a Baby HSA contribution is simply moving money from a taxable account to an HSA: it’s still your money!

Last, an HSA deduction/exclusion is better than a deduction/exclusion for a traditional 401(k) contribution. In exchange for the upfront tax benefit, the traditional 401(k) will be fully taxable when withdrawn later on. Not so with the HSA. As long as the HSA is used to pay qualified medical expenses and/or to reimburse PUQME, the money comes out tax-free. No wonder I’m so fond of HSAs!

One additional benefit for retirees is the $1,000 deducted for a Baby HSA is $1,000 more of Roth conversions that can be slotted in at a low tax rate. The HSA deduction also lowers both adjusted gross income and “modified adjusted gross income” for Premium Tax Credit purposes, making it valuable for early retiree tax planning.

One Spouse Under Age 55

What happens if one of the spouses is under age 55? Here’s an example:

Example 3: Steven (age 56) and Holly (age 52) are married and covered by a family high deductible health plan provided by Holly’s employer for all of 2024. Thus, Holly has an HSA contribution limit of $8,300. Steven has an HSA contribution limit of $9,300, computed as a $8,300 normal contribution limit plus a $1,000 catch-up contribution limit. Holly maxes out her 2024 HSA ($8,300) through payroll withholding. When looking at Steven’s normal contribution limit, we must look at what Holly has contributed to her HSA for 2024. Since Holly maxed out her HSA, Steven’s normal contribution limit is $0. However, Steven’s catch-up contribution limit is still $1,000, since it is not reduced for contributions Holly made to her HSA.

Because Steven was 55 or older during the year, he still gets to contribute $1,000 to his Baby HSA. Holly’s age and contributions are irrelevant because the catch-up contributions of one spouse are not limited by the age and contributions of the other spouse. 

Watch me discuss the Baby HSA on YouTube. Stay to the end to see me butcher some 80’s movie trivia.

Conclusion

The Baby HSA is a nice tax planning tactic for married individuals with a HDHP as their only medical insurance between turning age 55 and going on Medicare. While limited in scale, the Baby HSA can provide real tax benefits and later tax-free growth. Of note, some ACA plans qualify as HDHPs. This means that the Baby HSA opportunity will exist for some using ACA plans in early retirement, as well as those covered by a HDHP through an employer. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

TikTok Tax Advice

There’s tax advice available on TikTok. Is it worth following? Does it miss the big picture?

Retirement Saving Through Various Forms of Life Insurance

TikTok tax advice often boils down to something like the following: don’t save in traditional retirement accounts where you will get crushed by taxes in retirement. Rather, save for retirement through permanent life insurance products (such as indexed universal life insurance policies) to get tax free growth and tax free withdrawals during retirement. 

Watch me discuss two problems with TikTok tax advice on YouTube.

This advice is not just offered on TikTok, though, anecdotally, it appears TikTok is at least something of a hub for promoting indexed universal life (“IUL”) and other forms of permanent life insurance. 

One recent example of this sort of advice posits a retired couple making $160,000 a year in IRA/401(k) distributions and $40K in Social Security/pension income and worries that the couple will have a terrible tax problem. 

But is that really the case? Let’s play it out with a detailed example.

Sally and Joe both turn age 75 in 2022. They are California residents. During their working years, they were prodigious savers in their workplace 401(k) plans, and their employers offered generous matching contributions. As a result, in 2022 they have required minimum distributions (“RMDs”) of $160,000. They also will have $40,000 of Social Security income, $4,000 of qualified dividend income, and $1,000 of interest income. Further, being tax savvy, they contribute $500 a month to their church through qualified charitable distributions (“QCDs”) from their traditional IRAs. They claim the standard deduction as their home is paid off and thus have no mortgage interest deductions. 

Alright, let’s see what Sally and Joe’s 2022 tax picture (all numbers are estimates) looks like:

First, their rough 2022 federal income tax return:

Federal Income Tax Return
RMDs$ 160,000
Social Security$ 40,000
15% Social Security Exclusion$ (6,000)
Interest$ 1,000
Qualified Dividends$ 4,000
QCD RMD Exclusion$ (6,000)
Adjusted Gross Income (“AGI”)$ 193,000
Standard Deduction$ (25,900)
Additional SD Age 65+$ (2,800)
Federal Taxable Income$ 164,300

Let’s turn to what their $164,300 federal taxable income means in terms of federal and California income taxes paid and their 2022 cash flow:

2022 Income Taxes and Cash Flow (Estimated)
Federal Income Tax$ 27,100
Effective Tax Rate on AGI14.04%
Marginal Federal Income Tax Rate22%
California Taxable Income (Approximate):$ 149,000
California Income Tax (Approx.)$ 7,862
Effective CA Income Tax Rate on Fed AGI4.07%
Marginal CA Income Tax Rate9.30%
Total Fed & CA Effective Income Tax Rate18.11%
Cash Flow After Fed & CA Income Tax & QCDs$ 164,038

By my math, after paying both income taxes and charitable contributions, this retired couple has $164,000 in cash flow for living expenses. Considering that, like many retirees, they live in a paid-off home, do we really believe there is a significant risk they will not be able to pay their bills? This couple ought to be able to enjoy a very pleasant, comfortable lifestyle, including recreational activities and travel.

Are Sally and Joe really getting crushed by income taxes? As residents of a high tax state, they do pay about $35K in combined federal and state income taxes. Sure, if $35K was on the table in front of you, you’d grab it pretty quick. But considering the $200K plus in cash flow they generated during the year, paying $35K in income taxes to the IRS and California is hardly financially debilitating. 

Most retired couples, even financially successful couples, will not have federal adjusted gross income of $193,000. If Sally and Joe are not crushed by income taxes (paying just an 18.11% estimated effective rate even living in a high-tax state), it is likely most retirees will be able to withstand the tax hits at retirement from having significant savings in traditional deferred retirement accounts. 

The Trade-Off Unstated on TikTok

TikTok tax advice often presents the boogeyman of taxes in retirement. It says “don’t invest in your 401(k) because it will get crushed in retirement.” Even if that were true, it usually neglects an important consideration: the upfront benefit of investing in a 401(k). 

During their working careers, it is likely that Joe and Sally were subject to marginal income tax rates of 24% or more federal and 9.3% California. Had they used permanent life insurance to save instead of using their 401(k)s, they would have lost 33 cents (or more) on every dollar in immediate tax savings, as there is no tax deduction for amounts contributed to life insurance policies.

The existence of the tax deduction for amounts contributed to a traditional 401(k) does not automatically mean that using permanent life insurance products for retirement is a bad idea. However, in weighing the tax benefits of the traditional 401(k) approach compared to the permanent life insurance approach, one must consider the immediate, and potentially substantial, tax benefits of traditional 401(k) contributions. 

One consideration in weighing the pros and cons of each: traditional 401(k) contributions generally get a tax benefit at the taxpayer’s marginal tax rate, while withdrawals from traditional 401(k)s and IRAs are more generally taxed at a taxpayer’s lower effective rate. On the way out, withdrawals are taxed through the relatively progressive tax brackets existing today, getting the benefits of the 10%, 12%, and 22% federal income tax brackets. 

Uncertainty

But, Sean, what about future tax rate increases! The federal government is running a huge deficit and it’s not getting any better.

This is a valid point. But let’s consider a few things. First, in my example, Sally and Joe were subject to a 33.3% marginal tax rate during their working years, and barely over an 18% effective tax rate during their retirement. For the math to work out to make permanent life insurance more attractive (tax-wise) than traditional 401(k)s for them, tax rates would need to be increased substantially, by over 80%. Thus, even if tax rates on retirees such as Joe and Sally were to increase 85% from current levels, the tax math might only marginally favor using permanent life insurance instead of a traditional 401(k). 

Second, if there are going to be income tax rate increases, they are more likely to be to the upper tax brackets. There are fewer taxpayers (read: voters) subject to the higher tax brackets, so those are the ones the politicians are more likely to increase. Increasing the 10%, the 12%, and/or the 22% tax brackets will impact more voters and lead to more election risk for the politicians.

Third, recent history suggests that the politicians are not likely to target retirees. It’s true that Social Security went from being tax free to being largely subject to taxation, up to 85% taxable. Interestingly enough, the second Social Security tax increase, which subjected Social Security to possibly being 85% taxable, passed through a Democratic Congress in 1993. The following year the Democrats suffered historic losses in the House and Senate elections. Many factors came into play, but it is interesting that since 1994 tax policy has generally benefited retirees (no more tax increases on Social Security, increasingly progressive tax brackets, and the increased standard deduction). 

Perhaps the politicians in both parties have learned a lesson when it comes to retiree taxation.

Is there zero risk that retirees could be subject to higher taxes in the future? Absolutely not. But, is that risk great enough to eschew traditional 401(k) contributions in favor of permanent life insurance? Not in my opinion.

Further, there are simpler, less costly planning techniques other than permanent life insurance that those using 401(k)s for retirement planning can avail themselves of, including Roth accounts and health savings accounts. 

Roth Accounts

Savers worried about future tax rate hikes have a simple, easy to implement tool to hedge against future tax rate increases: the Roth IRA. The Roth IRA solves the same tax problem that permanent life insurance solves for. In today’s environment, Roth IRAs are available at a vast array of financial institutions with very low fees. 

As I have previously discussed, many savers will benefit from the combination of a maxed out traditional 401(k) and a maxed out annual Roth IRA. 

Many will point out the possibility of much greater contributions to an indexed universal life insurance policy than to a Roth IRA. While true, many of those concerned with getting large amounts into tax-free accounts while working can turn to the Roth 401(k), which has significantly greater annual contribution limits than the Roth IRA. 

Roth Conversions

Many in the FIRE community have access to Roth conversions during what are likely to lower taxable income years. The tax idea behind retiring early is to load up on traditional 401(k) contributions during working years, and then convert amounts inside traditional retirement accounts to Roth accounts during early retirement years prior to collecting Social Security. 

In early retirement years, many in the FIRE movement appear, at least initially, to be poor on their tax return. No longer working, and not yet collecting Social Security, one’s tax return only includes interest income, dividend income, and some capital gains income. If that income is relatively low (which it is likely to be for many early retirees), it likely leaves room for Roth conversions at the 10% or 12% tax brackets during early retirement. 

This is tax rate arbitrage. First, deduct 401(k) contributions in the 24% or greater federal income tax brackets during one’s working years. Then, during early retirement, convert amounts in the traditional retirement accounts at a 10%, 12%, or perhaps 22% marginal federal income tax rate. 

Two observations: A) using permanent life insurance instead of traditional 401(k) contributions followed by early retirement Roth conversions denies members of the FIRE community a significant tax rate arbitrage opportunity. While there is no taxable income inclusion when withdrawing from a permanent life insurance policy, there is also no tax deduction for contributions to IULs, whole life insurance, and other permanent life insurance policies. 

B) By doing Roth conversions during early retirement, FIRE members reduce the uncertainty risk described above. FIRE members face a shorter time frame during which significant savings are in traditional retirement accounts, as the goal is (generally speaking) to get the money (mostly) converted to Roths prior to age 70.

The Roth conversion tool reduces the risk that future tax increases will crush savers who mostly use traditional 401(k)s during their working years. While this is true for all savers, it is most especially true for members of the FIRE community. 

A note on tax optimization: Imagine Joe and Sally were retired at age 55, today’s tax laws existed, and they had many years with artificially low taxable income. Say they did not do Roth conversions during this time. Is that a mistake? From a tax optimization perspective, absolutely. They would have likely been able to do Roth conversions at a 10% or 12% federal income tax rate, which is lower than both their retirement 22% marginal federal income tax rate and 18.11% combined effective income tax rate. While they are not tax optimized, they are something more important in my example: financially successful. Yes, tax optimization is important, but it is not the be-all and end-all. My guess is that financially successful individuals do not regret the failure to tax optimize on their deathbeds, though I look forward to reading Jordan “Doc G” Grumet’s new book to be sure. 

Conclusion

I’m not here to tell you exactly how to save for retirement. But I am concerned that TikTok tax advice has two deficiencies. First, it overstates the problem of taxation in retirement. Is there a potential problem? Yes. Is it as severe as some make it out to be? Not under today’s laws. Further, there are tactics such as annual Roth IRA contributions and Roth conversions during early retirement that can address the problem. Second, TikTok tax advice understates the current benefit of deductible traditional 401(k) contributions during one’s working years. 

Further Reading

Forbes has recently published two articles on the sorts of insurance policies frequently promoted on TikTok. They are available here and here. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Mystery of the Disappearing Tax Basis

Tax loss harvesting is all the rage in a down stock market. Did you know that it can create a mystery worthy of the Hardy Boys? Read on to find out how tax basis can disappear because of tax loss harvesting and the wash sale rule. 

Tax Loss Harvesting

I’ve previously written about tax loss harvesting. The idea is to sell a stock, bond, mutual fund, ETF, or other asset at a loss and report that loss on a tax return. That loss can offset other capital gains, and after having done that, it can offset ordinary income (W-2 income, interest income, etc.) up to $3,000 per year. Unused capital losses can be carried forward to subsequent tax returns indefinitely.

Tax loss harvesting is a nice tactic and in the right circumstances can be beneficial. That said, tax loss harvesting should not be a primary driver of one’s investment portfolio allocation. 

The Wash Sale Rule

The opportunity presented by tax loss harvesting has a major hurdle: the wash sale rule. Any acquisition of the same asset or a “substantially identical” asset 30 days before or 30 days after the sale at a loss denies the loss on the tax return. This is a very logical rule, considering the potential for abuse. Here’s an example:

Example 1: Sal owns 30 shares of Acme Corporation stock. He purchased it for $200 per share, and it is now worth $140 per share. Without the wash sale rule, Sal could sell all 30 shares for $140 on December 1st (triggering a $1,800 loss on his tax return) and then purchase 30 shares of Acme Corporation on December 2nd for its current value and have very little change in his economic position. 

Seen through the lens of Sal’s example, the wash sale rule makes sense. Why should Sal get to claim a loss on 30 shares of Acme stock he owns at year-end?

However, the wash sale rule can be implicated in less clear cut situations. Here’s one example:

Example 2: Cate owns 500 shares of IBM stock* in her taxable brokerage account. She purchased each share for $150 per share. On July 6, 2022, she sold 300 shares for $140 per share, realizing a $3,000 capital loss (300 times $10 loss per share). On July 29, 2022, IBM paid a dividend of $3 per share ($600 total on Cate’s remaining 200 shares), which Cate automatically reinvested in IBM stock, now valued again at $150 per share. 

In Cate’s case, the dividend reinvestment purchased 4 shares of IBM stock within the 61-day wash sale window. The taxable loss on 4 shares of the 300 sold ($40 total) is disallowed by the wash sale rule, and Cate will only be able to claim a taxable loss of $2,960 on the July 6th sale. 

* All values used in this blog post are hypothetical for purposes of the example. I did not look up IBM’s actual stock prices on these dates. The IBM dividend is also made up for the sake of the example.

One interesting tidbit about the wash sale rule in today’s environment: as the rule only applies to “securities” it does not apply to cryptocurrencies. Thus, an investor can sell a cryptocurrency at a loss on one day and repurchase it a day later and claim the entire loss on his or her tax return. There are proposals to do away with this treatment and subject cryptocurrencies to the wash sale rule. 

Retirement Accounts and the Wash Sale Rule

Let’s change Cate’s example just a bit, by having the repurchase occurring inside a Roth IRA.

Example 3: Cate owns 300 shares of IBM stock in her taxable brokerage account. She purchased each share for $150 per share. On July 6, 2022, she sold all 300 shares for $140 per share, realizing a $3,000 capital loss (300 times $10 loss per share). Separately, Cate owns 200 shares of IBM in her Roth IRA. On July 29, 2022, IBM paid a dividend of $3 per share ($600 total on Cate’s remaining 200 shares), which Cate’s Roth IRA automatically reinvested in IBM stock, now valued again at $150 per share. 

What result? The IRS has issued a Revenue Ruling, Rev. Rul. 2008-5, ruling that if the repurchase occurs inside the taxpayer’s Roth IRA or traditional IRA, the wash sale rule applies. Cate would suffer the exact same $40 wash sale rule loss disallowance. 

Note that a Revenue Ruling is not binding on taxpayers and the courts. Of course, a judge or appellate court may agree with the conclusion the IRS reaches in a Revenue Ruling, but they are not obligated to do so based solely on the IRS having issued the ruling. Rev. Rul. 2008-5 cites two 1930s court cases as authority for the conclusion reached in the ruling. Those cases involve a taxpayer using a controlled corporation to attempt to get around the wash sale rule, and the courts ruled that the wash sale rule applied regardless. 

In my research, I have not found any published court cases which have weighed in on Rev. Rul. 2008-5. The wash sale rule, as found in Section 1091, does not explicitly deem a retirement account and its owner to be the same person. Thus, there is at least some (perhaps quite small) risk to the IRS that a court would deem the primary result in Rev. Rul. 2008-5 to be too much of a stretch. That said, I certainly would not recommend taking a position counter to the ruling. I would struggle to advise that the wash sale rule does not apply if the security is repurchased in a retirement account. 

Disappearing Basis?

The wash sale rule disallows a loss, but it does not disallow basis. Section 1091(d) of the Internal Revenue Code and Treasury Regulation Section 1.1091-2 provide for a tax basis adjustment so that taxpayers are ultimately made whole after the application of the wash sale rule. Broadly speaking, the tax rules allow the disallowed loss to be added to the basis of the repurchased asset. In my Example 2 above, the basis of the 4 shares Cate repurchased is their historic cost ($150 per share) increased by the $10 per share disallowed loss. Thus, if Cate later sells those 4 shares, she will have a basis of $160 in those shares for purposes of determining gain or loss. 

In theory, the wash sale rule is simply a timing rule. It is inappropriate to allow a taxpayer to currently claim a loss when they wind up holding the exact same stock or securities. But, over time the tax basis rules should work out such that ultimately the correct amount is taxed to the taxpayer. 

What about basis adjustments when the wash sale occurs because of a repurchase made inside a retirement account? Rev. Rul. 2008-5 states that there is no basis adjustment with respect to a retirement account. There is an argument that Section 1091(d) should create Pro-Rata Rule basis in a traditional IRA. However, considering how highly technical and structured IRAs are, that is not a very likely outcome were the issue ever to be litigated. Further, that outcome would (quite oddly) give the taxpayer a different basis result based on whether they repurchased in a Roth retirement account or a traditional retirement account.

So what becomes of the basis? Does it just disappear? If the basis vanishes, the taxpayer obtains a worse wash sale result by repurchasing inside a retirement account. It seems odd that a taxpayer would receive a worse outcome for doing a repurchase through a retirement account instead of through a taxable brokerage account. 

Solving the Disappearing Basis Mystery

I have a theory that might solve the mystery. 

To get us started, consider that neither the Revenue Ruling nor Example 3 above discuss the “replacement property” in the taxable brokerage account. Here are two examples to ponder.

Example 4: Tim owns 1,000 shares of Domestic Equity Mutual Fund A (worth $50,000) he purchased for $60,000. It is held in a taxable brokerage account. On December 1, 2022, he sold Domestic Equity Mutual Fund A for $50,000 cash. He used the cash received to fund living expenses (food, clothing, heating bills, travel expenses, insurance, gasoline, etc.). On December 2, 2022, Tim purchased 1,000 shares of Domestic Equity Mutual Fund A in his Roth IRA. 

Example 5: Tim owns 1,000 shares of Domestic Equity Mutual Fund A (worth $50,000) he purchased for $60,000. It is held in a taxable brokerage account. On December 1, 2022, he exchanged all of his Domestic Equity Mutual Fund A for $50,000 worth of International Equity Mutual Fund B. On December 2, 2022, Tim purchased 1,000 shares of Domestic Equity Mutual Fund A in his Roth IRA. 

The wash sale rule disallows the $10,000 capital loss in both Example 4 and Example 5. But does Tim lose $10,000 of basis permanently? If he does, it’s an odd result considering that had he repurchased Domestic Equity Mutual Fund A in a taxable brokerage account (instead of in a retirement account), he would not lose that basis. 

I believe that there is a reasonable possibility that a court would rule that the $10,000 of basis shifts to the replacement property received in the wash sale. In Example 4, that conclusion leads Tim to no better position: he uses the cash for personal expenses, and there is no tax deduction for personal expenses. Further, I can’t imagine a court would give a step up in basis in Tim’s functional currency, the U.S. dollar. 

As applied to Example 5, where there has been a reinvestment in a taxable brokerage account, the equities of the situation might encourage some judges to find that Tim’s International Equity Mutual Fund B basis at a later sale is $60,000, not $50,000. 

Tim originally had $60,000 of basis in the system. While it is appropriate for a current loss to be disallowed, it is not appropriate for Tim’s basis in the system to be diminished in a situation where his overall taxable investment has not changed.

It’s one thing for the wash sale rule to operate to deny Tim a current loss deduction. It’s entirely another thing to interpret the wash sale rule to both deny current loss recognition and to permanently deny Tim $10,000 of basis. In its enactments of the wash sale rule and of the basis rules, Congress never manifested an intention for this one-two punch to bite Tim twice. If Tim sells the International Equity Mutual Fund B shares and recovers only $50,000 of basis he is inappropriately overtaxed. 

I believe some judges might determine that the IRS cannot have its cake (wash sale loss disallowance) and eat it too (permanent basis reduction). Basis exists to appropriately tax property transactions. Allowing Tim only $50,000 of future basis recovery over-taxes a later sale of his International Equity Mutual Fund B shares. While the IRS has a good argument that the wash sale rule disallowance should be spread to retirement account repurchases, it does not have a good argument that the overall result should be worsened if the repurchase occurs inside a retirement account.

Further, there is at least some risk to the IRS that a court would consider them to have reached just a bit by applying the wash sale rule to a repurchase inside a retirement account. The court might determine that what is good for the goose is good for the gander: if the IRS can reach a bit to apply the wash sale rule, the taxpayer can reach a bit to adjust the basis of the newly acquired securities in the taxable account.

The policies behind the rules point in the direction of allowing a taxpayer to add the disallowed loss to the basis of any replacement capital asset obtained through a direct exchange or a close-in-time use of the sales proceeds.

My proposed resolution has basis behave as it does in more familiar contexts. Say you received $50 from your grandmother when you were 12 years old. If you spent it on movie tickets and going bowling, the basis vanished for tax purposes. What if, instead, you purchased one share of stock of a publicly traded company for that $50? You’d get $50 of basis in that share of stock. Same with your first job: if you spend your first $1,000 W-2 paycheck on rent and groceries, tax basis disappears. But if you take that $1,000 and buy shares of ABC Mutual Fund in a taxable brokerage account, the basis stays attached to the mutual fund shares. Basis surviving when assets are reinvested in capital assets is a logical outcome.

Conclusion

Does anyone know for sure what happens to basis when the wash sale rule is tripped due to a repurchase in a retirement account? I believe it is still an unsolved mystery. 

Does basis vanish into the night? Or can it be preserved if the taxpayer reinvests in a capital asset in a brokerage account, as I have suggested?

Remember, the text of the Revenue Ruling does not affirmatively state that the basis simply disappears. Rather, all it says is that the basis does not get added to the taxpayer’s basis in the retirement account. To my mind, that’s a clue. It is not a definitive answer to the mystery. 

Now that we are 14 years removed from the issuance of Rev. Rul. 2008-5, it might be time for the IRS and Treasury Department to revisit the basis issue. The government could issue a regulation or another Revenue Ruling addressing the basis result in a situation similar to my Example 5. 

Of course, for taxpayers, this mystery is best avoided if possible. Repurchases should either (i) occur outside of the 61-day wash sale window or (ii) be of securities that are not the same or substantially identical to the sold securities.

I’ve also posted a video on YouTube with thoughts on this topic.

Lastly, the above is simply my technical analysis. It is not legal advice applicable to any one particular taxpayer or real life situation. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Four Ways to Fight Inflation

Decisions you make today can subject you to more inflation tomorrow! Read below about ways to increase or decrease your exposure to inflation tomorrow.

Watch me discuss fighting back against inflation.

Tax Planning

As a practical matter, most Americans have the majority of their retirement savings in traditional, pre-tax vehicles such as the 401(k). Having money in a traditional 401(k) is not a bad thing. However, the traditional 401(k) involves trade offs: an upfront tax deduction is the primary benefit in exchange for future taxation when there is a withdrawal or Roth conversion.

Having money inside traditional retirement accounts subjects future inflation to taxation. Some of the future growth in a traditional retirement account is likely to be attributable to inflation, and thus there will be a tax on inflation. Further, there are no inflation adjustments when it comes to the taxation of traditional IRA and traditional 401(k) withdrawals. 

An antidote to this problem is the tax free growth offered by Roth accounts and health savings accounts. Getting money into Roths and HSAs excuses future growth from taxation, including growth attributable to inflation. 

Roth 401(k) versus Roth IRA

Of course, inflation is only one consideration. Many will do some traditional retirement account contributions and some Roth retirement account contributions. The question then arises: which Roth account to use? 

My view is that for many a Roth IRA contribution (whether a direct annual contribution or a Backdoor Roth IRA) is better than a Roth 401(k) contribution. Many do not qualify to deduct a traditional IRA contribution but can deduct a traditional 401(k) contribution. Considering that reality, why not combine a deductible traditional 401(k) contribution and a Roth IRA contribution? 

Long Term Fixed Rate Debt

Often we discuss how inflation hurts Americans, and we should be concerned about the bad effects of inflation. However, there is a way to become a beneficiary of inflation: using long-term, low interest fixed rate debt to your advantage.

That’s right: hold onto that low rate 30 year mortgage like it’s a life raft! Okay, that’s a bit hyperbolic, but the overall point holds. Inflationary environments are great for debtors, particularly those debtors who have locked in a low interest rate for a long term.

Here is an example: Sarah and Mike have a 30 year, $400,000 mortgage on their primary residence at a 2.9% fixed interest rate. By paying the required monthly payment, and no more, they benefit from any future inflation. By paying off the mortgage later rather than sooner, they are using devalued future money to pay the mortgage rather than more valuable current day dollars. 

Sarah and Mike benefit from inflation! Are there reasons to pay off a mortgage early? Sure. But in an inflationary environment, paying off the mortgage early gives the bank more valuable dollars to satisfy the debt.

To my mind, a fixed rate, long term mortgage is a great hedge against inflation.

That said, there are few perfect financial planning tactics. Most involve risk trade offs. One risk Sarah and Mike assume by not paying down the mortgage early is the risk of deflation. To obtain this inflation hedge, they expose themselves to the risk of deflation. If the U.S. dollar starts to deflate (i.e., it appreciates in value), Sarah and Mike will find themselves paying more valuable dollars to the bank in the future. 

Travel Rewards

Travel rewards can help fight inflation. One way is using sign-up bonuses and other accrued points to pay for hotel room nights or flights. Using points gets out of cash paying and thus inflation of the dollar hurts a bit less.

However, keep in mind that travel reward points are subject to their own inflation! The hotel chain or airline can devalue the redemption value of points at any time. Thus, if everything else is equal, those with significant travel rewards point balances might want to spend those points sooner rather than later for travel. 

A second consideration are the features of credit cards. Some travel branded credit cards come with certificates for free nights or a companion pass for a companion to receive free or discounted flights. If flighting inflation is a key goal, favoring cards that offer free-night certificates or companion passes can be a way to fight inflation. 

Spending that Leads to More or Less Future Spending

We’re used to assessing the price tag. $28,000 for that brand new car: “that’s a great deal!” or “that’s a terrible deal!” But the price tag is only one part of the financial picture.

If you buy a black cup of coffee at Starbucks, it might cost you $2.65. Fortunately, that’s it. The cup of coffee isn’t likely to cause you to incur later costs.

What about a $45,000 SUV? That purchase will cause later costs, many significant. For example, the cost to insure a $45,000 SUV might be significantly more than insuring a $22,000 sedan. What about gas? By purchasing a larger, less fuel-efficient car, you lock in more future spending, and thus more exposure to future inflation. 

Think about buying a large home with a pool in the backyard. That square footage attracts property tax, heating and cooling costs, and inflation in both costs. The pool in the backyard requires constant upkeep, subjecting the homeowner to another source of inflation. 

To my mind, food is a big one in the fight against inflation. What you eat today could very well translate into medical costs tomorrow, exposing you to significant inflation. Spending on foods with vegetable oils and sugars today is likely to increase your future exposure to medical expense inflation. 

The lesson is this: you can use today’s spending to reduce your exposure to future inflation. 

Conclusion

Is there a perfect answer to inflation? No. But with some intentional planning and spending today, Americans can reduce their exposure to the harmful effects of future inflation. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Sean Discusses the Four Percent Rule on the ChooseFI Podcast

Why was your grandparents’ furniture horribly out of date? There’s a reason that has to do with financial independence!

I had a great conversation about grandparents’ furniture, inflation, and the four percent rule with Brad and Jonathan on the ChooseFI podcast. You can access the episode on all major podcast players or on the ChooseFI website: https://www.choosefi.com/the-four-backstops-to-the-four-percent-rule-sean-mullaney-ep-376/

During the episode, we reference my recent blog post, The Four Backstops to the Four Percent Rule.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Tax Increase in SECURE 2.0

There’s a tax increase in the new SECURE Act 2.0 legislation. Unfortunately, it falls largely on those least equipped to shoulder it.

Catch-Up Contributions

Since enacted in 2001, “catch-up” contributions have been a great feature of 401(k) plans. Currently, they allow those age 50 or older to contribute an additional $6,500 annually to their 401(k) or similar plan. Those contributions can be traditional deductible contributions, Roth contributions, or a combination of both.

The idea is that by age 50, workers have much less time to make up for deficiencies in retirement savings. Thus, the law allows those workers to make catch-up contributions to have a better chance of financial success in retirement.

Other than age (must be at least 50 years old), there are no limits on the ability to make catch-up contributions. That could be viewed as a give-away to the rich. However, it is logical to keep retirement savings rules simple, especially those designed to help older workers behind in retirement savings.

Watch me discuss SECURE 2.0’s tax increase on catch-up contributions

Catch-Up Contributions for Those Behind in Retirement Savings

For those behind in retirement savings, deducting catch-up contributions usually makes the most sense. First, many in their 50s are in their highest earning years, and thus tax deductions are their most valuable. Second, those behind in retirement savings are not likely to be in a high tax bracket in retirement. With modest or low retirement income, they are likely to pay, at most, a 10% or 12% top federal income tax rate in retirement.

Here is an example of how that works:

Sarah, single and age 55, is behind in her retirement savings, so she maxes out her annual 401(k) contribution at $27,000 ($20,500 regular employee contribution and $6,500 catch-up contribution). Sarah currently earns $130,000 a year and lives in California. Since she deducts her catch-up contributions, she saves $2,165 a year in taxes ($6,500 times 24% federal marginal tax rate and 9.3% California marginal tax rate). That $2,165 in income tax savings makes catching up on her retirement savings much more affordable for Sarah.

Sarah’s approach is quite logical. If things work out, Sarah can make up the deficit in her retirement savings. Doing so might push her up to the 12% marginal federal tax bracket and the 8% marginal California tax bracket in retirement.

For someone like Sarah who is behind in their retirement savings, the Roth option on catch-up contributions is a very bad deal!

SECURE 2.0 and Catch-Up Contributions

SECURE 2.0 disallows the tax deduction that people like Sarah rely on. It requires all catch-up contributions to be Roth contributions. For the affluent, this makes some sense. Why should someone with very substantial assets get a tax deduction when they already have a well-funded retirement?

Sadly, many Americans in their 50s and 60s do not have well-funded retirements. Removing the tax deduction for catch-up contributions increases their taxes. These are people who can least afford to shoulder a new tax. The goal should be to make it easier for those behind in retirement savings to catch-up. Taking away this tax deduction makes it more difficult to build up sufficient savings for retirement.

Fortunately, as of this writing SECURE 2.0 has only passed the House. It has not passed the Senate. Hopefully this provision will be reconsidered and will not ultimately become law.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Four Backstops to the Four Percent Rule

Introduction

Worried about an early retirement based on the Four Percent Rule? Might the 4% Rule work because of natural backstops most early retirees enjoy? 

The 4% Rule

The 4% Rule is a rule of thumb developed by the FI community. For example, JL Collins writes extensively about the 4% Rule in Chapter 29 of his classic book The Simple Path to Wealth.

Boiled down, the rule of thumb states that an investor can retire when he or she (or a couple) has 25 times their annual expenses invested in financial assets (equities and bonds). They would then spend down 4% of their wealth annually in retirement. The first year’s withdrawal forms a baseline and is increased annually for inflation.

The idea behind the 4% Rule is that the retiree would have a very strong chance of funding retirement expenses and never running out of money in retirement. As a result, some refer to 4% as a safe withdrawal rate. 

Here’s how it could look:

Maury is 50. He has $1M saved in financial assets. He can spend $40,000 in the first year of retirement. If inflation is 3% at the end of his first year of retirement, he increases his withdrawal by 3% ($1,200) to $41,200 for the second year of retirement.

The 4% Rule has a nice elegance to it. Most investors aim for a greater than 4% return. In theory, with a 5% return every year, the 4% Rule would never fail a retiree. If you spend approximately 4% annually, and earn approximately 5% annually, you have, in theory, created a perpetual money making machine and guaranteed success in retirement.

Watch me discuss the Four Backstops to the 4% Rule

The theory is great. But in practice we know that investors are subject to ups and downs, gains and losses. What happens if there is a large dip in equity and/or bond prices during the first year or two of retirement? What if there are several down years in a row during retirement? 

As a result of these risks, and stock market highs in late 2021, some are worried that the 4% Rule is too generous for many retirees. Christine Benz discussed her concerns on a recent episode of the Earn and Invest podcast. 

This post adds a wrinkle to the discussion: the four backstops to the 4% Rule for early retirees. What if worries about the adequacy of the 4% Rule for early retirees can be addressed by factors outside of the 4% Rule safe withdrawal rate? And what if those factors quite naturally occur for early retirees?  

Resources for the Four Percent Rule

These are links to articles addressing the 4% Rule and safe withdrawal rates

Cooley, Hubbard, and Waltz (Trinity University) 2011

Bengen 1994

Below I discuss what I believe to be the four natural backstops to the 4% Rule. 

Spending

A 4 percent spending rate in retirement is not preordained from on-high. Spending in retirement can be adjusted. Those adjustments can take on two flavors.

The first flavor are defensive spending reductions.  As Michael Kitces observed on an episode of The Bigger Pockets Money podcast, retirees will not blindly spend 4 percent annually without making adjustments in down stock markets.

See that the stock market is down 10 percent this month? Okay, take a domestic vacation for 6 days instead of an international vacation for 9 days. Buy a used car instead of a new car. Scale down and/or delay the kitchen remodel.

There are levers early retirees can pull that can help compensate for declines in financial assets while not too radically altering quality of life. 

The second flavor is, from a financial perspective, even better. As early retirees age, there will be natural reductions in spending. How many 80 year-olds decide to take a 12 hour flight to the tropics for the first time? There is a natural reduction in energy and interest in certain kinds of spending as one ages. It is likely that many retirees will experience very natural declines in expenses as they age. 

Social Security

For the early retiree under 62 years old, the 4% Rule must disregard Social Security. Why? Because Social Security does not pay until age 62, and many in the financial independence community delay Social Security payments beyond age 62, perhaps all the way to age 70 (to increase the annual payment).

Here is an example of how that works.

Melinda is 55. She has accumulated $1.5M in financial assets and can live on $60,000 per year. If she retires at age 55 and lives off $60,000 a year increased annually for inflation, the only financial resources she has are her financial assets (what I refer to as her 4% assets). She cannot live off Social Security payments until age 62, and may choose to defer receiving Social Security up to age 70. 

If Melinda defers Social Security until age 70, and receives $2,500 per month at age 70 from Social Security, her 4% assets now do not need to generate the full 4% once she turns 70, since Social Security will pay her $30,000 a year at age 70.

In theory, under the 4% Rule, Melinda’s Social Security is play money. Melinda funds her lifestyle with withdrawals from her financial assets, and now she’s getting additional Social Security payments. But, if her portfolio is struggling to produce the amount Melinda needs to live off of, Social Security payments provide a backstop and can help make up the difference. 

You might think “but wait a minute, didn’t Melinda significantly lower her Social Security benefits by retiring early by conventional standards? The answer is likely no, as I described in more detail in my post on early retirement and Social Security. First, only the 35 highest years of earnings count for Social Security benefits. At age 55 is it possible Melinda has 35 years of work in. 

Second, and more importantly, Social Security benefits are progressive based on “bend points.” The first approximately $12,000 of average annual earnings are replaced by Social Security at a 90 percent rate. The next approximately $62,000 of average annual earnings are replaced by Social Security at a 32 percent rate, and remaining annual earnings are replaced at a 15 percent rate. This is a fancy way of saying that reducing later earnings, for many workers, will sacrifice Social Security benefits at a 15 percent, or maybe a 32 percent, replacement rate. Even early retirees are likely to have secured all of their 90 percent replacement bend point and a significant amount of their 32 percent replacement bend point. 

I previously wrote the following example:

Chuck is 55 years old and has 32 years of earnings recorded with Social Security. Those earnings, adjusted for inflation by Social Security, total $2,800,000. Divided by 35, they average $80,000. This means Chuck has filled the 90 percent replacement bend point (up to $12,288) and filled the 32 percent replacement bend point (from $12,288 to $74,064) of average annual earnings. If Chuck continues to work, his wages will be replaced at a 15 percent replacement rate by Social Security. 

An additional year of work for Chuck at a $130,000 salary netted Chuck only $557 more in annual Social Security benefits at full retirement age! 

Real Estate

Most early retirees own their own primary residence, usually with either significant equity or no mortgage. That primary residence can be a backstop to the 4% Rule.

For example, a retiree might live in a 2,000 square foot, $500,000 home with no mortgage. During their retirement, they might decide they don’t want to maintain such a large home, so they sell the 2,000 square foot home and move into a 1,000 square foot condominium at a cost of $350,000. The $150,000 difference in sale prices can become a financial asset to backstop 4% Rule assets and help the retiree succeed financially.

Alternatively, the early retiree could sell the $500,000 home and move into a smaller apartment with a $2,000 per month rent. While the retiree has increased their expenses, they also have created $500,000 worth of financial wealth to help pay that rent and fund their other expenses.

A third option is a reverse mortgage where the retiree stays in their primary residence but gets equity out of the home from a bank. 

Real estate can serve as a natural backstop to help ensure retirees have financial security and success.

Death

It’s wet blanket time. You may be considering a 30, 40, or 50 year retirement. Unfortunately, there is a good chance that you will not live that long. Sadly, not all early retirees have a long retirement. 

As demonstrated in these tables, there is a real chance that an early retiree will not live for 25 or 30 years. That factors into whether or not the 4% Rule will work for an early retiree. 

Let’s consider a 55 year old considering early retirement using the 4% Rule. He believes that he will live 30 more years and there is a 95% chance that his assets will last 30 years. He believes that the 4% Rule has a 5% chance of failing him. Further, assume that he believes there is a 30% chance that he will die prior to age 85.

His own potential death reduces the chance that the 4% Rule will fail. Remember, failure requires that he has to both run out of assets and live long enough to run out of assets. By his estimation, the odds that both events will occur are just 3.5 percent. To figure this estimated probability, multiply the probability that he will run out of assets (5%) by the probability that he will live long enough to run out assets (70%). 

A not insignificant number of early retirees will have an early retirement that lasts (sadly) only 10 years, 15 years, or 20 years. That (again, sadly) backstops the 4% Rule. 

Early Retirees vs. Conventional Retirees

I’ve contended that early retirees have four natural backstops to the 4% Rule. What about more conventional retirees? I’ll define a “conventional retiree” as one who collects Social Security soon after retiring. 

I believe conventional retirees enjoy three of the four backstops. Sadly, they “enjoy” the mortality backstop to a greater degree than early retirees. 

Conventional retirees retiring on Social Security do not enjoy Social Security as a backstop to the 4% Rule in most cases. Here’s an example:

Robert is age 65 and is planning to retire on financial assets and Social Security. He will collect $36,000 a year in Social Security and will spend a total of $76,000 a year. To facilitate this, he will initially withdraw $40,000 from his $1M portfolio.

In Robert’s case, Social Security is not a backstop to the 4% Rule. Rather, the 4% Rule is simply one of two necessary but not sufficient sources of funds for his retirement. A failure of the 4% Rule in Robert’s case would not be backstopped by Social Security. 

Conclusion

While there are no guarantees when it comes to safe withdrawal rates in retirement and the 4% Rule, it is possible that many early retirees will succeed with the 4% Rule, for two reasons. First, the 4% Rule may, by itself, be successful for many early retirees. The second reason is that even if the 4% Rule fails, there are four natural backstops in place for many early retirees that can step in and help retirees obtain financial success even if the 4% Rule fails on its own.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

House Passes SECURE Act 2.0

It appears some changes are likely coming to the tax-advantaged retirement savings landscape, as the House of Representatives passed (by a 414-5 vote) the Securing a Strong Retirement Act of 2022. It now goes the Senate where the Senate Finance Committee is likely to offer their own version of the bill. Commentators have referred to this bill as the SECURE Act 2.0 or SECURE 2.0.

Here is the bill text.

This bill is not a paradigm shift in retirement saving and planning. Rather it makes many changes to the tax-advantaged retirement savings rules, most of which are small changes.

Here is a some brief points to consider:

My thinking about the bill

What expanding Roths (“Rothification”) means to the FI/FIRE community

The bill does not include the repeal of the Backdoor Roth IRA.

Deloitte materials on SECURE 2.0.

A good Twitter thread from Ed Zollars.

A nice summary of the most important points from Jamie Hopkins.

Post on ten provisions in the bill.

Stay Tuned: Some version of SECURE 2.0 is likely to be enacted in 2022, but it could get seriously changed in the U.S. Senate.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Early Retirement and Social Security

UPDATE October 20, 2023: This post has been updated for the 2024 Social Security numbers.

I can’t retire early! I’ll destroy my Social Security!

Is that true? What happens to Social Security benefits when retirees retire early? Are significantly reduced Social Security benefits a drawback of the financial independence retire early (FIRE) movement? 

Below I explore how Social Security benefits are computed and the effects of retiring early on Social Security.

Social Security Earnings

Form W-2 reports to the government one’s earnings during the year. For the self-employed, the Schedule SE performs this function. The Social Security Administration tracks those earnings. 

Only a limited amount of earnings every year count as Social Security earnings. There is an annual maximum on the amount of earnings that can go on one’s Social Security record, regardless of the number of jobs one has. For 2024, the Social Security cap is $168,600. The cap is increased most years for inflation. Payroll taxes for Social Security (FICA for W-2 workers, self-employment taxes for the self-employed) are not due on earnings above the cap.

Social Security Benefits

A few very general rules need to be established as we consider the amount Social Security pays.

  1. Only the highest 35 years of earnings during one’s working years count in determining Social Security benefits.
  1. For most Americans reading this, full retirement age is 67. This means a person can collect his or her “full” Social Security benefits at age 67.
  1. Social Security benefits can be collected as early as age 62 and can be deferred as late as age 70. Collecting early reduces annual benefits (by roughly 5 to 7 percent per year) and collecting late increases benefits (by 8 percent per year).
  1. Annual earnings used in determining benefits are inflation adjusted through age 59. Earnings earned at age 60 and later are not inflation adjusted for purposes of computing Social Security benefits. 
  1. Very roughly speaking, the annual benefit is computed as follows: accumulated earnings (computed based on the rules described above) in the high 35 years are summed and then divided by 35. The resulting average annual earnings are applied against the Social Security “brackets” or “bend points.” Up to $14,088 (using 2024 numbers) of computed average annual earnings is replaced by Social Security at a 90% rate. The next $70,848 of average annual earnings are replaced at a 32% rate. Any additional amount of average annual earnings is replaced at a 15% replacement rate. The bend points are adjusted for inflation.

One need not be an expert on Social Security to see directionally how early retirement might impact Social Security benefits. Because of the progressive nature of Social Security benefits, leaving work early (by conventional standards) tends to reduce benefits less than one might initially expect. Additional earnings later in life tend to only slightly increase Social Security benefits.  

Early Retirement Social Security Example

Here’s an example to help us understand the impact of an early retirement on Social Security benefits. 

Chuck is 55 years old and has 32 years of earnings recorded with Social Security. Those earnings, adjusted (thus, nominally increased) for inflation by Social Security, total $3,100,000 as of 2024. Divided by 35, they average $88,571. This means Chuck has filled the 90 percent replacement bend point (up to $14,088) and filled the 32 percent replacement bend point (from $14,088 to $84,936) of average annual earnings. If Chuck continues to work, his wages will be replaced at a 15 percent replacement rate by Social Security. 

If Chuck retires now and earns nothing more, his annual Social Security benefits, expressed in 2024 dollars, will look something like this at full retirement age:

Replacement RateReplaced Annual IncomeAnnual Social Security at Full Retirement Age
90%$14,088$12,679
32%$70,848$22,671
15%$3,635$545
Total$88,571$35,896

Note that I rounded each bend point’s calculation. With the cents Chuck gets in each bend point, his total is increased by almost a full dollar. Similar rounding applies to the examples below as well.

At age 67, Chuck’s annual Social Security will be $35,896 (expressed in 2024 dollars).

If Chuck continues to work for one more year at a $130,000 salary, and then retires his annual Social Security benefits at full retirement age, expressed in 2024 dollars, looks something like this:

Replacement RateReplaced Annual IncomeAnnual Social Security at Full Retirement Age
90%$14,088$12,679
32%$70,848$22,671
15%$7,349$1,102
Total$92,285$36,453

Interestingly, an additional year of work only increased Chuck’s annual Social Security benefit by $557. Why is that? Remember that every dollar earned is divided by 35 for purposes of computing Social Security benefits. You can see that Chuck’s replaced income increased by $3,714 (from $88,571 to $92,285). By earning $130,000 in 2024, Chuck increased his Social Security average annual income by $3,714, which is $130,000 divided by 35.

Multiplying the increase in replaced income ($3,714) by the replacement rate (15%) gets us the additional $557 in annual Social Security benefits. 

Okay, but what about three more years of earnings. Say Chuck can work for three more years at an average annual salary of $135,000. What result (in 2024 dollars) then? 

Replacement RateReplaced Annual IncomeAnnual Social Security at Full Retirement Age
90%$14,088$12,679
32%$70,848$22,671
15%$18,920$2,838
Total$103,856$38,188

Where I come from, $1,735 ($38,188 minus $36,453) in increased annual Social Security benefits at full retirement age is not nothing. But is it worth delaying retirement for three full years if one is otherwise financially independent? To my mind, probably not. 

Spousal Benefits

What if Chuck is married to Mary? How does that impact the analysis?

During Chuck and Mary’s joint lifetimes, it depends on whether Mary collects spousal benefits. If Mary has Social Security earnings of greater than 50 percent of Chuck’s Social Security earnings, she will likely collect benefits under her own earnings record, and not a spousal benefit. Thus, Chuck’s Social Security earnings will be irrelevant to the Social Security benefit Mary collects.

If, however, Mary’s lifetime Social Security earnings are less than 50 percent of Chuck’s, Mary is likely to collect a spousal benefit of roughly half of Chuck’s annual benefit. In this case, Chuck working 3 more years creates $2,603 of additional annual Social Security income ($1,735 for Chuck and $868 as Mary’s spousal benefit). Even $2,603 in additional annual income isn’t likely to justify Chuck working for three more years.

At Chuck’s death, assuming Chuck predeceases Mary, Mary will collect the greater of her own Social Security benefit or Chuck’s Social Security benefit. Thus, Chuck increasing his Social Security earnings could increase Mary’s Social Security benefit as a widow.

I’ve got a plan to save Social Security and Medicare.

Resource

Most people I know cannot tell you their Social Security earnings record off the top of their head. But, this information is accessible by creating an account at ssa.gov. From there, Americans can obtain their Social Security statement which includes their Social Security earnings (though the statement does not adjust those annual earnings for inflation). The 2024 factors to increase annual earnings for inflation can be found by entering “2024” in the search box at the bottom of this SSA.gov website.

Conclusion

There are many factors to consider before retiring early. It is helpful to understand how Social Security benefits are computed so early retirees can understand the potential impact of retiring on their Social Security benefits. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Two New Personal Finance Videos

To celebrate my new YouTube Channel’s one month anniversary, I posted two new videos this weekend. Enjoy!

Current events can inspire personal finance content creation. But should they change your financial plan?
Exploring the tax consequences of owning VTIAX.

You may notice some new background art, which I purchased from the StolitronArtDesign Etsy store.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post, and all videos, text, and comments on my YouTube channel, are for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Recipe for Reporting a Backdoor Roth IRA

When it comes to the Backdoor Roth IRA, I’ve seen it all. Reporting a Backdoor Roth IRA on tax returns remains confusing for both taxpayers and tax return preparers. Here’s the recipe I recommend using to report the Backdoor Roth IRA on the tax return and avoid overpaying taxes.

Watch me discuss reporting Backdoor Roth IRAs on tax returns.

Let’s consider a hypothetical Backdoor Roth IRA on a 2021 tax return.

Example: On January 1, 2021, John Smith contributed $6,000.00 to a traditional IRA. On February 1, 2021, John Smith converted the entire amount in his traditional IRA, $6,001.00, to a Roth IRA. On December 31, 2021, John Smith had a zero balance in all his traditional IRAs, SEP IRAs, and SIMPLE IRAs. John Smith’s income is such that he qualifies for neither a deductible traditional IRA contribution nor a regular annual Roth IRA contribution. John has no existing basis in traditional IRAs as of January 1, 2021. 

Ingredients

Dry Ingredients

  • Taxpayer & Spouse Form W-2 and/or self-employed retirement contributions
  • The prior year’s Form 8606 (if the taxpayer has existing traditional IRA basis – most Backdoor Roth IRA taxpayers do not)

Wet Ingredients

  • Forms 5498 from financial institutions
    • If not available, substitute (i) end-of-year balances in all traditional IRAs, SEP IRAs, and SIMPLE IRAs and (ii) taxpayer knowledge or IRA account statement
  • Forms 1099-R from financial institutions

Directions

First, Enter the Dry Ingredients

In order to ensure that the tax return software has all the information to properly report the Backdoor Roth IRA, the taxpayer’s and spouse’s Forms W-2 (if any) should be properly entered into the tax return software. In particular, if Box 13 is checked, that should be indicated in the tax return software. Any qualifying self-employed retirement plan (Solo 401(k), SEP IRA, SIMPLE IRA) contributions should also be entered into the software. This requires the computation of the Schedule C to validate the correctness of the self-employment retirement contributions. 

Lastly, any established and still existing traditional IRA basis reported on previously filed Forms 8606 must be entered into the software. For those who have properly done Backdoor Roth IRAs in the past, this is extremely rare, but not impossible. Most such taxpayers enter the year with $0 of such basis. 

None of these steps directly report the current year’s Backdoor Roth IRA. However, without properly completing them, the tax return software will be unlikely to report the Backdoor Roth IRA correctly. 

Second, Enter The Traditional IRA Contribution

The first step in the tax return process is entering the traditional nondeductible IRA contribution into the tax return software. In theory, this should come off the Form 5498 (Box 1). In practice, that is not likely. The Form 5498 is not required to be filed by the financial institution until May 31st. Vanguard, for example, provides these forms in mid-May. 

If the taxpayer has a Form 5498 when preparing their tax return (perhaps because they are filing the return on extension), Box 1 of the form should report the traditional IRA contribution. In most circumstances, taxpayers will use their own knowledge of the transaction or their IRA account statement to report that they made a $6,000 nondeductible traditional IRA contribution.

By entering the $6,000.00 traditional IRA contribution into the tax return software, John’s tax return should generate a Form 8606. This is crucial for two reasons. First, the nondeductible traditional IRA contribution must be reported. Second, the nondeductible contribution establishes the “basis” that keeps John’s Backdoor Roth IRA as almost entirely tax free. 

Note further that IRAs are a single person item, meaning that there is no such thing as a “joint” IRA. Each spouse must enter his or her information separately, and must file his or her own individual Form 8606 as needed. Where spouses can impact the calculations and reporting is the ability to deduct an IRA contribution where one spouse is covered by a workplace retirement plan and the other spouse is not. 

Third, Enter the Roth Conversion

This is where the tax return reporting can go a bit off the rails if one is not careful. Tax return software usually has an input for Forms 1099-R. The Form 1099-R should be entered into the tax return software. 

John’s Form 1099-R should look like this (please pretend it is for 2021):

It is important to input all of the boxes on the Form 1099-R in the tax return software to help ensure that the software understands the transaction and no penalties are charged (there should be none as the transaction is a Roth conversion).

Some worry about Box 2a reporting $6,001.00 as the “taxable amount.” It’s okay! The taxable amount is in fact $6,001.00. However, it must be remembered that taxpayers must pay tax on the taxable amount reduced by the allowed available basis. 

How do we know what the allowed available basis is? By preparing and filing the Form 8606! To prepare the Form 8606, we must have all the ingredients above. It will be important that the following information is input into the Form 8606:

  • Current year traditional IRA contribution ($6,000.00)
  • Current year Roth IRA conversion ($6,001.00)
  • Balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs on December 31, 2021 ($0 in John’s case)

At this point the first two data points are in the tax return software. The last one must now be added to the software. Assuming the tax return is prepared prior to May, the taxpayer needs to review all of their existing traditional IRAs, SEP IRAs, and SIMPLE IRAs to ensure that as of December 31, 2021 there were no balances in those accounts. If there were balances, they must be added up and reported on line 6 of the Form 8606.

The Finished Product

Here is what page 1 of John’s Form 8606 should look like out of the oven.

Because Line 6 is $0, John’s allowed available basis is $6,000, the amount of 2021 nondeductible traditional IRA contribution. Separately, I blogged about the result if there is a substantial amount on Line 6 (hint: the allowed available basis decreases sharply, see Example 2). 

Unfortunately, I know that at least one tax return preparation software references a worksheet instead of populating the form in the output that the taxpayer sees. The correct information is (apparently) communicated to the IRS through electronic filing, but I wish all software providers simply populated the form to make it easier for review. 

Having successfully completed the first page of the Form 8606, the odds are that page 2 will also be successfully completed. Here’s what it should look like:

The final check on all of this comes from page 1 of Form 1040. If the Form 8606 is not correctly prepared, page 1 of Form 1040 will not correctly reflect the taxation of the Backdoor Roth IRA.

Assuming the taxpayer completed a 2021 Backdoor Roth IRA as John Smith did, page 1 of Form 1040 should look like this:

The key lines are Line 4a and Line 4b. Line 4a will simply be the sum of all Box 1’s from Forms 1099-R. In John’s case, that is $6,001. Line 4b is where the confusion comes. If the Form 8606 is properly prepared, the correct amount from Line 18 of Form 8606 should be the taxable amount reported on Line 4b of Form 8606. 

Fixing Backdoor Roth IRA Errors

Errors in previously filed tax returns can be fixed! I previously blogged about amending previously filed tax returns in cases where a Backdoor Roth IRA has been mistakenly reported. 

2023 Tax Season Backdoor Roth IRA Tax Return Reporting

Watch me discuss Backdoor Roth IRA tax return reporting.

Conclusion

Getting Backdoor Roth IRA tax return reporting is the last vital step in successfully executing a Backdoor Roth IRA. While it is not a simple exercise, it can be navigated with educational resources such as this blog post.

While tax return preparation software is great, it does not replace a taxpayer’s own judgment. Ultimately it is up to the taxpayer to ensure that the tax return properly reports the Backdoor Roth IRA. In many cases it will be wise to use a professional tax return preparer to prepare a tax return if the taxpayer has done a Backdoor Roth IRA.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean on the Stacking Benjamins Podcast

I talk tax with Joe Saul-Sehy on today’s episode of the Stacking Benjamins podcast. Available on YouTube and all major podcast players. https://www.stackingbenjamins.com/stories-from-our-stackers-1158/

This post, podcast, and video are for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean Launches YouTube Channel

Enjoy videos on my brand new YouTube Channel. The channel will focus on tax and personal finance topics. I have ten tax videos up there to watch. My goal is to post a new tax or personal finance video every Saturday morning at 7AM Pacific.

Highlights include an update on 2022 Backdoor Roth IRAs, news on 72(t) payments, and one way to use tax planning to fight inflation.

Videos will usually be anywhere from 2 to 5 minutes.

I appreciate your viewing and liking my videos. Please subscribe to my channel.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post, and all videos, text, and comments on my YouTube channel, are for entertainment and educational purposes only. They do not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

What are Section 199A Dividends?

Did you receive a Form 1099-DIV which lists an amount in Box 5 “Section 199A dividends”? If so, you might be asking, what the heck are Section 199A dividends? 

You probably never came across the term “Section 199A dividends” in high school algebra. That’s okay. Below I discuss what a Section 199A dividend is and how to report it on your tax return. 

Watch me discuss how Section 199A Dividends are reported on tax returns.

Who Pays Section 199A Dividends?

Real estate investment trusts (“REITs”) pay Section 199A dividends. REITs are a special type of business entity. A REIT owns almost entirely real estate. Many office buildings, hotels, hospitals, malls, and apartment buildings are owned by REITs. Investors can own the stock of a single REIT, or they can own mutual funds or ETFs that are partly or entirely composed of REIT stock. For example, there are some REITs in the Vanguard Total Stock Market Index Fund (VTSAX). 

REITs are advantageous from a tax perspective. In exchange for paying 90 plus percent of its income out to investors as dividends, the REIT itself does not pay federal corporate income taxes. This results in REITs often paying higher dividends than companies in other industries. The dividends paid by the REIT are Section 199A dividends.

I discuss the Section 199A dividends paid by VTSAX in this video.

What is the Tax Benefit of a Section 199A Dividend?

A Section 199A dividend qualifies for the Section 199A qualified business income deduction. This is also referred to as the QBI deduction. The qualified business income deduction is a 20 percent federal income tax deduction. 

Here is an example of how the tax deduction works for Section 199A dividends.

Catherine owns shares of ABC REIT Mutual Fund. The mutual fund pays her $1,000.00 of dividends, all of which are Section 199A dividends reported to her in both Box 1a and Box 5 of Form 1099-DIV. She gets a $200 qualified business income deduction on her federal tax return (20 percent of $1,000.00) because of the $1,000.00 of Section 199A dividend.

There are several things to keep in mind when considering Section 199A dividends:

  1. Section 199A dividends are a slice of the pie of dividends. The full pie of dividends, “total ordinary dividends,” is reported in Box 1a of Form 1099-DIV. Since Box 1a reports all of the dividends, Box 5 must be equal to or less than Box 1a.
  1. There is no income limit (taxable income, MAGI, or otherwise) on the ability to claim the Section 199A qualified business income deduction for Section 199A dividends. The QBI deduction for self-employment income is generally subject to taxable income limitations on the ability to claim the deduction. Not so with the Section 199A dividends. Taxpayers can claim the QBI deduction for Section 199A dividends regardless of their level of income.
  1. Taxpayers get the Section 199A QBI deduction regardless of whether they claim the standard deduction or itemized deductions. 
  1. There is no requirement to be engaged in a qualified trade or business to claim the QBI deduction for Section 199A dividends. 
  1. The QBI deduction does not reduce adjusted gross income. Thus, it does not help a taxpayer qualify for many tax benefits, such as the ability to make an annual contribution to a Roth IRA. 
  1. Section 199A dividends are not qualified dividends (which are reported in Box 1b of Form 1099-DIV). They are taxed as ordinary income subject to the taxpayer’s ordinary income tax rates. They do not qualify for the preferred federal income tax rates for qualified dividends. 

Where Do I Report a Section 199A Dividend on My Tax Return?

Section 199A dividends create tax return reporting in three prominent places on a federal income tax return.

First, Form 1099-DIV Box 1a total ordinary dividends are reported on Form 1040 Line 3b. As Section 199A dividends are a component of Box 1a total ordinary dividends, they are thus reported on the Form 1040 on Line 3b. Section 199A dividends are not reported on Line 3a of Form 1040 because Section 199A dividends are not qualified dividends. 

Second, Section 199A dividends are reported on either Line 6 of Form 8995 or Line 28 of Form 8995-A. In most cases, taxpayers will file the simpler Form 8995 to report qualified business income and Section 199A dividends. By reporting Section 199A dividends on one of those lines most tax return preparation software should flow the dividends through the rest of the form as appropriate (but it never hurts to double check).

Third, the QBI deduction, computed on either Form 8995 or Form 8995-A, is claimed on Line 13 of Form 1040. 

Tax return software varies. Hopefully, by entering the Form 1099-DIV in full in the software’s Form 1099-DIV input form, all of the above will be generated. Ultimately, it is up to the taxpayer to review the return to ensure that the information has been properly input and properly reported on the tax return.

Conclusion 

Section 199A dividends create a taxpayer favorable federal income tax deduction. They are reported in Box 5 of Form 1099-DIV and should be reported on a taxpayer’s federal income tax return. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on X at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

72(t) Series of Substantially Equal Periodic Payments Update

The IRS and Treasury have recently issued two updates to the rules for payments which avoid the 10 percent early withdrawal penalty from retirement accounts. These payments are referred to as a series of substantially equal periodic payments, SEPP, or 72(t) payments. This post discusses the updated rules. 

72(t) Payments

Tax advantaged retirement accounts are fantastic. Who doesn’t love 401(k)s, IRAs, Roth IRAs, and the like?

However, investing through a tax advantaged account can have drawbacks. One big drawback is that taxable amounts withdrawn from a tax advantaged retirement account prior to the account owner turning age 59 ½ are generally subject to a 10 percent early withdrawal penalty. My home state of California adds a 2.5 percent early withdrawal penalty. 

There are some exceptions to this penalty. One of them is taking 72(t) payments. The idea is that if the taxpayer takes a “series of substantially equal periodic payments” they can avoid the penalty. 

72(t) payments must be taken annually. Further, they must last for the longer of (a) 5 years or (b) the time until the taxpayer turns age 59 ½. This creates years of locked-in taxable income. 

There are three methods that can be used to compute the amount of the annual 72(t) payments. These methods compute an annual distribution amount generally keyed off three numbers: the balance in the relevant retirement account, the interest rate, and the table factor provided by the IRS. The factor is greater the younger the account owner is. The greater the factor, the less the account owner can withdraw from a retirement account in a 72(t) payment.

New 72(t) Payment Interest Rates

In January 2022, the IRS and Treasury issued Notice 2022-6. Hat tip to Ed Zollars for the alert. This notice provides some new 72(t) rules. The biggest, and most welcome, change is a new rule for determining the interest rate.

Previously, the rule had been that 72(t) payments were keyed off 120 percent of the mid-term applicable federal rate (“AFR”). The IRS publishes this rate every month. In recent years, that has been somewhat problematic, as interest rates have been historically low. For example, in September 2020, the mid-term AFR was just 0.42 percent. This made relying on a 72(t) payment somewhat perilous. How much juice can be squeezed from a large retirement account if the interest rate is just 0.42 percent?

Here is what a $1M traditional IRA could produce, under the fixed amortization method, in terms of an annual payment for a 53 year old starting a 72(t) payment if the interest rate is just 0.42 percent:

120% of Sept 2020 MidTerm AFR0.42%
Single Life Expectancy Years at Age 5333.4
Account Balance$1,000,000.00
Annual Payment$32,151.93

Notice 2022-6 makes a very significant change. It now allows taxpayers to pick the greater of (i) up to 5 percent or (ii) up to 120 percent of mid-term AFR. That one change makes a 72(t) payment a much more attractive option, since periods of low interest rates do not as adversely affect the calculation. 

Here is what a $1M traditional IRA could produce, under the fixed amortization method, in terms of an annual payment for a 53 year old starting a 72(t) payment if the interest rate is 5 percent:

5% Interest Rate5.00%
Single Life Expectancy Years at Age 5333.4
Account Balance$1,000,000.00
Annual Payment$62,189.80

The new rule provides a 5 percent interest rate floor for those using the fixed amortization method and the fixed annuitization method to compute a 72(t) payment. Using a 5 percent interest rate under the fixed amortization method is generally going to produce a greater payment amount than using the required minimum distribution method for 72(t) payments. 

The interest rate change provides taxpayers with much more flexibility with 72(t) payments, and a greater ability to extract more money penalty free prior to age 59 ½. Taxpayers already have the ability to “right-size” the traditional IRA out of which to take a 72(t) payment to help the numbers work out. In recent years, what has been much less flexible has been the interest rate. Under these new rules, taxpayers always have the ability to select anywhere from just above 0% to 5% regardless of what 120 percent of mid-term AFR is. 

Watch me discuss the update to 72(t) payment interest rates.

New Tables

A second new development is that the IRS and Treasury have issued new life expectancy tables for required minimum distributions (“RMDs”) and 72(t) payments. Most of the new tables are found at Treasury Regulation Section 1.401(a)(9)-9, though one new table is found at the end of Notice 2022-6. 

These tables reflect increasing life expectancies. As a result, they reduce the amount of RMDs, as the factors used to compute RMDs are greater as life expectancy increases. 

From a 72(t) payment perspective, this development is a minor taxpayer unfavorable development. Long life expectancies in the tables means the tables slightly reduce the amount of juice that can be squeezed out of any particular retirement account.

This said, the downside to 72(t) payments coming from increasing life expectancy on the tables is more than overcome by the ability to always use an interest rate of up to 5 percent. These two developments in total are a great net win for taxpayers looking to use 72(t) payments during retirement. 

Use of 72(t) Payments

Traditionally, I have viewed 72(t) payments as a life raft rather than as a desirable planning tool for those retiring prior to their 59 ½th birthday. Particularly for those in the FI community, my view has been that it is better to spend down taxable assets and even dip into Roth basis rather than employ a 72(t) payment plan. 

These developments shift my view a bit. Yes, I still view 72(t) payments as a life raft. Now it is an upgraded life raft with a small flatscreen TV and mini-fridge. 😉

As a practical matter, some will get to retirement prior to age 59 ½ with little in taxable and Roth accounts, and the vast majority of their financial wealth in traditional retirement accounts. Notice 2022-6 just made their situation much better and much more flexible. Getting to retirement at a time of very low interest rates does not necessarily hamstring their retirement plans given that they will always have at least a 5 percent interest rate to use in calculating their 72(t) payments. 

72(t) Payments and Roth IRAs

As Roth accounts grow in value, there will be at least some thought of marrying Roth IRAs with 72(t) payments. 

At least initially, Roth IRAs have no need for 72(t) payments. Those retired prior to age 59 ½ can withdraw previous Roth contributions and Roth conversions aged at least 5 years at any time tax and penalty free for any reason. So off the bat, no particular issue, as nonqualified distributions will start-off as being tax and penalty free.

Only after all Roth contributions have been withdrawn are Roth conversions withdrawn, and they are withdrawn first-in, first-out. Only after all Roth conversions are withdrawn does a taxpayer withdraw Roth earnings.  

For most, the odds of withdrawing (i) Roth conversions that are less than five years old, and then (ii) Roth earnings prior to age 59 ½ are slim. But, there could some who love Roths so much they largely or entirely eschew traditional retirement account contributions. One could imagine an early retiree with only Roth IRAs. 

Being “Roth only” prior to age 59 ½ could present problems if contributions and conversions at least 5 years old have been fully depleted. Taxpayers left with withdrawing conversions less than 5 years old or earnings in a nonqualified distribution might opt to establish a 72(t) payment plan for their Roth IRA. Such a 72(t) payment plan could avoid the 10 percent penalty on the withdrawn amounts attributable insufficiently aged conversions or Roth earnings. Note, however, that Roth earnings withdrawn in a nonqualified distribution are subject to ordinary income tax, regardless of whether they are part of a 72(t) payment plan. 

See Treasury Regulation Section 1.408A-6 Q&A 5 providing that Roth IRA distributions can be subject to both the 72(t) early withdrawal penalty and the exceptions to the 72(t) penalty. The exceptions include a 72(t) payment plan. 

Additional Resource

Ed Zollars has an excellent post on the updated IRS rules for 72(t) payments here.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters.Please also refer to the Disclaimer & Warning section found here.

2022 Backdoor Roth IRA

The Backdoor Roth IRA lives! The proposal to repeal the Backdoor Roth IRA as of January 1, 2022 will not be enacted in 2021, as it is now abundantly clear that the Build Back Better legislative program will not be enacted anytime soon. 

But could the proposal come back in 2022? How does one do financial planning in this regard in this climate of uncertainty?

Below I discuss how I approach the issue of whether one should execute a Backdoor Roth IRA in early 2022. What follows is my opinion of the possibilities that could play out. They are simply one person’s opinion in the face of a somewhat uncertain situation. 

Nothing below is tax advice for any individual taxpayer to rely upon. 

Update February 5, 2022: Watch my updated assessment of the 2022 Backdoor Roth IRA landscape on YouTube.

Planning for Uncertainty

To tackle the issue of whether to execute a Backdoor Roth IRA in early 2022, I believe it is best to think of a hypothetical example and then consider all of the (currently known) possibilities in terms of law changes and their probabilities of occuring. So here’s a hypothetical example:

Single Nurse is 35 years old, single, and makes $170,000 at her W-2 job in 2022. She is covered by a 401(k) at work. Her 2022 modified adjusted gross income (“MAGI”) makes her ineligible to make an annual contribution to a Roth IRA. On January 1, 2022, Single Nurse contributes $6,000 to a traditional IRA. On January 5, 2022, Single Nurse converts the entire balance in her traditional IRA, $6,000.23, to a Roth IRA. Assuming Single Nurse takes no other action, she will have $0 in all traditional IRAs, SEP IRAs, and SIMPLE IRAs on December 31, 2022. 

Will Single Nurse be happy she executed a Backdoor Roth IRA early in 2022?

Let’s analyze the various possibilities in terms of new laws during 2022 and how they could impact Single Nurse’s 2022 Backdoor Roth IRA. Many thanks to Pixabay.com for the emoji reaction pictures and the featured image!

Note that Possible Outcomes #3 through #6 include the small possibility that Congress enacts a repeal of the Backdoor Roth IRA separate from the Build Back Better program.

Possible Outcome #1: No Portion of Build Back Better is Enacted in 2022

Sean’s Estimated Probability of Occurring: 70%

Under this outcome, Single Nurse is quite pleased with her 2022 Backdoor Roth IRA. She’s happy she executed it, even though she could have done it much later in the year.

Single Nurse’s reaction:


Possible Outcome #2: A New Version of Build Back Better is Enacted in 2022 Which Does Not Repeal the Backdoor Roth IRA

Sean’s Estimated Probability: 15%

Single Nurse is again quite pleased with her 2022 Backdoor Roth IRA in January, even though she could have waited. 

Single Nurse’s reaction:


Possible Outcome #3: A New Version of Build Back Better is Enacted in 2022 Which Repeals the Backdoor Roth IRA Effective January 1, 2023

Sean’s Estimated Probability: 10%

Single Nurse is again quite pleased with her 2022 Backdoor Roth IRA in January, though she’ll miss the Backdoor Roth IRA in 2023. 

If Congress does enact legislation in 2022 to repeal the Backdoor Roth IRA, I agree with Steven Rosenthal that the most likely effective date is January 1, 2023, which would be the easiest to implement. Changing tax laws during a year creates needless complexity and confusion, and thus I believe a January 1, 2023 effective date is the most likely effective date. 

Single Nurse’s reaction:


Possible Outcome #4: A New Version of Build Back Better is Enacted in 2022 Which Repeals the Backdoor Roth IRA Effective On the Date of Enactment

Sean’s Estimated Probability: 3%

Single Nurse breathes a huge sigh of relief! If she had waited until later in 2022 to execute her 2022 Backdoor Roth IRA, she would not have been able to. She got her 2022 Backdoor Roth IRA in under the wire, and is very happy she executed the Backdoor Roth IRA early in January. 

Single Nurse’s reaction:

Possible Outcome #5: A New Version of Build Back Better is Enacted in 2022 Which Repeals the Backdoor Roth IRA Effective January 1, 2022 and the IRS Treats an Early 2022 Backdoor Roth IRA as a Correctable Excess Contribution to a Roth IRA

Sean’s Estimated Probability: 1.6%

This is where it gets really interesting. First of all, a law retroactively repealing a tax law benefit would likely face some sort of legal challenge were to be enforced retroactively. For now, I will put an analysis of that outcome to the side. 

How would the IRS enforce a repeal of the Backdoor Roth IRA as applied to Backdoor Roth IRAs executed prior to the law change but after a January 1, 2022 effective date? Single Nurse’s Backdoor Roth IRA is both post-effective date and prior to the enactment of the law change. 

This situation would require an administrative transition rule from the IRS and Treasury. I believe the only feasible transition rule would be for the IRS to treat any pre-enactment/post-effective date 2022 Backdoor Roth IRA as an excess contribution to a Roth IRA. Under the excess contribution rules, excess contributions are generally correctable.

This treatment would give Single Nurse three potential courses of action:

  1. Withdraw the $6,000 and the growth on the $6,000 from the Roth IRA (a corrective distribution) by October 16, 2023.* Any growth on the $6,000 originally contributed is taxable to Single Nurse as ordinary income in 2022; or
  2. Recharacterize the $6,000 and the growth on the $6,000 as a traditional IRA by October 16, 2023. This will result in Single Nurse having a traditional IRA with a basis of $6,000; or,
  3. If neither Option 1 or Option 2 is timely executed by October 16, 2023, Single Nurse owes a six percent penalty on the $6,000 excess contribution ($360) and will owe an additional six percent penalty for every additional year the $6,000 Roth contribution (but not the earnings) is not withdrawn from the Roth IRA. 

I do not see another administratively feasible alternative for the IRS to enforce a retroactive repeal of the Backdoor Roth IRA in 2022. 

I believe the IRS and Treasury would also apply this treatment (or a similar treatment) to any split-year Backdoor Roth IRAs completed in 2022 for the 2021 tax year.

*Update 1/6/2022: Upon further reflection, I believe remedial action to correct an excess Roth IRA contribution in this hypothetical situation can occur by the extended tax return due date. See the bottom of page 42 of IRS Publication 590-A. An earlier version of this post used April 15, 2023 as the deadline date for all three remedial courses of action.

This outcome is not all that bad for Single Nurse. An opportunity taken away for sure, but the “downside” consequences are not all that deleterious. The downside appears limited to ordinary income tax on a few months of growth on $6,000. 

Single Nurse’s reaction:

Possible Outcome #6: A New Version of Build Back Better is Enacted in 2022 Which Repeals the Backdoor Roth IRA Effective January 1, 2022 and the IRS Treats Early 2022 Backdoor Roth IRAs in a Different Manner

Sean’s Estimated Probability: 0.4%

This outcome accounts for the unknown. The IRS and Treasury might take a different approach than the one I outline in Possible Outcome #5. To my mind, the absolute worst outcome would be the six percent penalty tax on an excess contribution. Even then, it is difficult to imagine a scenario where the IRS would not allow remedial action to avoid the six percent penalty.

Single Nurse’s reaction:

Single Nurse’s Assessment

Single Nurse will need to make a subjective assessment of the possibilities and the risks. She is likely to assign somewhat different probabilities to the various possible outcomes than I do. Further, she will have to determine how much she values the possible benefit of an early Backdoor Roth IRA (Possible Outcome #4 in particular, and Possible Outcomes #1 through #3) versus the costs of an early Backdoor Roth IRA (Possible Outcomes #5 and 6). 

My own assessment is that Single Nurse is more likely to benefit from executing an early Backdoor Roth IRA than she is to be (slightly) harmed by it, because I believe that Possible Outcome #4 is more likely than Possible Outcomes #5 and #6. 

Conclusion

Of course, none of the above is advice for any particular taxpayer. Rather, it serves to illustrate how one financial planner would go about systematically assessing the probabilities, risks, and rewards associated with an early 2022 Backdoor Roth IRA.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

The End of the End of the Backdoor Roth IRA?

Update as of December 20, 2021: I originally posted this article on Saturday morning, December 18th. On Sunday, developments occurred which called into question the use of a question mark in the article’s title.

Senator Joe Manchin appeared on Fox News Sunday and very publicly indicated he is a No on Build Back Better. He followed that with a written statement outlining his opposition to Build Back Better. The White House issued a statement in response to Senator Manchin.

A fair assessment indicates the parties are not at all close on this one. This is not a situation where Senator Manchin is bargaining to get A, B, and C into the bill and the White House is hoping to only have to give B and C. While anything is possible with tax legislation, it is quite difficult to argue that the Build Back Better program (which includes Backdoor Roth IRA repeal) has a realistic possibility of passage in this Congress in anything resembling its current form.

Update February 5, 2022: Watch my updated assessment of the lay of the land on 2022 Backdoor Roth IRAs.

Below is the original post posted on December 18, 2021.

There’s an early Christmas present for tax efficient investors. The proposal to end the Backdoor Roth IRA is on life support, and as of now (December 18, 2021) it appears that even if the proposal passes, it will not pass until 2022 at the earliest.

Latest Developments

The White House has now issued a written statement that the so-called Build Back Better program will not be signed into law this year. The proposal to repeal the Backdoor Roth IRA is one of many tax proposals contained within the overall Build Back Better legislative program. As this Deloitte write-up discusses, it is clear the Senate will not pass the legislation any time in the near-term. Thus, for the time being, the Backdoor Roth IRA is in the clear. 

Prospects for 2022

Update December 28, 2021: Read my assessment of 2022 Backdoor Roth IRAs.

There is a reason the Build Back Better program will not be enacted during 2021: it’s not broadly popular. This is reflected in the current opposition of all 50 Senate Republicans and Democrat Senator Joe Manchin. Further, it is not at all clear that Democrat Senator Kyrsten Sinema will ultimately support Build Back Better. 

If the Build Back Better program were to become popular, the dynamics in the U.S. Senate would likely change. But one must ask: is there something that could occur in early 2022 that would make the legislation popular then when it was not popular in late 2021? 

Another issue the legislation has is the unlikelihood of any potential tax increase passing during an election year. New tax laws have proponents and opponents: in recent years Congress has hesitated to create opponents during election years by enacting significant tax legislation. 

What If?

What if the legislation is enacted in early 2022? What happens to Backdoor Roth IRAs? That is highly, highly speculative. My guess is that if the legislation (at that point) bans Backdoor Roth IRAs, either (i) Backdoor Roth IRAs will be prohibited as of January 1, 2023 (instead of January 1, 2022 in the current legislation) or (ii) prohibited as of the enactment of the law. 

But all sorts of alternative possibilities exist. A much smaller version of the Build Back Better program could be enacted, and that version could omit the Backdoor Roth IRA repeal. Or there will be no legislation enacted at all. 

Why Are We Here?

Is the Backdoor Roth IRA gimmicky? Absolutely it is!

But there is a bigger issue. Why the heck is there any income limitation on the ability to make a $6,000 annual contribution to a Roth IRA? Consider these two examples.

Wealthy Investor controls a large public company and is known for his ability to earn good investment returns. He is worth billions of dollars and is 80 years old. He can direct the large public company to offer a Roth 401(k), and on January 1st of 2022 he can have payroll issued to him, of which he can put $27,000 into his Roth 401(k). 

Single Nurse, age 35, is a nurse and earns $170,000 from her W-2 job. Her employer offers a traditional 401(k) but no Roth 401(k). Single Nurse earns too much (due to the Roth IRA modified adjusted gross income limit) to make an annual $6,000 contribution to a Roth IRA. As a result, Single Nurse’s annual Roth contributions are limited to $0.

Wealthy Investor can contribute $27,000 to a Roth 401(k) but Single Nurse can’t contribute $6,000 to a Roth IRA?

To borrow an exasperated quote from Cosmo Kramer, “What’s going on!!!”

The Backdoor Roth IRA solves this problem for Single Nurse and many other Americans. This workaround does not work for all Americans, as I have previously written. 

The simplest solution is to eliminate the modified adjusted gross income limit for all Roth IRA contributions. So some very wealthy Americans will get a few thousand dollars into Roth IRAs every year. Is this a horribly worrisome outcome considering many very wealthy Americans already have access to much greater workplace retirement plan contributions with absolutely no income limitation?

Once the income limit on the ability to make a Roth IRA contribution is repealed, there will be no need for Backdoor Roth IRAs. 

Conclusion

The only constant in the tax world is change. We shall see what the future holds for the Backdoor Roth IRA, but the coast appears to be clear for the rest of the year. Stay tuned!

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

FI Tax Guy Featured on the Optimal Finance Daily Podcast

Today and tomorrow my year-end tax planning post will be featured on the Optimal Finance Daily podcast.

Listen to today’s episode on podcast players and here.

Read my year-end tax planning blog post here.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Sean Talks Tax with DocG

Listen to my discussion with DocG on the latest episode of the Earn and Invest podcast. Available on all major podcast players and at this link: https://www.earnandinvest.com/episodes/five-tax-questions-you-must-ask

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Tax Planning for Inflation

In recent years, inflation existed but was not significant. Significant inflation was associated with wide lapels and eight-track tapes and thought to be left behind in the late 1970s and early 1980s.

But, sure enough, significant inflation is back. Inflation is 6.2 percent for the 12 months ending October 2021.  

Inflation has a tax angle. How does one use tax planning to minimize the impact of inflation? In this post, I review the issues associated with inflation and tactics to consider if one is concerned about inflation.

Inflation: The Tax Problem

Inflation increases the nominal (i.e., stated) value of assets without a corresponding increase in the real value of the asset. Here is an example:

Larry buys $100,000 worth of XYZ Mutual Fund on January 1, 2022. During the year 2022, there is 10 percent inflation. On January 1, 2023, the XYZ Mutual Fund is worth $110,000. Inflation-adjusted, the position has the same real value as it did when Larry purchased it. However, were Larry to sell the entire position, he would trigger a $10,000 capital gain ($110,000 sales price less $100,000 tax basis), which would be taxable to him. 

Hopefully you see the problem: Larry has not experienced a real increase in wealth. Larry’s taxable “gain” is not a gain. Rather, it is simply inflation! Larry will pay tax on inflation if he sells the asset. Ouch!

While inflation increases the nominal value of assets, there is no inflation adjustment to tax basis! Thus, inflation creates artificial gains subject to income tax. 

There are other tax problems with inflation. Inflation artificially increases amounts received as wages, self-employment income, interest, dividends, and retirement plan distributions. Those artificial increases are not real increases in income (as they do not represent increases in value) but they are subject to income tax as though they were real increases in income.

The tax law does provide some remedy to address the problem of taxing inflation. The IRS provides inflation adjustments to increase the size of progressive tax brackets. In addition, the standard deduction is adjusted annually for inflation. Recently the IRS released the inflation adjustments for 2022.  

IRS inflation adjustments are helpful, but they do not excuse inflation from taxation. Rather, they only soften the blow. Thus, they are not a full cure for the tax problems caused by inflation. 

Inflation and Traditional Retirement Accounts

Inflation is detrimental to traditional retirement accounts such as pre-tax 401(k)s and IRAs. Holding assets inside a traditional retirement account subjects the taxpayer to income tax on the growth in the assets caused by inflation.

Inflation artificially increases amounts in these accounts that will ultimately be subject to taxation. Inflation can also limit the opportunity to do Roth conversions in early retirement. Greater balances to convert from traditional to Roth accounts and increased dividend, capital gain, and interest income triggered by inflation makes early retiree Roth conversion planning more challenging. 

Inflation and Real Estate

There are several tax benefits of rental real estate. One of the main benefits is depreciation. For residential real estate, the depreciable basis is deducted in a straight-line over 27.5 years. For example, if the depreciable basis of a rental condo is $275,000, the annual depreciation tax deduction (for 27.5 years) is $10,000 (computed as $275,000 divided by 27.5). That number rarely changes, as most of the depreciable basis is determined at the time the property is purchased or constructed. 

Over time, inflation erodes the value of depreciation deductions. Inflation generally increases rental income, but the depreciation deduction stays flat nominally and decreases in real value. Increasing inflation reduces the tax benefits provided by rental real estate. 

Planning Techniques

There are planning techniques that can protect taxpayers against the tax threat posed by inflation. 

Roth Contributions and Conversions

Inflation is yet another tax villain the Roth can slay. Tax free growth inside a Roth account avoids the tax on inflation. 

Once inside a Roth, concerns about inflation increasing taxes generally vanish. Properly planned, Roths provide tax free growth and tax free withdrawals. Thus, Roths effectively eliminate the concern about paying tax on inflation. 

For those thinking of Roth conversions, inflation concerns point to accelerating Roth conversions. The sooner amounts inside traditional retirement accounts are converted to Roth accounts, the less exposure the amounts have to inflation taxes. 

Roth contributions and conversions provide tax insurance against the threat of inflation. For those very concerned about inflation, this consideration moves the needle toward the Roth in the ongoing Roth versus traditional debate. 

Watch me discuss using Roth accounts to help manage an investor’s exposure to inflation.

Health Savings Accounts

A Health Savings Account, like its Roth IRA cousin, offers tax free growth. HSAs also protect against taxes on inflation. Inflation is another argument to take advantage of an HSA. 

Basis Step Up Planning

There is another tax planning opportunity that can wipe away the taxes owed on years of inflation: the basis step up at death. At death, heirs receive a basis in inherited taxable assets which is usually the fair market value of the assets on the date of death. For taxable assets, death provides an opportunity to escape the tax on inflation.

It is important to note that traditional retirement accounts do not receive a basis step up. Inflation inside a traditional retirement account will eventually be subject to tax (either to the original owner or to a beneficiary after the original owner’s death). 

During one’s lifetime, there is the tax gain harvesting opportunity to step up basis and reduce inflation taxes. The tactic is to sell and repurchase an investment with a built-in gain at a time when the investor does not pay federal income tax on the capital gain. If one can keep their marginal federal income tax rate in the 12% or lower marginal tax bracket, they can pay a 0% federal income tax rate on the gain and “reset” the basis to the repurchase price of the sold and then repurchased asset. 

There is a second flavor of tax gain harvesting: triggering a capital gain (at an advantageous time from a tax perspective) by selling an asset and reinvesting the proceeds in a more desirable asset (essentially, investment reallocation). 

One inflation consideration with respect to tax gain harvesting: as inflation increases interest and dividends, there will be less room inside the 12 percent taxable income bracket to create capital gains that are federal income tax free.

Conclusion

Inflation is yet another tax planning consideration. As we are now in a period of significant inflation, taxpayers and advisors will need to weigh inflation’s potential impact on tax strategies. 

None of the above is advice for any particular taxpayer. Hopefully it provides some educational background to help assess the tax impact of inflation and consider tactical responses to inflation.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean Discusses Year-End Tax Planning on the ChooseFI Podcast

Listen to me discuss year-end tax planning with Brad and Jonathan on the ChooseFI podcast. The episode is available on all major podcast players, YouTube, and on the ChooseFI website (https://www.choosefi.com/year-end-tax-planning-2021-ep-351/).

During the conversation we referenced this blog post.

As always, the discussion is general and educational in nature and does not constitute tax, investment, legal, or financial advice with respect to any particular individual or taxpayer. Please consult your own advisors regarding your own unique situation. Sean Mullaney and ChooseFI Publishing are currently under contract to publish a book authored by Sean Mullaney.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Roth 401(k) vs Roth IRA

Many taxpayers ask the question: should I contribute to a Roth 401(k) or contribute to a Roth IRA? While there is no universal answer to this question, for many in the financial independence (FI/FIRE) community, I believe there is a clear answer. 

Roth Accounts

What is not to love about Roths? If withdrawn properly, they promise tax free growth and tax free withdrawals. Further, Roths (be them 401(k)s or IRAs) give taxpayers tax insurance: income tax increases in the future are not a problem with respect to money invested in a Roth account. Roths even provide some ancillary benefits during retirement if the United States ever adopts a value added tax (a “VAT”). 

Roth IRAs

Roth IRAs are an individual account and can be established at a plethora of financial institutions. Most working taxpayers qualify to make annual contributions to a Roth IRA. However, the ability to make an annual contribution to a Roth IRA phases out at certain income levels and is completely eliminated at $140,000 (single) or $208,000 (married filing joint) of modified adjusted gross income (2021 numbers). 

The maximum annual contribution to a Roth IRA is $6,000 (if under age 50) or $7,000 (if age 50 or older) (2021 and 2022 numbers). 

I have previously written about my fondness for Roth IRAs. One reason for my fondness is that annual contributions can be withdrawn from the Roth IRA at any time for any reason tax and penalty free. Thus, Roth IRAs can perform double duty as both a retirement savings vehicle and as an emergency fund. This is an advantage of Roth IRAs over Roth 401(k)s. 

Of course, considering their tax free growth, it is usually best to keep amounts in a Roth IRA for as long as possible. 

Roth 401(k)s

Roth 401(k)s are a workplace retirement plan. Contributions can be made through payroll withholding. Many employers offer a Roth 401(k), though they are far from universally adopted. 

The Roth 401(k) does enjoy some advantages when compared to its Roth IRA cousin. First, there is no income limit to worry about. Regardless of income level, an employee can contribute to a Roth 401(k). Second, the contribution limits are much higher than the contribution limits for Roth IRAs. As of 2021, the annual Roth 401(k) contribution limit is $19,500 (under age 50) or $26,000 (age 50 and older). 

The Roth 401(k) is not a good account for emergency withdrawals. Withdrawals occurring prior to both the account holder turning 59 ½ years old and the account turning 5 years old generally pull out a mixture of previous contributions and taxable earnings.

Roth 401(k) vs Roth IRA

So which one should members of the FI/FIRE community prioritize? Contributions to a Roth 401(k) or contributions to a Roth IRA?

To help us answer that question, let’s consider a young couple pursuing financial independence:

Stephen and Becky are both age 30, married (to each other), and pursuing financial independence. They both would like to retire at least somewhat early by conventional standards. They each have a W-2 salary of $90,000. They have approximately $2,000 of annual interest and dividend income. They claim the standard deduction. At this level of income, they have a 22 percent marginal federal income tax rate. Stephen and Becky each have access to a traditional 401(k) and a Roth 401(k) at work. They would like to maximize their retirement plan contributions. 

How should Stephen and Becky allocate their retirement plan contributions? Should they contribute to a Roth 401(k) and/or to a Roth IRA?

To my mind, the best play here is to contribute to a Roth IRA ($6,000 each) and contribute to a traditional 401(k) ($19,500 each). Stephen and Becky should not contribute to a Roth 401(k). 

There is a significant tax opportunity cost to making a Roth 401(k) contribution: the ability to deduct a traditional contribution to a 401(k). Remember, the Roth 401(k) shares the $19,500 annual contribution limit with the traditional 401(k). Every dollar contributed to a Roth 401(k) is a dollar that cannot be contributed to a traditional 401(k). 

For Stephen and Becky, the hope is that in early retirement tax laws either stay the same as they are today or at least keep today’s flavor. The idea is to take a deduction while working at a 22 percent marginal tax rate (by contributing to the traditional deductible 401(k)). Then, in early retirement, they convert amounts in the traditional 401(k) to a Roth. At that point, hopefully they have a marginal federal income tax rate of 10 percent or 12 percent. Many early retirees have an artificially low taxable income (and thus, a low marginal income tax rate) prior to collecting Social Security. 

Contrast the significant tax opportunity cost of making a Roth 401(k) contribution to the tax opportunity cost of making a Roth IRA contribution: practically nothing. 

Stephen and Becky have no ability to deduct a traditional IRA contribution because of their income level and the fact that they are covered by a workplace retirement plan. Thus, they aren’t losing much, from a tax perspective, by each making a $6,000 annual Roth IRA contribution. 

Situations Where the Roth 401(k) Contributions Make Sense

For those in the financial independence community, generally there are four situations where choosing to contribute to a Roth 401(k) makes sense. In three of these situations, the tax rate arbitrage play available to Stephen and Becky isn’t available. In the fourth situation (tax insurance), there is a separate consideration causing the taxpayer to forgo an initial tax deduction to get assurance as to the tax rate they will be subject to. 

In the situations below, a Roth 401(k) contribution is likely preferable to a traditional 401(k) contribution. As compared to a Roth IRA contribution, (a) the first contributions should generally be to the Roth 401(k) to secure the employer match, and then after that, (b) generally both the Roth 401(k) and the Roth IRA work well. To my mind, the emergency-type fund feature of the Roth IRA, which I’ve previously discussed, is probably the tiebreaker in favor of making the next contributions to a Roth IRA.

Transition Years

Think about a year one graduates college, graduate school, law school, or medical school. Usually, the person works for only the last half or last quarter of the year. Thus, they have an artificially low taxable income (since they only work for a small portion of the year). Why take a tax deduction for a contribution to a traditional 401(k) in such a year, when one’s marginal federal income tax rate might only be 10 percent or 12 percent?

Transition years are a great time to make Roth 401(k) contributions instead of traditional 401(k) contributions. 

Young Earners with Low Incomes

Many careers start with modest salaries early but have the potential to experience significant salary increases over time. My previous career in public accounting is one example. Medicine is another example. Young accountants and doctors, among others, making modest starting salaries should consider Roth 401(k) contributions at the beginning of their careers. As their salaries increase, they should consider shifting their contributions to a traditional 401(k). 

As a *very general* rule of thumb, those in the 10 percent or 12 percent marginal federal income tax rate (particularly those not subject to a state income tax) should consider prioritizing Roth 401(k) contributions (regardless of occupation).

No Hope

Picture a charismatic franchise NFL quarterback. He’s got a $40M plus annual NFL contact, endorsement deals, business ventures, and likely a long TV career after his playing days are done. For him, there is no hope ( 😉 ). He will probably be in the top federal income tax bracket the rest of his life. He might be well advised to “lock-in” today’s low (by historical standards) 37% federal income tax marginal tax rate by choosing to contribute to a Roth 401(k) instead of to a traditional 401(k).

Tax Insurance

We really do not know what the future holds. That includes future federal and state income tax rates. 

Thus, some workers may want to buy tax insurance. Roth 401(k) contributions are a way to do that. The extra tax paid (because the taxpayer did not deduct traditional 401(k) contributions) is an insurance premium. That insurance premium ensures that the taxpayer won’t be subject to future income tax (including potential tax rate increases) on amounts inside the Roth 401(k) and the growth thereon. 

Remember, none of this is “all or nothing” planning. Some may want to allocate a piece of their workplace retirement plan contributions to the Roth 401(k) to get some insurance coverage against future tax rate increases. 

Conclusion

In the FI community, a maxed out traditional 401(k) and a maxed out Roth IRA (whether through a regular annual contribution or through a Backdoor Roth IRA) can be the dynamic duo of retirement savings. This combination can provide tax flexibility while maximizing current tax deductions. Roth 401(k) contributions often have a significantly greater tax opportunity cost as compared to the tax opportunity cost of Roth IRA contributions. In such situations, the Roth IRA is preferable to my mind. 

Of course, each individual is unique and has different financial and tax goals and priorities. The above isn’t advice for any particular individual, but hopefully provides some educational insight regarding the issues to consider when allocating employee retirement account contributions. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

2021 YEAR-END TAX PLANNING

It’s time to think about year-end tax planning. Year-end is a great time to get tax planning ducks in a row and take advantage of opportunities. This is particularly true for those in the financial independence community. FI principles often increase one’s tax planning opportunities.  

Remember, this post is for educational purposes only. None of it is advice directed towards any particular taxpayer. 

Backdoor Roth IRA Deadline 2021

As of now (December 7, 2021), the legal deadlines around Backdoor Roth IRAs have not changed: the nondeductible 2021 traditional IRA contribution must happen by April 18, 2022 and there is no legal deadline for the second step, the Roth conversion. However, from a planning perspective, the practical deadline to have both steps of a 2021 Backdoor Roth IRA completed is December 31, 2021. 

This is because of proposed legislation that eliminates the ability to convert nondeductible amounts in a traditional IRA effective January 1, 2022. As of December 7th, the proposed legislation has passed the House of Representatives but faces a very certain future in the Senate. Considering the risk that the Backdoor Roth elimination proposal is enacted, taxpayers planning on completing a 2021 Backdoor Roth IRA should act to ensure that the second step of the Backdoor Roth IRA (the Roth conversion) is completed before December 31st. 

Taxpayers on the Roth IRA MAGI Limit Borderline

In years prior to 2021, taxpayers unsure of whether their income would allow them to make a regular Roth IRA contribution could simply wait until tax return season to make the determination. At that point, they could either make the regular Roth IRA contribution for the prior year (if they qualified) or execute what I call a Split-Year Backdoor Roth IRA.  

With the proposed legislation looming, waiting is not a good option. The good news is that taxpayers executing a Backdoor Roth IRA during a year they actually qualify for a regular annual Roth IRA contribution suffer no material adverse tax consequences. Of course, in order for this to be true there must be zero balance, or at most a very small balance, in all traditional IRAs, SEP IRAs, and SIMPLE IRAs as of December 31, 2021. 

December 31st and Backdoor Roth IRAs

December 31st is a crucial date for those doing the Roth conversion step of a Backdoor Roth IRA during the year. It is the deadline to move any balances in traditional IRAs, SEP IRAs, and SIMPLE IRAs to workplace plans in order to ensure that the Roth conversion step of any Backdoor Roth IRA executed during the year is tax-efficient. 

This December 31st deadline applies regardless of the proposed legislation discussed above. 

IRAs and HSAs

Good news on regular traditional IRA contributions, Roth IRA contributions, and HSA contributions: they don’t have to be part of an end-of-2021 tax two-minute drill. The deadline for funding an HSA, a traditional IRA, and a Roth IRA for 2021 is April 18, 2022. 

Solo 401(k)

The self-employed should consider this one. Deadlines vary, but as a general rule, those eligible for a Solo 401(k) usually benefit from establishing one prior to year-end. The big takeaway should be this: if you are self-employed, your deadline to seriously consider a Solo 401(k) for 2021 is ASAP! Usually, such considerations benefit from professional assistance. 

Something to look forward to in 2022: my upcoming Solo 401(k) book!

Charitable Contributions

For those itemizing deductions in 2021 and either not itemizing in 2022 or in a lower marginal tax rate in 2022 than in 2021, it can be advantageous to accelerate charitable contributions late in the year. It can be as simple as a direct donation to a qualifying charity by December 31st. Or it could involve contributing to a donor advised fund by December 31st.  

A great donor advised fund planning technique is transferring appreciated securities (stocks, bonds, mutual funds, or ETFs) to a donor advised fund. Many donor advised fund providers accept securities. The tax benefits of making such a transfer usually include (a) eliminating the built-in capital gain from federal income taxation and (b) if you itemize, getting to take a current year deduction for the fair market value of the appreciated securities transferred to the donor advised fund. 

The elimination of the lurking capital gain makes appreciated securities a better asset to give to a donor advised fund than cash (from a tax perspective). Transfers of appreciated securities to 501(c)(3) charities can also have the same benefits.

The 2021 deadline for this sort of planning is December 31, 2021, though taxpayers may need to act much sooner to ensure the transfer occurs on time. This is particularly true if the securities are transferred from one financial institution to a donor advised fund at another financial institution. In these cases, the transfer may have to occur no later than mid-November, though deadlines will vary.

Early Retirement Tax Planning

For those in early retirement, the fourth quarter of the year is the time to do tax planning.  Failing to do so can leave a great opportunity on the table. 

Prior to taking Social Security, many early retirees have artificially low taxable income. Their only taxable income usually consists of interest, dividends, and capital gains. In today’s low-yield environment, without additional planning, early retirees’ taxable income can be very low (perhaps even below the standard deduction). 

Artificially low income gives early retirees runway to fill up lower tax brackets (think the 10 percent and 12 percent federal income tax brackets) with taxable income. Why pay more tax? The reason is simple: choose to pay tax when it is taxed at a low rate rather than defer it to a future when it might be taxable at a higher rate.

The two main levers in this regard are Roth conversions and tax gain harvesting. Roth conversions move amounts in traditional retirement accounts to Roth accounts via a taxable conversion. The idea is to pay tax at a very low tax rate while taxable income is artificially low, rather than leaving the money in deferred accounts to be taxed later in retirement at a higher rate under the required minimum distribution (“RMD”) rules. 

Tax gain harvesting is selling appreciated assets when one is in the 10 percent or 12 percent marginal tax bracket so as to incur a zero percent long term capital gains federal tax rate on the capital gain. 

Early retirees can do some of both. In terms of a tiebreaker, if everything else is equal, I prefer Roth conversions to tax gain harvesting, for two primary reasons. First, traditional retirement accounts are subject to ordinary income tax rates in the future, which are likely to be higher than preferred capital gains tax rates. Second, large taxable capital gains in taxable accounts can be washed away through the step-up in basis at death. The step-up in basis at death doesn’t exist for traditional retirement accounts. 

One time to favor tax gain harvesting over Roth conversions is when the traditional retirement accounts have the early retiree’s desired investment assets but the taxable brokerage account has positions that the early retiree does not like anymore (for example, a concentrated position in a single stock). Why not take advantage of tax gain harvesting to reallocate into preferred investments in a tax-efficient way?

Long story short: during the fourth quarter, early retirees should consider their taxable income for the year and consider year-end Roth conversions and/or tax gain harvesting. Planning in this regard should be executed no later than December 31st, and likely earlier to ensure proper execution. 

Roth Conversions, Tax Gain Harvesting, and Tax Loss Harvesting

Early retired or not, the deadline for 2021 Roth conversions, tax gain harvesting, and tax loss harvesting is December 31, 2021. Taxpayers should always consider timely implementation: these are not tactics best implemented on December 30th! 

For some who find their income dipped significantly in 2021 (perhaps due to a job loss), 2021 might be the year to convert some amounts in traditional retirement accounts to Roth retirement accounts. Some who are self-employed might want to consider end-of-year Roth conversions to maximize their qualified business income deduction. 

Stimulus and Child Tax Credit Planning

Taxpayers who did not receive their full 2021 stimulus may want to look into ways to reduce their 2021 adjusted gross income so as to qualify for additional stimulus funds. I wrote in detail about one such opportunity in an earlier blog post. Lowering adjusted gross income can also qualify taxpayers for additional child tax credits. 

There are many factors you and your advisor should consider in tax planning. This opportunity may be one of them. For example, taxpayers considering a Roth conversion at the end of the 2021 might want to hold off in order to qualify for additional stimulus and/or child tax credits. 

Accelerate Payments

The self-employed and other small business owners may want to review business expenses and pay off expenses before January 1st, especially if they anticipate their marginal tax rate will decrease in 2022. Depending on structure and accounting method, doing so may not only reduce income taxes, it could also reduce self-employment taxes. 

State Tax Planning

For my fellow Californians, the big one here is property taxes. It may be advantageous to pay billed (but not yet due) property taxes in late 2021. This allows taxpayers to deduct the amount on their 2021 California income tax return. In California, the standard deduction ($4,601 for single taxpayers, $9,202 for married filing joint taxpayers) is much lower than the federal standard deduction, so consideration should be given to accelerating itemized deductions in California, regardless of whether the taxpayer itemizes for federal income tax purposes.

Required Minimum Distributions (“RMDs”)

They’re back!!! RMDs are back for 2021. The deadline to withdraw a required minimum distribution for 2021 is December 31, 2021. Failure to do so can result in a 50 percent penalty. 

Required minimum distributions apply to most retirement accounts (Roth IRAs are an exception). They apply once the taxpayer turns 72. Also, many inherited retirement accounts (including Roth IRAs) are subject to RMDs, regardless of the beneficiary’s age. 

Planning for Traditional Retirement Accounts Inherited in 2020 and 2021

Those inheriting traditional retirement accounts in 2020 or later often need to do some tax planning. The end of the year is a good time to do that planning. Many traditional retirement account beneficiaries will need to empty the retirement account in 10 years (instead of being on an RMD schedule), and thus will need to plan out distributions over the 10 year time frame to manage taxes rate on the distributions.

2021 Federal Estimated Taxes

For those with small business income, side hustle income, significant investment income, and other income that is not subject to tax withholding, the deadline for 2021 4th quarter estimated tax payments to the IRS is January 18, 2022. Such individuals should also consider making timely estimated tax payments to cover any state income taxes. 

Review & Update Beneficiary Designation Forms

Beneficiary designation forms control the disposition of financial assets (such as retirement accounts and brokerage accounts) upon death. Year-end is a great time to make sure the relevant institutions have up-to-date forms on file. While beneficiary designations should be updated anytime there is a significant life event (such as a marriage or a death of a loved one), year-end is a great time to ensure that has happened. 

2022 and Beyond Tax Planning

The best tax planning is long term planning that considers the entire financial picture. There’s always the temptation to maximize deductions on the current year tax return. But the best planning considers your current financial situation and your future plans and strives to reduce total lifetime taxes. 2022 is as good a time as any to do long-term planning.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean Presentation at CampFI

My presentation to CampFI Southwest in October 2021.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

The Backdoor Roth IRA and December 31st

New Year’s Eve is an important day if you do a Backdoor Roth IRA. Read below to find out why.

The Backdoor Roth IRA

I’ve written before about the Backdoor Roth IRA. It is a two step process whereby those not qualifying for a regular Roth IRA contribution can qualify to get money into a Roth IRA. Done over several years, it can help taxpayers grow significant amounts of tax free wealth.

One of the best aspects of the Backdoor Roth IRA is that it does not forego a tax deduction. Most taxpayers ineligible to make a regular Roth IRA contribution are also ineligible to make a deductible traditional IRA contribution. In the vast majority of cases, the choice is between investing money in a taxable account versus investing in a Roth account. For most, a Roth is preferable, since Roths do not attract income taxes on the interest, dividends, and capital gains investments generate. 

The Basic Backdoor Roth IRA and the Form 8606

Let’s start with a fairly basic example. 

Example 1

Betsy, age 40, earns $300,000 from her W-2 job in 2021, is covered by a workplace 401(k) plan, and has some investment income. Betsy has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA.

At this level of income, Betsy does not qualify for a regular Roth IRA contribution, and she does not qualify to deduct a traditional IRA contribution. 

Betsy contributes $6,000 to a traditional IRA on May 20, 2021. The contribution is nondeductible. Because the contribution is nondeductible, Betsy gets a $6,000 basis in her traditional IRA. Betsy must file a Form 8606 with her 2021 tax return to report the nondeductible contribution.

On June 5, 2021, Betsy converts the entire balance in the traditional IRA, $6,003, to a Roth IRA. As of December 31, 2021, Betsy has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA.

Betsy has successfully executed a Backdoor Roth IRA. Here is what page 1 of the Form 8606 Betsy should file with her 2021 income tax return should look like. 

Notice here that I am using the 2020 version of the Form 8606 for this and all examples. The 2021 Form 8606 is not yet available as of this writing. 

The most important line of page 1 of the Form 8606 is line 6. Line 6 reports the fair market value of all traditional IRAs, SEP IRAs, and SIMPLE IRAs Betsy owns as of year-end. Because Betsy had no traditional IRAs, SEP IRAs, and SIMPLE IRAs as of December 31, 2021, her Backdoor Roth IRA works and is tax efficient. This important number ($0) on line 6 of the Form 8606 is what ensures Betsy’s Backdoor Roth IRA is tax efficient. 

Note that Betsy’s Backdoor Roth IRA creates an innocuous $3 of taxable income, which is reported on the top of part 2 of the Form 8606. 

The Pro-Rata Rule and December 31st

But what if Betsy did have a balance inside a traditional IRA, SEP IRA, or SIMPLE IRA on December 31, 2021? Would her Backdoor Roth IRA still be tax efficient? Probably not, due to the Pro-Rata Rule.

The Pro-Rata Rule tells us just how much of the basis in her traditional IRA Betsy can recover when she does the Roth conversion step of the Backdoor Roth IRA. Betsy’s $6,000 nondeductible traditional IRA creates $6,000 of basis. As we saw above, Betsy was able to recover 100 percent of her $6,000 of basis against her Roth conversion. 

But the Pro-Rata Rule says “not so fast” if Betsy has another traditional IRA, SEP IRA, or SIMPLE IRA on December 31st of the year of any Roth conversion. The Pro-Rata Rule allocates IRA Basis between converted amounts (in Betsy’s case, $6,003) and amounts in traditional IRAs, SEP IRAs, and SIMPLE IRAs on December 31st. Here’s an example. 

Example 2

Betsy, age 40, earns $300,000 from her W-2 job in 2021, is covered by a workplace 401(k) plan, and has some investment income. Betsy has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA.

Betsy contributes $6,000 to a traditional IRA on May 20, 2021. The contribution is nondeductible. Because the contribution is nondeductible, Betsy gets a $6,000 basis in her traditional IRA. Betsy must file a Form 8606 with her 2021 tax return to report the nondeductible contribution.

On June 5, 2021, Betsy converts the entire balance in the traditional IRA, $6,003, to a Roth IRA. 

On September 1, 2021, Betsy transfers an old 401(k) from a previous employer 401(k) plan to a traditional IRA. On December 31st, that traditional IRA is worth $100,000. The old 401(k) had no after-tax contributions. 

This one 401(k)-to-IRA rollover transaction dramatically changes both the taxation of Betsy’s Backdoor Roth IRA and her 2021 Form 8606. Here’s page 1 of the Form 8606.

Line 6 of the Form 8606 now has $100,000 on it instead of $0. That $100,000 causes Betsy to recover only 5.67 percent of the $6,000 of basis she created by making a nondeductible contribution to the traditional IRA. As a result, $5,663 of the $6,003 transferred to the Roth IRA in the Roth conversion step is taxable to Betsy as ordinary income. At a 35% tax rate, the 401(k) to IRA rollover (a nontaxable transaction) cost Betsy $1,982 in federal income tax on her Backdoor Roth IRA. Ouch!

Quick Lesson: The lesson here is that prior to rolling over a 401(k) or other workplace plan to an IRA, taxpayers should consider the impact on any Backdoor Roth IRA planning already done and/or planned for the future. One possible planning alternative is to transfer old employer 401(k) accounts to current employer 401(k) plans.

There is an antidote to the Pro-Rata Rule when one has amounts in traditional IRAs, SEP IRAs, and SIMPLE IRAs. It is transferring the traditional IRA, SEP IRA, or SIMPLE IRA to a qualified plan (such as a 401(k) plan) before December 31st. Here is what that might look like in Betsy’s example. 

Example 3

Betsy, age 40, earns $300,000 from her W-2 job in 2021, is covered by a workplace 401(k) plan, and has some investment income. Betsy has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA.

Betsy contributes $6,000 to a traditional IRA on May 20, 2021. The contribution is nondeductible. Because the contribution is nondeductible, Betsy gets a $6,000 basis in her traditional IRA. Betsy must file a Form 8606 with her 2021 tax return to report the nondeductible contribution.

On June 5, 2021, Betsy converts the entire balance in the traditional IRA, $6,003, to a Roth IRA. 

On September 1, 2021, Betsy transfers an old 401(k) from a previous employer to a traditional IRA. The old 401(k) had no after-tax contributions. 

On November 16, 2021, Betsy transfers the entire balance in this new traditional IRA to her current employer’s 401(k) plan in a direct trustee-to-trustee transfer. 

Here is Betsy’s 2021 Form 8606 (page 1) after all of these events:

Betsy got clean by December 31st, so her Backdoor Roth IRA now reverts to the optimized result (just $3 of taxable income) she obtained in Example 1. 

Pro-Rata Rule Clean Up

Implementation 

From a planning perspective, it is best to clean up old traditional IRAs/SEP IRAs/SIMPLE IRAs prior to, not after, executing the Roth conversion step of a Backdoor Roth IRA. I say that because things happen in life. There is absolutely no guarantee that those intending to roll amounts from IRAs to workplace qualified plans will get that accomplished by December 31st. 

Further, transfers from one retirement account to another are usually best done through a direct “trustee-to-trustee” transfer to minimize the risk that the money in the retirement account accidentally is distributed to the individual, causing potential tax and penalties. 

Before cleaning up old traditional IRAs, SEP IRAs, and SIMPLE IRAs, one should consider the investment choices and fees inside their employer retirement plan (such as a 401(k)). If the investment options are not good, and/or the fees are high, perhaps cleaning up an IRA to move money into less desirable investments is not worth it. This is a subjective judgment that must weigh the potential tax and investment benefits and drawbacks. 

Tax Issues

Amazingly enough, the Pro-Rata Rule is concerned with only one day: December 31st. A taxpayer can have a balance in a traditional IRA, SEP IRA, or SIMPLE IRA on any day other than December 31st, and it does not count for purposes of the Pro-Rata Rule. Perhaps December 31st should be called Pro-Rata Rule Day instead of New Year’s Eve. 😉

Betsy’s November 16th distribution from her traditional IRA to the 401(k) plan does not attract any of the basis created by the nondeductible traditional IRA contribution earlier in the year. This document provides a brief technical explanation of why rollovers to qualified plans do not reduce IRA basis. 

Extra care should be taken when cleaning up (a) large amounts in any type of IRA and (b) any SIMPLE IRA. While it is fairly obvious that significant sums should be moved only after considering all the relevant investment, tax, and execution issues, the SIMPLE IRA provides its own nuances. Any SIMPLE IRA cannot be rolled to an account other than a SIMPLE IRA within the SIMPLE IRA’s first two years of existence. Thus, SIMPLE IRAs must be appropriately aged before doing any sort of Backdoor Roth IRA clean up planning. 

Spouses are entirely separate for Pro-Rata Rule purposes, even in community property states. Cleaning up one spouse, or failing to clean up one spouse, has absolutely no impact on the taxation of the other spouse’s Backdoor Roth IRA.

Lastly, non spousal inherited IRAs do not factor into a taxpayer’s application of the Pro-Rata Rule. Each non spousal inherited IRA has its own separate, hermetically sealed Pro-Rata Rule calculation. The inheriting beneficiary does a Pro-Rata Rule calculation on all IRAs he/she owns as the original owner, separate from any inherited IRAs. In addition, non spousal inherited IRAs cannot be rolled into a 401(k).

Mega Backdoor Roth

Good news: the concerns addressed in this blog post generally do not apply with respect to the Mega Backdoor Roth (sometimes referred to as a Mega Backdoor Roth IRA, though a Roth IRA does not necessarily have to be involved). Qualified plans such as 401(k)s are not subject to the Pro-Rata Rule. 

While 401(k)s are not subject to the Pro-Rata Rule, amounts within a particular 401(k) plan’s after-tax 401(k) are subject to the “cream-in-the-coffee” rule I previously wrote about here. Thus, if there is growth on Mega Backdoor Roth contributions before they are moved out of the after-tax 401(k), generally speaking either the taxpayer must pay income tax on the growth (if moved to a Roth account) or the taxpayer can separately roll the growth to a traditional IRA (which could then create a rather small Pro-Rata Rule issue with future Backdoor Roth IRAs). Fortunately, the cream-in-the-coffee rule has a much narrower reach than the Pro-Rata Rule.

Backdoor Roth IRA Tax Return Reporting

Watch me discuss Backdoor Roth IRA tax return reporting.

Conclusion

Get your IRAs in order so you can enjoy New Year’s Eve! 

December 31st is an important date when it comes to Backdoor Roth IRA planning. It is important to plan to have no (or at a minimum, very small) balances in traditional IRAs, SEP IRAs, and SIMPLE IRAs on December 31st when planning Backdoor Roth IRAs. 

None of what is discussed in this blog post is advice for any particular taxpayer. Those working through Backdoor Roth IRA planning issues are often well advised to reach out to professional advisors regarding their own tax situation.

Further Reading

I did a blog post about Backdoor Roth IRA tax return reporting here.

I did a deep dive on the taxation of Roth IRA withdrawals here.

I did a deep dive on the Pro-Rata Rule here.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The End of the Backdoor Roth IRA?

Is the backdoor closing? If a recently released proposal from the House Ways & Means Committee is enacted, then yes it is.

My analysis and commentary below is just my initial take on the proposed new laws: it is subject to revision.

UPDATE December 18, 2021

The update as of December 18, 2021 can be read here. Turns out that as of now (December 18th) my predictive analysis offered in November appears rather spot on. But remember, things can change.

Here’s what I wrote in November: On November 19, 2021, the House of Representatives passed the proposals discussed below. To my mind, the passage of this legislation is a 26.2 mile marathon: Passage in the House is the first mile, and passage in the Senate is the next 25.2 miles. There are absolutely no guarantees as to whether the proposals ultimately become law. My view is that passage in the Senate is going to be much more difficult than passage in the House.

Backdoor Roths

The Backdoor Roth IRA has been a popular transaction for over a decade. It allows those unable to make a direct Roth IRA contribution to get an annual contribution into a Roth IRA through a two-step process. There is a 401(k) version popularly referred to as the Mega Backdoor Roth IRA, which allows taxpayers to move significant amounts into Roth accounts using after-tax 401(k) contributions.

House Ways & Means Proposal

On September 13, 2021, the House Ways and Means committee released legislative text and an explanation of proposed new rules that would change the Roth landscape.

Elimination of Backdoor Roth IRAs and Mega Backdoor Roth IRAs

Effective in 2022, after-tax amounts in IRAs could not be converted to Roth IRAs. This rule would apply to all taxpayers regardless of their level of adjusted gross income. This rule would eliminate the Backdoor Roth IRA, as amounts contributed to a nondeductible traditional IRA (the first step of a Backdoor Roth IRA) could not be converted to a Roth IRA.

The bill would also eliminate after-tax contributions to qualified plans. As a result, workplace plans such as 401(k)s could no longer offer the Mega Backdoor Roth.

Effect on 2021 Backdoor Roth IRAs

In a twist, the new rule would effectively impose a deadline on all 2021 Backdoor Roth IRA planning: December 31, 2021. If the new law is passed, both the nondeductible traditional IRA contribution step and the Roth conversion step for a Backdoor Roth IRA would need to be completed by 2021 in order to do a 2021 Backdoor Roth IRA.

Usually, the deadline to worry about from a Backdoor Roth IRA perspective is the deadline to make the nondeductible traditional IRA contribution, usually April 15th of the following year. There is no particular deadline to complete the Roth conversion step. By prohibiting Roth conversions of after-tax money in traditional IRAs beginning January 1, 2022, Congress effectively makes December 31, 2021 the deadline to execute the Roth conversion step of a 2021 Backdoor Roth IRA.

I wrote about how the legislative proposal impacts the approach to 2021 Backdoor Roth IRA planning and deadlines here.

I have previously written about late or “split-year” Backdoor Roth IRAs under current law here.

Update on Legislative Proposals (As of November 4, 2021)

On October 28th, a new tax proposal came out which did not have the Backdoor elimination proposals. However, a second new tax proposal issued on November 3rd did contain the Backdoor Roth elimination proposals. Based on the current political landscape, there is significant doubt as to whether any tax proposal is enacted during this Congress. However, there is at least some chance the Backdoor Roth proposals are enacted.

Elimination of Roth Conversions for High Income Taxpayers Beginning in 2032

The legislative proposal also eliminates Roth conversions in any year a taxpayer’s adjusted taxable income is $400K (single filers) or $450K (married filing joint) starting in the year 2032.

A couple of observations about this rule. First, this rule would have no practical effect on the FI community. Usually, those in the FI community avoid taxable Roth conversions during high income years. Taxable Roth conversions (such as the so-called Roth Conversion Ladder strategy) are usually executed during early retirement before collecting Social Security. Those years often have artificially low taxable income, so a high income cap on the ability to do a Roth conversion is a rule without consequence for the FI community.

Second, you might be wondering: why the heck are they changing the tax law 10 years in the future? Why not now? The answer lies in how Congress “scores” tax bills. Taxable Roth conversions, particularly in the near term, increase tax revenue. An immediate repeal of Roth conversions would “cost” the government money in the new few years. But by delaying implementation for 10 years, Congress is able to predict that taxpayers, facing a future with no Roth conversions, will increase Roth conversions in 2030 and 2031, increasing tax revenues in those years.

Outlook

Congress is closely divided. There is absolutely no guarantee this bill will pass both houses of Congress and be signed by the President. That said, these proposed rules are now “out there” and being “out there” is the first step towards a tax rule becoming law.

I will Tweet and blog about any future developments in this regard.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Tax Deductions for Individuals

Tax deductions can be a confusing topic considering the many types of tax deductions and the terminology for them. Below I explain the different types of tax deductions you can claim on your tax return. You may be taking several of these types without even knowing it.

Types of Individual Tax Deductions

Exclusions

Many things we think of tax deductions are not treated as tax deductions on a tax return. Instead, they are excluded from taxable income. An exclusion from taxable income has the exact same effect as a tax deduction.

The most common exclusion is the exclusion for employer provided benefits, including health insurance, retirement plan contributions, and health savings accounts contributions. Here is an example:

Example: Mark has a salary of $100,000. He contributes ten percent ($10,000) of his salary to his employer’s 401(k) plan. His W-2 for the year will report wages of $90,000, not $100,000, and he will enter $90,000 as wages on his Form 1040. The $10,000 Mark contributed to his 401(k) is excluded from his gross income. This exclusion has the same income tax effect as a deduction.

Exclusions are a great form of deduction in that they are generally unlimited on your tax return, though they may have their own limitations. For example, in 2021 the most an employee under age 50 can exclude for contributions to a 401(k), 403(b), or a 457 is $19,500.

For those at least 70 1/2 years old, the qualified charitable distribution (“QCD”), which I wrote about here, can be a great tax planning technique. 

Exclusions also reduce adjusted gross income (“AGI”). Items that reduce AGI are great because AGI (or modified AGI, “MAGI”) is usually the measuring stick for whether a taxpayer qualifies for many tax benefits (such as eligibility for making a deductible contribution to an IRA or making a contribution to a Roth IRA). Lowering AGI is an important tax planning objective, since lower AGI opens the door to several tax benefits. 

Business Deductions

Business deductions include trade or business deductions generated from self-employment and investments in partnerships and rental property. On a Form 1040, these deductions are reported on Schedule C or Schedule E. Business deductions include salaries, rent, depreciation (deducting the cost of a business asset over a useful life), and other ordinary and necessary expenses.

Business deductions are generally great tax deductions because they are subject to relatively few limitations on your tax return. That said, limitations such as the passive activity loss rules and the at-risk limitations can limit a taxpayer’s ability to claim some business losses. Further, business deductions reduce not only income tax but also self-employment income, and thus, self-employment tax.

Business deductions are also valuable because they reduce AGI.

“For AGI” or “Above the Line” Deductions

On your Form 1040 you deduct certain expenses from your gross income to determine your AGI. Prior to tax returns filed for 2018 and later, these deductions were at the bottom of page 1 of the Form 1040. Starting with tax returns for 2018, these deductions are presented on Schedule 1 which accompanies Form 1040.

Examples of these deductions include one-half of self-employment tax paid by self-employed individuals, deductible contributions to IRAs, and contributions to certain self-employed retirement plans.  

Capital losses, generally up to $3,000 on any one tax return, can be deducted for computing AGI. Capital losses in excess of $3,000 are carried over to future tax years to be deducted against capital gains and against up to $3,000 per year of ordinary income. 

Health Savings Accounts (“HSAs”) are their own special breed. If contributions to an HSA are made through workplace payroll withholding, they are excluded from taxable income. If contributions to an HSA are made through another means (such as a check or wire transfer to the HSA), the contributions are for AGI deductions reported on Schedule 1. Which is better? From an income tax perspective, there is no difference. But from a payroll tax perspective, using payroll withholding is the clear winner. Amounts contributed to an HSA through payroll withholding are not subject to the FICA tax, creating another HSA tax win!

Standard Deduction or Itemized Deductions

Tax reform changed the landscape of itemized deductions. As a result of the tax reform bill enacted in December 2017, far fewer taxpayers will claim itemized deductions, and will instead claim the standard deduction.

The most common itemized deductions are state and local taxes (income, property, and in some cases, sales taxes), charitable contributions, and mortgage interest.

Taxpayers generally itemize if the sum total of itemized deductions (reported on Schedule A) exceed the standard deduction. Tax reform did two things to increase the chance that the standard deduction will exceed a taxpayer’s itemized deductions. First, the amount of the standard deduction increased. It went from $6,350 for single taxpayers in 2017 to $12,000 for single taxpayers in 2018. For married filing joint taxpayers, the standard deduction went from $12,700 in 2017 to $24,000 in 2018.

The standard deduction for 2021 is $12,550 (single) and $25,100 (MFJ) for most taxpayers. 

In addition, several itemized deductions were significantly reduced. For example, starting in 2018 there is a deduction cap of $10,000 per tax return ($5,000 for married filing separate tax returns) for state and local taxes. This hits married taxpayers particularly hard and increases the chance that if you are married filing joint you will claim the standard deduction, since you will need over $15,100 in other itemized deductions to itemize (using the 2021 numbers).

In addition, miscellaneous deductions, such as unreimbursed employee expenses and tax return preparation fees, were eliminated as part of tax reform.

Thus, many taxpayers will find that they will often claim the standard deduction. As discussed below, there will be planning opportunities for taxpayers to essentially push many itemized deductions (such as charitable contributions) into one particular tax year, itemize for that year, and then claim the standard deduction for the next several years.

Neither the standard deduction nor itemized deductions reduce AGI.

Special Deductions

In a relatively new development in tax law, there are now deductions that apply only after AGI has been determined and separate and apart from the standard deduction or itemized deductions. 

QBI Deduction

Tax reform created an entirely new tax deduction: the qualified business income deduction (also known as the QBI deduction or the Section 199A deduction). I have written about the QBI deduction here and here. Subject to certain limitations, taxpayers can claim, as a deduction, 20 percent of qualified business income, which is generally income from domestic business activities (not wage income), income from publicly-traded partnerships, and qualified REIT (real estate investment trust) dividends.

The QBI deduction does not reduce AGI.

Taxpayers can claim the QBI deduction regardless of whether they elect itemized deductions or the standard deduction.

Special Deduction for Charitable Contributions

For the 2021 tax year, taxpayers who do not claim itemized deductions are eligible for a special deduction for charitable contributions. The deduction is limited to $300 for single filers and $600 for MFJ filers.

As discussed by Jeffrey Levine, this deduction, like the QBI deduction, neither reduces AGI nor is an itemized deduction. 

The statutory language for this new deduction is found at Section 170(p). I believe that there is a very good chance that this deduction is extended to years beyond 2021, though as of now, it is only applicable to the 2021 tax year. 

Planning

Tax deductions provide a great opportunity for impactful tax planning. Here are some examples.

Timing

If your marginal income tax rate is the same every year, then you generally want to accelerate deductions. Thus, if you have a sole proprietorship and are a cash basis taxpayer, you are generally better off paying rent due on January 1, 2022 on December 31, 2021 instead of January 1, 2022 since the deduction saves the same amount of tax regardless of which tax year you pay it, but you’ll get the cash tax benefit sooner – on your 2021 income tax return instead of on your 2022 income tax return.

But there can be situations where you anticipate that your marginal tax rate will be greater next year than this year. In those cases, it makes sense to delay deductions. For example, perhaps you would make a large charitable contribution next year instead of before the end of the current year. Or, in the above example, you would pay the rent on January 1, 2022 to ensure the deduction is in 2022 instead of 2021.

Bunching

For some taxpayers, it may make sense to bunch deductions to maximize the total benefit of itemizing deductions versus claiming the standard deduction over several years. My favorite example of this is the donor advised fund. I’m not alone in my fondness of the donor advised fund. It allows you to contribute to a fund in one year, claim a charitable deduction for the entire amount of the contribution, and then donate from that fund to charities in subsequent years. The big advantage is that you get an enhanced upfront deduction in the first year and then claim the standard deduction in several subsequent years. This strategy only works if the amount of the deduction for the contribution to the donor advised fund is sufficient such that your itemized deductions in the year of the contribution exceed the standard deduction by a healthy amount.

Deadlines, Deadlines, Deadlines!!!

Different deductions have different deadlines. Many deductions have December 31st deadlines, so it is important to make the contribution by year-end. For charitable contributions, it is best to make the contribution online with a credit or debit card before January 1st if you are running really late, though if you place the contribution in a U.S. Postal Service mailbox prior to January 1st that counts as prior to the near year (though it makes it harder to prove you beat the deadline if you drop it in the mailbox on December 31st).

For employee contributions to a 401(k), the deadline is December 31st. Thus, if you are reading this on December 5th and you want to significantly increase your 401(k) contribution for 2021, you ought to get in touch with your payroll administrator and increase your contribution rate for your last paycheck ASAP.

By contrast, the deadline for a 2021 contribution to a deductible IRA or a non-payroll 2021 contribution to a HSA is April 15, 2022 (the date tax returns are due).

Self-employed retirement plans have their own sets of deadlines that should be considered.

Conclusion

Tax deductions present several important tax planning considerations. These considerations should include the taxpayer’s current marginal tax rate and future marginal tax rate. They should also include consideration of maximizing the combination of itemized deductions and the standard deduction over multiple taxable years.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Roth IRAs and the VAT Boogeyman

The Roth IRA: tax free retirement income. What’s not to love? 

But wait a minute. What Congress gives Congress can take away, right? Might Congress, looking for tax revenues to pay off the debt, simply make Roth distributions in retirement taxable? Not very likely. 

While I have no evidence to support this proposition, my guess is that Roth account owners vote at very high rates. Voting to tax Roth withdrawals in retirement seems to be a good way to create a motivated constituency to deny members of Congress re-election. I’m hardly the first person to argue that it is very unlikely that Congress will ever subject Roth withdrawals to income taxation.

The Value Added Tax

There are indirect ways for Congress to attack Roths and tax some of that otherwise tax free account value. One way some worry about is the value-added tax, otherwise known as the VAT. The VAT is a consumption tax on goods and services. The EU has a website here describing the VAT in the European Union. A VAT functions like a sales tax and can be added at any or all levels of production. Many developed countries have a VAT, but the United States does not. 

Roths and the VAT

A VAT has the potential to increase the price of goods and/or services, and thus, to potentially eat away at value inside Roth accounts. 

Here is a simplified example of how that would work. 

Maria is retired. Her annual consumption is approximately $95,000, $5,000 of which is property taxes. She lives off $25,000 a year in Social Security income and $70,000 a year in withdrawals from her Roth IRA. She pays no income taxes on those withdrawals. If a 10 percent VAT were enacted on retail sales, she would need to withdraw approximately $9,000 (10 percent of her current $90,000 non-property tax annual consumption) more from her Roth IRA to pay for her current level of consumption. Instead of using an income tax, the government collects $9,000 from her Roth IRA annually by imposing a VAT.

The VAT functions as a tax on a Roth IRA. As Maria has to withdraw more from her Roth to maintain the same level of consumption, the VAT also reduces the value of amounts inside a Roth IRA. Does this mean a Roth IRA is less desirable?

For the reasons argued below, I believe that the answer is No. First, it should be remembered that were a VAT to be implemented, is almost certain to be implemented in addition to the current federal income tax. Sure, if the United States were to switch from an income tax to a VAT traditional IRA owners would win big (having previously received an income tax deduction without a later income tax charge) and Roth IRA owners would lose big. But a switch from an income tax to a VAT is almost certainly not happening. 

Second, when assessing the value of Roth accounts in a United States with a VAT, one must compare them to the alternatives: traditional retirement accounts and taxable accounts. 

Traditional Versus Roth with a VAT

Let’s start out by examining the difference between a Roth IRA and a traditional IRA if there is a federal VAT. Here is an example. 

Joe is 65 years old and retired. He is a lifelong New York Jets fan, and decides he wants to go Super Bowl LVI, to see his Jets, presumably the AFC representatives in the game. One ticket costs $10,000 and Joe’s only source of funds for the purchase is his retirement account. Joe’s marginal federal income tax rate is 22 percent. Here are the results if Joe has a traditional IRA and a Roth IRA both without a federal VAT on the ticket and with a 5 percent federal VAT on the ticket:

No VATNo VAT5% VAT5% VAT
IRA TypeAmount NeededIncome Tax DueAmount NeededIncome Tax Due
Traditional$12,821$2,821$13,462$2,962
Roth$10,000$0$10,500$0

Hopefully you can see what is going on in the table. With a traditional IRA, one cannot simply withdraw $10,000 to pay for a $10,000 expense. There will be income tax due on the withdrawal. In order to net out $10,000 to pay for the ticket, Joe must withdraw $12,821, which covers the cost of the ticket and the 22 percent federal income tax (assume Joe lives in Florida so there’s no state income tax). This is computed as the amount needed ($10,000) divided by 1 minus the tax rate (1 minus .22), which equals $12,821. 

With a 5 percent VAT, Joe must pay $10,500 for the Super Bowl ticket. From his traditional IRA, he must withdraw $13,462, computed as the amount needed ($10,500) divided by 1 minus the tax rate (1 minus .22). 

As we are about to learn, paying a VAT with a traditional IRA creates a new tax: income tax on the VAT. Paying a VAT with a Roth IRA avoids this new tax.

If Joe pays for his Super Bowl ticket with a traditional IRA, he needs $641 more from his traditional IRA in a VAT environment to pay for the Super Bowl ticket. He must pay $141 in additional income tax to cover this additional withdrawal. The income tax on the VAT is $110 (22 percent of $500), the income tax on the income tax on the VAT is $24 (22 percent of $110), and there is approximately $7 of income tax on the remainder of the income tax required. 

See this spreadsheet for the income tax calculation. Incredibly, it is possible to pay income tax on the income tax on the income tax on the income tax on the VAT if you pay the VAT from a traditional IRA. It will get much worse as expenses increase beyond the $10,000 tackled in this example. 

The first lesson: a VAT hurts those with traditional IRAs, since they will have to increase their taxable withdrawals to pay for goods and services subject to the VAT. When paid with a traditional retirement account, VAT creates several new taxes: the VAT itself, the income tax on the VAT, the income tax on the income tax on the VAT, etc.

The second lesson: if a VAT is enacted, the Roth protects retirees from the income tax payable on the VAT. The 5 percent VAT increases the total tax cost of the $10,000 ticket by $641 if one uses a traditional IRA but only by $500 if one uses a Roth IRA. Having a Roth protects against income tax on the VAT itself. This makes a Roth an even more desirable planning alternative if there is a VAT than if there is no VAT. 

The income tax on the VAT is another tax villain the Roth can successfully defeat.

Roth Versus Taxable with a VAT

I believe the logic applied in the Roth versus Traditional VAT environment applies in assessing Roths versus taxable accounts in a VAT environment. To fund consumption, retirees will have to sell more of their taxable brokerage accounts to pay for the now increased price of goods and services, resulting in higher capital gains (and thus, more capital gains taxes) in many cases. Using a Roth withdrawal to pay a VAT protects against those additional capital gains taxes. 

Planning

If one believes that a VAT is coming, there is not much, to my mind, to be done from a financial planning perspective, other than increasing amounts in Roth accounts. One might purchase durable goods in advance of the enactment of a VAT, but that sort of planning is of limited value. How many refrigerators can you stockpile for your future use? For those worried about a VAT, the tactics that appear effective are to increase Roth contributions and/or conversions.

While a VAT would not be good news, it makes the Roth planning decision more likely to be the advantageous planning decision.

Paying a VAT out of a Roth avoids the income tax on the VAT (and the resulting additional income taxes) retirees incur when paying the VAT out of a traditional IRA. A Roth also avoids increased capital gains taxes resulting from using taxable brokerage accounts to pay a VAT. 

Conclusion

A VAT is not good news for Roth IRA owners, but it is worse news for traditional IRA owners. Roths limit the tax damage of a VAT to the VAT itself in a way neither traditional retirement accounts nor taxable accounts are capable of. In the age-old traditional versus Roth debate, the possibility of a future VAT moves the needle (if ever so slightly) in the direction of the Roth. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Qualified Business Income Deduction Update

For those interested in tax planning for the FI community, some interesting news came from the Senate this week. Senator Ron Wyden, a Democrat and the Chairman of the Senate Finance Committee, released a proposal to modify the Section 199A qualified business income (“QBI”) deduction.

My view is that this is very good news, for reasons I will discuss below.

QBI Deduction

The Section 199A QBI deduction provides small business owners a deduction of up to 20 percent of their “qualified business income.” Usually, this is income from self-employment (reported on Schedule C) or income from a partnership or S corporation (reported on Form K-1). The deduction is subject to a host of limitations which tend to kick in hard for upper income taxpayers. 

I’ve written plenty on the Section 199A QBI deduction. My introductory post is here, and a more advanced post is here. 

The QBI deduction is good for the financial independence community. It lowers the federal income tax burden on those with small businesses and side hustles. 

Expiration

But there is one lurking issue with the QBI deduction: will it last? There are two reasons to worry that it will not. First, it was enacted by Republicans in late 2017 in a polarized political environment. While that means Washington Republicans generally support the deduction, it also means Washington Democrats may have no particular political reason to support it. Second, the deduction has an expiration date: December 31, 2025: The deduction is not available in tax years beginning after that date. 

While there are few things more permanent than a temporary tax deduction, obviously it is worrisome that if nothing else happens, we only have four and a half more years of the tax deduction. 

Wyden Proposal

Senator Wyden introduced a proposal to modify the Section 199A QBI deduction. The legislative language is available here and a summary of the legislation from Senator Wyden’s staff is available here.

I am still reviewing the language, so at this point (July 21, 2021) I only have a basic understanding of it. Please take the below as a preliminary analysis subject to change. 

The bill keeps the QBI deduction, but appears to eliminate it entirely (as related to qualified business income itself) if taxable income reported on the tax return is $500,000 or more. Between $400K and $500K of taxable income, the QBI deduction is phased out. It appears single taxpayers do very well with this provision, as the limits apply per tax return, and are not doubled for married filing joint taxpayers. 

The Wyden proposal eliminates the ability for married filing separately taxpayers and estates and trusts to claim the QBI deduction. 

The bill also eliminates the concept of a “specified service trade or business.” This simplifies the QBI deduction and will help many self-employed professionals qualify for the deduction where under current law they would not. 

See the example of Jackie I posted here. Without a deduction for Solo 401(k) contributions Jackie did not qualify for any QBI deduction at all because he was a single lawyer with a taxable income over $215K. If the Wyden proposal is enacted as written, Jackie could have up to $400K in taxable income and claim a full QBI deduction. Single moderate to high income professionals appear, at first glance, to be the big winners if the Wyden proposal is enacted. Some married professionals will also benefit from this provision. 

Section 199A Dividends

The proposed bill appears to keep the 20 percent deduction for “Section 199A dividends” which are dividends paid by real estate investment trusts (“REITs”) and mutual funds and ETFs which own REITs. It appears, however, that a taxpayer’s ability to deduct Section 199A dividends would phase out between $400K and $500K of taxable income. Under current law there is no taxable income limit on the ability to deduct 20 percent of Section 199A dividends. 

Expiration 

The Wyden proposal does not eliminate the expiration date, December 31, 2025. To my mind, that is not too surprising. Eliminating the expiration date would increase the “cost” of the Wyden proposal and thus, under Congressional budgeting procedures, likely require cutting spending or raising other taxes. 

The Good News

To my mind, the Wyden proposal is good news for those fond of the QBI deduction. Instead of eliminating the QBI deduction, we now have a powerful Washington Democrat embracing large parts of the deduction, and expanding its availability for some taxpayers. If this were to pass (and that is very speculative), then both Republicans and Democrats would have passed a version of the QBI deduction. At that point, it is unlikely that either party would want to be responsible for the deduction dying in full in 2026. 

This legislative proposal is simply a first step: stay tuned for further developments. But for the FI community, I see a powerful Washington Democrat embracing a large portion of the QBI deduction to be a positive development. 

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Sean on The Struggle is Real Podcast

I chatted with Justin Peters on The Struggle is Real Podcast regarding tax issues for those in their 20s to consider. You can access the episode here: https://justinleepeters.podbean.com/e/what-you-need-to-know-about-taxes-in-your-20s-e39-sean-mullaney/

As always, the discussion is general and educational in nature and does not constitute tax, investment, legal, or financial advice with respect to any particular individual or taxpayer. Please consult your own advisors regarding your own unique situation.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

S Corporations for Beginning Solopreneurs

Last month the blog discussed the beginning of the self-employment journey. Specifically, it discussed how one pays taxes when they become self-employed. This post goes further. It explores a potentially powerful tax planning for self-employed solopreneurs, the S corporation. 

None of the below is tax advice for any particular taxpayer. Note that if you are considering an S corporation, you are generally well advised to work with a tax professional before and during the process of implementing an S corporation. 

The S Corporation Concept

Generally speaking, a corporation is subject to federal income tax at a 21 percent rate. For example, if Acme Incorporated has $100,000 of taxable income for the year, it owes the IRS $21,000 of federal income tax. Further, the shareholders are subject to taxes on the receipt of dividends from the corporation. If Acme Incorporated pays its after tax profit of $79,000 to its shareholders, generally its shareholders must include the receipt of the dividend in taxable income (though the dividend may qualify for the favorable qualified dividend income rates). 

Based on both the corporation and the shareholders having to pay tax on the same income, it is said that many corporations (so-called “C corporations”) are subject to double tax. 

For smaller businesses, this can be very problematic. The tax rules recognize this, and thus, for certain small business entities, allow an “S corporation” election (meaning that the corporation is taxed under the rules of Subchapter S of the Internal Revenue Code).

S corporations are generally subject to only one level of tax, as all of the tax items of the S corporation (taxable income, gain, loss, credits, etc.) are reported and taxed on the shareholder(s) individual tax returns. The S corporation itself usually does not pay federal income tax. 

Most states replicate this treatment to a large extent. For example, in my home state of California, S corporation income is reported on the shareholders’ tax returns, but the S corporation itself is subject to a 1.5% income tax (with a minimum annual tax due of $800 regardless of income). 

The Self-Employment Tax Savings and Reasonable Compensation

There is another wrinkle to S corporations which can make them advantageous to solopreneurs. The S corporation must pay owner-employees reasonable compensation as W-2 salary. However, the rules generally allow the owner-employee to take some of the earnings of the S corporation as a dividend. This has the rather interesting effect of, in many cases, reducing the overall payroll tax liability of the solopreneur. 

Here’s a quick example of how that could work:

Aurora works as a private detective. After business expenses, she has a net income of $110,000. The payroll taxes she pays will depend on whether the business is organized as a sole proprietorship or an S corporation. 

If she is operating as a sole proprietorship, she will pay $15,543 in self-employment taxes, as computed on Schedule SE (roughly, 14.13% of her profits are due in self-employment taxes). 

Things are different if the business is organized as an S corporation. Assume, just for the sake of this example, that the S corporation pays Aurora $55,000 in W-2 compensation and this is reasonable. The FICA tax she and the S corporation together pay is 15.3% of that amount, $8,415. 

In this example, Aurora saves over $7,000 in payroll taxes by electing to operate out of an S corporation.

Of course, compensation must be reasonable. S corporation owner-employees who pay themselves very small W-2 salaries can have dividend payments recharacterized as W-2 salary, prompting disputes with the IRS and state taxing agencies and the collection of back payroll taxes.

Solopreneur Requirements for an S Corporation

Below I discuss, very broadly, the general requirements to establish and maintain an S corporation for a solopreneur who does not employ other people. Those items with a single asterisk can (but does not have to) apply to a Schedule C sole proprietorship (for example, for solopreneurs a limited liability company can be either a Schedule C sole proprietorship or an S corporation). The item with a double asterisk also applies to a sole proprietorship, but perhaps to a somewhat lesser extent. 

Entity Formation*

To have an S corporation, one must operate out of a legal entity. Generally, the legal entity can be a corporation or a limited liability company (an “LLC”). Corporations and LLCs are creatures of state law. Each state has its own formation and regulation procedures, requirements, and fees. Often it is wise to consult with legal counsel when forming a legal entity.

Under the federal income tax rules, an S corporation generally must have 100 or fewer shareholders and only a single class of stock outstanding. 

Tax Election

Electing S corporation status requires the filing of a Form 2553 with the IRS with the signatures of all the shareholders. In community property states, usually one’s spouse is considered a shareholder. Taxpayers omitting a spouse’s signature where the S corporation stock is community property can fix the omission under the procedure available under Revenue Procedure 2004-35. 

Entity Maintenance*

Legal entities have requirements for maintenance. These vary by state, and can include annual fees, annual shareholders’ meetings, and meetings of a Board of Directors. Consultations with legal counsel can be helpful in this regard. 

Separate Books, Records, and Bank Accounts**

A legal entity should have its own bank account to collect revenue and pay expenses. Most solopreneurs operating out of either a sole proprietorship or an S corporation are well advised to hire a (very likely virtual) bookkeeper to track revenues and expenses. 

Separate Federal Income Tax Return

S corporations must file an annual income tax return with the federal government, the Form 1120-S. Included in this Form is a Form K-1. Form K-1 reports to both the shareholders and the IRS the ordinary income and other tax results of the S corporation for the year that must be reported on the income tax returns of the shareholders.

Generally speaking, the Form 1120-S is due March 15th, but can be extended to September 15th. 

Separate State Income Tax Return

In most states, S corporations have to file income tax returns. There can be entity level taxes on S corporations (such as California’s 1.5% income tax, $800 minimum tax) and in most states the shareholders will need to report the S corporation’s income on their own state income tax return. 

Running W-2 Payroll/Reasonable Compensation

S corporations must pay their employees, including solopreneur owners, reasonable compensation. This requires running W-2 payroll, including federal and state payroll tax withholding and remittance. There are payroll processors that specialize in providing payroll services for small S corporations. 

As discussed above, W-2 compensation must be reasonable. 

Forms W-2, W-3, 940, and 941

There are both quarterly and annual payroll tax returns that must be filed to report salaries paid and payroll taxes withheld and remitted. The Form 941 is filed for each quarter and is generally due one month after the end of the quarter. 

Forms W-2, W-3, and 940 are filed on an annual basis and generally due January 31st.

Tracking Distributions and S Corporation Stock Basis

Shareholders must track their “basis” in their S corporation stock. Generally speaking, dividends from an S corporation are not taxable to the shareholder. However, they reduce the shareholder’s basis in their S corporation stock. If the shareholder receives a distribution at a time he or she does not have basis in their S corporation stock, it triggers a taxable gain to the shareholder.

Basis should generally be tracked as part of the tax return preparation process. However, basis should also be tracked during the year prior to the shareholder taking significant dividends from the S corporation. 

Increased Professional Fees

Operating out of an S corporation generally increases the professional fees a solopreneur pays. This absolutely can be worth it, but in many cases there needs to be professional assistance regarding reasonable compensation, tax filings, legal maintenance, and payroll processing. 

Tax Planning

In a world without two of my favorite tax topics, the qualified business income deduction and the Solo 401(k), the analysis was usually somewhat straightforward. Estimate business income and run it through the filters of income and self-employment tax if reported on a Schedule C versus income and payroll tax if reported through an S corporation. This yielded an estimate of the overall tax savings obtained using an S corporation structure. 

To make the “S corporation or Schedule C” decision, the taxpayer would then, for the most part, compare the estimated annual tax savings versus the additional administrative burden and costs associated with the S corporation. 

Today, we live in a world with the qualified business income deduction and the Solo 401(k). These planning opportunities make the “S corporation or Schedule C” question more nuanced. At a minimum, solopreneurs should work with their tax advisors to model out what the income tax, self-employment tax, qualified business income deduction, and retirement plan results look like at their anticipated business income level and desired retirement plan contribution level to determine whether the S corporation or the Schedule C route is better. 

Operating through an LLC

One option available to solopreneurs is operating out of an LLC as the sole owner. LLCs provide a legal entity out of which to conduct business. Properly operated, an LLC can provide a solopreneur with liability protection and reputational advantages. One great feature of LLCs is their tax flexibility. They default to disregarded status, meaning that for a solopreneur, the default option is that the taxable income of the LLC is simply reported on their Schedule C. However, using the Form 2553, a solopreneur can elect to have the LLC treated as an S corporation.

Those looking to work through an LLC should consider hiring legal counsel regarding the establishment and maintenance of their legal entity. 

Conclusion

Operating out of an S corporation is a significant additional operational commitment. There are instances where it can make a great deal of sense for a solopreneur. Those considering using an S corporation should understand the administrative commitment involved and should work with advisors as appropriate to ensure they make an informed decision. 

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean Discusses Tax Planning on the ChooseFI Podcast

I was honored to discuss using tax returns as a springboard to tax planning on a recent episode of the ChooseFI podcast. Click here for the episode website.

During the conversation we referenced this blog post.

As always, the discussion is general and educational in nature and does not constitute tax, investment, legal, or financial advice with respect to any particular individual or taxpayer. Please consult your own advisors regarding your own unique situation. Sean Mullaney and ChooseFI Publishing are currently under contract to publish a book authored by Sean Mullaney.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Paying Taxes When You’re Self-Employed

Thinking of shifting to self-employment? If you’re thinking about starting a business and being your own boss, one of the things you need to do is figure out how to pay taxes. The transition from W-2 work to self-employment significantly alters the tax landscape. 

Below I discuss the taxes self-employed solopreneurs are subject to and how to pay them. As always, the below is for educational purposes only and is not tax advice for any particular taxpayer. 

Taxes Paid by the Self-Employed

Federal Income Tax

The first tax is the exact same tax you paid as a W-2 worker: federal income tax. The determination of how much of your income is subject to this tax is a bit different. As a W-2 employee, you received a Form W-2, and, generally speaking, Box 1 of Form W-2 told you how much of your income was subject to federal income taxes. 

As a self-employed individual, you now need to track the income and expenses of your business. Solopreneurs should strongly consider practices such as having a separate bank account for the business and hiring a bookkeeper, possibly a virtual one. 

Income and expenses of the solopreneur’s business are reported annually on a Schedule C filed with Form 1040 every year. The amount of income computed on Schedule C is taxable on Form 1040.

Federal Self-Employment Tax

Congratulations on the transition to self-employment! You just signed up for a new tax: the federal self-employment tax. It’s actually (roughly speaking) the same FICA tax you paid as a W-2 employee, but now you pay it yourself (instead of through employer W-2 withholding), and you pay both halves of it. 

Here is an example of federal self-employment tax:

Leslie reports self-employment income of $80,000 on her Schedule C. Leslie has no W-2 income. Her self-employment tax is $11,304, computed as 14.13 percent of $80,000.

One’s self-employment tax will not always be approximately 14.13 percent of self-employment income. That said, in many cases 14.13 percent will be the approximate percentage. Self-employment tax is computed and reported annually on Schedule SE. Schedule SE is filed with the annual Form 1040. 

To account for the fact that the self-employed pay both halves of the payroll tax (the employee side and the employer side), they receive an income tax deduction (from adjusted gross income) on Schedule 1, line 14 for the “employer” half of the payroll tax. 

State Income Tax

Most states have an income tax, and the self-employed must pay it too, no different than when one is a W-2 employee. 

Local Taxes

Localities have various taxes solopreneurs may be subject to. First, there may be a general business tax which is often either a flat annual fee or a small percentage of revenue. Especially with the latter, there may be an exemption amount (usually, a revenue threshold) below which the solopreneur does not owe the tax. It is usually important to register with your locality to be able to claim any exemption from these taxes.

Second, localities sometimes impose a separate sales tax on particular industries or goods.

It is best to look into these taxes upfront. Localities know that sometimes small businesses miss these taxes and are usually willing to work with those who apply for relief for any missed filings or payments.

Paying Taxes

Now that we’ve discussed the broad categories of taxes the self-employed are subject to, the next step is to determine how and when to pay those taxes.

Federal Income Tax and Self-Employment Tax

This is one stop shopping. The federal tax rules require the self-employed to pay estimated taxes in quarterly payments (referred to as estimated tax payments). The dates they are due for each quarter of the year are as follows (assume the estimated tax payments account for Year 1):

QuarterDate Estimated Tax Payment is Due
First QuarterApril 15, Year 1
Second QuarterJune 15, Year 1
Third QuarterSeptember 15, Year 1
Fourth QuarterJanuary 15, Year 2

Note that if a payment due date occurs on a weekend or federal holiday, generally the due date is moved to the next day that is not a weekend and/or a federal holiday.

Generally speaking, the estimated tax payment must include both the estimated income tax due and the estimated self-employment tax due. Further, it must account for all taxable income (interest, dividends, capital gains, etc.), not just self-employment income.

Failure to pay in sufficient amounts on time can lead to an underpayment penalty computed on Form 2210. Usually, the amount required to avoid an underpayment penalty is the lesser of (i) 90 percent of the current year tax due (paid in timely, equal payments) or (ii) 110 percent of the previous year tax due (paid in timely, equal payments). These two standards are often referred to as safe harbors.

Note that if previous year adjusted gross income was less than $150,000, the 110 percent safe harbor drops to 100 percent. 

For those with growing incomes, the 110 percent safe harbor often works best. Those who have filed your Year 1 tax return by April 15, Year 2 (or at least have it just about ready to go) can take the total tax due number from the Form 1040, multiply it by 1.1, and divide it by 4 to get the amount of the required quarterly estimated tax payment to be good to go. Here is an example:

Josh is self-employed and filed his Year 1 tax return on April 1, Year 2. His business is growing. His total federal tax for Year 1 (including income tax and self-employment tax) was $45,000. Josh believes that his self-employment income could significantly increase in Year 2, so he has decided to rely upon the 110 percent safe harbor to pay his estimated tax. He multiplies $45,000 by 1.1 and then divides that product ($49,500) by 4 to get his quarterly estimated tax payment of $12,375). He makes four $12,375 payments to the IRS no later than April 15, Year 2, June 15, Year 2, September 15, Year 2, and January 15, Year 3.

The nice thing about this strategy is that Josh is now protected against the underpayment penalty even if he wins the lottery during Year 2. He simply makes those estimated payments and then, with his Year 2 Form 1040, he pays the IRS the balance due, which could be quite large. But regardless of the balance due, Josh’s underpayment penalty is $0. 

Taxpayers who might be subject to the underpayment penalty can request relief from it on the Form 2210 and/or “annualize” their income on Form 2210 to prove that the majority of their income came from later in the year (and thus estimated taxes paid later in year are sufficient for the current year’s estimated tax). Using the 110 percent safe harbor generally eliminates the need to look to mitigation tactics. 

Paying the IRS

Solopreneurs can mail estimated taxes to the IRS with a Form 1040-ES. Alternatively, solopreneurs can use the IRS DirectPay system and pay electronically at this IRS website. 

State Income Taxes

States with income taxes also generally require periodic or quarterly estimated tax payments. Many follow some or all of the IRS rules. My home state of California has its own timing rules for estimated tax payments. It generally requires taxpayers to pay 30 percent of their estimated income tax liability during the first quarter (April 15th due date), the next 40 percent of their estimated income tax liability during the second quarter (June 15th) and the remaining 30 percent after the end of the fourth quarter (the following January 15th). 

States, like the IRS, generally have website portals where solopreneurs can make estimated tax payments. 

The Transition Year

Transitions from W-2 work to solopreneurship presents many challenges and opportunities. One potential opportunity is the need to pay less or possibly no estimated taxes for the year of the transition. This can be true for several reasons. 

It may be that based on the W-2 withholding collected prior to leaving full time employment, the new solopreneur had enough withheld to cover the tax on their annual income. W-2 withholding generally assumes a full year of employment, but if one leaves full time employment and experiences start-up expenses and lower self-employment income as they build a business, it may be the case that they need to make little or no estimated tax payments in that first year.

Another source of tax payments is spousal W-2 withholding. If filing jointly with a spouse, the spouse’s W-2 withholding combined with the new solopreneur’s partial year W-2 withholding might be enough to cover the estimated taxes for the transition year. 

EINs and Forms 1099

In most cases, it makes sense for sole proprietors to obtain an employer identification number (“EIN”) from the IRS for their sole proprietorship. This EIN is used on the business’s Schedule C. Further, this number is used (instead of a Social Security number) to file any required Forms 1099s paid with respect to the business. Forms 1099 (such as the Form 1099-NEC) are required for cash payments of $600 or more during the year to individuals in the course of business. 

The IRS has an internet portal here for taxpayers to apply online for EINs. 

Tax Planning

The transition from W-2 employment to self-employment can provide several tax planning challenges and opportunities. Here is a brief overview of several challenges and opportunities.

Qualified Business Income Deduction

The Section 199A qualified business income deduction is a relatively new deduction for small businesses, including solopreneurs. I have previously blogged about this deduction here and here. 

Roth Conversions for the Self-Employed

The transition to self-employment may present Roth conversion opportunities, for two reasons. First, as a business starts up, the soloprenuer’s taxable income might be very low, and thus a start up year might be a great time to execute a Roth conversion (i.e., moving amounts from traditional IRAs/401(k)s etc. to Roth accounts) and enjoy a low marginal federal income tax rate on the converted amount.

Second, there are instances where Roth conversions by the self-employed can benefit from the Section 199A qualified business income deduction. I blogged about that opportunity here. 

S Corporations

Many solopreneurs will have the opportunity to operate out of what is referred to as an “S corporation” for U.S. federal tax purposes. There are several advantages to operating out of an S corporation, but there are also some disadvantages. 

Next month’s blog post discusses S corporations and some of the planning considerations involved. 

Solo 401(k)s

Solopreneurs are responsible for their own workplace retirement account. The Solo 401(k) is a great opportunity for many solopreneurs to stash significant amounts into tax-advantaged retirement accounts. 

As I announced in March, I’m currently working on a book about Solo 401(k)s, which is tentatively set to be published in early 2022. 

Hiring Professionals

To my mind, the shift from W-2 employment to self-employment often signals the need to hire a tax return preparer, and possibly a (virtual) bookkeeper as well. Self-employment significantly increases the complexity of one’s tax return and thus it is often wise for the self-employed to hire a tax return preparer and a bookkeeper.

Conclusion

The shift to self-employment is both exciting and challenging. Yes, the self-employed have a more complicated tax picture. But with some intentional planning, managing and ultimately optimizing the tax picture is very much possible. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

QCDs and the FI Community

Qualified charitable distributions (“QCDs”) are an exciting tax planning opportunity, particularly for the FI community. Below I describe what a qualified charitable distribution is and how members of the FI community should think about them when tax planning.

Of course, this post is educational in nature. Nothing in this blog post is tax advice for any particular taxpayer. Please consult your own tax advisor regarding your unique circumstances. 

Qualified Charitable Distributions

QCDs are transfers from a traditional IRA directly to a charity. Up to $100K annually, they are (a) not included in the taxpayer’s taxable income, (b) not deductible as charitable contributions, and (c) qualify as “required minimum distributions” (“RMDs”) (to the lesser of the taxpayer’s required minimum distribution or the actual distribution to the charity). Here is an example:

Example 1: Jack and Jill are 75 years old and file their tax return married filing joint. Jack has a RMD from his traditional IRA of $40,000 in 2021. Jack directs his traditional IRA institution to transfer $40,000 during 2021 to a section 501(c)(3) charity. Jack and Jill recognize no taxable income on the transfer, and Jack does not have to take his 2021 RMD (the $40K QCD having covered it). Further, Jack and Jill receive no charitable contribution deduction for the transfer.

Considering that Jack & Jill (both age 75) enjoy a standard deduction of $27,800 in 2021, they get both the standard deduction and a $40K deduction for the charitable contribution from the traditional IRA (since they do not have to include the $40K in their taxable income). This is the best of both worlds. Further, excluding the $40K from “adjusted gross income” (“AGI”) is actually better than taking the $40K as an itemized deduction, since many tests for tax benefits are keyed off of AGI instead of taxable income. 

Important QCD Considerations

Take QCDs Early

Generally speaking, it is best that QCDs come out of the traditional IRA early in the year. Why? Because under the tax rules, RMDs come out of a traditional IRA first. So it is usually optimal to take the QCD early in the year so it can fulfill all or part of the required minimum distribution for the year. Then you can do Roth conversion planning (if desired), so long as the full RMD has already been withdrawn (either or both through a QCD and a regular distribution) from the traditional IRA first. 

No Trinkets

I don’t care how much you love your PBS tote bag: do not accept any gift or token of appreciation from the charity. The receipt of anything (other than satisfaction) from the charity blows the QCD treatment. So be sure not to accept anything from the charity in exchange for your QCD.

QCDs Available Only from Traditional IRAs

In order to take advantage of QCD treatment, the account must be a traditional IRA. 401(k)s and other workplace plans do not qualify for QCDs. Further, SIMPLE IRAs and SEP IRAs do not qualify for QCD treatment. 

As a practical matter, this is not much of an issue. If you want to do a QCD out of a 401(k) or other tax advantaged account, generally all you need to do is rollover the account to a traditional IRA. 

QCD Age Requirement

In order to take advantage of the QCD opportunity, the traditional IRA owner must be aged 70 ½ or older. 

Inherited IRAs

QCDs are available to the beneficiary of an inherited IRA so long as the beneficiary is age 70 ½ or older. 

QCDs For Those Age 70 ½ and Older

If you are aged 70 ½ or older and charitably inclined, the QCD often is the go-to technique for charitable giving. In most cases, it makes sense to make your charitable contributions directly from your traditional IRA, up to $100,000 per year. QCDs help shield RMDs from taxation and help keep AGI low. 

QCDs and the Pro-Rata Rule

If you have made previous non-deductible contributions to your traditional IRA, distributions are generally subject to the pro-rata rule (i.e., the old contributions are recovered ratably as distributions come out of the traditional IRA). 

However, QCDs are not subject to the pro-rata rule! This has a positive effect on future taxable distributions from the traditional IRA. Here is an example of how this works:

Example 2: Mike is age 75. On January 1, 2021, he had a traditional IRA worth $500,000 to which he previously made $50,000 of nondeductible contributions. If Mike makes a $10,000 QCD to his favorite charity, his traditional IRA goes down in value to $490,000. However, his QCD does not take out any of his $50,000 of basis from nondeductible contributions. This has the nice effect of reducing the tax on future taxable distributions to Mike from the traditional IRA, since the QCD reduces denominator (by $10K) for determining how much basis is recovered, while the numerator ($50K) is unaffected. 

QCDs for Those Under Age 70 ½

Those in the FI community considering early retirement need to strongly consider Roth conversions. The general idea is that if you can retire early with sufficient wealth to support your lifestyle, you can have several years before age 70 during which your taxable income is artificially low. During those years, you can convert old traditional retirement accounts Roth accounts while you are taxed at very low federal income tax brackets.

For the charitably inclined, the planning should account for the QCD opportunity. There is no reason to convert almost every dime to Roth accounts if you plan on giving significant sums to charity during your retirement. Why pay any federal or state income tax on amounts that you ultimately will give to charity?

If you are under the age of 70 ½ and are charitably inclined, QCDs should be part of your long term financial independence gameplan. You should leave enough in your traditional retirement accounts to support your charitable giving at age 70 ½ and beyond (up to $100K annually). These amounts can come out as tax-free QCDs at that point, so why pay any tax on these amounts in your 50s or 60s? Generally speaking, a Roth conversion strategy should account for QCDs for the charitably inclined. 

Conclusion

For the charitably inclined, QCDs can be a great way to manage taxable income and qualify for tax benefits in retirement. QCDs also reduce the pressure on Roth conversion planning prior to age 72, since it provides a way to keep money in traditional accounts without having to pay tax on that money. 

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean on the How to Money Podcast

I recently discussed tax planning, financial independence, and entrepreneurship on the How to Money podcast. Please click the below link to listen. https://www.howtomoney.com/smart-tax-planning-moves-with-sean-mullaney/

FI Tax Guy can be your financial planner Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Sean Discusses the Roth 401(k) on the ChooseFI Podcast

Watch my recent segment on the ChooseFI podcast discussing the Roth 401(k)

I was privileged to join Brad and Jonathan on a recent episode of the ChooseFI podcast to discuss the Roth 401(k).

You can access the episode (Episode 289) on all major podcast players and here: https://www.choosefi.com/a-smorgasbord-of-fi-ep-289/

I have also blogged on the Roth 401(k). Here are two posts:

Roth 401(k)s for Beginners

Roth 401k Withdrawals

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Luck, Credit, and the FIRE Movement

Recently, the FIRE movement has come in for some criticism. Here is one prominent example. While I don’t want to speak for the critics, some of the arguments boil down to a version of the following: FI or FIRE (I prefer FI, but let’s not argue over terminology) overemphasizes personal responsibility and individualism, as most financial outcomes are the result of luck and the work of others. For example, if you invest $250,000 in real estate and local property values skyrocket such that your investment is now worth $600,000, most of the value of your investment is not attributable to anything you did.

While I appreciate the perspective provided by these commentators, I respectfully disagree with the criticisms. 

My Journey with FI

Before I address the criticisms, I thought it would be helpful to share a bit of my perspective on FI. My journey with personal finance mostly starts in college, when I began to become interested in some of the tactics of personal finance. Things like the Roth IRA and passive investing. 

For me, the tactics were like the quartz countertops, cabinets, and ceiling beams on a home construction site: shiny objects drawing attention, but by themselves not all that impactful. As applied to personal finance, when you add in the FI framework, you transform shiny objects into a house. Having the FI framework and goals ultimately drives better choices and better luck. 

Getting introduced to FI in 2017 flipped a switch for me. It gave meaning to the personal finance tactics. More important, it encouraged me to make better choices. For me, it’s not about a FI number or a retirement deadline.* And it has never been about anyone who retired at a particularly early age. Rather, to me FI is all about making better choices that give me and my family more options and better financial luck. 

This is why I don’t believe “financial literacy” is an adequate substitute for FIRE. You can teach people about 401(k)s and HSAs until you’re blue in the face. Without something akin to the FI framework, financial knowledge by itself does not often materially improve choices and outcomes. Financial literacy without a framework and goals is sort of like teaching algebra in high school. There’s nothing wrong with it, but how much did algebra affect your adult life? 

Having shared a bit of my own FI journey, here are my thoughts on the recent criticisms of the FIRE movement. 

* Note: For some, FI is about hitting a FI number and/or retiring by a certain date. That’s great–to each their own. 

The Role of Luck

Michael Jordan won six NBA Championships. Wouldn’t we all say that he was a great basketball player?

But wait a minute. Wasn’t almost all of his success attributable to luck? First, Dr. James Naismith invented the sport of basketball. Then players, promoters, and team owners spread the sport throughout the United States such that professional leagues could become a way to earn an income. Then the founders, players, coaches, owners, television executives, and fans of the National Basketball Association had to build it and sustain it through some very challenging times. Without the work and support of countless people, Michael Jordan would not have been able to make a living playing basketball, much less win six championships playing basketball.

And what about Jordan’s height, good health, parents, coaches, and teammates? Talk about lucky . . .

Most of us, when confronted with all the luck Michael Jordan had in his basketball career, would simply acknowledge that luck played a role, but that in no way diminishes all the hard work he put into his craft and the fact that he was a great basketball player. 

In all situations, luck plays an important role. There is little anyone can do to avoid being subject to a significant degree of luck. All you can do is make choices based on judgment and what experience and history teach. Often, you will enjoy more good luck as you make better choices. 

Luck and choices are not entirely unrelated. The better financial choices you make, the more likely it is you will have good financial outcomes and enjoy better luck along the way. For example, you can’t get lucky with an investment if you don’t make the investment! 

Investment growth could** be thought of as luck. But without an individual financial choice (the decision to invest), you get absolutely none of that luck! The FIRE movement simply says “we have hundreds of years of economic data: we know diversified baskets of productive investments generally tend to grow over long periods of time, so start investing!”

FI provides a framework for capturing financial luck. Why shouldn’t there be a “movement” (if you want to call it that) of people who are intentional about making better choices that increase the odds that they and others will experience financial luck and success? 

** Note: I do not believe investment growth is luck. I simply acknowledge that some might think of investment growth as luck. 

Credit versus Choices

The FIRE movement is not about claiming credit for financial outcomes. It’s about encouraging good financial choices. 

To my mind, arguing that the FIRE movement is lacking because most of the credit belongs to others misses the point. The point of the Financial Independence movement is not to “deserve” financial success. Rather, the point is to make choices that increase the odds of financial success and having more financial options. 

If I wear a seatbelt, I’m making a choice that increases my odds of staying safe. 

I (hopefully) don’t demand credit for being safe. Rather, I simply make an informed choice that makes my life incrementally better. 

That is what the FIRE movement is all about: make good choices in your financial life, and, generally speaking, your financial life tends to have good outcomes. If someone wants to give you credit for the resulting outcomes, that’s fine, but that credit is not what the FIRE movement is all about.

None of this makes financial independence easy, and financial independence as an end goal will be more difficult for some than for others. 

But practically everyone has financial choices to make. Thus, the FIRE movement can speak to everyone. The FIRE movement offers a framework and encouragement to make good choices. Regardless of the luck you have had up to now, it is better to be intentional about your financial choices and seek to improve your future financial choices. 

Room for Improvement

Is everything perfect in the FIRE movement? Surely not. For example, extreme examples of FIRE tend to get overemphasized in the media and within the movement (in my opinion). 

Overemphasizing certain stories causes a distorted view of financial independence. But podcasts, YouTube, blogs, and other forums help all sorts of FI stories to get out there. The FIRE movement is constantly developing and different FIRE voices appeal to different listeners (and hopefully to a growing number of listeners). 

My hope is that the movement and the media reduce the emphasis on some of the more extreme FIRE examples (while still acknowledging their validity) and choose to promote a diverse array of FIRE perspectives. No one has all the answers, but everyone can make a contribution. 

The Future of FI

In May, I published the following: 

FI/FIRE will survive out of economic necessity. What else are people to do? Tie their entire economic future to one job that can be gone in an instant? The economic downturn occurring due to Coronavirus demonstrates that you need multiple sources of economic support. Part of FI (or FIRE) is that you ultimately build up so many sources of support (essentially, a well-diversified portfolio) that your job becomes an unnecessary source of support.

I stand by that. Some argue that FIRE is unrealistic. I’d argue that tying your financial future to a single job (or, more broadly, to your ability to always earn an income from your labor) is unrealistic. 

The FIRE movement provides a framework for improving your financial condition through better choices. That is a movement worth staying in. 

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Sean on the Earn & Invest Podcast

Really enjoyed this year-end tax planning conversation with Doc G on the Earn & Invest podcast. Stay tuned to the end for some candid behind the scenes podcast recording.

https://www.earnandinvest.com/episodes-2/year-end-tax-moves-that-count

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post (and this podcast episode) is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Roth IRA Withdrawals

The Roth IRA is 25 years old as of 2023 (its birthday was January 1st). Yet there is still confusion about the rules applicable whenever someone withdraws money from a Roth IRA prior to turning 59 ½. This blog post attempts to correct some misconceptions on the taxation of nonqualified Roth IRA withdrawals.

Watch me discuss Roth IRA withdrawals.

Roth IRAs: The Basics

A Roth IRA is a tax-advantaged account that generally offers tax-free growth for invested amounts. Taxpayers receive no upfront tax deduction for putting money into a Roth IRA. If properly executed, taxpayers can withdraw money from a Roth IRA entirely tax and penalty free, and can enjoy years of tax-free growth on the amounts invested in a Roth IRA.

I have previously blogged about why I believe the Roth IRA is a great tax-advantaged account in my An Ode to the Roth IRA.

Roth IRA Funding

How does one move money into a Roth IRA? There are three ways.

Annual Contributions

Generally speaking, if your income is below certain limits, you can contribute up to the lesser of $6,500 or your earned income (2023 limits) to a Roth IRA. If you are aged 50 or older, the limits are the lesser of $7,500 or earned income (2023 limits). 

I discussed Roth IRA annual contributions, including the income limits on the ability to make Roth IRA contributions, in this post. 

Conversions

Amounts can be converted from traditional retirement accounts into a Roth IRA. Any taxpayer can convert amounts from a traditional retirement account to a Roth IRA. There are no restrictions based on level of income and/or having had earned income. 

Conversions are taxable in the year of the conversion. 

There are several reasons you might want to do a Roth IRA conversion. One might be the anticipation of paying tax at a higher rate in the future. The planning concept is to “lock in” the lower tax rate in the year of the conversion rather than tomorrow’s (anticipated) higher tax rate, and to get all of the earnings on the contribution out of income taxation.

Unlimited Roth IRA conversions form the backbone of the Backdoor Roth IRA planning concept. 

Note that inherited traditional IRAs cannot be converted to Roth IRAs.

Transfers from Workplace Retirement Accounts

A third way to get money into a Roth IRA is by using workplace retirement accounts. Amounts in Roth 401(k)s and other workplace Roth accounts can be transferred into a Roth IRA. Generally, it is best to use direct “trustee-to-trustee” transfers to accomplish this. 

Further, after-tax contributions in workplace retirement plans can be directly transferred to Roth IRAs, as discussed in Notice 2014-54. The ability to transfer after-tax contributions into a Roth IRA has facilitated the use of the Mega Backdoor Roth IRA planning technique. 

Roth IRA Withdrawals: The Confusion

You may have heard that you cannot take money out of a Roth IRA if the account is not 5 years old without paying tax and a penalty. Not true!

There are not one, but two, five (5) year rules applicable to Roth IRAs. But neither one of them prohibit you from taking money out of a Roth IRA you have previously contributed through annual contributions. First, I will illustrate the default Roth IRA withdrawal rules, and then I will discuss the two 5 year rules. 

Quick Thought: Most of this blog post addresses situations where the taxpayer does not qualify for a qualified distribution. Generally, a taxpayer fails to qualify for a qualified distribution if he or she has not attained the age of 59 ½, and/or if he or she has not owned a Roth IRA for 5 years. The advantage of a qualified distribution is that it is automatically tax and penalty free. 

Roth IRA Withdrawals: The Layers

Here is the default order of distributions that come out of a Roth IRA. These are the rules that apply in cases where the taxpayer does not qualify for a qualified distribution. All Roth IRAs (other than inherited Roth IRAs) the taxpayer owns are aggregated for purposes of determining his or her Roth IRA layers.

First Layer: Tax-free return of Roth IRA contributions

Second Layer: Roth IRA conversions (first-in, first-out)

Third Layer: Roth IRA earnings

Each layer must come out entirely before the subsequent layer is accessed.

Here’s a brief example:

Example 1: Samantha opened her only Roth IRA in 2018. Samantha has made three prior $5,000 contributions to her Roth IRA (one for each of 2018, 2019, and 2020). She also made a $5,000 conversion from a traditional IRA to a Roth IRA in 2018. In 2021, at a time when her Roth IRA is worth $30,000 and Samantha is 50 years old, she takes a $10,000 withdrawal from her Roth IRA. All $10,000 will be a recovery of her previous contributions (leaving her with $5,000 remaining of previous contributions). Thus, the entire $10,000 distribution from the Roth IRA will be tax and penalty free.

The Roth IRA contributions come out tax and penalty free at any time for any reason! The 5 year rules have nothing to do with whether a taxpayer can recover their previous Roth IRA contributions tax and penalty free!

For those wanting to dig deeper into the tax law, please refer to this technical slide deck discussing why the Roth IRA contributions are distributed tax and penalty free regardless of the 5 year rules. 

Note that aggregation rules always apply. In making an analysis like the one provided in Example 1, one must account for all their Roth IRAs and treat all of their Roth IRAs as a single Roth IRA to determine their own Roth IRA layers. Roth 401(k)s and inherited Roth IRAs are not included in the analysis. 

5 Year Rule for Roth IRA Earnings

The first five-year rule for Roth IRAs applies only to a withdrawal of earnings from a Roth IRA. If the account owner has not owned a Roth IRA for at least 5 years, the earnings withdrawn from the account are subject to ordinary income tax (and possibly a penalty). 

Example 2: Joe is 62 years old in 2024. He has owned a Roth IRA since 2021. In 2024, after having made $14,000 in prior annual contributions to his Roth IRA, he withdrew $17,000 from the Roth IRA. Because Joe has not owned a Roth IRA for 5 years, the withdrawal is not a qualified distribution. Joe recovers his first $14,000 tax free as a return of contributions. The next $3,000 of earnings is taxable to Joe as ordinary income (because of the first five-year rule). Because Joe is over age 59 ½, he does not owe the ten percent penalty on the distribution. If Joe had not attained the age of 59 ½, he would owe the 10 percent penalty on the $3,000 of earnings he received. 

5 Year Rule for Roth IRA Conversions

There is a five-year rule applicable to taxable money converted from a traditional retirement account to a Roth IRA (what I will colloquially refer to as the “second five-year rule”). The idea behind the second five-year rule is to protect the 10% early withdrawal penalty applicable when someone has a traditional retirement account. Here is an illustrative example.

Example 3: Milton has $100,000 in a traditional IRA, no basis in any IRA, and is age 50. If he were to withdraw $1,000 from his traditional IRA (assuming no penalty exception applies), he would owe (in addition to ordinary income tax) a $100 penalty (ten percent) on the withdrawal. 

Okay, but what if Milton first converts that money from a traditional IRA to a Roth IRA (assume Milton has no other balance in a Roth IRA)? Would that get him out of the 10 percent penalty? No, it won’t, because of the second five-year rule.

Example 4: Milton has $100,000 in a traditional IRA, no basis in any IRA, has no Roth IRAs, and is age 50. In September 2024, he converts $1,000 to a Roth IRA. In October 2024, he withdraws $1,000 from that Roth IRA. Because of the five-year rule applicable to Roth IRA conversions, Milton will still owe the $100 penalty on the withdrawal from the Roth IRA. 

Had Milton waited until 2029 or later, he would not have owed the penalty on the withdrawal of that $1,000.

The 5 Year Rule for Roth IRA Conversions and the Backdoor Roth IRA

The Backdoor Roth IRA is subject to the second five-year rule, but the penalty effect turns out to be very minor (or non-existent) if the Backdoor Roth IRA has been properly executed.  

Conversions, the second layer of the Roth IRA stack, come out first-in, first out. Further, the taxable amount (potentially subject to the 10 percent penalty upon withdrawal) of any one particular Roth IRA conversion comes out first within the conversion amount. Thus, the second layer (the conversion layer) can be composed of several mini-layers.

Here is a quick example:

Example 5: Denzel made $6,000 nondeductible traditional IRA contributions on January 1, 2019 and January 1, 2020. On February 2, 2019 and February 2, 2020, Denzel converted the entire balance of the traditional IRA ($6,010 each time) to a Roth IRA. As of December 31, 2019 and December 31, 2020, Denzel had $0 balances in all traditional IRAs, SEP IRAs, and SIMPLE IRAs.

In 2021, at a time when Denzel is 35 years old and has made no other contributions or conversions to a Roth IRA, he withdraws $3,000 from his Roth IRA. The first $10 of the withdrawal will be from the taxable amount of his 2019 Roth conversion, and thus, will be subject to the 10 percent penalty as it violates the second five-year rule (Denzel will owe $1 in penalties). The next $2,990 is attributable to the non-taxable portion of his 2019 Roth conversion, and as such, will not be subject to the 10 percent penalty. None of the $3,000 will be subject to ordinary income tax. 

Penalty Exceptions

From time to time you will hear things such as “you can withdraw only $10,000 from a Roth IRA for a first-time home purchase.” Does that mean everything else discussed above does not apply?

Fortunately, the answer is no! 

So what is the $10,000 rule getting at? It is getting at amounts withdrawn from a Roth IRA that would otherwise be subject to the penalty (and possibly income taxes — see The Super Exceptions below). 

There are several penalty exceptions applicable to taxable converted amounts and earnings that are withdrawn from a Roth IRA in a nonqualified distribution. But the penalty exception rules generally apply on top of the usual layering rules, not instead of the usual Roth IRA layering rules. 

In a discussion on social media, I used a version of the following example.

Example 6: Jane Taxpayer, age 30, has had a Roth IRA since 2017. In 2020, she withdraws $30,000 from her Roth IRA to acquire her first home, and has never used traditional IRA and/or Roth IRA money for such a purchase. She has previously made $20,000 in annual contributions to the Roth IRA. The first $20,000 of the withdrawal is a tax-free return of those contributions (see the layers above). The next $10,000 is out of earnings (see the layers above). This $10,000 is taxable to her as ordinary income. But, because of the $10,000 “qualified first-time homebuyer distribution” exception, she does not owe the 10 percent penalty on the withdrawal of those earnings.

In this case, withdrawals used to fund certain home purchases can qualify for a penalty exception (the first-time homebuyer exception is subject to a $10,000 cap). Please visit this website for a list of the possible penalty exceptions applicable to withdrawals from a traditional IRA and a Roth IRA.

The Super Exceptions

If the taxpayer is relying on the disability, age 59 ½, death, or qualified first-time home purchase penalty exceptions, the earnings also come out income tax free so long as the taxpayer has owned a Roth IRA for five years. See slide 5 of the above referenced technical slide deck. 

As applied to Jane Taxpayer in Example 6 above, if she had owned a Roth IRA since any time in 2015 or earlier, the distribution of $10,000 of earnings would not only have been penalty free, it would have also been income tax free. 

60 Day Rollovers

A taxpayer might take money out of a Roth IRA and then reconsider. Perhaps he or she wants the money to grow tax-free. Or perhaps the taxpayer dipped into earnings and the distribution is not a qualified distribution, meaning that it will likely be subject to both ordinary income and a ten percent penalty. 

He or she might be able to roll the money back into the Roth IRA. However, the tax rules allow only one 60 day rollover every 12 months. The IRS has a website here discussing some of the issues. 

Because of the one-rollover-per-year rule, I generally advise against doing 60 day rollovers unless you need to. Generally, it is best to avoid them, and then have the option available as a life raft if money somehow comes out of a Roth IRA (or other IRA) when it should not have.

Required Minimum Distributions

There are no required minimum distributions from a Roth IRA! Every other non-HSA tax-advantaged retirement account, including the Roth 401(k), has required minimum distributions. 

Note that required minimum distributions are generally required once the Roth IRA becomes an inherited Roth IRA (in the hands of anyone but certain surviving spouses). 

Tax Planning

Okay, so taxpayers always have tax and penalty free access to old Roth IRA annual contributions. So what of it? As a practical matter, maybe nothing. 

In most cases, it makes sense to simply keep the money in the Roth IRA and let it grow tax free!

That said, there can be instances where, as part of a well crafted financial plan, it can make sense to withdraw previous Roth IRA contributions prior to age 59 ½. Further, it is good to know that, in an emergency situation, those old Roth IRA contributions are accessible.

Of course, prior to taking an early withdrawal from a Roth IRA, it is usually best to consult with your own financial advisor and/or tax advisor. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Transferring a Primary Residence to Children

How do you pass your family’s house to your children? It’s a pressing question and involves significant tax, legal, and emotional considerations. Unfortunately, it is a topic about which there is much confusion.

This blog post discusses some of the important considerations. But as a blog post, it can only scratch the surface. Anyone looking to efficiently pass on their home is well advised to consult with their own lawyer, tax professional, and in some cases, their banker as well.

Minor Children

To my mind, the primary planning objective of married couples with minor children vis-a-vis their home is to account for what happens if both spouses die. Such couples would want their children taken care of in the most flexible manner possible.

Generally speaking, in such situations, it is often best to work with a lawyer to transfer the primary residence to a revocable living trust (explained below). In the event of both spouses’ deaths, the house would be held by the trust and managed by the trustee of the trust. It could be sold or rented for the benefit of the children, or kept so the children and their guardian(s) could live in the house. 

This resolution is generally preferable to leaving a house directly to minor children. 

Revocable Living Trusts

What is a revocable living trust? It is generally a written trust (drafted by a lawyer) that owns property the grantor(s) or settlor(s) transfers to the trust. For this sort of planning, usually spouses (the grantors) transfer their home to the trust and designate themselves as the primary beneficiaries of the trust. The trust provides that the grantors’ minor children are the successor beneficiaries. Upon both spouses’ deaths, the trust becomes irrevocable, and a trustee holds the assets and manages them on behalf of the beneficiaries (the minor children).

The best thing about a revocable living trust: as long as the grantor(s) is/are alive, the trust is fully revocable! So mistakes can be easily fixed (working with a lawyer). 

Revocable living trusts also generally avoid probate. 

Tax Effect

One nice thing about a revocable living trust is that it doesn’t change the grantor’s tax situation. All the income of the trust assets remain the taxable income of the grantor. Generally speaking, the grantor’s tax return does not change at all. Further, favorable tax rules, such as the $250K per person exclusion for capital gains on qualified primary residences, apply unchanged.

Parents placing their primary residence in their own revocable living trust does not necessitate the filing of a federal gift tax return (Form 709).

Upon inheriting a house as the beneficiary of a revocable living trust, the child takes a fair market value tax basis in the house (the so-called “step-up in basis”). This makes using a revocable living trust a tax-efficient way of passing a house to the next generation. 

Adult Children

Okay, but what about adult children? It’s readily apparent that five-year olds should not own real estate outright. But what about grown children? If a primary goal is simply avoiding probate, why not use a joint tenancy with rights of survivorship instead of a revocable living trust?

Putting an adult child’s name on the title of the parent(s) primary residence (and thus, creating a joint tenancy with rights of survivorship) can lead to a host of issues, but perhaps not the issues that initially come to mind. 

Capital Gains Tax

What about the adult child’s capital gain upon the sale of the house after the parent’s death? Is that a reason to use a revocable living trust to house the house (pun intended)? 

Well, it turns out the answer is generally No. Assuming the adult child did not contribute to the acquisition of the house, the adult child can take a full fair market value basis in a house acquired from a joint tenancy. Here is an example very loosely based on the example on page 10 of IRS Publication 551:

Example: Joan and Jane owned, as joint tenants with rights of survivorship, Joan’s home. Joan paid $300K for it, Jane paid nothing for it. Upon Joan’s death, the home has a fair market value of $600K. Jane inherits (as the surviving joint tenant) the house from Joan with a $600K basis (a fully stepped-up basis).

If interested, I’ve prepared a technical analysis as to why the surviving non-contributing non-spouse joint tenant receives a full step-up in basis here. 

Note that the above full stepped-up basis does not obtain if the gift of a portion of the house was through a tenancy-in-common (instead of through a joint tenancy with rights of survivorship). However, there is little reason to use a tenancy-in-common to transfer a house, because the original owner’s remaining share simply remains in his/her name, and absent other arrangements, passes through probate.

Other Problems with Joint Tenancies

If the capital gains tax upon the original owner’s death isn’t an issue, why not use a joint tenancy to transfer your house to your adult children? Here are some of the considerations.

Capital Gains Tax

Wait, what? I thought you said capital gains taxes were not an issue. They generally aren’t an issue after the original owner’s death. But they can be an issue before his or her death.

What if, during the owner’s lifetime, the house is sold? What if there’s a pressing need to sell the house, perhaps to help pay for long-term care? 

The owner/occupant is at least somewhat protected by the $250K per person primary residence gain exclusion. But the adult child is not protected by that exclusion if the home is not their primary residence. The adult child could have to pay capital gains tax (based on their share of the proceeds less their share of the owner’s historic tax basis) on the transaction if the house is sold prior to the owner/occupant’s death.  

Loss of Control

Simply put, transferring an interest in your home to another person relinquishes some of your control over the property. You never know if you will need that control in the future. Proceed with significant caution, and consult a trusted lawyer, prior to putting anyone else on the title of your home.

Gift Tax

While not a horrible problem, adding an adult child to the title of a house as a gift requires the filing of a Form 709 gift tax return. Due to the high estate and gift tax exemptions, in most cases it is highly unlikely the transfer would trigger actual gift tax. 

Disputes Among Adult Children

Adding multiple adult children to the title as joint tenants with rights of survivorship can create issues after the parent’s death. If siblings cannot agree amongst themselves how to handle and/or dispose of the house, the disagreement can be difficult to resolve. Using a revocable living trust (which becomes irrevocable upon the parent’s death) gives the parent the opportunity to work with their lawyer to put in place a trustee and ground rules for how the house is to be managed and/or disposed of after death.

Children’s Issues

Adult children are people. And people have problems. Divorces, liabilities, bankruptcies, etc. Putting an adult child on the title of a home could subject the home to the adult child’s creditors in a problematic manner. 

Summary

The above are just some of the considerations to weigh before adding adult children to the title of a home as a joint tenant with rights of survivorship.

Revocable living trusts keep control with the original owner. Further, they facilitate transferring real estate to the next generation in a tax-efficient manner. Based on these advantages and the issues that exist with joint tenancies, I generally prefer revocable living trusts over joint tenancies for primary residences. Using a will can also be effective from a tax perspective, but should be discussed with a lawyer considering state and local real estate laws. Some states have transfer-on-death type real estate deeds, which also should be considered with a lawyer (if that sort of deed is available).

Outright Gift

You might be saying, well, I have only one child I want to give my house to. Further, I don’t need to own my house. Why not simply give the house outright to that child during my life and avoid any legal events/issues occurring at my death? 

Besides some of the issues discussed above and the full loss of control (which are troublesome enough), an outright gift creates a significant capital gains tax issue for the adult child. This capital gains tax issue exists both before and after the original owner’s death.

Previously, I wrote this example on the blog illustrating the issue:

William lives in a house he purchased in 1970 for $50,000. In 2019 the house is worth $950,000. If William gifts the house to his son Alan in 2019, Alan’s basis in the house is $50,000. However, if William leaves the house to Alan at William’s death, Alan’s basis in the house will be the fair market value of the house at William’s death.

Giving William’s house to Alan during William’s lifetime could increase the capital gains taxable to Alan by $900K! Ouch!

So, whatever you do (a) consult with your lawyer before determining how to pass your house to your children and (b) be very, very hesitant to outright give your house to your child. 

Conclusion

There are various ways in which you can transfer your home to your children. In many cases, I believe revocable living trusts are a great way to leave a house to children. You are always well advised to consult with your lawyer before making any decisions on how you want to title your house and how you want to transfer your house. If you do inherit a house from your parents, you should consult with a lawyer regarding titling issues and with your tax professional regarding the tax implications of selling the inherited home. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Roth 401(k)s for Beginners

Roth 401(k)s are gaining prominence as a tax-advantaged workplace retirement account. This post provides introductory information regarding Roth 401(k)s and their potential benefits as a retirement savings account.

Two important introductory notes. First, not all 401(k) plans offer a Roth option, so for some employees, a Roth 401(k) contribution is not an option. Second, this post is for educational purposes only and is not advice for any particular taxpayer. 

Traditional 401(k) versus Roth 401(k)

In an ideal world, contributions by an employee to a traditional 401(k) result in a tax deduction when contributed, and taxable income when withdrawn.

Example 1: Tony makes $100,000 from his employer in W-2 wages in 2021. Tony contributes $15,000 during the course of 2021 to his employer’s traditional 401(k). Tony will receive a W-2 from his employer reporting $85,000 of taxable W-2 wages for 2021.

In an ideal world, contributions by an employee to a Roth 401(k) result in no tax deduction when contributed, and no taxable income when withdrawn.

Example 2: Rudy makes $100,000 from his employer in W-2 wages in 2021. Rudy contributes $15,000 during the course of 2021 to his employer’s Roth 401(k). Rudy will receive a W-2 from his employer reporting $100,000 of taxable W-2 wages for 2021.

Roth 401(k) Contributions

Employees can contribute the lesser of their earned income or $19,500 (2021 limit) to a Roth 401(k) in “employee deferrals.” For those 50 years old or older, the 2021 limit is the lesser of earned income or $26,000.

The employee deferral limit factors in both traditional 401(k) employee contributions and Roth 401(k) employee contributions. Here’s an illustrative example.

Example 3: Sarah, age 35, earns $100,000 in W-2 income in 2021 at Acme Industries, Inc. Sarah contributes the maximum to her 401(k) plan. Assuming Acme offers both a traditional 401(k) and a Roth 401(k), that maximum $19,500 contribution can be split up however Sarah chooses ($13,000 to the traditional 401(k) and $6,500 to the Roth 401(k), $5,000 to the traditional 401(k) and $14,500 to the Roth 401(k), etc.). 

Any combination (including all in the traditional or all in the Roth) is permissible as long as the total does not exceed $19,500 (using 2021’s limits).

Roth 401(k) Contributions: Income Limits

There’s good news here. Unlike their Roth IRA cousins, Roth 401(k) contributions have no income limits. In theory, one could make $1 billion annually in W-2 income and still contribute $19,500 to a Roth 401(k). 

Matching Contributions

Employer matching contributions are one of the best benefits of 401(k) plans. 

It is important to keep in mind that matching contributions, profit sharing contributions, and forfeitures must go into employee accounts as traditional contributions. This is true regardless of whether the employee’s own contributions are traditional, Roth, or both. 

Example 4: Elaine, age 35, works at Perry Publishing. She earns a salary of $50,000. Perry matches 50% of the first 6% of salary that Elaine contributes to her 401(k). Elaine decides to contribute $3,000 (6 percent) of her salary to the 401(k) as a Roth contribution. Perry contributes $1,500 as a matching contribution. The $1,500 employer match goes into the 401(k) as a traditional contribution. The $3,000 and its growth are treated as a Roth 401(k), and the $1,500 and its growth are treated as a traditional 401(k). 

Matching contributions may be subject to vesting requirements, as described in this post. Employee contributions to a 401(k) (whether traditional or Roth) are always 100% vested. 

Roth 401(k) Withdrawals

The greatest benefits of a Roth 401(k) are tax-free growth and tax-free withdrawals. Tax-free withdrawals are generally the goal, but they are not automatic. Recently, I wrote a post on Roth 401(k) withdrawals. 

One important consideration regarding Roth 401(k) withdrawals: Roth 401(k)s are subject to the required minimum distribution rules starting at age 72. Thus, you must start withdrawing money from a Roth 401(k) at age 72. As a result, you will have less wealth growing tax-free. For this reason, many consider rolling Roth 401(k)s to Roth IRAs prior to age 72. 

Conclusion

Roth 401(k)s provide a great opportunity to save and invest for retirement. Taxpayers should consider their own circumstances, and often consult with tax professionals, in deciding their own investment program. 

Further Reading

For more information about 401(k) plans, please read this post. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Roth 401k Withdrawals

We live in a Roth IRA world (or, at least I wish we did). We also live in a world where increasing numbers of people invest through a Roth 401(k). 

The Roth 401(k) is still a relatively new account. Taxpayers and practitioners alike are still learning its contours. Things get even more complicated when you roll money from a workplace Roth 401(k) to a Roth IRA.

To get our feet wet, first I will illustrate the ordering rules for withdrawals from a Roth IRA. Then we will explore withdrawals from a Roth 401(k).

Note that much of this post discusses withdrawals before age 59 ½. In most cases, it is not wise to take a withdrawal from a retirement account before age 59 ½ unless (a) there is an emergency or (b) it is part of a well crafted financial plan.

Watch me discuss Roth 401(k) withdrawals.

Default Rule for Roth IRA Withdrawals: The Layers

Unless the distribution qualifies as a “qualified distribution” (see below), amounts come out of Roth IRAs in layers. Only after one layer has been exhausted can the next layer come out.

Here is the order of distributions that come out of a Roth IRA:

First Layer: Roth IRA contributions

Second Layer: Roth IRA conversions (first-in, first-out)

Third Layer: Roth IRA earnings

Here’s a brief example:

Example 1: Steve has made five $5,000 contributions to his Roth IRA in previous years. He also made a $10,000 conversion from a traditional IRA to a Roth IRA in 2014. In 2021, at a time when his Roth IRA is worth $60,000 and Steve is 45 years old, he takes a $10,000 withdrawal from his Roth IRA. All $10,000 will be a recovery of his previous contributions (leaving him with $15,000 remaining of previous contributions). Thus, the entire distribution from the Roth IRA will be tax and penalty free.

The Roth IRA contributions come out tax and penalty free at any time for any reason!

A qualified distribution from a Roth IRA is usually one where the account holder both (i) has owned a Roth IRA for at least 5 years and (ii) is at least 59 ½ years old. If either condition is not satisfied, the default layering rules described above apply. Qualified distributions from a Roth IRA are tax and penalty free regardless of the layers inside the Roth IRA.

See page 31 of IRS Publication 590-B for more information about qualified distributions from Roth IRAs.

Roth 401(k) Withdrawals

First, a practical note: employers may restrict in-service Roth 401(k) withdrawals before age 59 1/2. Consider that before thinking about how the tax rules apply to withdrawals.

Default Rule: Cream-in-the-Coffee

Generally speaking, Roth 401(k)s have (1) investment in the contract (“IITC”), which is generally previous contributions and conversions and (2) earnings. 

Unlike the sequenced layering of Roth IRA withdrawals, Roth 401(k) withdrawals generally default to what Ed Slott refers to as the “cream-in-the-coffee” rule (see Choate — discussed below, page 140).

As a result, withdrawals default to carrying out both some IITC and some earnings. Here’s an example:

Example 2: Lilly has made five $6,000 contributions to her Roth 401(k) in previous years. She also made a $10,000 conversion from a traditional 401(k) to her Roth 401(k) in 2014. In 2021, at a time when her Roth 401(k) is worth $60,000 and Lilly is 45 years old, she takes a $10,000 withdrawal from her Roth 401(k). Two-thirds ($6,667, computed as the fraction $40,000 divided by $60,000 times the withdrawal) of the $10,000 will be a recovery of her IITC (entirely tax and penalty free), and one-third ($3,333, computed as the fraction $20,000 divided by $60,000 times the withdrawal) of the $10,000 will be earnings, which are subject to both ordinary income taxation and a 10 percent penalty.

Quick Thought: Had Lilly’s Roth conversion occurred in 2017 or later, the portion attributable to the conversion ($1,667) would be subject to the 10 percent early withdrawal penalty (but not to ordinary income taxation). See Section 402A(c)(4)(D) and Section 408A(d)(3)(F). Note an earlier version had “2018 or earlier” where the bolded words are in error. I regret the error.

Quick Thought: The cream-in-the-coffee rule does not factor in amounts in traditional 401(k) accounts, even if they are within the same 401(k) plan.

Solving the Cream-in-the-Coffee Issue

We see that the cream-in-the-coffee rule has bad effects. It does not allow exclusive access to tax-favored amounts when there are non-tax favored amounts in an account. So what to do? There are three primary exceptions to the cream-in-the-coffee rule. 

Exception 1: Wait for a Qualified Distribution

The cream-in-the-coffee rule can be waited out.

A qualified distribution from a Roth 401(k) is a withdrawal that occurs when the owner is age 59 ½ (see Treas. Reg. Sec. 1.402A-1 Q&A 2(b)(2)) and has had that particular Roth 401(k) account for five years (see Treas. Reg. Sec. 1.402A-1 Q&A 2(b)(1) and Q&A 4). Other qualified distributions can occur upon death or disability (if the 5 year test is satisfied), but for our purposes, we will assume for the rest of the article that any qualified distributions are qualified distributions occurring at or after age 59 ½ and after five years of ownership.

The owner of a Roth 401(k) who qualifies for a qualified distribution does not need to roll the Roth 401(k) to a Roth IRA to take a tax free withdrawal. Once the owner qualifies for a qualified distribution he or she can simply withdraw amounts from the Roth 401(k) tax-free.

However, as a practical matter, it is often the case that Roth 401(k)s are rolled into Roth IRAs (for several reasons). If the rollover from the Roth 401(k) to the Roth IRA would qualify as a qualified distribution if taken directly, then the entire amount in the Roth 401(k) (IITC and earnings) goes into the Roth IRA as a contribution. Ian Berger discussed this issue in an August 11, 2022 response to a question. His answer applies the rule in Treas. Reg. Sec. 1.408A-10 Q&A 3 (the sentence beginning with “Thus,”).

Up to the amount rolled into the Roth IRA can be distributed tax and penalty free. So long as the taxpayer has met the 5 year rule with respect to any Roth IRA, any future earnings beyond the amount rolled in can be withdrawn tax free at any time.

Quick Thought: I would be remiss if I didn’t insert the standard tax planner advice that rollovers from Roth 401(k)s to Roth IRAs are best accomplished through a direct trustee-to-trustee transfer.

There is one five year rule nuance to consider. If the taxpayer has never had a Roth IRA, he or she must wait 5 years (regardless of their age) to access later earnings generated by rollover contribution tax free. Here’s a quick example:

Example 3: John is 60 years old. He has never had a Roth IRA. He has had a Roth 401(k) with his employer for over five years. He has made $100,000 of contributions to the Roth 401(k) which has grown to $200,000. He does not need to roll his Roth 401(k) into a Roth IRA to take out money entirely tax and penalty free.

If John chooses to roll all $200,000 in his Roth 401(k) into a Roth IRA, all $200,000 goes into the Roth IRA as a contribution. If John withdraws more than $200,000 from the new Roth IRA before the Roth IRA turns 5 years old, those withdrawals of new earnings would be subject to income tax (though, of course, penalty free since John is over 59 ½ years old).

As a practical matter, as long as the taxpayer does not plan on withdrawing more than the rolled over amount in the first five years, this nuance is not likely to be a gating issue in determining whether the Roth 401(k) should be rolled over to a Roth IRA.

Exception 2: Roth 401(k) Rollover then Withdraw

The second strategy to overcome the cream-in-the-coffee rule is to rollover the Roth 401(k) to a Roth IRA without waiting.

If either the taxpayer is less than 59 ½ years old and/or has not held that particular Roth 401(k) for at least five years, the nonqualified distribution rules apply to the rollover. The Roth 401(k) goes into the Roth IRA as “contributions” to the extent of the IITC in the Roth 401(k), and as “earnings” to the extent of growth in the Roth 401(k).

Recall the example of Lilly above. Here is how it changes if she rolls the Roth 401(k) into a Roth IRA and then takes the withdrawal.

Example 4: Lilly has made five $6,000 contributions to her Roth 401(k) in previous years. She also made a $10,000 conversion from a traditional 401(k) to her Roth 401(k) in 2014. In 2021, at a time when her Roth 401(k) is worth $60,000 and Lilly is 45 years old, she rolls her Roth 401(k) over to a Roth IRA (her first ever). A month later, Lilly takes a $10,000 withdrawal from her Roth IRA. All $10,000 will be a recovery of her previous contributions (leaving her with $30,000 remaining of previous contributions). Thus, the entire withdrawal will be tax and penalty free.

While rollovers of nonqualified distributions do not eliminate Roth 401(k) earnings, they do eliminate the cream-in-the-coffee rule. As a result, Roth 401(k) to Roth IRA rollovers often make sense.

The Five Year Roth Earnings Rule

Where such rollovers can be disadvantageous is the five year rule as applied to earnings. Recall that being age 59 ½ is a necessary, but not sufficient, condition to withdrawing Roth earnings tax free. You also need to meet a 5 year rule.

If you have a Roth 401(k) that is 5 years old but have never had any Roth IRA, and you are less than 5 years away from attaining age 59 ½, rolling into a Roth IRA could subject withdrawals of earnings (after age 59 ½) in excess of IITC to ordinary income taxation. That said, often withdrawals do not exhaust contributions in the first five years after a rollover. Thus, often this will not be a gating issue.

Exception 3: Roth 401(k) Withdrawal then Rollover

There is a third way to overcome the cream-in-the-coffee rule. It is to take a withdrawal from the Roth 401(k) and then rollover the earnings component to a Roth IRA. Let’s see how that would affect Lilly:

Example 5: Lilly needs $10,000 and has decided to access it from her Roth 401(k). Lilly has made five $6,000 contributions to her Roth 401(k) in previous years. She also made a $10,000 conversion from a traditional 401(k) to her Roth 401(k) in 2014. In 2021, at a time when her Roth 401(k) is worth $60,000 and Lilly is 45 years old, Lilly takes a $15,000 withdrawal from her Roth 401(k). Based on her Roth 401(k) consisting of two-thirds IITC and one-third earnings, $5,000 of the withdrawal is taxable and subject to an early withdrawal penalty. However, Lilly can, within 60 days, rollover the $5,000 of earnings into a Roth IRA. The earnings will go into the Roth IRA as earnings, and Lilly avoids the tax and penalty on the withdrawal.

Note that if Lilly does this partial rollover, the rollover piece is not subject to the cream-in-the-coffee rule. The partial rollover attracts earnings before attracting any IITC (see Treasury Regulation Section 1.402A-1 Q&A 5). 

Note further that if Lilly has no other Roth IRAs, she now has a Roth IRA that consists only of earnings. She will not (generally speaking) be able to touch this Roth IRA without ordinary income tax and a penalty until age 59 ½.

As a practical matter, the “withdraw then rollover” strategy may not be available to Lilly. The 401(k) plan may not allow partial distributions pre-age 59 1/2 after separation from service.

Coordination with the Rule of 55

Many like the Rule of 55, which is a rule that allows taxpayers to take amounts from workplace retirement plans such as 401(k)s without the early withdrawal penalty. It applies when a taxpayer separates from service at age 55 or older (up to age 59 ½, when withdrawals become penalty free), and the plan allows partial withdrawals.

So the question becomes, if you are in the 4.5 year Rule of 55 window (ages 55 to 59 ½) and you separate from service, should you leave a Roth 401(k) in the plan or roll it into a Roth IRA if you need to withdraw from it? Let’s consider an example.

Example 6: James is 56 years old and leaves his employment. He has contributed $100,000 over more than five years to his Roth 401(k), and it is currently worth $200,000. If he keeps the amounts in the Roth 401(k), every dollar he takes out will be half recovery of IITC (tax-free) and half a withdrawal of earnings (taxable, but qualifies for a penalty exception). If, instead, James follows the “rollover then withdraw” strategy and rolls his Roth 401(k) to a Roth IRA, the first $100,000 he withdraws before age 59 ½ will be a return of contributions, and only if he exceeds $100,000 in withdrawals will he have ordinary income and a penalty. A second option for James would be to do the “withdraw then rollover” strategy whereby James would direct half of each distribution (the earnings half) to a Roth IRA in order to avoid ordinary income taxation on the earnings portion.

This illustrates that numbers matter in this regard. It also shows that as long as the pre-age 59 ½ withdrawals will be less than the previous Roth 401(k) contributions, it is generally better to take the withdrawals from a rollover Roth IRA than from a Roth 401(k) penalty protected by the Rule of 55.

However, if one employs the “withdraw then rollover” strategy, keeping money in the Roth 401(k) can work as effectively as rolling over to a Roth IRA. 

A Note on Rollovers

Any designated Roth account (401(k), 403(b), and/or 457) can be rolled into a Roth IRA. Designated Roth accounts can be rolled into other designated Roth accounts, though note there can some be some complexity in this regard.

Roth IRAs cannot be rolled into a designated Roth account, including a Roth 401(k).

The IRS has a handy rollover chart accessible here. 

SECURE 2.0 Update

SECURE 2.0 makes three changes relating to Roth 401(k)s. First, it eliminates required minimum distributions (“RMDs”) from Roth 401(k)s during the owner’s lifetime. This change has little practical effect, as many Roth 401(k)s will ultimately be rolled to Roth IRAs anyway in order for the owner to obtain more investment choice and control of the account.

Second, SECURE 2.0 mandates that beginning in 2024, employee catch-up contributions to 401(k) accounts must be Roth contributions if the employee made more than $145,000 in wages the prior year.

Third, SECURE 2.0 allows employer contributions to Roth 401(k)s.

I suspect that based on the second and third changes, more employers may offer Roth 401(k)s in addition to traditional 401(k)s.

Further Reading

For those interested in seeing more information on distributions out of Roth IRAs after rollovers of Roth 401(k)s, please see Treasury Regulation Sec. 1.408A-10. For more information on rollovers of distributions from Roth 401(k)s into Roth IRAs, please see Treasury Regulation Sec. 1.402A-1.

Natalie B. Choate’s treatise Life and Death Benefits for Retirement Planning (8th Ed. 2019) is an absolutely invaluable resource regarding retirement account withdrawals, including Roth 401(k) withdrawals.

Conclusion

The rules around Roth 401(k)s are complex, and different than those applicable to Roth IRAs. This blog post only presents an educational introduction to those rules. Taxpayers should exercise extra caution, and often consult with tax professionals, before moving money out of a Roth 401(k).

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

An Ode to the Roth IRA

It won’t surprise many to find out that a tax-focused financial planner is fond of the Roth IRA. Below is a brief review of the advantages of a Roth IRA.

Tax Free Growth

Amounts in Roth IRAs grow tax free. Considering many Americans may now live into their 80s, 90s, and beyond, this is a tremendous benefit. 

The only caveat is that in order for all distributions from Roth IRAs to be tax and penalty free, they generally have to be either (a) a return of contributions or of sufficiently aged conversions (see below), or (b) a distribution of earnings made in the Roth IRA (or other amounts in the Roth IRA) at a time when the owner of the account is 59 ½ or older and has owned a Roth IRA for at least five years.

The rules for ordering distributions out of a Roth IRA generally provide that contributions come out first, and then the oldest conversions come out next. This means that in many cases Roth IRA distributions, even those occurring before age 59 ½, are tax and penalty free. 

N.B. Generally speaking, you want to only take a distribution from a Roth IRA before age 59 ½ if it is either (i) a serious emergency or (ii) part of a well crafted, very intentional financial plan. 

Ease of Administration and Withdrawal 

There are many financial institutions that provide Roth IRAs. Investment expenses in low-cost index funds at financial institutions that provide Roth IRAs are approaching zero. Vanguard, Fidelity, and Schwab are among the very good providers of low-cost Roth IRAs (and there are others). 

It is also relatively easy to access money inside a Roth IRA. This makes the Roth IRA a great account to have in an emergency. Of course, it is generally best to leave money inside a Roth IRA to let it grow tax free, but it is good to know that you can access money in a Roth IRA relatively easily if an emergency arises. 

Tax Free Withdrawals of Contributions

This is a great benefit of the Roth IRA. Contributions to a Roth IRA can be withdrawn at any time for any reason tax and penalty free. Further, the first money deemed distributed from a Roth IRA is a contribution. Here is a quick example:

Mark is 35 years old in 2025. He made $6,000 contributions to his Roth IRA in each of 2020, 2021, 2022, 2023, and 2024 (for $30,000 total). In 2025, when his Roth IRA is worth $41,000, Mark withdraws $10,000 from his Roth IRA in 2025. All $10,000 will be deemed to be a return of contributions, and thus entirely tax free and penalty free.

The only exception is a taxpayer favorable exception: a timely withdrawal of an excess contribution (and related earnings) occurs before regular contributions are considered withdrawn. 

N.B. Roth 401(k)s, 403(b)s, and 457s have different distribution rules — most pre-age 59 ½ distributions will take out some taxable earnings.

Tax Free Withdrawals of Sufficiently Aged Converted Amounts 

If you convert an amount into a Roth IRA, you start a five year clock as of January 1st of the year of the conversion. Quick example:

Mike is 35 years old in 2025. Mike converts $10,000 from a traditional IRA to a Roth IRA on July 2, 2025. His five year conversion clock starts January 1, 2025. On January 1, 2030, Mike can withdraw the entire $10,000 he converted in 2025 tax and penalty free. 

This feature of the Roth IRA, the tax free withdrawal of sufficiently aged conversions, is the basis for the Roth Conversion Ladder strategy. Sufficiently aged converted amounts are deemed to come out after contributions are exhausted and before more recent conversions and earnings come out.  

No Required Minimum Distributions

During an account holder’s lifetime, there are no required minimum distributions from a Roth IRA. You can live to 150 and never be required to take money from a Roth IRA.

Creditor Protection

In federal bankruptcy proceedings, Roth IRAs are (as of 2024), protected up to $1,512,350. 

Where there can be differences in liability protection are state general creditor claims (i.e., creditor protection in non-bankruptcy situations). In some states, Roth IRAs receive a level of creditor protection similar to that of ERISA plans. Generally, such protection is absolute against all creditors except for an ex-spouse or the IRS. 

In other states, Roth IRAs receive no or limited creditor protection. In my home state of California, Roth IRAs are only creditor protected up to the amount necessary to provide for you and your dependents in your retirement (as determined by the court). Such protection is valuable but hardly airtight. 

A Sneaky Way to Contribute More to Your Retirement

Yes, in theory everyone should save for retirement based on exacting calculations (i.e., I estimate I need $X in retirement, so based on projections I save $A in traditional accounts and $B in Roth accounts this year). That’s the theory.

In practice, it’s “I maxed out this account and that account” or “I put $C into this account and $D into that account.” There isn’t that much wrong with how we practically save for retirement, as long as we are saving sufficient amounts for retirement.

But not all “maxing out” is created equal. We know this because if Jane has $100,000 in a traditional IRA and Mary has $100,000 in a Roth IRA, who has more wealth? Mary! Unless Jane can always be in a zero percent income tax bracket, Mary has more than Jane, even though they both nominally have $100,000. 

A Great Account to Leave to Heirs

While non-spouse heirs will have to take taxable required distributions from inherited IRAs (in many cases beginning in 2020 they will need to drain the account within 10 years of death), heirs are never taxed on distributions from Roth IRAs. This makes a Roth IRA a great account to leave to your heirs. 

Compare with Other Retirement Accounts

No other retirement account combines ease of administration and withdrawal, low costs, significant tax benefits, creditor protection, and great emergency access the way the Roth IRA does. Most workplace retirement plans have some restrictions on withdrawals. Traditional account withdrawals do not have the tax advantages of a Roth IRA. Distributions from a traditional IRA, even one at a low-cost, easy to use discount brokerage, will trigger ordinary income taxes, and possible penalties, if withdrawn for emergency use. 

Financial Planning Objectives

Personal finance is indeed personal. But I submit the following: pretty much every individual has some desire (and/or need) to not work at some point in his/her lifetime and every individual needs to be prepared for emergencies. Further, these are two very important financial planning objectives for most, if not all, individuals.

If the above is true, then we must ask “which account type best supports the combination of these two pressing financial planning objectives?” It appears to me that the answer is clearly the Roth IRA. 

None of this is to say that a Roth IRA is the only way to plan for retirement and plan for emergencies, but rather, it is to say that, generally speaking, a Roth IRA ought to be a material element in such planning. Other tools, such as other retirement accounts, insurances, investments in taxable accounts, and sufficiently funded emergency funds are likely needed in addition to a Roth IRA. 

Retirement Accounts and Emergencies

Let’s examine how a Roth IRA might help someone facing a very serious emergency. 

Picture Jack, who is 52 years old, and has a full time job. He has $1M in a traditional 401(k) and $10,000 in cash in a taxable account. That’s it. Then picture Chuck, also 52 with a full time job. Chuck has $700,000 in a traditional 401(k), $250,000 in a Roth IRA, and $10,000 in cash.

Who is better situated to deal with an emergency? Far and away the answer is Chuck. 401(k)s are difficult to access in an emergency. First of all, the 401(k) plan might not allow in-service distributions, and it might not allow taking out a loan. 

Even if the 401(k) allows in-service distributions, distributions from 401(k)s are immediately taxable, and often subject to penalties (10% federal, 2.5% in California, for example) if you are under age 59 ½. Loans, while not immediately taxable, can become taxable if not paid back. 

Long story short, a 401(k) may be a tough nut to crack in an emergency.

What about a Roth IRA? In Chuck’s case, he can access his prior Roth IRA contributions and sufficiently aged contributions tax and penalty free at any time for any reason! And his Roth IRA is easy to access, particularly if it is at a low-cost discount brokerage.

When you combine tax-free growth, no requirement to take required minimum distributions during the account holder’s lifetime, and the best emergency access of any tax-advantaged retirement account, it is difficult to see why working adults should not have at least some money in a Roth IRA. 

When a Roth IRA Doesn’t Make Sense

The short answer is: not often! I struggle to come up with profiles of individuals that would not benefit from having some amount in a Roth IRA. 

I can think of two profiles. The first, a rare case, is someone with very large legal liabilities such that all of their wealth would benefit from the creditor protections offered by an ERISA retirement plan (such as a 401(k)) and who needs almost all of their wealth shielded from creditors. 

First, if you have built up 6 figures or more in wealth, having creditors able to claim your entire wealth is relatively rare. Second, in most cases, good insurance coverage, including adequate medical insurance, professional liability insurance (as applicable), home and automobile insurance, and personal umbrella liability insurance, should protect the vast majority of people such that they could withstand any liability exposure caused by having money in a Roth IRA instead of an ERISA protected plan. 

The second profile is someone with incredibly high income currently and very little anticipated income in the future (such that their future tax rate is much lower than today’s rate). This too is a bit of a unicorn – people with high income today tend to have decent income tomorrow (even in the FI community).

Health Savings Accounts

It will also come as no surprise that I am fond of health savings accounts. Health savings accounts share some of the attributes that make the Roth IRA such a winner for both retirement savings and emergency planning.

But, there are some drawbacks. First, the distribution ordering rules are not as taxpayer friendly. While it may be the case that you have sufficient old medical expenses that you can reimburse yourself for (and thus not pay tax and a penalty on the HSA distribution), that is not always going to be the case, and even if it is, does add a layer of complexity.

Second, the HSA is not for everyone. If a high deductible health plan is not good medical insurance for you, an HSA is generally off the table.

So, that leaves the HSA as a fantastic option for those who qualify for and use a high deductible health plan (and usually an option that should be part of a comprehensive financial plan if you use a HDHP). But it also means that the HSA is not quite as good as a tool for the combination of retirement saving and emergency planning. 

Conclusion

Assuming that an individual (a) has retirement planning and emergency preparedness as financial planning objectives and (b) is not in a position where legal liabilities would cripple them without ERISA creditor protection, it is hard to argue against having at least some material amount in a Roth IRA. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Split-Year Backdoor Roth IRAs

Can I contribute to a Roth IRA? Can I do a Backdoor Roth IRA? These are two questions I often hear as a tax-focused financial planner.

Perhaps you find yourself preparing your 2020 tax return in early April 2021. You have not contributed anything to a traditional IRA or a Roth IRA yet for 2020. Do you have time to perhaps do a Roth IRA or a Backdoor Roth IRA? The answer is, “Absolutely!” if you have the right facts in place. Let’s discuss a comprehensive example:

Example 1: Jack is single, 35 years old, participates in a 401(k) at work, and has self-prepared his 2020 tax return but not yet filed it. It is April 9, 2021, and his tax-return software indicates that he does not qualify for a Roth IRA, as his modified adjusted gross income for 2020 is $150,000. Jack has no traditional IRAs, SEP IRAs, or SIMPLE IRAs. Jack just learned about the existence of the Backdoor Roth IRA. 

What can Jack do? Can he do a Backdoor Roth IRA for 2020? The answer is, Yes! 

First, Jack should, by April 15, 2021, make a traditional, non-deductible IRA contribution of $6,000. When he does this, he should designate the contribution as being for 2020. With his soon-to-be-filed 2020 federal income tax return, he should file a Form 8606 which will report the $6,000 traditional, non-deductible IRA contribution. Easy enough. 

Assuming Jack contributed to his 2020 traditional, non-deductible IRA in April 2021, in May of 2021 Jack should convert the entire balance in his traditional IRA to a Roth IRA. Third, he should ensure he has no balance in traditional IRAs/SEP IRAs/SIMPLE IRAs as of December 31, 2021. 

Jack can also do a Backdoor Roth IRA for 2021, which may be advisable if (a) his modified adjusted gross income exceeds the Roth IRA contribution thresholds and (b) he will have no balance in traditional IRAs/SEP IRAs/SIMPLE IRAs as of December 31, 2021. 

Assume Jack makes a traditional, non-deductible contribution to an IRA for 2021 on June 1, 2021, and on July 2, 2021, he converts the amounts in the traditional IRA to a Roth IRA. Further assume (a) the amounts converted in May and July were $6,001 and $6,002, respectively, and (b) Jack has no balance in traditional IRAs/SEP IRAs/SIMPLE IRAs as of December 31, 2021. 

When Jack files his 2021 tax return, Page 1 of his Form 8606 should look like this:

Page 1 of the Form 8606 reflects the total basis in traditional IRAs (without considering the Roth conversions). Note that I had to use the 2019 version of the Form 8606, as the 2021 version has not yet been released. Please adjust all dates in your mind’s eye accordingly.

Page 2 (reporting the 2021 Roth IRA conversions) of the Form 8606 should look like this:

The gross amount of the Roth IRA conversions are taxable, but Jack gets to recover his $12,000 of traditional IRA basis.

Post Tax Return Filing Split-Year Backdoor Roth IRA

Example 2: Jim is single, 35 years old, participates in a 401(k) at work, and has self-prepared his 2020 tax return and filed it on March 15, 2021. Jim’s modified adjusted gross income for 2020 is $150,000. Jim has no traditional IRAs, SEP IRAs, or SIMPLE IRAs. It is April 9, 2021 and Jim just learned about the existence of the Backdoor Roth IRA. 

Can Jim still do a Backdoor Roth IRA for 2020? Absolutely!

First, Jim should, by April 15, 2021, make a traditional, non-deductible IRA contribution of $6,000. When he does this, he should designate the contribution as being for 2020. So far, everything is the same as Example 1.

But here is where things change. Jim should also, by April 15, 2021, file a standalone Form 8606 with the IRS and be sure to sign the form on page 2. The Form 8606 will report the contribution to the traditional, non-deductible IRA. Jim will have to paper file the Form 8606 and mail it to the IRS Service Center that he would mail his Form 1040 to (if he were to paper file his Form 1040). 

Jim could then convert the traditional IRA to a Roth IRA to successfully complete the Backdoor Roth IRA. He should also ensure he had no balance in a traditional IRA, SEP IRA, or SIMPLE IRA on December 31, 2021. 

Advanced Split-Year Backdoor Roth IRA

Example 3: Jill is married to Joe, 35 years old, participates in a 401(k) at work, and has self-prepared their 2020 tax return but not yet filed it. Jill and Joe’s modified adjusted gross income for 2020 is $250,000. Jill has a traditional IRA with a balance of $100,000 (and no previous non-deductible contributions). It is April 9, 2021 and Jill just learned about the existence of the Backdoor Roth IRA. 

Jill’s example is a bit more challenging than Jack and Jim’s previous example. Yes, it is possible that Jill could successfully complete a Backdoor Roth IRA for 2020. But it involves much more execution risk – the risk that the proper steps will not be completed in time. While taxpayers engaging in any sort of tax planning should consider engaging professional assistance, Jill is in a position where that is even more so the case. 

Here is how Jill could successfully execute a Backdoor Roth IRA for 2020. Jill should go to her workplace benefits website and download and review the “Summary Plan Description” for the 401(k) plan (sometimes initialized “SPD”). 

It may be the case that Jill’s workplace 401(k) plan will accept a roll-in of her traditional IRA. Many 401(k)s do, but many do not. Some plans will only accept roll-ins of other qualified plans (401(k)s, 403(b)s, etc.), and some plans will only accept roll-ins of qualified plans and so-called “conduit IRAs” i.e., IRAs that consist only of money that was formerly in a qualified plan. However, there are some plans that will accept roll-ins of both old qualified plans and any type of traditional IRA (though note that in all events 401(k) plans cannot accept roll-ins of amounts representing non-deductible IRA contributions).

If Jill’s workplace 401(k) plan will accept a roll-in of the $100,000 traditional IRA, then Jill could transfer (in a direct trustee-to-trustee transfer) her traditional IRA (other than the amount of any nondeductible contributions, including a $6,000 2020 contribution) to the 401(k). If she fails to do that by December 31, 2021, then any Backdoor Roth IRA would be very tax inefficient (and unavisable) – you can read more here in the “Jennifer” example. 

This is one reason I say that there is “execution risk” – perhaps Jill does the “Backdoor Roth IRA” steps but neglects the transfer of the old traditional IRA to the 401(k) until after December 31, 2021. If that happens, Jill’s Backdoor Roth IRA will now be very tax inefficient.

Some might say “couldn’t Jill start a side hustle, open a Solo 401(k) for it, and then roll the traditional IRA into the Solo 401(k)?” To my mind, that is a dangerous path. Jill’s side hustle might not rise to the level of a trade or business for tax purposes. If it does not, then it is not eligible to have a Solo 401(k). Any transfer of a traditional IRA to a plan that does not qualify as either an IRA, 401(k), 403(b), or similar plan is simply a taxable distribution subject to full income tax and a 10 percent early withdrawal penalty. Ouch!!!

Jill should not over think it. If she can easily roll her old traditional IRA into her workplace 401(k), then she should consider doing so and doing a Backdoor Roth IRA. But if she cannot, then fine, there are plenty of other ways to become financially independent and/or achieve retirement planning goals. Not having the Backdoor Roth IRA tool available is no killer to her future plans and goals. 

Note further that if Jill’s balance was in a SIMPLE IRA that was less than 2 years old, she could not roll the SIMPLE IRA into anything other than a SIMPLE IRA for the first two years of her SIMPLE IRA’s existence without incurring a 25% penalty.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

From Tax Returns to Tax Planning

Many colloquially refer to the Winter and early Spring as “tax season.” To my mind, that is short sighted. Yes, for most the time from late January to mid-April are when their tax return is prepared and filed. But the most impactful tax work is not tax return preparation — it’s tax planning!

Below I discuss ways to use your current tax return as a springboard to tax planning. 

Before we get started, two notes. First, there is some tax planning that can be “do it yourself” and some tax planning that is best considered and implemented with the help of a tax planning professional. When in doubt, the concept is probably the latter. Second, it is helpful to keep in mind the correct use of this blog or any other blog–as a tool to raise awareness. Blogs are not a substitute for professional advice, and are not advice for any particular person. Rather, this post and others should be viewed as a way to increase knowledge and help faciliate more informed conversations with professionals. 

Your 2020 Tax Return

Your 2020 tax return is a great springboard for tax planning. Look at the following items on your tax return to jump start your tax planning.

Schedule D Line 13 Capital Gain Distributions

Everyone should review their own tax returns for the past few years and look at this line. If there is a substantial number on this line, it should raise a red flag.

I previously discussed capital gain distributions here. Generally, they come from mutual funds and ETFs in taxable accounts. These financial securities pass gains out to the shareholders, creating capital gains income on the shareholders’ tax returns. Actively managed funds tend to have much greater capital gain distributions than passively managed index funds.

The planning opportunity is to review the accounts that are generating significant capital gain distributions. If the realized gain in such accounts is low (or if there is a realized loss in those accounts), it might be advisable to sell the holding and replace it with a fund likely to have lower capital gain distributions. Taxpayers considering this strategy should be sure to fully understand the gain or loss in the securities before selling. Financial institutions do not have to report to investors (and the IRS) basis in mutual funds purchased prior to 2012, so sometimes it can be difficult to determine the taxable built-in gain or loss on older holdings.

Form 8889 Line 14c Distributions

Form 8889 is the tax return form for a FI favorite: the health savings account. Amounts other than $0 on Line 14c of Form 8889 should appear, in my opinion, only if the taxpayer is elderly or found themselves in a dire situation during the tax year. It is generally not optimal, from a tax perspective, to take distributions from an HSA to fund medical expenses when one is neither elder nor in a dire situation. 

Amounts other than $0 on Line 14c can be a learning and planning opportunity. Future routine medical expenses are usually best paid from one’s checking account (a regular taxable account), and taxpayers should save the receipt. In the future, taxpayers can reimburse themselves tax free from their HSA for that expense. In the meantime, the money has grown in the HSA and enjoyed many years of tax free compounding. 

Form 1040 Line 4b IRA Distributions Taxable Amount

Taxpayers who did a Backdoor Roth IRA and have a large amount on Line 4b of Form 1040 should review their transactions to make sure everything was correctly reported. Part of the idea behind a Backdoor Roth IRA is that, if properly executed, it should result in a very small amount of taxable income (as indicated on Line 4b). 

It may be the case that the tax return improperly reported the Backdoor Roth IRA (and thus, the taxpayer should amend their return to obtain a refund). Or, it may be the case that the taxpayer did the steps of the Backdoor Roth IRA at a time they probably should not have (because they had a significant balance in a traditional IRA, SEP IRA, or SIMPLE IRA). 

Discovering the problem can help effectively plan in the future, and if necessary take corrective action. 

For those executing Roth Conversion Ladders, a large amount on Line 4b is the equivalent of Homer Simpson’s Everything OK Alarm. Roth Conversion Ladders are intended to create a significant amount of taxable income, and Line 4b is where that income is reported on Form 1040. Note further that all Roth IRA conversions require the completion of Part II of the Form 8606. 

Schedule A Line 17 Total Deductions

Those who claimed itemized deductions in 2020 should review Line 17 of Schedule A. Is the number reported for the total itemized deductions close to the standard deduction amount (for 2021, single taxpayers have a standard deduction of $12,550 and married filing joint taxpayers have a standard deduction of $25,100)?

If so, there a tax planning opportunity. Why is that number what it is? Is it because of charitable contributions? If so, the donor advised fund might be a good opportunity. Here’s how it might work:

Example: Joe and Lisa file married filing joint. In 2020, they itemized based on $10K of state taxes, $9K of mortgage interest, and $6K of charitable contributions ($500 a month to their church). Thus, at $25,000 of itemized deductions, they were barely over the threshold to itemize. In 2021, they move a sizable amount into a donor advised fund ($25,000). They use the donor advised fund to fund their 2021, 2022, 2023, and 2024 monthly church donations. 

From a tax perspective, Joe and Lisa itemize in 2021 (claiming total deductions of $44K – the state taxes, mortgage interest, and a $25K upfront deduction for contribution to the donor advised fund). In 2022, 2023, and 2024, they would claim the standard deduction, which is (roughly speaking) almost equivalent to their 2020 itemized deductions. 

By using the donor advised fund, Joe and Lisa get essentially the same deduction in 2022 through 2024 that they would have received without the donor advised fund, and they get a tremendous one year increase in tax deductions in 2021. 

Form 8995 or Form 8995-A Line 2

Those with any amount on Line 2 of the Form 8995 or the Form 8995-A should likely consider some tax planning. This line indicates that the taxpayer has qualified trade or business income that may qualify for the new Section 199A qualified business income deduction. Taxpayers in this situation might want to consider consulting with a professional, as there are several planning opportunities available to potentially increase any otherwise limited Section 199A qualified business income deduction.

2021 Adjusted Gross Income Planning to Maximize Stimulus Payments

Taxpayers should review line 11 (adjusted gross income or “AGI”) on their Form 1040 in concert with reviewing their stimulus checks. For those taxpayers who did not receive their maximum potential stimulus payments in 2021, there can be opportunities to lower AGI so as to qualify for additional stimulus payments and/or increased child tax credits. I blogged about one planning opportunity in that regard here.

The Shift to Tax Planning

Tax planning can take many shapes and sizes. But it needs to be driven by goals, not by tactics. Bad tax planning begins something like this: “I need a Solo 401(k), how do I set it up?” N.B. Opening a Solo 401(k) when you do not qualify for one is a great way to create a tax problem for yourself. 

Good tax planning begins more like this: “I want to achieve financial independence. How do I best save for retirement in a tax advantaged way? I’ve heard a Solo 401(k) is a great option. As part of this process, we should consider it as a possible way to help me achieve my goal.”

Another point: I find there is far too much focus on “I had to pay [insert perceived sizable amount here] this year in taxes” and far too little focus on lifetime taxes. To my mind, the goal should not be to pay less tax in any one year. Rather, the goal should be to legitimately reduce lifetime tax burden. Sure, there can be tax planning that does both, but the best tax planning (whether DIY or with the help of a professional) places reducing lifetime tax burden as its primary goal.

Below are just some areas where taxpayers can begin their tax planning considerations.

Retirement Planning

This is a big one. Taxpayers should understand whether they contribute to a traditional IRA and/or Roth IRA, and why or why not. This post helps explain whether taxpayers qualify to make an annual contribution to a traditional IRA and/or a Roth IRA. 

Taxpayers should consider their workplace retirement plans, which can provide several planning opportunities. 

Small Business/Self-Employment Income

For those with a small business and/or significant self-employment income, tax planning is very important. I have written several posts about just some of the tax planning available to those with small businesses. People with small businesses often benefit from professional, holistic tax and financial planning. 

Stock Options

Stock options and employer stock grants provide some good tax planning opportunities. I’ve previously written about ISOs, but all kinds of stock option programs can be an opportunity to do some tax planning, which often should be with a professional advisor. 

Conclusion

Filing timely, accurate tax returns is important. But the best way to optimize one’s tax situation is to do quality, intentional tax planning. Tax planning should prioritize goals over tactics. There is some tax planning that can be done by yourself, but many areas of tax planning strongly benefit from professional assistance.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Understanding Your Form 1099-DIV

If you’re reading this in the Winter of 2024, you may have already received a bill from your financial institution. It’s called a Form 1099-DIV. Oddly, the financial institution isn’t demanding a penny of payment. Rather, your 1099-DIV prompts the IRS and your state tax agency (in most states) to expect the payment of income tax with respect to your financial assets.

A Form 1099-DIV is a great window into your taxable investments. By learning how to read the major boxes of your 1099-DIV, you can gain valuable insights about your investments and their tax efficiency.

VTSAX Form 1099-DIV 2024 Update

The Basics

Form 1099-DIV exists so that taxpayers and the IRS know the income generated by financial assets in dividend paying accounts. These include stocks, mutual funds, and exchange traded funds (“ETFs”). The financial institution prepares the Form 1099-DIV and submits a copy to the IRS and a copy to the taxpayer. 

Let’s be clear about what we are talking about. We are not talking about assets in retirement accounts (401(k)s, IRAs, Roth accounts, HSAs, etc.). You do not receive a Form 1099-DIV from a retirement regardless of how much money the account earned during the year. This is one of the advantages of saving through a retirement account. Dividends and other income generated by assets in a retirement account are not taxable to the account holder when generated (so long as the funds stay in the retirement account).

Dividends

Corporations pay dividends to their shareholders as a return to the shareholders of their portion of some or all of the earnings of the corporation. The corporation’s Board of Directors vote from time to time to pay dividends to the shareholders. Boards determine dividends based on a variety of factors, including the company’s profitability, industry, stage in the corporate life cycle, and business cash needs.

All shareholders of a corporation receive dividends. Some of those shareholders are themselves mutual funds or ETFs. Mutual funds and ETFs distribute out dividends and certain other income they receive (such as interest) to their shareholders as dividends.

Box 1a and Box 1b

Box 1a lists the so-called “total ordinary dividends” received from the account. That is all of the dividends paid by the stocks, mutual funds, and ETFs in the account. 

Box 1a should be understood as the entire pie. It represents all of the dividends received in the taxable account. The amounts in Box 1a are reported on line 3b of the Form 1040 (and on Schedule B if required).

Box 1b qualified dividends should be understood as a slice of the pie. It represents the portion of the total ordinary dividends that qualify for the long-term capital gains rates. Dividends create “ordinary income” for U.S. federal income tax purposes. However, certain “qualified dividends” (referred to as “QDI”) are taxed at preferential long term capital gains rates. As I have previously written, “[g]enerally, two requirements apply for the dividend to qualify for favorable QDI tax treatment. Very generally stated, they are:

  • The shareholder must own the stock for 60 of the 121 days around the “ex-dividend” date (the first date on which the stock sells without the right to receive the upcoming dividend); and,
  • The paying corporation must be incorporated either in the United States or in a foreign country with which the United States has a comprehensive income tax treaty.

Shareholders can obtain QDI treatment for stock owned through mutual funds and ETFs.

It may be that your qualified dividend slice is the entire pie. In most cases, there are usually some dividends that do not qualify for QDI treatment. 

Amounts reported in Box 1b are reported on line 3a of the Form 1040.

Box 2a Capital Gain Distributions

Box 2a is the danger zone of the Form 1099-DIV. In a way, it is unavoidable to recognize dividends (even if such dividends are QDI) if one wants to invest in a broad based portfolio of equities in a taxable account. Eventually corporations pay out dividends. While younger companies tend not to pay dividends, as companies mature they tend to start paying dividends.

What are much more avoidable (at least to a degree) are capital gain distributions. Capital gain distributions come from mutual funds and ETFs (they do not come from individual stocks).

Capital gain distributions occur when fund managers sell individual holdings at a gain. The fund is required to (usually toward year end) pay out those gains to the shareholders. The paid out gains are reported in Box 2a.

Three things tend to increase capital gain distributions: 1) active management; 2) a bull market; and 3) fund redemptions.

Active Management

Usually, this is the most significant factor in capital gain distributions. In order to actively manage a mutual fund or ETF, fund managers generally need to buy and sell different holdings. The selling of holdings is what creates capital gain distributions.

Frequent trading can make certain actively managed mutual funds and ETFs very tax inefficient, because they trigger capital gain distributions that are currently taxed to the owner at capital gains rates. 

From this, we can deduce the secret tax advantage of index funds. Index mutual funds and ETFs seek to simply replicate a widely known index. Other than occasional mergers and acquisitions of companies in the index, index fund managers rarely need to sell a holding to meet an investment objective. Thus, in many cases holding index funds in taxable accounts is tax efficient and will be better from a tax perspective than holding an actively managed fund.

Bull Market

Mutual funds and ETFs pass out capital gain distributions, not capital loss distributions. But in order for the shareholders to have a capital gain distribution, the mutual fund or ETF must (a) sell a holding and (b) must realize a gain on that sale.

In bear markets, it is often the case that the second requirement is not satisfied. The fund often realizes a loss on the sale of holding, meaning that the portfolio turnover does not generate a capital gain distribution reported in Box 2a. However, bear markets don’t always mean there will be no capital gain distributions, as active management and fund redemptions can still trigger capital gain distributions.

Fund Redemptions

There is an important distinction between mutual funds and ETFs in this regard. ETFs trade like public company stock — other than IPOs and secondary offerings, generally you buy and sell the stock of a public company and an ETF with an unrelated party that is not the issuer itself. 

Mutual funds, on the other hand, are bought and sold from the issuer. If I own 100 shares of the XYZ mutual fund issued by Acme Financial, when I redeem my 100 shares, Acme Financial buys out my 100 shares.

In order to buy out mutual fund shares, the mutual fund must have cash on hand. If it runs out of cash from incoming investments into the fund, it will have to sell some of its underlying holdings to generate the cash to fund shareholder redemptions. This creates capital gain distributions for the remaining shareholders. 

Interestingly, Vanguard has created a method to reduce the tax impact of mutual fund redemptions. Further, in recent times, fund redemptions have not caused significant capital gain distributions in many cases because in this current bull market mutual fund inflows often exceed outflows. 

Box 3 Nondividend Distributions

There are occasions where corporations make distributions to shareholders during a time where the corporation does not have retained earnings (i.e., it either has not made net income or it has previously distributed out is net income). Such distributions are not taxable as dividends. Rather, such dividends first reduce the shareholder’s basis in their stock holding. Once the basis has been exhausted, the distribution causes a capital gain.

Box 5 Section 199A Dividends

Section 199A dividends are dividends from domestic real estate investment trusts (“REITs”) and mutual funds that own domestic REITs. These dividends are reported on Form 8995 or Form 8995-A and qualify for the Section 199A QBI deduction. The good news is that the taxpayer (generally) gets a federal income tax deduction equal to 20 percent of the amount in Box 5. This deduction does not reduce adjusted gross income but does reduce taxable income.

Section 199A dividends are another slice of the pie of Box 1a ordinary dividends.

Watch me explain Section 199A dividends

Box 7 Foreign Tax Paid

An amount in Box 7 is generally good news from a federal income tax perspective. Many countries impose a tax on the shareholder when the corporation pays a dividend is a non-resident shareholder. The corporation withholds a percentage of the dividend and then remits the net amount of the dividend to the shareholder. 

The amount in Box 7 usually creates a foreign tax credit that reduces federal income tax dollar for dollar. If you have $300 or less in foreign tax credits ($600 or less if married filing joint) you can simply claim the foreign tax credit on your Form 1040 without any additional work. If your foreign tax credits exceed these amounts, you will also need to file a Form 1116 to claim the foreign tax credit.

The ability to claim foreign tax credits is a reason to hold international equities in taxable accounts.

Watch me discuss how VTIAX might generate a foreign tax credit on a US income tax return.

Boxes 11 and 12 Exempt-Interest Dividends and Private Activity Bond Interest

Box 11 represents all of the tax-exempt dividends received in the taxable account. Typically this is generated by state and municipal bond interest received by the mutual fund or ETF and passed out to the shareholders. This income is tax-exempt for federal income tax purposes.

This income may not be tax-exempt for state tax purposes. For example, in my home state of California, this income is taxable unless it is established that 50 percent or more of the funds assets are invested in California state and municipal bonds. In that case, the exempt-interest dividend attributable to California state and municipal bonds is tax-exempt for California purposes. The financial institution must separately provide the percentage of income attributable to California bonds to the shareholder in order to compute the amount of exempt-interest dividend exempt from California income tax. 

Box 12 is a subset of Box 11 (Box 11 is the whole pie, Box 12 is a slice). Box 12 dividends are those attributable to private activity bonds. The significance is for alternative minimum tax (“AMT”) purposes. While this income is tax-exempt for regular federal income tax purposes, it is not tax-exempt for AMT purposes (and thus is subject to the AMT). After the December 2017 tax reform bill this issue still exists, though it affects far fewer taxpayers.

Conclusion

The Form 1099-DIV conveys important information, all of which must be properly assessed in order to correctly prepare your tax return. It can also provide valuable insights into the tax-efficiency of your investments. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

The SECURE Act’s Impact on the FI Community

In late December 2019 the President and Congress enacted the SECURE Act. The SECURE Act makes some significant revisions to the laws governing IRAs, 401(k)s, and other retirement accounts. This post discusses the impacts of these changes on those pursuing financial independence.

The Big Picture

The SECURE Act is a big win for the FI community, in my opinion. 

The FI community significantly benefits from IRAs, 401(k)s, and other tax-advantaged retirement accounts. However, the federal government is facing increasing debts and annual deficits. That puts tax-advantaged accounts in the crosshairs. What Congress gives in tax benefits Congress can take away.

So what does the SECURE Act do? First, it actually gives us a couple more tax advantages during our lifetimes (see “Opportunities” below). Second, it significantly reduces the tax advantages of inherited retirement accounts for our heirs.

For those either with large retirement account balances or planning to have large retirement account balances, any change in tax laws is a potential problem. We should be glad that this round of tax law changes has occurred without our own retirement accounts being negatively impacted. Congress has passed the bill to our heirs, which, right or wrong, is a victory for us. 

When you see people in the financial press squawking about how awful the SECURE Act is, remember, it could be a whole lot worse–your retirement account could have been more heavily taxed during your lifetime! 

For those pursuing FI, the ability to use tax-advantaged retirement accounts remains the same, and in a couple small ways, has been enhanced. The next generation still has all those retirement account opportunities, even if they won’t be able to benefit from inheriting retirement accounts as much as they do under current law. 

Opportunities

Traditional IRA Contributions for those 70 ½ and Older

Starting in 2020, those aged 70 ½ and older will be able to contribute to a traditional IRA. This will open up Backdoor Roth IRA planning for those 70 ½ and older and still working. For those still working (or doing side hustles) at age 70 ½ or older, this is a nice change.

Remember, regardless of age, in order to contribute to an IRA, you or your spouse must have earned income. 

RMDs Begin at 72

For those attaining age 70 ½ after December 31, 2019, the age at which they will need to take RMDs will be 72, not 70 ½. This gives retirement accounts a bit more time to bake tax-deferred. It also slightly expands the window to do Roth conversions before RMDs begin. However, this last benefit is tempered by the fact that you must take Social Security no later than age 70. Roth conversion planning to reduce taxable RMDs should be mostly completed well before age 70 ½, regardless of this change in the law. 

Note that taxpayers can still make qualified charitable distributions (“QCD”) starting when they turn age 70 ½. While pre-age 72 QCDs won’t satisfy RMD requirements, they will (a) help optimize charitable giving from a tax perspective (by keeping adjusted gross income lower and avoiding the requirement to itemize to deduct the contribution) and (b) reduce future RMDs.

Annuities in 401(k)s

The new law provides rules facilitating annuities in 401(k) plans. This one requires proceeding with extreme caution. If your 401(k) plan decides to offer annuity products, you need to carefully assess whether an annuity is the right investment for you and you need to fully understand the fees charged. 

Remember, just because the law changed doesn’t mean your asset allocation should change!

Leaving Retirement Accounts to Heirs

This is the where the SECURE Act raises taxes. The SECURE Act removes the so-called “stretch” for many retirement plan beneficiaries. For retirement accounts inherited after December 31, 2019, only certain beneficiaries will be able to stretch out distributions over their remaining life (or based on the age of the decedent if over 70 ½ at death). For nonqualified beneficiaries, the rule will simply be that the beneficiary must take the account within 10 years of the owner’s death (the “10-year rule”).

My overall opinion on the SECURE Act stated above, planning for the next generation is important. Particularly if you are already financially independent and want to help your children become financially independent, the SECURE Act has significant ramifications.

Spouses

If your current estate plan features your spouse as your retirement account primary beneficiary, the SECURE Act should in no way change that aspect of your plan. Fortunately, the many advantages applicable to spouses inheriting retirement accounts will not change. Spouses remain an excellent candidate to inherit a retirement account. 

Minor Children

If you leave your retirement account to your minor children, they are exempt from the 10-year rule (and can generally take distributions based on IRS RMD tables that are generous to younger beneficiaries) while they are still minors. Once your children reach the age of majority, they will have ten years to empty the retirement account. 

The exception to the 10-year rule applies only to your minor children. It does not apply to your grandchildren, your adult children, and the children of others (including nieces and nephews). 

Other Eligible Beneficiaries

The exceptions to the 10-year rule apply to your spouse, your minor children, the disabled, the chronically ill, and persons not more than 10 years younger than you at your death. All others will need to empty retirement accounts within 10 years of inheritance. This will require some significant planning in cases where the beneficiary has inherited a traditional retirement account to strategically empty the account over the 10 year window to manage adjusted gross income, taxable income, and total tax. 

Planning

For those of you with estate plans involving adult children, the passage of the SECURE Act may well require revisions to your plans. First off, as a practical matter, your revocable living trust may need modifications. Many have designated a trust as a retirement account beneficiary. To do so properly requires conforming with specific income tax rules. Those with trusts as the beneficiary of their retirement account would be well advised to, at a minimum, consult with their lawyer to determine if the language of the trust needs updating.

Second, understanding that inheriting a traditional retirement account will now mean accelerated, and possibly significantly increased, taxation for their heirs, many will want to consider Roth conversion planning. Roth accounts will be subject to the 10-year rule, but the good news is that the beneficiary can keep the assets in the Roth account for 10 years, let it grow tax free, and then take out the money in 10 years tax free. Not too bad.

Roth conversion planning to optimize your heirs’ income tax picture is now even more important. However, it should not be done if it will impose a financial hardship on the account owner during their lifetime. The first priority should be securing the account owner’s retirement. Only if the account owner is financially secure should they consider Roth conversion planning to reduce their heirs’ tax liability.

Conclusion

Tax rules are always changing. This round of changes is a victory for those pursuing financial independence. Any tax law change that does not negatively impact your path to financial independence is a win. 

For those considering the financial health of their heirs, particularly their adult children, the SECURE Act should prompt some reconsideration of estate plans. Often it is wise to consult with professional advisors in this regard. 

FI Tax Guy can be your financial advisor! FI Tax Guy can prepare your tax return! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. 

Roth Conversions for the Self-Employed

Are you self-employed? Is your self-employment income your primary source of income? If so, you might want to consider doing a Roth conversion before the end of the year.

Takeaways

  • If most of your taxable income is self-employment income (either reported on Schedule C or from a partnership), you might want to consider year-end Roth conversions to maximize your QBI deduction and pay a lower-than-expected federal income tax rate on the conversion.
  • To optimize this strategy, convert traditional IRAs to Roth IRAs (or do in-plan traditional 401(k) to Roth 401(k) conversions) to increase your QBI deduction. 

Why? Because of the still relatively new qualified business income (“QBI”) deduction (also known as the Section 199A deduction). 

QBI Deduction and Initial Limitation

Starting in 2018, there is a deduction for “qualified business income.” This is generally income from a qualified trade or business received from a sole proprietorship (and reported on Schedule C), from a partnership, or from a S Corporation (in these cases, generally reported to the taxpayer on a Form K-1 and reported on the Schedule E with the tax return). 

Important for this purpose is the initial limit on the QBI deduction. It is the lesser of following two amounts:

  1. 20 percent of taxable income less “net capital gain” which is generally capital gains plus qualified dividend income (“QDI”) (the “Income Limit”) or
  2. 20 percent of QBI (the “QBI Limit”).

As a practical matter, in most cases the limit will be determined by the second limitation (such taxpayers are what I call “QBI Limited”). Many taxpayers will have much more taxable income than they have QBI. Consider spouses where one has self-employment income and the other has W-2 income. Unless the W-2 income is very small, their combined taxable income is likely to be in excess of their combined QBI, and thus they will be QBI Limited.

Alternatively, consider a situation where a single person has QBI from an S corporation (say $50,000) and the S corporation also pays him or her a W-2 salary (say $60,000). In such a case the QBI is $50,000 (20% of which is $10,000) and the taxable income might be $97,450 ($110,000 total from the S corporation less a $12,550 standard deduction), 20% of which is $19,490. This taxpayer would also be QBI Limited. 

Income Limited

But what if you are not QBI Limited, but rather, limited by the Income Limit listed above (what I call “Income Limited”)? Here is an illustrative example.

Example 1: Seth is single and self-employed. He claims the standard deduction in 2021. He reports a business profit of $100,000 on his Schedule C. He also has $1,000 of interest income.

His Income Limit is computed as follows:

Schedule C Income: $100,000

Interest Income: $1,000

Deduction for ½ Self-Employment Taxes: ($7,065)

Standard Deduction: ($12,550)

Taxable Income: $81,385

20% Limit: $16,277

Seth’s QBI Limit is computed as follows:

Schedule C Income: $100,000

Deduction for ½ Self-Employment Taxes: ($7,065)

QBI: $92,935

20% Limit: $18,587

In this case, Seth’s QBI deduction is only $16,277 (he is Income Limited), the lesser of these two calculated limits. 

Roth Conversion Planning

Is there anything Seth can do to increase his limitation and optimize his QBI deduction?

Imagine Seth has $20,000 in a traditional IRA (with zero basis). He could convert some of that traditional IRA to a Roth IRA by December 31, 2021. This would create taxable income, which would increase Seth’s Income Limit. Here is how that could play out:

Without Roth Conversion

Schedule C Income$ 100,000
Interest Income$ 1,000
Deduction for ½ Self-Employment Taxes$ (7,065)
Adjusted Gross Income$ 93,935
Standard Deduction$ (12,550)
Qualified Business Income Deduction (see above)$ (16,277)
Taxable Income$ 65,108
Federal Income Tax$ 10,072

With Roth Conversion

Schedule C Income$ 100,000
Interest Income$ 1,000
Deduction for ½ Self-Employment Taxes$ (7,065)
Roth IRA Conversion$ 11,550
Adjusted Gross Income$ 105,485
Standard Deduction$ (12,550)
Qualified Business Income Deduction$ (18,587)
Taxable Income$ 74,348
Federal Income Tax$ 12,105

What has the $11,550 Roth IRA conversion done? First, it has made the Income Limit ($18,587) the exact same as the QBI Limit ($18,587). Thus, Seth’s QBI deduction increases from $16,227 to $18,587. 

Second, notice that Seth’s taxable income has increased, but not by $11,550! Usually one would expect that a Roth IRA conversion with no basis recovery would simply increase taxable income by the amount converted. But not here! The interaction with the QBI deduction caused Seth’s taxable income to increase only $9,240 ($74,348 minus $65,108). 

This example illustrates that, under the right circumstances, a Roth IRA conversion can receive the benefit of the QBI deduction!

As a result, at Seth’s 22 percent marginal federal income tax bracket, his total federal income tax increased only $2,033. In effect, Seth pays only a 17.6 percent rate on his Roth IRA conversion ($2,033 of federal income tax on a $11,550 Roth IRA conversion). This is true even though Seth is in the 22 percent marginal tax bracket. His Roth IRA conversion is only 80 percent taxable. This is the flip-side of the 80% deduction phenomenon I previously blogged about here. 

Is it advantageous for Seth to convert his traditional IRA? Well, it depends on Seth’s expected future tax rates. If Seth’s future marginal tax bracket is anticipated to be 22 percent, then absolutely. Why not convert at a 17.6 percent instead of face a 22 percent rate on future traditional IRA withdrawals?

Strategy

Seth’s Roth IRA conversion is optimized. The takeaway is that the Roth IRA conversion gets the benefit of the QBI deduction, but only for amounts that increase the Income Limit up to the QBI Limit.

A *very general* rule of thumb for solving for the optimal Roth conversion amount is to multiply the difference between the QBI Limit and the Income Limit (without a Roth conversion) by 5. In Seth’s case, that was $18,587 minus $16,277 (which equals $2,310) times 5.

In this case, converting exactly $11,550 made Seth’s Income Limit exactly equal his QBI Limit. As long as the Roth conversion increases the Income Limit toward the QBI Limit, the conversion benefits from the QBI deduction.

But the first dollar of the Roth conversion that pushes the Income Limit above the QBI Limit does not receive the benefit. If Seth converted $11,551 from his traditional IRA to his Roth IRA, that last dollar above $11,550 would be taxed at Seth’s full 22 percent federal marginal tax bracket. 

Note that instead of / in addition to a Roth IRA conversion, Seth could do an in-plan traditional 401(k) to Roth 401(k) conversion, if he had sufficient funds in a traditional 401(k), and the 401(k) plan permits Roth 401(k) conversions.

Also note that the strategic considerations with QBI deductions become much more complicated once taxpayers exceed the initial QBI taxable income limitations (in 2021, those are $164,900 for single taxpayers and $329,800 for married filing joint taxpayers). 

Conclusion

Taxpayers whose taxable income consists mostly or exclusively of self-employment income should consider Roth conversions toward year-end. This is often an area that benefits from consulting with a professional tax advisor before taking action.

Further Reading

I have blogged about the QBI deduction and retirement plans here. After the IRS and Treasury provided some QBI deduction regulations in January 2019, I provided some QBI deduction examples and lessons here. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Top 5 HSA Tips

For those with a health savings account, December is a great time to review how it has been used and to see if there are ways to better optimize the account.

One: Let it Grow!!!

When it comes to HSAs, often the best advice is Let it Grow, Let it Grow!!! Sing it to the tune of the popular Disney movie song if it helps you to remember.

Adding an “r” and a “w” would make Elsa a tremendous HSA advisor.

Spend HSA money only if one of the following two adjectives apply: DIRE or ELDERLY. Those neither in a dire situation nor elderly should think twice before spending HSA money! Instead, Let it Grow!

The tax benefits of an HSA are so powerful that funds should stay in the HSA (to keep growing tax free) and only be removed in dire (medical or financial) circumstances or by the elderly. Unless you leave your HSA to your spouse or a charity, HSAs are not great assets of leave to heirs. Thus, HSAs are great to spend down in your later years (after years of tax-free growth). 

Two: Max Out Payroll Contributions by December 31st

While you can contribute via non-payroll contribution by April 15, 2020 for 2019, contributing to your HSA through payroll deductions is generally optimal since it secures both an income tax deduction and a payroll tax deduction for the money contributed.

If you didn’t max out your HSA through payroll deductions in 2019 and your employer allows HSA payroll deductions, write the check to your HSA in early 2020 (for 2019) and set up your 2020 payroll elections so as to max out your HSA through payroll deductions in 2020.

Three: Review HSA Investment Allocation

Those with low-cost diversified investment choices in their HSA are generally well advised to invest in higher growth assets inside their HSAs. The HSA is a great tax-protected vehicle. That tax protection is best used for high growth assets. 

Those who have invested their HSA funds solely or mostly in cash should consider reassessing their HSA investment strategy.

Four: Track Medical Expenses 

Medical expenses incurred after coverage begins under a high deductible health plan (a “HDHP”) can be reimbursed to you from an HSA many years in the future. There is no time limit on the reimbursement. Unless you are elderly, long-delayed reimbursement (instead of directly paying medical expenses with a HSA) is usually the tax-optimal strategy. Keep a digital record of your medical expenses and receipts to facilitate reimbursements out of the HSA many years in the future. 

Five: Properly Report HSA Income (CA, NJ, NH, TN)

HSAs are tax-protected vehicles for federal income tax purposes and in most states. On your federal tax return, you need to report your HSA contributions and distributions (see Form 8889). However, you are not taxed on the interest, dividends, and capital gains earned in the HSA, and you do not need to report these amounts. 

It is very different if you live in California and New Jersey. Neither California nor New Jersey recognize HSAs as having any sort of state income tax protection. They are simply treated as taxable accounts in those states. In preparing your California or New Jersey state tax return, you must (1) increase your federal wages for any excluded HSA contributions, (2) remove any deduction you took for HSA contributions (non-payroll contributions to your HSA), and (3) report (and pay state income tax on) your HSA interest, dividends, capital gains, and capital losses.

This last step will generally require accessing your HSA account online and pulling all of the income generating activity, including asset sales, in order to properly report it on your California or New Jersey tax return. 

Tennessee and New Hampshire do not impose a conventional income tax, but do tax residents on interest and dividends above certain levels. HSA interest and dividends are included in the interest and dividends subject to those taxes.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Fixing Backdoor Roth IRAs

Watch me discuss Backdoor Roth IRA tax return reporting on YouTube.

The word is out. The Backdoor Roth IRA is a powerful tax planning tool. You may believe that by previously executing Backdoor Roth IRAs, you have planned well and received a great tax benefit while building retirement savings.

Is it possible you are mistaken? It is possible you did not complete the Backdoor Roth IRA correctly? 

It may be true that you have successfully completed the two independent steps of a Backdoor Roth IRA: a traditional, non-deductible IRA contribution followed by a later Roth IRA conversion. It may also be true that you had no balances in a traditional IRA, SEP IRA, and/or SIMPLE IRA as of December 31st of the year you did the Backdoor Roth IRA. 

Year-end tip: The deadline to clean out traditional/SEP/SIMPLE IRAs (by rolling them into employer retirement plans such as 401(k)s) so as to optimize a Backdoor Roth IRA is December 31st of the year of the Roth IRA conversion step. As a practical matter, you should not complete the Roth IRA conversion step until you have cleaned out the traditional/SEP/SIMPLE IRAs. Life happens; there is simply no guarantee you complete the clean out before December 31st. Failing to do so will significantly increase the tax on your Backdoor Roth IRA. 

But you may not have correctly reported the Backdoor Roth IRA on your tax return. This last step is too-often overlooked. Below I discuss how to properly report a Backdoor Roth IRA, a potential tax return mistake that could have cost you thousands in erroneous taxes, and ways to fix the mistake. 

Backdoor Roth IRA Example

Charlie is single and 35 years old. He is covered by a retirement plan at work. In 2018 his W-2 salary was $200,000, and thus he did not qualify to make a Roth IRA contribution for 2018. He has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA. He decides to do a Backdoor Roth IRA. 

On September 2, 2018, Charlie contributed $5,500 to a traditional, non-deductible IRA. On October 10, 2018, he converted the entire balance in the traditional IRA, then $5,510, to a Roth IRA. 

So far, so good with the Backdoor Roth IRA! But Charlie’s not done yet. Let’s look at how the Charlie should file his tax return and the pitfalls he should avoid.

Backdoor Roth IRA Tax Return Reporting

Early in the year, Charlie should receive a Form 1099-R that looks like the following from his financial institution.

Charlie’s Backdoor Roth IRA Form 1099-R should look something like this. Note that the “taxable amount” is the full conversion amount ($5,510) and the box indicating that the taxable amount has not been determined is checked.

This requires precise tax return reporting to ensure Charlie increases his taxable income by the correct amount to account for the Backdoor Roth IRA. An error in the tax return reporting could erroneously overstate his adjusted gross income and thus cause him to pay significantly more to the IRS and state tax agency than he owes.

There are two places Charlie needs to report the Backdoor Roth IRA: Pages 1 and 2 of Form 8606 and lines 4a and 4b of the Form 1040.

Let’s start with the Form 8606. Below is the correct way for Charlie to file Page 1 of his Form 8606.

Lines 1, 6, and 11 of the Form 8606 are crucial to properly reporting a Backdoor Roth IRA and computing the nontaxable portion of the Roth IRA conversion.

Notice a few things about this form. First, on line 1 Charlie reports his traditional, non-deductible IRA contribution of $5,500. Second, on line 6, Charlie reports the total combined value of his traditional IRAs, SEP IRAs, and SIMPLE IRAs as of December 31, 2018. He can find this number on the Forms 5498 that his financial institutions send him and the IRS regarding his IRA accounts. To have a very efficient Backdoor Roth IRA, ideally Charlie should no balance in these accounts on December 31, 2018, and thus Charlie can, and does, report zero on line 6. If Charlie has any such balances the total must be reported here and it will cause his Backdoor Roth IRA to be partially (maybe mostly) taxable. 

Next, Charlie reports his Roth IRA conversion amount on line 8. This is the total taxable amount he converted, reported to him in Box 2 of the Form 1099-R, $5,510. The mechanics of the Form 8606 then lead to lines 11 and 13, the nontaxable portion of Charlie’s Roth IRA conversion. In Charlie’s case, this is $5,500. This is because he is entitled to recover all $5,500 of basis he has in his traditional IRA (as computed in this part of the Form 8606). This $5,500 number is required to correctly prepare Page 2 of the Form 8606 and line 4b of the Form 1040.

Form 8606 Line 18 should be reported on Line 4b of Form 1040 for a 2018 Backdoor Roth IRA.

Page 1 computed how much of Charlie’s basis he can recover and the nontaxable portion of his Roth IRA conversion. Page 2 answers the second question: How much of Charlie’s Roth IRA conversion is taxable? Line 16 is simply line 8, and line 17 is simply line 11. Subtracting the nontaxable portion of the Roth IRA conversion from the total converted amount yields the amount of the Roth IRA conversion that is taxable. In Charlie’s case, it is only $10. This amount goes to Charlie’s Form 1040, line 4b. 

This is how a Backdoor Roth IRA should look on your Form 1040. Notice the very small number on Line 4b.

The Wrong Way

The following is what Charlie’s Form 1040 might look like if his Backdoor Roth IRA is misreported. 

Heed the warning of my chicken scratch: a four figure number on Line 4b after a Backdoor Roth IRA is likely an indication that either the tax planning or the tax reporting is off.

How might this happen? It could be that a Form 8606 simply was not prepared, or it was incorrectly prepared. Sometimes the Form 1099-R is misunderstood. People see that $5,510 is the “taxable amount” in line 2 of the Form 1099-R and believe that must be the taxable amount reported on line 4b. But remember, the Form 1099-R has a box checked indicating that the taxable amount is not determined. The Form 8606 is what determines the taxable amount created by the Backdoor Roth IRA (in Charlie’s case, $10). 

As a check, you should ensure that the Lines 18 of your previously filed Forms 8606 agree to the appropriate line on the Form 1040 (line 4b in 2018). If there are discrepancies (and/or a Form 8606 was not filed for a Backdoor Roth IRA), that is an indication there is likely an error on the tax return. If Line 18 on the Form 8606 is a four-figure or greater number after a Backdoor Roth IRA, it is very likely that either the tax planning or the tax return reporting went wrong somewhere.

We can see how deleterious this error is for Charlie. If he filed his tax return the wrong way, his federal taxable income is overstated by $5,500. In his case, this caused him to erroneously owe $1,760 more in federal income tax ($43,613 minus $41,853 — hat tip to ProConnect Tax Online for the tax calculations). If Charlie lives in a state with a state income tax, he will also overpay his state income taxes because of this error. 

Filing an Amended Tax Return

Imagine that Charlie filed his tax return as pictured in the Wrong!!! picture above. What can Charlie do?

Charlie’s remedy is to file an amended return. This entails refiling the Form 1040 and all of its related forms and schedules (including the Form 8606) with the correct amounts. It also entails filing a Form 1040X. This form presents amounts as originally filed and as corrected, with the difference illustrated. It also requires a narrative submission explaining the changes made on the amended tax return.

There are several things to keep in mind when filing an amended tax return. First, a taxpayer filing an amended return is under an obligation to correctly report amounts. If, as part of the exercise of fixing a Backdoor Roth IRA through an amended tax return, the taxpayer learns that other amounts on the originally filed tax return were incorrect, he or she must correct those amounts if they choose to file an amended return. 

Second, there is a deadline for amending a federal income tax return (the so-called statute of limitations). Generally, the deadline is three years from the later of the tax return due date (if originally filed on or prior to the initial tax return due date) or the filing date (if filed after the initial tax return due date). This later deadline applies anytime the taxpayer files after the initial due date (including, for example, a timely post-April 15th tax return filing made after filing for an extension). 

If the amended return claiming the refund (because of the corrected Backdoor Roth IRA tax return reporting) is filed after this three year deadline, the IRS cannot and will not issue a refund to the taxpayer due to the statute of limitations. There are limited exceptions to this rule (such as when the IRS and the taxpayer have mutually agreed to extend the statute of limitations). 

States have their own statutes of limitations, which may or may not be the same as the federal statute of limitations. In my home state of California, it is a four-year statute of limitations instead of a three-year statute of limitations. 

The statute of limitations means the clock is ticking to correct Backdoor Roth IRAs not correctly reported on previously filed tax returns. In many cases, taxpayers learning they have incorrectly filed a tax return (for whatever reason, including an erroneously reported Backdoor Roth IRA) are well advised to seek professional assistance in amending their tax returns. 

Further Reading

I have previously blogged about Backdoor Roth IRAs for beginners here and about tactics to employ if you want to do a Backdoor Roth IRA but currently have a balance in a traditional IRA, SEP IRA, and/or SIMPLE IRA.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

IRS Identity Protection PIN

UPDATE (January 13, 2021): The IRS has expanded the PIN program to all Americans. See https://www.irs.gov/newsroom/all-taxpayers-now-eligible-for-identity-protection-pins Hat Tip to Ed Zollars for the update: https://www.currentfederaltaxdevelopments.com/blog/2021/1/13/ip-pin-program-available-to-all-taxpayers

The post below has NOT been updated for the January 13, 2021 update. Please use the below for general background purposes only and refer to the IRS website and Mr. Zollars’ article.

Identity theft continues to be a significant 21st century concern. It can happen in many ways. One particularly nefarious way is that your identity might be stolen to file a tax return with the IRS. Below I discuss a relatively new program that the IRS has made available to many Americans to help prevent identity theft with the IRS. If you are eligible, you should give strong consideration to opting into the program.

Identity Theft and Tax Returns

Obviously identity theft is bad. But why would someone use your identity with the IRS?

The answer is a tax refund. The scam often works like this: a scammer steals your identity and files a tax return with your name and Social Security number early in the year, before you have a chance to file your tax return for the prior year. The scammer will report taxable income and tax payments such that the tax return claims you have a significant income tax refund due from the IRS. The phony tax return will direct the refund such that the scammer gets the tax refund.

This becomes a nightmare for the victim. Once the IRS accepts the tax return and issues the scammer a refund, the victim will not be able to file a tax return. The IRS will reject the valid return and will not issue any tax refunds owed to the victim. The victim now faces what is likely months of remedial action to correct the situation.

Identity Protection PINs

The IRS is aware of this problem. They have an optional program that allows certain people to obtain an Identity Protection Personal Identification Number (PIN). The PIN functions to protect a taxpayer. 

If a taxpayer has an Identity Protection PIN issued with the IRS, the IRS will only accept that taxpayer’s electronic tax return if the tax return provides the Identity Protection PIN. That stops the sort of scams described above. For paper returns, a missing or incorrect PIN will delay the IRS accepting the tax return while the IRS takes additional steps to verify that the tax return came from the taxpayer whose name and Social Security number appear on the tax return. Either way, obtaining a PIN provides a level of protection against tax return identity theft.

Spouses each separately apply for their own PIN and the IRS will issue each spouse a unique PIN. If the spouses file jointly, both PINs are included on the tax return. If you have an Identity Protection PIN and use a paid tax preparer, it is important that your paid tax preparer include the PIN on your tax return. 

Eligibility

You are eligible to apply for an Identity Protection PIN from the IRS if:

Arizona, California, Colorado, Connecticut, Delaware, District of Columbia, Florida, Georgia, Illinois, Maryland, Michigan, Nevada, New Jersey, New Mexico, New York, North Carolina, Pennsylvania, Rhode Island, Texas, and Washington.

The yellow states below are the ones in which all taxpayers may apply for an IRS Identity Protection PIN (hat tip to 270toWin.com).

PLEASE SEE UPDATE FROM JANUARY 13, 2021 ABOVE: NOW ALL AMERICANS CAN POTENTIALLY QUALIFY.

Application

To obtain an IRS Identity Protection PIN, you can start at this website.

You will need to establish an IRS electronic account. The IRS website will guide you through the process and will use some credit history information to verify your identity. Once you have your IRS electronic account, you can easily obtain an IRS Identity Protection PIN. 

Future Years

Your PIN changes every year. At the beginning of the year, the IRS will put your new PIN (for use in filing the prior year’s tax return) in your IRS electronic account and they will mail your PIN to your last address of record. This makes it crucial to file a Form 8822 with the IRS to officially change your address with the IRS anytime you move, so that any PIN related correspondence (including retrievals in the event you lose your PIN) are directed to your correct address. 

The IRS will change your PIN every year, so it is important to ensure you use the correct PIN when filing your tax return. A PIN received in October 2019 will be for 2018 and you will need to use the PIN issued early in 2020 to file your 2019 tax return. 

Conclusion

Taxpayers eligible for the IRS Identity Protection PIN program should strongly consider applying for a PIN. It can help protect you from the serious headache of having your identity stolen and used to file a false tax return in your name. 

Further Reading

Kay Bell wrote a great post about the IRS Identity Protection PIN program here. 

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

The Tax Challenges of ISOs

Incentive stock options (“ISOs”) are a great employee benefit. ISOs are very powerful because they provide the possibility of compensating employees at preferential long term capital gains rates instead of at ordinary income tax rates, and they avoid Social Security and Medicare taxes. ISOs can also help build wealth by allowing employees to purchase employer stock at a discount. However, ISOs can create several tax challenges, and reporting them on your tax return can be confusing.

Incentive Stock Options

Employers grant employees incentive stock options as an incentive to stay with the company. The company grants the employee an option to purchase the stock of the company at a certain price (the “exercise price” or the “strike price”). That price is no less than the company’s current stock price (i.e., the stock price on the grant date, defined below). 

There is a $100,000 annual limit on the fair market value of stock subject to ISO treatment per employee. If an employee leaves the employer’s employment, he or she must exercise or forfeit their ISOs within three months.

Three dates matter when considering ISOs. 

Grant Date: The date the employee is granted the option (i.e., the first date the employee has the option to purchase the stock at the strike price).

Exercise Date: The date the employee exercises the ISO (i.e., the date the employee purchases the stock of the company under the terms of the ISO at the strike price). 

Disposition Date: The date the employee sells the stock acquired by the previous exercise of the ISO.

Tax Treatment

Grant: There is no tax consequence to the employee upon the grant of the ISO.

Exercise: Upon exercise, there is no income tax consequence to the employee. However, the difference between the fair market value of the ISO and its strike price is an adjustment that creates income for alternative minimum tax purposes (the dreaded AMT). Fortunately, the late-2017 tax reform bill increased AMT exemptions (i.e., the amount of income below which the AMT does not apply), thus reducing, but not eliminating, the potential negative impact AMT can have on ISO exercises. 

Further, the AMT issue is removed if the exercise and later stock disposition occur in the same year. As a practical matter, it is often the case that the later stock disposition occurs almost instantaneously after exercise, which takes the AMT issue off the table. 

Dispositions: ISOs have very favorable tax treatment upon disposition if the disposition of the shares satisfies both of the following rules.

  1. The disposition is at least two years from the grant date; and,
  2. The disposition is at least one year from the exercise date.

If both rules are satisfied, the employee has long term capital gain or loss upon the disposition of the shares. Long term capital gains are taxed at preferential rates for federal income tax purposes.

Example: Gary works for Acme Explosives, Inc. Acme grants Gary 10,000 ISOs at an exercise price of $10 per share on January 1, 2018. Gary exercises the ISOs on June 1, 2018 at a time when the fair market value of the stock is $15 per share. On February 1, 2020, Gary sells each share acquired through the ISO exercise at a price of $20 per share. Assume that Gary was not subject to AMT in 2018. 

Because Gary sold the Acme shares at least one year after exercise and at least two years after the ISO grant, Gary’s sale qualifies entirely for long term capital gain treatment (creating a $100,000 capital gain — $200,000 sales proceeds less $100,000 basis) and creates no taxable ordinary income.

Early Dispositions

Often employees will dispose the ISO stock before the time required to get favorable income tax treatment. As a practical matter, employees often exercise the ISO and immediately sell the stock. 

Employees are exposed to the economic performance of their employer through their job and possibly other equity holdings. Thus, they often want to reduce the risk associated with their employer’s performance and dispose of their ISO stock as soon as possible. Most view the tax cost as well worth it considering that (i) the employee immediately pockets (net of tax) the difference between the fair market value of the stock and the strike price, and (ii) the diversification benefits of investing the ISO proceeds into other investments.

If the employee disposes of the ISO stock early (referred to as a “disqualifying disposition”), what result? The difference between the strike price and the fair market value of the stock at exercise becomes ordinary income to the employee reported to the employee as compensation income included in Box 1 of the employee’s Form W-2. The remaining amounts create long or short term capital gain or loss.

Example: Angela works for Acme Anvils, Inc. Acme grants Angela 10,000 ISOs at an exercise price of $10 per share on January 1, 2019. Angela exercises the ISOs on June 1, 2019 at a time when the fair market value of the stock is $15 per share. On December 1, 2019, Angela sells each share acquired through the ISO exercise at a price of $20 per share. 

Because Angela’s December 2019 sale violates both timing tests, Angela’s sale does not qualify for long term capital gain treatment. Thus, Angela has $50,000 of compensation income ($15 fair market value less $10 strike price times 10,000 shares) of ordinary compensation income. The remaining $50,000 of gain is short term capital gain. 

Fortunately, the compensation income is not included in compensation income for purposes of Social Security and Medicare payroll taxes (and, thus, is not included in Boxes 3 and 5 on the Form W-2). Because Angela sold the ISO shares in the same year she exercised the ISOs, there will not be a separate AMT consequence of the ISOs. 

Tax Reporting

Staying with Angela’s example, the $50,000 of ordinary income will be reported as compensation income in Angela’s Form W-2 Box 1, but not in Boxes 3 and 5. Box 14 should indicate “ISO DISQ” and $50,000 as the amount.

Angela should also receive two other tax reporting documents. First, Angela should receive a Form 1099-B. The form should indicate $200,000 of sales proceeds ($20 per share times 10,000 shares) and should indicate a basis of $100,000 (Angela’s historic cost basis, as she paid $10 per share for 10,000 shares). Angela should also receive a Form 3921. This form should indicate the exercise price per share ($10) and the fair market value per share on the date of the exercise ($15).

The IRS will expect to see at least two numbers on Angela’s tax return. First, the compensation income must be reported on Angela’s Form 1040 box 1. Second, the $200,000 stock sale should be reported on Schedule D and on Form 8949. 

This is where it gets interesting. If Angela simply reports $200,000 as gross proceeds and $100,000 as basis on her Schedule D and her Form 8949, she is going to have a very bad tax result. Why? Angela’s W-2 includes $50,000 of the overall $100,000 of income she recognized on the ISO exercise and disposition. If she simply reports a $100,000 gain on her Schedule D/Form 8949, her total reported income will be $150,000, creating $50,000 in over-reported taxable income. 

Thus, Angela must increase the basis she reports on Schedule D and Form 8949 by the $50,000 of ordinary compensation income reported on her Form W-2. Her Schedule D and Form 8949 should report both the $200,000 of gross proceeds and $150,000 of basis in the disposed of Acme shares. 

Estimated Taxes

Even though the gain on a disqualifying disposition of an ISO is taxable as ordinary income in Box 1 of the Form W-2, there is no requirement that the employer withhold any income tax with respect to the gain. Thus, the onus falls to the employee to ensure he or she pays the proper amount of federal and state estimated income tax to avoid penalties. The good news is that there is a safe harbor under which employees can avoid underpayment penalties. 

For federal income tax purposes, there will not be an underpayment of estimated tax penalty if the employee has paid in at least 90 percent of their current year total tax liability and/or 100 percent of their prior year total tax liability. If current year income is $150,000 or more, 100 percent becomes 110 percent. 

Regardless of whether there is a qualifying disposition triggering long term capital gain or a disqualifying disposition triggering ordinary income, the employee should endeavor through a combination of estimated tax payments, additional workplace withholding, and/or additional spousal workplace withholding to ensure that he or she has withheld enough during the year to avoid federal and state underpayment penalties. 

Conclusion

ISOs can be a great wealth building tool. But because of the tax rules and at times confusing tax reporting, they present a challenge. Anyone with ISOs (or with clients that own ISOs) should step back and fully understand the tax ramifications of selling them. It is often advisable to work with a professional advisor as you sell ISOs and manage the tax ramifications of the sale. 

Further Reading

The IRS provides some tax resources on ISOs starting on page 12 of Publication 525.

FI Tax Guy can be your financial advisor! FI Tax Guy can prepare your tax return! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters.

Defending HDHPs

In the financial independence community and beyond, high deductible health plans (“HDHPs”) have received significant criticism. Few downplay the significant tax benefits of their tag-team partner, the health savings account. But some have written that the HSA sweetener is not sufficient to make high deductible health plans desirable. 

Below I offer a different perspective. I write regarding the approach of anyone seeking financial independence, but I believe much of what is discussed below applies regardless of whether you are seeking financial independence. 

One quick caveat: the below assumes that you are relatively healthy when you select your medical insurance, and that you expect that you will most likely remain so. For those with significant, chronic medical conditions, an HDHP is not likely to be a good medical insurance choice.

HDHP Critiques

High deductible health plans have been criticized by both the national media and by financial independence writers. Several studies have found that those covered by HDHPs tend to delay or forego needed medical assistance when compared with the population at large. This study found that those with HDHP insurance tend not to take advantage of free preventive services. Based on these study findings, there is a concern that the use of HDHPs can cause long term harm and worsen medical and health outcomes. 

Financial Independence Mentality

Those actively seeking financial independence (“FIers”) embrace two beliefs. First, they believe they are not constrained by others’ failures. While FIers understand that others’ failures can be indicative of difficulties they themselves might face, FIers believe that with intentional action they can overcome those difficulties.

FI exists because people see what the “average” or “typical” person does (for example, a very low savings rate) and say, “wait a minute, I’m going to do something very different.” FIers acknowledge a societal trend and then pursue a different path with intention. 

Second, FIers prioritize valuable purchases over immediate bottom-line results. Being financially independent (or seeking FI) frees you from the tyranny of any particular financial number when considering necessary expenses.

Health Insurance and Behavior

Your medical insurance should not determine whether you seek medical care. Only your current condition should determine whether you seek medical care. Assuming, only for the sake of argument, that the studies’ findings are correct, should those findings deter someone pursuing FI from using an HDHP as their medical insurance? I argue that they should not, for several reasons.

First, the studies probably did not include you. Why would you have a limiting belief about your own future behavior based on studies of other people? Even if you were in one of the studies and delayed or forwent necessary medical treatment, is it not possible that you could change your behavior?

Second, why not simply accept that cost will deter some people from obtaining needed medical assistance, but resolve that you will not act in such a shortsighted fashion. Many FIers seek to obtain financial assets of $1 million, $1.5 million, $2 million or more to fund the rest of their lives. Neither an unanticipated $300 medical expense nor an unanticipated $5,000 medical expense will derail your plans to achieve financial independence. 

If you commit to FI, you are committing to acting very differently than most people when it comes to spending and saving. Why then would you believe you will act like the average study subject when it comes to obtaining medical treatment for a medical need? 

Third, there is nothing preventing those with HDHPs from taking advantage of free preventive services. Many workers do not take advantage of the employer match to their 401(k). That outcome does not make a 401(k) a bad retirement plan. Rather, it illustrates that in many areas of life, people should be more intentional about taking advantage of what is offered to them. Suboptimal human behavior does not make 401(k)s and HDHPs bad, and others’ mistakes should not limit your insurance choices.

Finally, financial independence exists in part to make personal finances revolve around what needs to happen, and not to have what needs to happen revolve around personal finances. FIers ought to make medical care decisions based on their health, and not based on avoiding a medical bill that is ultimately minor in the grand scheme of things.

The Role of Insurance

What the studies appear to illustrate is a widespread misunderstanding of medical insurance. Insurance does not exist to determine whether you obtain medical assistance. Insurance exists to prevent financial ruin. 

Might an unexpected medical situation be expensive if you have an HDHP? Yes, absolutely. But should it be ruinous? It should not be. Your annual out-of-pocket maximum for medical expenses will be high: imagine in your mind’s eye that it is $10,000. In the event of a medical calamity, you will pay $10,000 in expenses annually. Then your finances are protected. 

Does an unexpected $10,000 expense hurt? Absolutely. But if your FI plan was to build $1.5 million in assets to fund the rest of your life, is not possible that you instead build $1.51 million in assets? Why would you put off necessary medical care to avoid a very slight increase in the assets you will need to build up to become financially independent? Are you much worse off in this situation than someone with zero-deductible medical insurance? Their “FI number” is $1.5 million; yours is $1.51 million. 

You might argue “but might my insurance company deny my claim?” That is a valid concern with insurance. But it is a concern whether you have a gold-plated, zero-deductible insurance plan, an HDHP, or any other type of medical insurance. Thus, the possibility that you might have to fight with your insurance company to get an expense covered is not a reason to avoid HDHPs. 

Risk/Reward Trade-off

When you use an HDHP, you assume additional risk. Put simply, you risk paying annual medical expenses up to the higher deductible. Two things should be noted about that risk. First, it is capped, as described above. A capped risk is the sort of risk that those building up assets should usually be willing to take on, as long as there is sufficient benefit to doing so.

Second, you are compensated for taking that risk. While your future annual medical expenses are uncertain, the benefits of using an HDHP are largely certain and immediate. Namely, they are:

  1. Lower insurance premiums
  2. Income and payroll tax savings (if the HSA is properly funded)
  3. Employer contributions to the HSA on your behalf
  4. Tax-deferred or (if withdrawn correctly) tax-free growth of the investments in the HSA

For taking on the risk of medical expenses up to the annual out-of-pocket maximum, there are two or three measurable, guaranteed benefits every pay period for using the HSA/HDHP combination. And while the fourth benefit can vary greatly (depending on the length of tax-free growth, future tax rates, etc.), it too is a significant benefit.

When evaluating an insurance plan, the risk/reward trade-offs and the costs are what should be evaluated. When comparing an HDHP with a lower deductible insurance plan, you must weigh the assumption of a speculative, capped risk in exchange for the benefits listed above. Based on the protection against very high annual medical expenses and the four benefits listed above, an HDHP appears to be, in many cases, a good risk/reward trade-off for those without expensive, chronic medical conditions. 

Conclusion 

The studies have not found that an HDHP is suboptimal from a risk trade-off perspective. Rather, they have found suboptimal consumer behavior. That’s where FI comes back in. FI is all about turning around suboptimal saving, investing, and consumer behavior and re-ordering financial priorities. Why shouldn’t obtaining necessary medical care be among the highest financial priorities? Why can’t you examine your own healthcare purchasing behavior and improve it? 

There can be good reasons not to select an HDHP based upon your particular circumstances. Perhaps you have a chronic condition, you do not like the HDHP’s particular insurance carrier, and/or you do not believe the risk trade-off benefits are sufficient. But don’t eschew an HDHP because of a limiting belief about something under your own control: your behavior as a patient and medical consumer. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Health Savings Accounts

Health savings accounts (“HSAs”) are a tremendous wealth building tool. For healthy individuals and families, a health savings account paired with a high deductible health plan (“HDHP”) can be a great way to manage medical costs and grow tax advantaged wealth. 

HSA Basics

A health savings account is a tax advantaged account. Contributions to an HSA are tax deductible. The interest, dividends, capital gains, and other income generated by assets in an HSA is not currently taxable (the same as with a 401(k) or IRA). If withdrawn for qualified medical expenses (or to reimburse the owner for the payment of qualified medical expenses), withdrawals from an HSA are not taxable. 

The HSA combines the best of a traditional retirement account (deductible contributions) and the best of Roth retirement accounts (tax-free withdrawals) if done properly. 

The annual HSA contribution limits (including both employer and employee/individual contributions) are $3,650 for an individual HDHP and $7,300 for a family HDHP in 2022. Those aged 55 or older can make annual catch-up contributions of an additional $1,000 to their HSA. 

HSA Eligibility

Who is eligible to contribute to an HSA? Only those currently covered by a high deductible health plan. As a general matter, a high deductible health plan is medical insurance with an annual deductible of at least $1,400 (for individuals) or $2,800 (for families) (using 2021 numbers). The insurance plan document should specifically state that the plan qualifies as a high deductible health plan. You must be covered on the first day of the month in order to contribute to a HSA in that month.

Once you cease to be covered by a HDHP, you keep your HSA and can use the money in it. The only thing you lose is the ability to make further contributions to the HSA.

HDHPs may not be a good insurance plan if you have certain chronic medical conditions or otherwise anticipate having high medical expenses. But if you are relatively healthy, HDHPs often make sense, particularly if you are young. 

There are some other eligibility requirements. Those also covered by other medical insurance plans, those enrolled in Medicare, and those who can be claimed as a dependent on someone else’s tax return are not eligible to contribute to a HSA.

Benefits of an HSA

Tastes Great and Less Filling

If done right, an HSA is a super-charged tax advantaged account. You get a deduction on the front end (when the money is contributed to the HSA), tax free growth, and no taxation if the money is used for qualified medical expenses or to reimburse the owner for qualified medical expenses. 

There’s no need to debate traditional versus Roth with an HSA. If done right, you get both!

HSA Payroll Tax Benefit

As a tax planner, this is one of my favorite benefits. There are many ways to legally reduce income taxes. Reducing payroll taxes, on the other hand, is more difficult. 

If you fund your HSA through payroll withholding, amounts contributed to the HSA are excluded from your salary for purposes of determining your Social Security and Medicare taxes. This results in saving on payroll taxes. HSA contributions enjoy this benefit while 401(k) elective deferrals do not.

Note that to qualify for the HSA payroll tax break, you must contribute to your HSA through payroll withholding. If, instead, you contribute through a direct personal contribution to your HSA, you do not get to deduct the contribution from your Social Security and Medicare taxable income, though you still get a federal income tax deduction for such contributions. 

Employer Contributions

Many employers offer a contribution to your HSA account. Often these employer contributions are a flat amount, such as $650 or $700 annually. This amounts to essentially free money given to you in a tax advantaged manner. 

Lower Insurance Costs

A great benefit of the combination of HDHPs and HSAs is lower medical insurance premium payments. By insuring with an HDHP, you usually save significant amounts on medical insurance. 

The healthier you are and the wealthier you are, the less financial protection you need against unanticipated medical expenses. Thus, HDHPs are often a good option for those fortunate enough to be relatively healthy and/or wealthy. 

Higher deductibles reduce the premium. The trade-off is that you self-fund more of your medical expenses. If those medical expenses are modest, the combination of saving on insurance premiums and the tax benefits can more than make up for the (potentially) higher medical expenses. 

HSA Reimbursements

Take note of when you first establish your HSA. Qualifed medical expenses incurred on that date or later can be reimbursed from your HSA.

Why is this important? Because if you track your qualified medical expenses, you can build up years of expenses that you can reimburse yourself, tax-free, from your HSA. There is no time limit to pay yourself a tax-free reimbursement from your HSA. Here is an example:

Keith established an HSA in 2011, when he was 30 years old. In 2015, he had a medical procedure and his total qualified medical expenses were $4,000. In 2018, Keith had $500 worth of qualified medical expenses for two medical appointments. In 2019, Keith had $3,500 in qualified medical expenses for a procedure and various doctors’ appointments. 

Assuming Keith had sufficient funds in taxable accounts when he incurred these expenses, Keith should (a) use those taxable funds to pay his medical expenses, (b) track his qualified medical expenses, and (c) after the money has had many years of tax-free growth, Keith should reimburse himself from his HSA for some or all of these $8,000 worth of qualified medical expenses. 

Unless you are financially strapped or in a dire medical situation, you should strive to use taxable funds to pay current medical expenses and allow the funds in your HSA to enjoy years, possibly decades, of tax-free growth. With no time limit on HSA reimbursements, you can access the funds later in life tax-free.

Note, however, that in the relatively rare cases where a taxpayer deducts medical expenses on their income tax return, expenses paid with HSA money cannot be deducted. In addition, if you have previously deducted medical expenses, those expenses are not “qualified medical expenses” that can be reimbursed tax-free from an HSA. Deducing medical expenses is rare because you can only deduct medical expenses if (i) you itemize your deductions and (ii) to the extent your medical expenses exceed 7.5 percent of your adjusted gross income (“AGI”).

No RMDs

Every tax advantaged retirement account (other than the Roth IRA) is subject to required minimum distributions (“RMDs”) during the account owner’s lifetime. HSAs, fortunately, are not subject to RMDs. They provide incredible flexibility for your financial future, particularly when you carefully track your reimbursable qualified medical expenses for many years. 

Qualified Medical Expenses

Qualified medical expenses are generally those expenses that qualify for the medical expense deduction. While this itself could be its own blog post, you can look to IRS Publication 502, which details which expenses qualify. 

Some items that you might not immediately think of, but are qualified medical expenses, are COBRA insurance premiums and Medicare Part B, Part D, and Medicare Advantage premiums. So if you ever pay COBRA premiums, it is great to pay them out of taxable accounts and keep a tally of the payments you made. Years later you can reimburse yourself for those premiums tax-free from your HSA (assuming you established the HSA prior to paying the COBRA premiums and you did not claim the COBRA premiums as an itemized deduction). 

Taxation of Non-Medical Withdrawals

If you are under age 65, withdrawals from HSAs that are not used for qualified medical expenses are subject to income tax and subject to an early withdrawal penalty of 20 percent. 

If you are under age 65, you can avoid these harsh tax results for an HSA withdrawal if you can find prior qualified medical expenses you can reimburse yourself for, and apply the withdrawal against those prior expenses. If such expenses do not exist, you can roll the money back into the HSA within 60 days (a 60-day rollover). Note you are limited to only one 60-day rollover during any 12 month period.

If you are age 65 or older, you are no longer subject to the 20 percent early withdrawal penalty. Withdrawals that are not for qualified medical expenses (or reimbursements thereof) are subject to income tax (in the same way a traditional IRA withdrawal would be). 

At age 65, an HSA remains an HSA and also becomes an optional IRA (in effect) without RMDs. This, combined with the ability to use HSA funds to pay Medicare Part B, Part D, and Medicare Advantage premiums tax-free, make an HSA a great account to own if you are age 65 or older. 

The Biggest HSA Mistake

Think twice before taking money out of an HSA!

An HSA and the investments in it can be analogized to an oven and a turkey. The HSA is like the oven. The investments are like the turkey. Putting the turkey in the oven is great. But it needs sufficient time to roast. If you take the turkey out of the oven too soon, you spoil it! The investments in your HSA are similar. They need time to bake tax-free in the HSA. If you take them out too soon, you spoil it!

Only the elderly, the financially strapped, and those facing medical emergencies and crises should withdraw HSA funds. Everyone else should keep money in an HSA to grow tax-free. If you are not in one of three listed categories, you should think long and hard before paying medical expenses with HSA money. 

Why waste the tremendous tax benefits of an HSA for minor, non-emergency medical expenses? Doing so is the biggest HSA mistake. Pay those expenses out of pocket, track them, and years later reimburse yourself tax-free from your HSA after the funds have grown tax-free for decades!

The only potential way to correct this mistake is to do a 60-day rollover of the withdrawn amounts back into an HSA. Note that rollovers are limited to one per any 12 month period. Other than the 60-day rollover, the mistake is not correctable. 

The Second Biggest HSA Mistake

The second biggest HSA mistake is not investing a significant percentage of your HSA funds in equities and/or bonds. According to this report, only four percent of HSAs had balances invested in something other than cash as of the end of 2017. Not good!

While I never provide investment advice on the blog, I do discuss the tax location of assets, in a general sense (not as applied to any particular investor). Cash is not a great asset to hold in an HSA. With today’s low interest rates, cash generates little in interest income. HSAs offer tax-free interest, dividends, capital gains, and growth!  That makes them great for high growth, high income assets. Why waste that incredibly favorable tax treatment on very low-yielding cash?

I call this the second biggest mistake (not the first) because unlike the first mistake, this mistake is easily correctable.

Of course, investors must evaluate their HSA investment options and their own individual circumstances to determine if the other investments are preferable to cash based on their particular circumstances.

State Treatment of HSAs

Two states do not recognize HSAs: California and New Jersey. For purposes of these two states, HSAs are simply taxable accounts. On California and New Jersey state income tax returns (a) there is no deduction/exclusion for HSA contributions, (b) interest, dividends, and capital gain distributions generated by HSA assets are taxable, (c) sales of assets in a HSA generate taxable capital gains and losses, and (d) nonqualifying withdrawals of money from an HSA have no tax consequence.

Tennessee and New Hampshire do not impose a conventional income tax. But they do tax residents on interest and dividends above certain levels. Interest and dividends generated by HSAs are included in the interest and dividends subject to those taxes.

HSAs and Death

This is the good news/bad news section of the article. 

First, the good news: HSAs are great assets to leave (through a beneficiary designation form) to a spouse or to a charity. If you leave your HSA to your spouse, he or she inherits it as an HSA and can use it (and benefit from it) just as you did. Charities also make for great HSA beneficiaries. They can use the money in the account and pay no tax on it. You will need to work with your financial institution to ensure the beneficiary designation form properly captures the charity as the intended beneficiary. 

The bad news: HSAs are terrible assets to leave to anyone else. If you leave an HSA to a non-spouse/non-charity, the recipient includes the entire balance of the HSA in their taxable income in the year of your death. 

Conclusion

With a little planning, an HSA can be a great asset to own, and can provide tremendous tax-free benefits. Generally speaking, time is a great asset if you own an HSA. Let your HSA bake tax-free for many years and you will be happy to receive tax-free money later in life to pay for medical expenses or as a reimbursement for many years of previous medical expenses.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

SEP IRA Versus Solo 401(k)

If you qualify for both a SEP IRA and a Solo 401(k), is there a clear winner? In the past, it was often the case that the tax benefits of a SEP IRA and a Solo 401(k) were similar, particularly if you also had access to a 401(k) plan at a full-time employer. Today the landscape has changed, and in most cases, there’s a clear winner.

This post discusses whether a SEP IRA or a Solo 401(k) is better in situations where the self-employed person qualifies for both plans.

Note that both plans have eligibility requirements. For example, under the tax rules, if you employ anyone other than your spouse for 1,000 hours or more during the year you are ineligible for a Solo 401(k). There are additional tax rules and separate (and additional) plan rules to consider to determine if you are eligible for a particular SEP IRA and/or Solo 401(k).

The Basics

Both the SEP IRA and the Solo 401(k) are self-employed retirement plans. They can be established by legal entities (in this context, often S corporations) or they can be established by individuals that have self-employed income. That self-employment income generally must come through a sole proprietorship or through a limited liability company (“LLC”) that is disregarded for tax purposes and reported on a Schedule C filed with the individual’s tax return. 

SEP IRAs

A SEP IRA allows only “employer” contributions. For this purpose, your own sole proprietorship or disregarded LLC can be your employer. 

Generally, the employer can make annual contributions of up to 25 percent of eligible W-2 compensation (from a corporation) or 20 percent of an individual’s self-employment income, limited to $66,000 of contributions in 2023.

Today, many financial institutions (including Fidelity, Schwab, and Vanguard) offer low-cost SEP IRA options.  

A SEP IRA can be established for a tax year by the deadline for filing that tax year’s tax return, including extensions. 

The administrative compliance burden of a SEP IRA is generally very manageable. 

History of the SEP IRA vs. the Solo 401(k)

Watch me discuss the history of both the SEP IRA and the Solo 401(k).

Solo 401(k)s

A Solo 401(k) (sometimes referred to as an “Individual 401(k)”) is a 401(k) plan established by a self-employed individual for their own benefit. 

The main advantage of the Solo 401(k) is that it allows annual contributions by the self-employed individual in his/her role as the “employee” and annual contributions by the self-employed individual (or S corporation) in his/her role as “employer.” 

Employee contributions are limited to the lesser of earned income or $22,500 ($30,000 if 50 or older) in 2023. Employer contributions are limited to up to 25 percent of eligible W-2 compensation (from a corporation) or 20 percent of an individual’s self-employment income, limited to $66,000 of contributions in 2023. Total employee and employer contributions are limited to $66,000 ($73,500 if age 50 or above) in 2022. 

Today, many financial institutions (including Fidelity, Schwab, and Vanguard) offer low-cost Solo 401(k) options.

The administrative compliance burden of a Solo 401(k) is generally very manageable, but note that once there are more than $250,000 in the plan and/or the plan is closed, a Form 5500-EZ must be filed.

The Clear Winner

At this point, you might be saying, “Great, both the SEP IRA and Solo 401(k) are attractive. Is there really a big difference between them? Should I care too much about which plan I establish?”

The answer is that in most cases, the Solo 401(k) is the much better option for a self-employed person. If you are considering a SEP IRA over a Solo 401(k) in a situation where you qualify for both, you ought to think twice about that decision.

Here are the main reasons why the Solo 401(k) is much better than the SEP IRA in most cases.

Employee Contributions

The Solo 401(k) allows employee contributions. If your self-employment income is relatively modest, this greatly increases the amount you could contribute. For example, if Jane, under age 50, has a side-hustle that earns her $10,000 in 2023 after the deduction for one-half of self-employment taxes is accounted for, her maximum Solo 401(k) contribution is $10,000, while her maximum SEP IRA contribution is only $2,000 (20% of $10,000).

Note that this assumes that Jane has contributed $12,500 or less to a workplace 401(k) or similar retirement plan. Using the 2023 limitations, $22,500 is the maximum total employee deferrals Jane can make to her 401(k) and similar plans, so Jane’s other employer retirement accounts should also be considered.

Section 199A and 80% Deductions

I have previously written about the new Section 199A qualified business income (“QBI”) deduction and its impact on self-employed retirement plans. Traditional contributions to both Solo 401(k) plans and SEP IRAs create, for many taxpayers, deductions that are only “80% deductions.” Here is an example.

After self-employment taxes, Joe, a single taxpayer, earns $120,000 from his sole-proprietorship. Joe makes a 10 percent employer contribution ($12,000) to either his Solo 401(k) or SEP IRA. In the 24 percent marginal tax bracket, he expects to save $2,880 ($12,000 times 24%) on his federal income taxes. He is surprised to learn that he only saved $2,304 on his federal income taxes. 

How is that possible? While Joe is correct that he receives a $12,000 retirement plan contribution tax deduction, he failed to consider that he lost $2,400 of his QBI deduction. A traditional Solo 401(k) contribution and a SEP IRA contribution is an 80% deduction. In Joe’s case, he received a net federal income tax deduction of only $9,600 (80 percent of $12,000). 

Why then would Joe prefer a Solo 401(k) to a SEP IRA? Because the Solo 401(k) gives him a planning option that avoid the 80% deduction issue. Instead of making traditional contributions to a Solo 401(k), Joe can make Roth employee contributions to a Solo 401(k).

Note further that Joe could possibly implement Mega Backdoor Roth IRA planning by making after-tax contributions to his Solo 401(k). Many Solo 401(k) plans do not offer this option, but some do.

The SEP IRA does not offer these options. 

Not all financial institutions offer the Roth Solo 401(k) and the after-tax Solo 401(k) contribution options. It is important to understand the features of any particular Solo 401(k) before you adopt it as your plan. 

For upper income taxpayers, the 80% deduction phenomenon may not be an issue, considering that the ability to claim the QBI deduction is reduced or eliminated above certain income thresholds. These taxpayers need not prefer the Solo 401(k) to a SEP IRA for QBI deduction reasons, but may prefer to have the increased planning ability, such as the ability to make Roth and/or after tax contributions to the Solo 401(k) that a SEP IRA does not offer. They may also prefer the Solo 401(k) for the reasons discussed below.

Backdoor Roth IRA Planning

The Backdoor Roth IRA is a great planning tool. But the Pro-Rata Rule can cause significant snags. For example, if you execute the two independent steps of a $6,500 Backdoor Roth IRA in a year when you have a separate significant traditional IRA, SEP IRA, or SIMPLE IRA at year-end, you will cause most of the Backdoor Roth IRA to be taxable. 

The SEP IRA is a significant roadblock to the ability to execute an efficient Backdoor Roth IRA. A Solo 401(k) does not cause this problem with the Backdoor Roth IRA. For this reason alone many will want to choose a Solo 401(k) instead of a SEP IRA, even if they plan on making traditional deductible contributions to the plan. 

Catch Up Contributions

If you are age 50 or older, you can make up to $7,500 (in 2022) in catch up employee contributions to a Solo 401(k).

This option does not exist for a SEP IRA. Thus, for high earning self-employed persons age 50 or older, a Solo 401(k) has an additional advantage over the SEP IRA.

Solo 401(k) Book

This post was originally published in 2019. In 2022 I published Solo 401(k): The Solopreneur’s Retirement Account, a book that goes into much more depth about Solo 401(k)s.

Conclusion

If you qualify for both, generally the Solo 401(k) is better than a SEP IRA. If you are going with a SEP IRA over a Solo 401(k), you should understand the reasons for doing so. Finally, self-employed retirement plans is an area that taxpayers usually benefit from receiving personal advice from a qualified tax advisor. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Sean on the ChooseFI Podcast

I’m honored to be the featured guest on this week’s ChooseFI podcast. Brad, Jonathan, and I discussed careers in accounting, my professional journey, and some tax planning. I’m glad to say that I’ll be back on the podcast to discuss tax issues and planning in the future.

I hope you enjoy this episode. It is available at this website, YouTube, and wherever you listen to podcasts. https://www.choosefi.com/how-to-fund-your-childs-roth-ira/

Understanding Your 401(k)

As an employee, your employer’s 401(k) plan can be your most important wealth building tool. Understanding how it functions will help you build your wealth in a tax efficient manner.

The Plan

A 401(k) plan is established by an employer. The employer provides the account, the account administration, and the investment choices. Usually, the investment options include a menu of stock and bond mutual funds and/or similar investments. In some plans, employer stock is one of the investment choices.

While the employer administers the plan, most of the assets in the plan (see Vesting below) belong the employees in individual accounts. Therefore, the employees, not the employer, enjoy the benefits and burdens of the economic appreciation and/or depreciation of the investments.

Creditor Protection

401(k) plans are subject to a host of rules, most of which (from a practical perspective) are the concern of the employer, not the employee. One important benefit of the rules for employees is that under ERISA, assets in a 401(k) plan are generally protected from creditors. During your lifetime only two creditors can access assets in your 401(k): the IRS and an ex-spouse.

Vesting

Contributions to a 401(k) made by the employee (referred to as “employee deferrals” and “after-tax contributions” — see numbers 1 and 3 below) are always immediately “100% vested.” This means that regardless of whether the employee leaves the employment of the employer tomorrow, he or she owns the money he or she contributed to the 401(k) and any related growth.

However, contributions to a 401(k) account made by the employer may be subject to a vesting schedule. Simply put, vesting means amounts become the property of the employee after the employee has been employed by the employer for a certain period of time.

Some plans use a gradual vesting schedule. The least generous of these is as follows:

Years of ServiceVesting Percentage
220%
340%
460%
580%
6100%

More generous (i.e., quicker) vesting is permissible.

Some plans use a “cliff” vesting schedule. This means that employer contributions go from 0% vested to 100% vested when the employee has been employed for a certain period. The longest permissible period is 3 years.

The growth associated with employer contributions is also subject to vesting.

Vesting incentivizes staying with the same employer for a sufficient period of time to capture all of the employer contributions to a 401(k) plan. It can also incentivize returning to a former employer if you have worked a number of vested years of service for them.

Some plans provide for 100% immediate vesting for employer contributions as well as employee contributions.

Contributions

There are five types of contributions to 401(k) plans, listed below in order of their prevalence (employee deferrals being the most prevalent).

1. Employee Deferrals

Employees can contribute, through payroll withholding, a portion of their salary to a 401(k) plan. All 401(k) plans offer “traditional” contributions, meaning employees can contribute amounts to the 401(k) plan and exclude those amounts from their taxable income for the year. Some plans, but certainly not all plans, also offer “Roth” contributions, which are not excludible from taxable income, but, if properly withdrawn, can be tax free in the future when withdrawn.

Employee deferrals are the only type of contribution to a 401(k) plan that can be done as a “Roth” contribution. All other contributions are “traditional” contributions.

Read here for more on the desirability of Roth contributions compared to traditional contributions.

Neither traditional nor Roth contributions reduce the amount of income subject to payroll (i.e., Social Security and Medicare) taxes.

2. Matching Contributions

Matching contributions are one of the most powerful ways employees can build wealth. Previously, I have written that if you participate in a 401(k) plan with an employer match, you must make it your top wealth building priority to contribute at least enough to your 401(k) to secure all of the employer match.

How does it work? Different employers have varying matching programs. There are two components: 1) the percentage of salary that is matched, and 2) the percentage of the match.

Here is an illustrative example:

Example 1: Elaine Benes works for Pendant Publishing. She is under 50 years old and earns $100,000 in annual W-2 wages. Pendant Publishing matches 100 percent of employee contributions up to 3 percent of salary, and matches 50 percent of employee contributions for the next 2 percent of salary. Based on this matching program, Elaine would be a fool not contribute at least 5 percent of her salary to Pendant Publishing’s 401(k) plan. Doing so will earn her $4,000 of matching contributions from Pendant Publishing on her $5,000 of employee contributions.

Employers vary in terms of when they match contributions. Some employers match employee contributions only once a year (usually at or after year-end). Other employers match employee contributions each pay period. If you work for an employer that does so, you need to be careful not to max-out your 401(k) early in the year, as each pay period requires an employee 401(k) contribution in order to obtain the match. Here is an example:

Example 2: The facts are the same as Example 1. In addition, Pendant Publishing’s matches 401(k) contributions every pay period, and has 24 pay periods per year. Elaine believes it is a good idea to accelerate her 401(k) contributions, and thus contributes $3,750.00 of her salary for each of the first 6 pay periods of the year ($22,500 total) and makes no contributions the rest of the year. For those 6 pay periods she receives an employee match of $166.67 each pay period ($100,000 divided by 24 times 4 percent) for a total annual match of $1,000. By doing this, Elaine misses out on $3,000 of her potential employer 401(k) match, because for the next 18 pay periods, she contributes nothing to her 401(k).

Some 401(k) plans adjust for this and would fully match Elaine’s contribution (in her case, by adding $3,000 to her 401(k) plan), but many do not. In Elaine’s case, she should have stretched out her contribution such that she contributed at least 5 percent of each pay period’s paycheck to her 401(k).

Note that employers are not required to provide a matching program. There are some employer 401(k) plans that provide no match at all.

Tax Treatment: Employer match contributions are traditional contributions. They are not subject to income tax when added to your 401(k), but they will be in the future when withdrawn (as will the growth on matching contributions). Matching contributions are not subject to payroll taxes.

3. After-Tax Contributions

Some 401(k) plans allow for employees to make so-called after-tax contributions to their 401(k) through payroll withholding. These contributions are not excluded from the employee’s taxable income, but do create basis in the 401(k) account. After-tax contributions are what make Mega Backdoor Roth IRA planning possible. Unless one is engaging in Mega Backdoor Roth IRA planning, in most cases after-tax contributions are not advisable.

Tax Treatment: After-tax contributions do not reduce the employee’s taxable income (for both income tax and payroll tax purposes). In the future after-tax contributions are taxable to the employee as withdrawn, but the employee can use the created basis to reduce the income inclusion. Depending on how the 401(k) account is disbursed, that basis recovery may be subject to the Pro-Rata Rule.

4. Profit-Sharing Contributions

Some 401(k) programs have a profit-sharing program, whereby the employer contributes additional amounts to each employee’s 401(k) account based on a formula.

Tax Treatment: Profit-sharing contributions are traditional contributions and are treated in the same manner as matching contributions, including being exempt from payroll tax.

5. Forfeitures

Because of vesting, employees forfeit unvested amounts in their 401(k)s when they leave the employer’s employment prior to fully vesting in the 401(k). When that happens, the unvested amounts must be accounted for. In some plans, the unvested amounts are used to offset plan administrative costs. In other plans, forfeited amounts are added to the remaining participants’ accounts.

Tax Treatment: Forfeitures are traditional contributions and are treated in the same manner as matching contributions, including being exempt from payroll tax.

Contribution Limits

Contribution limits get a bit complicated because there are two distinct 401(k) plan contribution limits, not one. Numerical limits are updated annually by the IRS to account for inflation. The numbers provided below are the numbers for 2023.

Employee Deferrals

There is an annual employee deferral limitation. For 2023, that limit is the lesser of $22,500 or total compensation (if under age 50) and the lesser of $30,000 or total compensation (if 50 or older). The limit applies to Roth employee contributions, traditional employee contributions, or any combination thereof.

This limit is per person, not per employer. Thus, those with side hustlers must coordinate employee deferrals to their large employer 401(k) plan with employee deferrals to their Solo 401(k). I discuss this topic in detail in my book, Solo 401(k): The Solopreneur’s Retirement Account.

All Additions

There is a second, less understood limitation on 401(k) contribution. The annual limit for all additions to 401(k) and other employer retirement accounts is the lesser of $66,000 or total compensation (if under age 50) and the lesser of $73,500 or total compensation (if 50 or older).

The all additions limit applies to the sum of numbers 1 through 5 above (employee deferrals through forfeitures) plus a sixth amount. The sixth amount is the amount which is contributed by your employer to another qualified retirement plan account on your behalf.

Some employers offer additional qualified retirement plans. These plans often provide for a contribution to an account by the employer based on a stated percentage of compensation. Employers use various names for these plans. Contributions may be subject to vesting and are traditional contributions that are not subject to payroll tax.

The all additions limit applies per employer, not per employee as the employee deferrals limit does.

Watch me discuss the all additions limit on YouTube.

Auto Enrollment

Many employers now auto-enroll new employees in a 401(k) plan. This has two components: contribution level and investment choice. In most cases, new employees should not simply settle for auto-enrollment. When you start a job, you should review your new 401(k) plan and make informed decisions regarding contribution level and investment choice.

Contribution Level

Auto-enrollment will set a contribution level. Not all employers set the contribution level at a level that maximizes employer matching. Even if the automatic contribution level is set at a level that maximizes the employer match, that level might not be the appropriate level for any particular person.

Investment Selection

Plans typically have a default investment plan for new 401(k) participants. It is best to review your investment options when you start a new job and select an appropriate investment allocation for your circumstances.

Withdrawals from Traditional 401(k)s

When a taxpayer is 59 ½ years old or older, they can withdraw amounts in a traditional 401(k) penalty free. Withdrawals are included in taxable income as ordinary income. Beginning at age 72, taxpayers must take out a required minimum distribution (“RMD”) for each year. The RMD is computed based on IRS tables.

If a taxpayer withdraws money from a 401(k) prior to age 59 ½, the withdrawal is not only taxable, it is subject to a 10 percent early withdrawal penalty, unless a penalty exception applies.

Taxpayers may transfer amounts in a 401(k) to another 401(k) to an IRA. Amounts in traditional 401(k)s and IRAs can be converted to Roth accounts. Such conversions create taxable income, but are not subject to the early withdrawal penalty.

Conclusion

Your workplace 401(k) plan is a vitally important wealth building tool. It is important to be an informed user of your 401(k) in order to build tax advantaged wealth.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Excess Contributions to an IRA

There are limits to how much can be contributed to traditional IRAs and Roth IRAs. This post describes how excess contributions happen and how to resolve them.

Three introductory notes. First, if you find that you have made an excess contribution, you may be well advised to seek professional advice. Second, please don’t panic, but make sure to act swiftly. Excess contributions are resolvable but do not benefit from delays. Third, you should not plan to make an excess contribution for a variety of reasons.

Traditional IRAs

There are (generally speaking) three situations that generate an excess contribution to a traditional IRA. They are:

  • Contributions are made for a year the taxpayer (and their spouse) does not have earned income.
  • Contributions are made in excess of the annual contribution limits.
  • Rolling into an IRA an amount that did not qualify to be rolled in.

This last category is not immediately obvious, but it does occasionally occur. For example, a taxpayer might inherit a taxable account and incorrectly roll it into an inherited IRA. Or a taxpayer might incorrectly roll an IRA they inherited into their own IRA. Or a taxpayer might attempt a 60-day rollover of amounts previously in an IRA and roll the money into an IRA after the 60-day deadline. Note that in some cases, this last mistake can be resolved by obtaining a private letter ruling from the IRS (doing so is beyond the scope of this post).

For 2019 and prior taxable years, there is an additional category: contributions to a traditional IRA when the taxpayer was 70 1/2 or older. The SECURE Act eliminates the prohibition on those 70 1/2 and older contributing to a traditional IRA.

Resolutions

Recharacterization

Prior to the 2020 tax year, if you qualified to make a contribution to a Roth IRA, but not to a traditional IRA, you could direct your financial institution to recharacterize the contribution to a Roth IRA. This scenario only applied in situations where the taxpayer was over age 70 ½ when the contribution was made to the traditional IRA.

Now there is no scenario where this would be relevant. Anyone not qualifying to make a contribution to a traditional IRA would also not qualify to make a contribution to a Roth IRA.

However, recharacterizations of contributions from traditional IRAs to Roth IRAs can make sense for some taxpayers for tax planning reasons, and are allowable if done properly.

To recharacterize, you must contact the financial institution and direct them to move the contribution and its earnings to a Roth IRA. This must be disclosed in a white paper statement attached to your federal income tax return. The recharacterization deadline is the extended due date of the tax return (generally October 15th).

Withdrawal

A second way to correct an excess contribution to a traditional IRA is to take a “corrective distribution” of the excess contribution and its earnings from the IRA. You will need to inform your financial institution of the excess contribution and request a corrective distribution of the excess contribution and the earnings attributable to the excess contribution. If the excess contribution is withdrawn prior to the extended filing deadline, the withdrawal of the contribution itself is generally not included in taxable income.

As observed in IRS Publication 590-A, page 34, in most cases the financial institution will compute the earnings attributable to the excess contribution. The earnings will be included in taxable income for the actual year the excess contribution was made. For example, if a 2023 IRA contribution is made in January 2024, and the taxpayer later takes a corrective distribution of that contribution and its earnings, the earnings will be includible in taxable income in 2024. In those cases where the taxpayer must compute the earnings, IRS Publication 590-A Worksheet 1-3 is a resource for figuring the earnings or loss.

See Example 1 in this article for insights on the reporting timing of earnings attributable to corrective distributions.

Up until the passage of SECURE 2.0, the earnings were also subject to the ten percent early withdrawal penalty (unless an exception otherwise applied). However, SECURE 2.0 Section 333 repealed the early withdrawal penalty with respect to withdrawals of earnings occurring pursuant to a corrective distribution. Note further that as of March 1, 2024 there is now some doubt as to the on going validity of SECURE 2.0.

If the corrective distribution occurs after the taxpayer files their tax return for the relevant taxable year, but before the extended filing deadline for the year (generally October 15th), the taxpayer must file an amended return which reports the corrective distribution.

A quick note on corrective distributions (as applied to both traditional IRAs and Roth IRAs): they can be done if the taxpayer has changed their mind. Natalie Choate makes this point in her excellent treatise Life and Death Planning for Retirement Benefits (8th ed. 2019, see page 132). Corrective distributions are not limited to simply those times when the taxpayer has made a contribution in excess of the allowed limits.

Apply the Contribution to a Later Year

You can keep an excess contribution in a traditional IRA and apply it to a later year, if you are eligible to make a traditional IRA contribution in that later year. This method does not avoid the six percent penalty discussed below for the year of the contribution, but it allows the taxpayer to avoid taking a distribution of the excess contribution and stops additional impositions of the six percent excess contribution penalty. Generally, this method is only effective if the amount of the excess contribution is relatively modest, since a large excess contribution cannot be soaked up by only one year’s annual IRA contribution limit.

Penalties

If you do not resolve the excess contribution prior to the extended deadline for filing your tax return, you must pay a six percent excise tax on the excess contribution annually until the excess contribution is withdrawn from the traditional IRA. You report and pay the excise tax by filing a Form 5329 with the IRS. Because this six percent tax is imposed each year the excess contribution stays in the traditional IRA, it is important to correct excess contributions to traditional IRAs promptly.

Note further that excess contributions withdrawn after the extended filing deadline are generally included in taxable income, though the taxpayer can recover a portion of any IRA basis they have under the Pro-Rata Rule.

Roth IRAs

There are (generally speaking) four situations that cause an excess contribution to a Roth IRA. They are:

  • Contributions are made for a year the taxpayer (and their spouse) does not have earned income.
  • Contributions are made in excess of the annual contribution limits.
  • Contributions are made for a year the taxpayer exceeds the modified adjusted gross income (“MAGI”) limitations to make a Roth IRA contribution)
  • Rolling into a Roth IRA an amount that did not qualify to be rolled in.

A rather common excess contribution occurs when taxpayers contribute to a Roth IRA in a year they earn in excess of the MAGI limits. That can happen for a host of reasons, including end of year bonuses or other unanticipated income.

Another somewhat common mistake in this regard is made by those subject to required minimum distributions (“RMDs”) when trying to convert traditional IRAs to Roth IRAs. In early January a taxpayer might convert a chunk of their traditional IRA to a Roth IRA. This creates a problem if the taxpayer did not previously take out their annual RMD for the year. There is a rule providing that RMDs are the first money to come out of an IRA during the year, and RMDs may not be converted to Roth IRAs. Thus, “converting” the first dollars out of a traditional IRA (an RMD) during the year creates an excess contribution to a Roth IRA.

Resolutions

Recharacterization

Assuming that the taxpayer qualifies to make a contribution to a traditional IRA, the excess contribution to a Roth IRA can be recharacterized as a contribution to a traditional IRA. Generally, the taxpayer must contact the financial institution and direct them to recharacterize the contribution and its earnings into a traditional IRA and must file a white paper statement with their tax return explaining the recharacterization.

When the taxpayer’s income puts him or her over the Roth IRA MAGI limits, recharacterization is often how excess contributions to Roth IRAs are resolved. In such cases, they will generally qualify to make a contribution to a traditional IRA, so a recharacterization is often the go-to method of correcting an excess contribution to a Roth IRA.

Note that the recharacterization deadline is the extended due date of the tax return (usually October 15th).

Withdrawal

A second way to correct an excess contribution to a Roth IRA is to take a corrective distribution of the excess contribution. You will need to inform your financial institution of the excess contribution and request a corrective distribution of the excess contribution and the earnings attributable to the excess contribution. The withdrawal of the excess contribution itself is generally not taxable.

The financial institution will compute the earnings attributable to the excess contribution. The earnings will be included in taxable income for the actual year the excess contribution was made. The same inclusion timing rules applicable to traditional IRA corrective distributions (discussed above) apply to the earnings from a Roth IRA corrective distribution.

If the corrective distribution occurs after the taxpayer files their tax return for the relevant taxable year, but before the extended filing deadline for the year (generally October 15th), the taxpayer must file an amended return which reports the corrective distribution and includes the earnings in taxable income (if the original contribution actually occurred in the year covered by the tax return).

Apply the Contribution to a Later Year

As with excess contributions to traditional IRAs, you can keep an excess contribution in a Roth IRA and apply it to a later year, if you are eligible to make a Roth IRA contribution in that later year. This method does not avoid the six percent penalty discussed below for the year of the contribution, but it allows the taxpayer to avoid taking a distribution of the excess contribution and stops additional impositions of the six percent excess contribution penalty. Generally, this method is only effective if the amount of the excess contribution is relatively modest, since a large excess contribution cannot be soaked up by only one year’s annual Roth IRA contribution limit.

Penalties

As with excess contributions to traditional IRAs, if you do not resolve the excess contribution to your Roth IRA prior to the extended deadline for filing your tax return, you must pay a six percent excise tax on the excess contribution annually until the excess contribution is withdrawn. It is best to resolve an excess contribution to a Roth IRA sooner rather than later to avoid annual impositions of the penalty.

Tax Return Considerations

Corrective measures applied to traditional IRA and/or Roth IRA contributions may require tax return reporting. Such reporting is discussed in various sources. Examples of such sources include IRS Publication 590-A, the Instructions to the Form 8606, and/or the Instructions to the Form 5329.

Conclusion

Excess contributions to IRAs and Roth IRAs happen. They are not an occasion to panic. They are an occasion for prompt, well considered action. Hopefully this article provides enough background for you to start your decision process and, if necessary, have an informed conversation with a competent tax professional.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Rental Real Estate Losses

Rental real estate has significant tax advantages. One of them is the ability to claim losses against other income in limited circumstances.

As a default, many taxpayers cannot claim tax losses generated by rental real estate because of the passive activity loss rules. This post describes the situations where the owner of rental real estate are able to claim real estate tax losses against other income.

The Passive Activity Loss Rules

The passive activity loss rules can be greatly oversimplified by saying “you can only deduct passive losses against passive income.” So what do we mean by “passive income”?

For this purpose, “passive income” is not necessarily what you may colloquially refer to as passive income. Portfolio income such as interest, dividends, and capital gains does not count as passive income. Wage income is also not passive income. Income from trade or business activities that the taxpayer does not materially participate in is generally passive income.

What is “material participation”? That could be its own blog post, but for our purposes, it is sufficient to know that, by itself, the activity of renting real estate is not “material participation” in a trade or business. Thus, in most instances, renting real estate will be considered a passive activity that generates passive income and passive losses.

Situations Where Real Estate Losses Can Offset Other Income

Other Rental Income

Passive income, including rental real estate income, can be offset by passive losses. Thus, if a taxpayer rents Condo A and Condo B, and Condo A has $5,000 of net taxable income during the year and Condo B has $4,000 of a net taxable loss during the year, the taxpayer will be able to offset $4,000 of Condo A’s income with Condo B’s loss on his tax return.

Real Estate Professionals

First, the wet blanket. Most taxpayers will not qualify as real estate professionals. If you have a full time job outside of real estate, you can forget about qualifying as a real estate professional.

Why would one want to be a so-called “real estate professional”? Real estate professionals are allowed to deduct losses generated by rental real estate unencumbered by the passive activity loss rules.

How does one qualify as a real estate professional? To qualify, generally one must work primarily in real estate trades or businesses they materially participate in (i.e., you must work more in real estate than in any other jobs or business activities) and must work at least 750 hours during the year in real estate activities.

Qualification could be its own blog post, but for purposes of this particular post it suffices to say that (a) “real estate professional” is a high threshold, and (b) it is great to qualify, because you are able to deduct rental real estate losses against other income unencumbered by the passive activity loss rules.

Active Participation

Taxpayers who are not real estate professionals, but actively participate in their rental real estate can deduct up to $25,000 in rental real estate losses if their modified adjusted gross income (“MAGI”) is below certain limits. The threshold for “active participation” is much lower than that for “material participation.” Generally speaking, the two main requirements are that the taxpayer makes decisions with respect to the activity (or hires someone to do so) and owns at least ten percent of the activity.

Thus, you can actively participate in renting out a house you own in your own name. You cannot actively participate in the renting of real estate by a partnership if you own less than 10 percent of that partnership.

If your MAGI is $100,000 or less, you can deduct up to $25,000 of active participation rental real estate losses. If your MAGI Is $150,000 or more, you cannot deduct any active participation rental real estate losses. In between those two amounts, the $25,000 potential maximum loss is reduced by fifty cents for every dollar above $100,000.

Here’s an example:

Shirley owns House A which she rents out. After taking into account depreciation and other tax deductions, in 2019 House A generates a $15,000 taxable loss reported on Schedule E of Shirley’s tax return. Shirley reports a MAGI of $125,000 on her 2019 tax return. Thus, she is able to claim $12,500 of the House A loss against her other income on her 2019 tax return. The remaining $2,500 of the House A loss will be a suspended passive loss that will carry forward to her 2020 tax return.

Future Passive Income

Previously suspended passive losses can offset future passive income.

Continuing with Shirley from above, in 2020 Shirley has a MAGI of $200,000 and House A reports a rental profit of $1,000 on Shirley’s Schedule E. Shirley can use $1,000 of her previously suspended $2,500 passive loss to offset the $1,000 in income generated by House A on her 2020 tax return. The remaining $1,500 of the House A loss will be a suspended passive loss that will carry forward to her 2021 tax return.

Dispositions

Dispositions of property used in a passive activity creates passive income or passive loss. A disposition of substantially all of a passive activity can trigger the use of all of that activity’s previously suspended passive losses.

One important point here: to trigger the use of all the previously suspended passive loss upon a disposition, the disposition must be of substantially all of the activity. Disposing of only part of the activity, even a significant part, is not enough to trigger the use of all of the previously suspended passive loss.

For example, imagine you and a partner are 50/50 partners in a partnership that invests in four rental properties. Unless you are trying to qualify as a real estate professional, it is usually advantageous to list each of the four rental properties from that partnership as its own separate activity on Schedule E, Part 2. That way, the future sale of one of the four properties will be sufficient to be the disposition of “substantially all” of that property and trigger any previously suspended passive losses related to that particular property.

If the partnership is instead listed as a single activity, the future disposition of any one (or two or three) property owned by the partnership will not be enough to constitute “substantially all” of the activity. While any gain from the disposition creates passive income which can be offset with previously suspended and/or current passive losses, the entire previously suspended loss with respect to that particular property is not necessarily usable because the one property is only a component part of a single activity.

Conclusion

The ability to use rental real estate losses against other income, in the limited circumstances described above, is a significant tax advantage of rental real estate. While tax losses should never be the driving factor in the decision to invest in rental real estate, potential real estate investors should go into the investment understanding the impact it will have on their taxes. Investors in rental real estate often benefit from consultations with tax professionals in order to maximize the potential tax benefits of the investment.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, investment, financial, legal, and tax matters.

Real Estate in Retirement Accounts

Should you hold rental real estate in a self-directed retirement account? Is real estate a great asset to own in a Roth IRA? Is holding real estate in a self-directed retirement account a hack that can help supercharge your path to financial independence? Below I discuss what it looks like to hold real estate in a self-directed IRA or 401(k), with a particular focus on those looking to achieve FI.

A Necessary Predicate

Before I proceed, I need to lay a necessary predicate. Those actively pursuing financial independence will fall into one of the two following groups:

Group 1: Invest in a diversified portfolio of equities and bonds.

Group 2: Invest in real estate and a diversified portfolio of equities and bonds.

Why is there no third group, real estate investors only? For two main reasons. First, many pursuing FI have no interest in owning rental real estate and/or desire to only own a small number of properties. Second, as a general rule, investing in only one sector of the economy (technology, financials, pharmaceuticals, utilities, real estate, etc.) leaves an investor dangerously undiversified and vulnerable to very particular risks to a degree diversified investors are not.

The rest of this post focuses on tax basketing for individuals in Group 2: those pursuing FI  and investing in rental real estate and a diversified portfolio of equities and bonds.

Stock Basis vs. Real Estate Basis

Recall that the basis of stock, bonds, mutual funds, and ETFs (what I will colloquially refer to as “stock basis”) is the amount you paid for the asset plus any distributions reinvested in the asset less any nondividend distributions (returns of capital). Stock basis is great, but for many in the FI community, its benefits are distant and significantly eroded by inflation.

Picture Jack and Jill, a married couple, each 25 years old and actively pursuing financial independence. They max out their IRAs and workplace retirement plans. They have a savings rate in excess of 50 percent, so they must invest in taxable accounts, and choose to invest in low-cost, well diversified index mutual funds. They target early retirement at age 40.

Other than very occasional tax loss harvesting, the basis Jack & Jill obtain in their taxable mutual fund accounts at age 25 will be meaningless to them until they are at least 40 years old. Even then, using something like the 4 percent withdrawal rule, they will touch only a small fraction of their basis every year. By then, the value of the basis they put in the mutual funds will have been significantly eroded by inflation.

But what if Jack and Jill instead decide that they will max out their IRAs and workplace retirement accounts (using stock and bond index funds), and then everything else will go into taxable rental real estate investments. What value does their basis have then? Much greater value, it turns out. Jack and Jill can immediately depreciate their rental real estate and start using their basis to reduce their taxable rental income from that property and other rental properties. Depending on their circumstances, they may be able to deduct some or all of any rental real estate loss against other taxable income.

When you invest in rental real estate in taxable accounts, your tax basis goes to work for you right away. When you invest in financial assets, your tax basis sits dormant, possibly for many years or the rest of your life. By the time you use your stock basis to obtain a tax benefit, the value of your stock basis (and thus the resulting tax benefit) may be severely diminished by inflation.

This strongly indicates you should house financial assets in retirement accounts and rental real estate in taxable accounts. House the rental real estate (pun intended) in taxable accounts where you can milk its basis for all it’s worth while housing the financial assets in retirement accounts.

Leverage and Tax Basis

You can use leverage to increase the tax value of rental real estate. A young couple will have to likely borrow some or all of the purchase price of their initial rental real estate investments. This can be advantageous from a tax perspective. Here’s an illustrative example:

Jack and Jill have $50,000 of cash to invest in a taxable account. They have decided to invest in a $250,000 fifth floor condominium to rent out. They borrow $200,000, purchase the property, and rent out the condo. In the first year they rent out the condo for a full year, they can get $9,091 ($250,000 divided by 27.5) in depreciation deductions and, assuming a 5% loan, almost $10,000 in interest deductions. Note this and all examples ignore any potential price allocation to land for simplicity.

Jack and Jill leveraged $50,000 into almost $19,000 in tax deductions in one year alone. Had they purchased $50,000 worth of financial assets, they would have received exactly nothing in tax deductions in the first full year, and the value of the $50,000 of basis would be eroding away to inflation. Even if they were able to tax loss harvest, at most the benefit would be a $3,000 deduction against their ordinary income.

In some cases, depreciation combined with other deductions causes rental real estate to produce a loss for tax purposes. Why put an asset that generates a tax loss in a retirement account?

If stock basis has such limited value, and rental real estate basis has such impactful, immediate value, why “exploit” stock basis in a taxable account while you neuter rental real estate basis in an IRA? It makes much more sense to utilize that rental real estate tax basis in a taxable account and put limited value stock basis in a retirement account.

Step-Up at Death

When you leave your heirs rental real estate in taxable accounts, the government gives your heirs hundreds of thousands of dollars worth of free tax deductions!

There’s no lack of content discussing the many tax benefits of real estate. Some of it discusses the step-up in basis at death and the ability to hold real estate in a self-directed retirement account. What little of this content acknowledges is that if you hold real estate in a self-directed retirement account, you lose the step-up in basis at death!

If you are at all concerned about Second Generation FI for your children, you need to consider this issue. The step-up in tax basis at death is an incredible opportunity for your heirs. Upon your death, your heirs get to re-depreciate your rental real estate based on the fair market value of the property at your death.

Here’s a comprehensive example.

Jake buys a small rental condo for $100,000 in 2019. He fully depreciates it over 27.5 years, saving significantly on his taxes. He dies in 2049 when the condo is worth $400,000. He leaves the condo to his adult son Jake Jr. He also leaves a Roth IRA with financial assets to Jake Jr. worth $400,000.

What result? Jake Jr. inherits the condo with a $400,000 tax basis and gets to depreciate that new $400,000 basis for 27.5 more years! This drastically reduces his taxable income from the property and may create a currently useable taxable loss. While Jake Jr. must withdraw the inherited Roth IRA within 10 years, the money from the Roth IRA is tax free to Jake Jr. And because Jake Jr houses the inherited Roth IRA at a discount brokerage (such as Vanguard, Fidelity, or Schwab), the Roth IRA pays minimal fees.

What if instead Jake had housed the financial assets in his taxable accounts and the rental property in his Roth IRA. First, the financial assets will produce interest, dividends, and capital gain distributions that will be taxable to Jake Jr. every year. Second, Jake Jr. will pay more in annual fees to a self-directed Roth IRA custodian. Further, Jake Jr. will lose the ability to claim any tax loss generated by the condo against his other income.

The effect is magnified if Jake Jr. leaves the rental property to his son, Jake III. Jake III will again get to step-up the basis in the condo to its fair market value when Jake Jr. dies and re-depreciate it! Over several generations the step-up in basis cycle can create potentially millions of dollars of tax depreciation deductions!

Rental Real Estate: Taxable Accounts and Retirement Accounts

If you are going to give up hundreds of thousands of dollars (possibly millions) of tax deductions for your heirs, you ought to have a compelling reason to do so. I do not believe there’s a compelling reason to house real estate in a retirement account and forego these free future tax deductions.

Roth IRAs are great for protecting the income generated by financial assets from taxation. The step-up in basis is great for protecting the income from rental real estate from taxation. Why waste a Roth IRA on real estate when your heirs will get a fantastic step-up in basis in your real estate to shield a significant portion of the income from taxation (and may possibly generate useable current real estate losses)?

All of this is magnified if the rental real estate is in a traditional IRA instead of a Roth IRA. Instead of depreciation and other deductions to shield rental income from taxation, every dollar you ever take from a traditional IRA will be subject to ordinary taxation (even if the underlying rental property is unprofitable). Combining this with self-directed retirement account custodian fees makes a traditional retirement account a terrible place to house rental real estate.

Stepped-Up Stock Basis

As discussed, the step-up in real estate basis is effective in reducing or eliminating taxable income rental real estate. But the step up in basis does nothing to reduce income from interest, dividends, and capital gain distributions generated by inherited financial assets. This further indicates that the step-up in basis is better used on real estate than on financial assets.

Other Considerations

Tax basis is not the only consideration in determining where to tax basket assets. Below is a run through of several other important considerations.

Costs

As of 2023, costs for investing in well diversified index funds in retirement accounts at discount brokerages are approaching zero. Costs for self-directed IRAs and 401(k)s are more substantial. Costs can include a set-up fee, annual account fees, one-off service fees, and fees for valuations.

Valuations

Starting at age 73, you must take RMDs from your traditional retirement accounts and employer Roth accounts. In the year after your death, certain heirs must take RMDs from your retirement accounts (including Roth IRAs). To do this, the recipient must know the value of each retirement account on December 31st of the prior year. For publicly-traded stock and bond based mutual funds and ETFs, the financial institution will simply report this information to you. For real estate, it is a very different ballgame. You will need to obtain a third party valuation, as the December 31st value of any particular piece of real estate is not readily apparent or known. This is an additional annual cost of owning real estate inside a retirement account.

Capital Gains

If you sell financial assets in a taxable account, you’re stuck with the capital gain, which will increase your federal (and possibly state) income tax bill. There are narrow and/or costly exceptions, including, the qualified opportunity zone program, which requires you to invest in a very specific type of investment that you may have absolutely no interest in investing in, for a minimum period of time. The qualified opportunity zone program can also apply to real estate capital gains.

The other exceptions to stock capital gain, including donations to charities, donor advised funds, and/or charitable trusts, are expensive, in that they require you to relinquish some or all of your economic ownership in order to avoid a taxable capital gain.

If you want to sell your rental real estate, you can use a Section 1031 “like-kind exchange” and simply exchange the rental property for another piece (or pieces) of rental real estate. This defers the capital gain on the sold property for as long as you hold onto the substitute property. Section 1031 exchange treatment is not available for financial assets.

While Section 1031 exchanges may not satisfy investors in every instance, the availability of Section 1031 exchanges is a reason to keep real estate in taxable accounts.

Rules, Rules, Rules

If you put your real estate in a retirement account, you voluntarily subject yourself to a whole host of rules. One is that you are not allowed to use the rental real estate for personal use. Another is that not allowed to personally manage or repair the property. Any violation of these rules can disqualify the retirement plan, resulting in a distribution of the property to the plan owner. This can result in a large taxable income hit and/or early distribution penalties if the owner is under age 59 ½.

Unrelated Debt Financed Income (“UDFI”) Tax

Is your rental property at all debt financed? If it is, and it is in an IRA, your IRA (including a Roth IRA) will be subject to income tax (the “unrelated business income tax”) on the portion of the taxable income that is attributable to the debt (the “unrelated debt financed income”). For example, if you have a condo that was purchased half with debt, half the income will be subject to tax (at the IRA level) as UDFI.

Further, as an entity your IRA is subject to taxation at very steep tax brackets. While the first $1,000 of UDFI is exempt from taxation, by the time the taxable UDFI exceeds $12,500, the IRA pays the highest individual marginal ordinary income tax rate (currently 37 percent) on the income.

There are UDFI workarounds. One is to roll a self directed IRA/Roth IRA to a self directed 401(k)/Roth 401(k). 401(k) plans are not subject to tax on UDFI generated by rental real estate. In order to move to a self directed 401(k)/Roth 401(k) plan, you must have a trade or business that can sustain the self directed 401(k) or self directed Roth 401(k).

If you roll from a Roth IRA to a self directed Roth 401(k), you solve your UDFI problem but you subject yourself to RMDs (and valuation issues) starting at age 73, reducing future tax free growth. You also added a requirement to file an annual Form 5500 tax return with the IRS if the self directed Roth 401(k) has $250,000 or more of assets. Another workaround is placing the real estate in the IRA/Roth IRA in a C corporation. This will lower the tax rate the UDFI is subject to down to 21 percent, but will also subject the non-UDFI income to that 21 percent tax rate.

Real Estate Losses

In some cases, depreciation combined with other deductions causes rental real estate to produce a loss for tax purposes. This can occur even if the property is “cash-flow positive” i.e., it produces cash income in excess of its cash expenses.

Why put an asset that generates a loss in a retirement account? Often times losses are suspended, meaning the rental property nets to zero on the tax return for that particular year. But the suspended loss is tracked and can be used in the future. Read this post for more information on deducting real estate losses.

Is the ability to use real estate losses from real estate held in taxable accounts limited? Absolutely. But it is fully eliminated if the real estate is in a retirement plan. Such losses can never be used on an individual’s tax returns.

Gilding the Lily

Discount brokerages have made this the best era to be a well diversified investor in equities and bonds. Costs associated with investing in index funds in retirement accounts are approaching zero.

This means equities and bonds reside in retirement accounts very well. Why do you need to gild the lily at that point? You have great investment options at a low cost.

To my mind, there is no compelling reason to reject this approach, particularly considering (1) depreciation and other tax advantages that help make rental real estate efficient in taxable accounts and (2) the burdens associated with housing real estate in retirement accounts.

Conclusion

In the vast majority of cases, if you want to own both financial assets (stocks/bonds/mutual funds/ETFs) and rental real estate as part of your portfolio, you are well advised to house your rental real estate in taxable accounts and save your retirement accounts for the financial assets.

It comes back to the tyranny of tactics. Real estate in an IRA sounds great, but when you peel back the onion, simplicity usually wins. Does this mean some with real estate in a retirement account will not achieve financial independence? Absolutely not. But the simpler path will keep your costs low and will likely be tax efficient.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Tax Basis for Beginners

What is Tax Basis?

To answer that question, let me posit two hypotheticals:

Hypothetical 1: Mark buys one share of Acme Industries stock for $100 on Monday. The following Monday he sells that share for $100.

Hypothetical 2: Judy buys one share of Kramerica Industries for $20 on Monday. On Thursday, Kramerica Industries announces the release of a new bottle that dispenses both ketchup and mustard, and the stock soars. On the following Monday, Judy sells her share of Kramerica Industries for $100.

What tax result? Do both Mark and Judy have $100 of taxable income? Of course not. We know that Mark has no taxable income and Judy has $80 of taxable income? But how do we know that? The answer: Basis!

Basis is the tax concept that ensures amounts are not taxed twice when they should not be. In Mark’s case, he has no real income when he sells the stock. Judy however, does have income. When she sells the Kramerica stock, she realizes the $80 gain.

Basis is what allows us to measure the appropriate gain or income to the seller of property. While we have a sense that Mark should not have had taxable income and Judy should have, without basis we have no way of measuring whether a disposition of property should trigger a taxable gain, loss, or nothing.

Generally, the basis of an asset is its historic cost, plus any capital improvements or additions made to the asset. In the case of a financial asset in a taxable account, basis is simply the purchase price plus reinvested distributions less any nondividend distributions (returns of capital).

Depreciation

Basis serves another function. Business assets are usually subject to a depreciation allowance on the theory that assets waste away from wear and tear over a useful life. The method and time period for depreciating an asset varies based on the asset. Residential real estate is depreciated in a straight line over 27.5 years. Most non-real estate property is depreciated using an accelerated method and over a shorter period. One business asset that never depreciated is land, on the theory that land has an indefinite useful life.

Each asset is depreciated based on its depreciable basis, which is generally historic cost plus capital improvements. For example, if you purchase a fourth floor residential condominium for $1,000,000 and rent it out, each full year it is used in the rental business you divide the $1,000,000 depreciable basis over 27.5 to come up with a depreciation deduction of $36,364, which lowers the taxable income from the rental activity, and may even be currently deductible against other income if the rental property produces a loss. Note that some of the basis may be attributable to land, which is good basis that can be recovered upon a sale, but it cannot be depreciated.

Step-up at Death

The tax code offers a tremendous benefit for those looking to facilitate Second Generation FI. The tax basis of inherited assets is “stepped-up” to the fair market value of the asset on the original owner’s date of death. This means, among other things, it is usually much better to leave an asset to an heir at death rather than to gift that asset to an heir during life. The asset left upon death has a stepped-up asset basis, while the gifted asset only has the original owner’s basis in the hands of the recipient.

I previously wrote an example of how this works:

William lives in a house he purchased in 1970 for $50,000. In 2019 the house is worth $950,000. If William gifts the house to his son Alan in 2019, Alan’s basis in the house is $50,000. However, if William leaves the house to Alan at William’s death, Alan’s basis in the house will be the fair market value of the house at William’s death.

Lastly, in order to qualify for the step-up at death, an asset must be held in a taxable account. Assets held in retirement accounts do not receive a step-up at death.

Tax Loss Harvesting

Basis is what makes tax loss harvesting possible. Picture Joey, who owns Blue Company stock worth $10,000. He purchased the stock a year ago for $13,000. He can sell his Blue Company stock and deduct the $3,000 loss on his tax return, realizing a nice benefit.

Tax loss harvesting is a neat tool in the tax planning tool box. But it’s a fools errand to succumb to the “tyranny of tactics” and arrange one’s portfolio around tax loss harvesting. At most, tax loss harvesting reduces your taxable income in any particular year by $3,000. Over the long run, that is not the way to build wealth and achieve financial freedom.

Sure, play the tax loss harvesting card when the right opportunity arises, but don’t structure your portfolio with dozens of holdings in the hopes you can get a $3,000 loss every year. Rather, structure your portfolio with your ultimate goal in mind, and if toward year-end an opportunity to do some tax loss harvesting arises, pounce on it.

Retirement Accounts

The term “basis” means something a bit different in the context of retirement accounts. Two points: First, it is possible to have basis in a traditional account. Generally this means that nondeductible, or “after-tax” contributions have been made to the account, and thus, in the future when there are taxable distributions a portion of the distribution will be offset by that basis.

Second, the assets inside of a retirement account (including a Roth account) do not have basis to the owner of the account. These assets do have basis, but that basis is never directly accessible to the owner of the account (in the way that depreciable basis or stock basis is accessible to the owner). Importantly, assets inside of a retirement account do not enjoy the step-up in basis at the owner’s death that assets in taxable accounts enjoy.

Conclusion

Tax basis is an important attribute to understand as you do tax planning. In two weeks I will build on this post to discuss in detail important implications of tax basis for those pursuing financial independence.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

What to Do if You Don’t Qualify for a Backdoor Roth IRA

In my last post, I discussed the basics of the Backdoor Roth IRA, which can be a great planning tool for some higher income Americans. But not everyone qualifies for a tax-efficient Backdoor Roth IRA. Recall Jennifer’s case:

Jennifer makes too much to qualify to make a Roth IRA contribution in 2022. She contributed $6,000 to a nondeductible traditional IRA on April 19, 2022. She also had a separate traditional IRA with no basis. As of December 31, 2022, that separate traditional IRA was worth $93,998.53.

If, in 2022, Jennifer were to convert the $6,000 that she put into the nondeductible traditional IRA to a Roth IRA she would increase her taxable income by over $5,600. Ouch!

Options

Jennifer has two possible options to qualify for a much more tax efficient Backdoor Roth IRA. The first option is to use her workplace 401(k), 403(b), or 457 plan. Some 401(k) plans and other workplace plans allow participants to “roll in” amounts in traditional IRAs. Workplace plans are not required to offer participants this option. If a workplace plan does, it can be worthwhile to consider this option in order to facilitate Backdoor Roth IRA planning.

Of course, there are considerations that go beyond income tax planning, including the quality of the investment choices available in a traditional IRA versus a workplace 401(k) or other retirement plan, and the expenses associated with each option.

A second option is rolling the traditional IRA into a Solo 401(k) plan. Jennifer must have a Solo 401(k) plan from self-employment and the plan must accept IRA roll ins in order for her to do this. As with workplace retirement plans, Solo 401(k) plans are not required to accept traditional IRA roll ins, and any decision must appropriately consider the relevant non-tax issues (as discussed above). Further, a Solo 401(k) plan has several requirements (including the conduct of a trade or business) that should be carefully considered before opening a Solo 401(k).

Considerations

Trustee-to-Trustee Rollover

If Jennifer wants to roll her traditional IRA into a workplace retirement plan or Solo 401(k), she should structure the transfer as a “trustee-to-trustee” direct rollover of the money between the financial institution holding the traditional IRA and the workplace retirement plan or Solo 401(k). If instead of a trustee-to-trustee direct rollover, Jennifer receives a check from her IRA financial institution payable to her, she has 60 days to roll over that check (i.e., to get it to her workplace retirement plan or Solo 401(k)). If she does not move the money within the 60 days, the distribution from the IRA is taxable, subject to early withdrawal penalties if Jennifer is under age 59 ½, and cannot be transferred into a retirement plan.

Timing

Roll ins should be completed by December 31st of the year of the Roth IRA conversion. Otherwise the pro-rata rule will bite, because there will be a balance in the taxpayer’s traditional IRAs at year-end. That balance will attract a sizable portion of the $6,000 of IRA basis established by the nondeductible traditional IRA contribution. This causes the Roth IRA conversion to grab little basis and thus be tax inefficient.

For simplicity’s sake, it is usually best to clean out traditional IRAs, SEP IRAs, and SIMPLE IRAs and then make the nondeductible traditional IRA contribution.

Basis

Prior to implementing a traditional IRA to 401(k) “roll-in” strategy, Jennifer should review all of her traditional IRAs to ensure that she has no basis in any existing traditional IRA. IRA basis amounts cannot be rolled into the 401(k) and must be left behind under the rule of Section 408(d)(3)(A)(ii) and this technical write up.

SIMPLE IRAs and SEP IRAs

Those with amounts in SIMPLE IRAs, need to be careful. During the first two years of the SIMPLE IRA account, it cannot be rolled into a plan other than another SIMPLE IRA plan. Doing so would create a taxable event, subject to both early withdrawal and excess contribution penalties (on the transfer to the non-SIMPLE IRA).

Thus, if Jennifer’s traditional IRA balance is in a SIMPLE IRA and she first deposited into the SIMPLE IRA less than two years ago, she must wait until the two year window has expired to roll her SIMPLE IRA into a workplace retirement plan or a Solo 401(k).

In addition, those with a SIMPLE IRA (beyond the two year window) or a SEP IRA from their current employer may not be allowed in-service distributions. Thus, they would not be able to roll over those accounts into a 401(k)/Solo 401(k)/403(b)/457. Additionally, amounts may be added to these accounts prior to December 31st. These considerations make it difficult to successfully execute Backdoor Roth IRA planning for those currently covered by an employer’s SIMPLE IRA or SEP IRA.

December 31st

Any Backdoor Roth IRA planning should involve an additional diligence step: ensuring that as of December 31st of the year of the Roth conversion step, the taxpayer has a zero balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs. This helps ensure the Backdoor Roth IRA is a tax-efficient tactic.

Illustrative Example

Jennifer expects to earn $300,000 from her W-2 job in 2022, is covered by a workplace 401(k) plan, and expects to have some investment income. On March 1, 2022, Jennifer has a $90,000 balance in a traditional IRA but otherwise has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA.

On March 2, 2022, Jennifer directs her workplace 401(k) plan and her IRA custodian to roll her traditional IRA to her workplace 401(k) plan. Her traditional IRA is rolled into her workplace 401(k) through a trustee-to-trustee direct rollover.

Jennifer contributes $6,000 to a traditional IRA on April 20, 2022. The contribution is nondeductible. Because the contribution is nondeductible, Jennifer gets a $6,000 basis in her traditional IRA. Jennifer must file a Form 8606 with her 2022 tax return to report the nondeductible contribution.

On May 2, 2022, Jennifer converts all the money in her traditional IRA to a Roth IRA (a Roth IRA conversion). At that time, Jennifer’s traditional IRA had a value of $6,001.47. Jennifer also ensures that as of December 31, 2022, she has a $0 balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs.

If Jennifer executes the above steps as described above, she will get the desired result. Done in this manner, the Roth IRA conversion step results in an increase in Jennifer’s taxable income of just $1.47 ($6,001.47 fair market value less $6,000 of traditional IRA basis).

Tactics vs. Goals

What if Jennifer’s workplace retirement plan does not accept roll ins? What if Jennifer doesn’t have access to a Solo 401(k)? What if Jennifer’s workplace retirement plan accepts roll ins but does not have quality investment options and/or charges high fees?

Remember, Jennifer’s ultimate goal is not to do a Backdoor Roth IRA. Her goal is financial independence! She should not let what I call the “tyranny of tactics” distract her from her ultimate goal.

The Backdoor Roth IRA is a great tactic to employ toward achieving that goal. But it’s okay if you can’t use this particular tactic. Plenty of people have and will achieve financial independence without executing a Backdoor Roth IRA.

If you can’t use the Backdoor Roth IRA for whatever reason, simply use other appropriate tactics, including but not limited to a high savings rate, to achieve your financial goals.

Further Reading

I discuss how to properly report a Backdoor Roth IRA on a tax return and what to do if has been incorrectly reported here.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Backdoor Roth IRAs for Beginners

If you read enough FI blogs, you will eventually come across the term “Backdoor Roth IRA.” This post answers the question “What’s the deal with Backdoor Roth IRAs?”

Why Do a Backdoor Roth IRA?

Why would someone do a Backdoor Roth IRA? The Backdoor Roth IRA gets money into a Roth IRA in cases where the taxpayer earns too much to make a direct annual contribution to a Roth IRA. Doing the Backdoor Roth IRA gets money that would have been invested in a taxable account into a tax-free Roth account. Further, the money in the Roth account gets better creditor protection than money in a taxable account.

History of the Backdoor Roth IRA

Before 2010, what is now referred to as a Backdoor Roth IRA would have been permissible and/or necessary in only relatively limited circumstances, and then only in years prior to 2008. But a 2006 change in the law opened up the Backdoor Roth IRA in the form we know now (starting in 2010).

Two fundamental concepts must now be addressed. The first is a Roth IRA contribution.

Roth IRA Contributions

This post discusses Roth IRA contributions in detail. Simplified, U.S. citizens and residents with earned income can make an annual Roth IRA contribution of up to $7,000 in 2024 ($8,000 if 50 or older). Done for many years, it can be a tremendous wealth building tool, since it moves wealth into an account that is tax-free (if properly executed).

The one catch is that your “modified adjusted gross income” (or “MAGI”) must be below a certain threshold in order to make a Roth IRA contribution. To make a full contribution in 2024, your MAGI must be less than $146,000 (if single) or $230,000 (if married filing joint).

Because of these limits, many taxpayers are unable to make a Roth IRA contribution. Further, based on the qualification rules for traditional deductible IRA contributions, most taxpayers unable to make a Roth IRA contribution are also unable to make a deductible traditional IRA contribution.

Roth IRA Conversions

The second fundamental concept is a Roth IRA conversion. A Roth IRA conversion is a movement of amounts in traditional accounts to a Roth IRA. This creates a taxable event. The amount of the Roth IRA conversion, less any “basis” in the traditional account (more on that later), is taxable as ordinary income on the taxpayer’s tax return.

Prior to 2010, only taxpayers with a modified adjusted gross income of $100,000 or less were allowed to do a Roth IRA conversion. This amount was not indexed for inflation and applied per tax return, making it particularly difficult for many married couples to qualify.

In 2006, Congress changed the law, effective beginning in 2010. As of January 1, 2010, there is no modified adjusted gross income limitation on the ability to do a Roth IRA conversion. The richest, highest earning Americans now qualify to do a Roth IRA conversion just as easily as anyone else.

The Backdoor

Okay, so there’s no MAGI limitation on the ability to execute a Roth IRA conversion. So what? Aren’t they taxable? What’s the advantage of doing one?

Recall I mentioned a taxpayer’s basis in a traditional account. Basis in an IRA occurs when a taxpayer makes a nondeductible contribution to a traditional IRA. Here is an example.

Mike expects to earn $300,000 from his W-2 job in 2024, is covered by a workplace 401(k) plan, and expects to have some investment income. Mike has no balance in a traditional IRA, SEP IRA, or SIMPLE IRA.

Mike contributes $7,000 to a traditional IRA on April 20, 2024. The contribution is nondeductible. Because the contribution is nondeductible, Mike gets a $7,000 basis in his traditional IRA. Mike must file a Form 8606 with his 2024 tax return to report the nondeductible contribution.

The “backdoor” opens because of the confluence of two rules: the ability to make a nondeductible traditional IRA contribution and the ability to do a Roth IRA conversion regardless of your income level. Let’s extend Mike’s example a bit.

On May 2, 2024, Mike converts all the money in his traditional IRA to a Roth IRA (a Roth IRA conversion). At that time, Mike’s traditional IRA had a value of $7,011.47.

What result? To start, all $7,011.47 is taxable. All money converted in a Roth IRA conversion is taxable. Uh oh! But there’s good news for Mike. Mike gets to offset the $7,011.47 that is taxable by the $7,000 of basis in his traditional IRA. Thus, this Roth IRA conversion will only increase Mike’s taxable income by $11.47 ($7,011.47 minus $7,000).

The combination of these two separate, independent steps (a nondeductible traditional IRA contribution and a later Roth IRA conversion) is what many now refer to as the Backdoor Roth IRA. Notice this is only possible because of the repeal of the MAGI limitation on Roth IRA conversions. Under the rules effective prior to 2010, Mike would have been allowed to make the nondeductible traditional IRA contribution, but his income (north of $300,000) would have prohibited him from a Roth IRA conversion.

The Backdoor Roth IRA allows Mike to obtain the benefits of an annual Roth IRA contribution without qualifying to make a regular annual Roth IRA contribution.

December 31st

Any Backdoor Roth IRA planning should involve an additional diligence step: ensuring that as of December 31st of the year of the Roth conversion step, the taxpayer has a zero balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs. This helps ensure the Backdoor Roth IRA is a tax-efficient tactic.

The Pro-Rata Rule

The Backdoor Roth IRA works well for someone with Mike’s profile. But it does not work well for everyone. Let’s change up the example a bit.

Jennifer’s story is the same as Mike’s story above, except that she had a separate traditional IRA before she did her 2024 nondeductible IRA contribution. That separate IRA had no basis. As of December 31, 2024, that separate traditional IRA was worth $92,988.53.

This one change in facts dramatically increases Jennifer’s taxable income from the Roth IRA conversion. Jennifer must apply the so-called Pro-Rata Rule to the Roth IRA conversion. Even though her two IRAs are in separate accounts, they are treated as one IRA for purposes of determining how much of Jennifer’s $7,000 of basis she recovers upon her Roth IRA conversion.

Jennifer starts with $7,011.47 of income (the amount she converts). To determine the amount of her $7,000 of basis she gets to recover against the proceeds of the Roth IRA conversion, we must multiply that $7,000 times the amount converted ($7,011.47) divided by the sum of the amount converted and her traditional IRA balance at the end of the year ($7,011.47 plus $92,988.53). Thus, Jennifer gets to recover 7.00147 percent of the $7,000 of basis, which is only $490.80. This results in Jennifer’s Roth IRA conversion increasing her taxable income by $6,520.67 ($7,011.47 minus $490.80).

What was a great idea for Mike becomes a horrible idea for Jennifer when she has a significant balance in another traditional IRA.

Note further that Jennifer would have the same bad outcome if that $92,988.53 traditional IRA was instead in a traditional SEP IRA or in a traditional SIMPLE IRA.

Tax Reporting

Assume Mike did his Roth IRA conversion and did not have any other money in traditional IRAs in 2024. He will get a Form 1099-R from his financial institution. In box 1 it will report a gross distribution of $7,011.47 (the amount of the Roth IRA conversion).

In box 2a the Form 1099-R will say that the “taxable amount” is $7,011.47 and box 2b will be checked to indicate that the “taxable amount not determined.” Wait, what? How can $7,011.47 be the taxable amount while the next box claims the taxable amount is not determined? The answer is the basis concept discussed above.

Mike’s financial institution does not know the rest of Mike’s story (his income, retirement plan coverage at work, IRAs at other institutions, etc.), so it has no way of determining how much basis, if any, Mike recovers when he did the Roth IRA conversion. Box 2b simply means that Mike might have recovered some basis, but the institution is not in a position to determine if he did.

Form 8606 helps complete the tax reporting picture. By filing that form, Mike establishes that he was entitled to $6,000 of traditional IRA basis and how the pro-rata rule applies (if at all) to his Roth IRA conversion. It is important that Mike file a properly completed Form 8606 with his timely-filed 2024 federal income tax return.

When Mike files his 2024 Form 1040, he puts $7,011.47 on line 4a (“IRA distributions”) and $11.47 on line 4b (“Taxable amount”). Most tax return preparation software will round cents to the nearest whole dollar.

Note that failing to report the transactions on the Forms 8606 and 1040 in this way can result in Mike paying an incorrect amount of tax.

Further Reading

This post discusses what you can do if you find yourself in Jennifer’s situation to get a result similar to Mike’s result. I discuss how to properly report a Backdoor Roth IRA on your tax return and what to do if has been incorrectly reported here.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.


Section 199A and Retirement Plans

Previously I have blogged about small business retirement plans. This post (revised in January 2020) folds the new Section 199A qualified business income (“QBI”) deduction into the discussion.

For an introduction to Section 199A, please read this. For more on Section 199A, please read this additional post.

The Basics

Section 199A, enacted in December 2017 as part of tax reform, gives owners of businesses (including partners, owners of S corporations, and sole proprietors) that generate QBI a deduction in the amount of 20 percent of the QBI.

In January 2019, the IRS and Treasury issued regulations providing detailed rules under Section 199A. Those rules define QBI. As part of the definition of QBI, taxpayers must subtract contributions to self-employment retirement plans from QBI.

80% Deductions

When a self-employed individual contributes to a traditional retirement plan, they generally reduce the amount of their QBI deduction (because the retirement plan contribution lowers QBI).

Here’s a quick example (using 2018 tax numbers) of how that works.

Example: Mike makes $50,000 from his sole proprietorship (as reported on Schedule C). He pays $7,065 in self-employment tax (Social Security and Medicare). He deducts half of his self-employment tax ($3,533) from his taxable income and his QBI. Mike is married to Jane. Jane has $34,000 of W-2 wages. Mike and Jane file jointly and take the $24,000 standard deduction.

Mike thus receives a QBI deduction of $9,293 (20% of $46,467). This makes Mike and Jane’s taxable income $47,174 ($50,000 less $3,533 plus $34,000 less $24,000 less $9,293).

Let’s assume that Mike wants to make a $10,000 employee contribution to his Solo 401(k) to lower his taxable income by $10,000. Sure enough, the math does not work that way due to the QBI deduction. Mike’s QBI is now $36,467 (the original QBI of $46,467 less the $10,000 traditional Solo 401(k) contribution). Thus, his QBI deduction is now reduced to $7,293 (20% of $36,467). This makes Mike and Jane’s taxable income $39,174 ($50,000 less $3,533 plus $34,000 less $24,000 less $10,000 less $7,293).

Notice that $39,174 is $8,000 less than $47,174, not $10,000 less than $47,174. The interaction of Section 199A and the small business retirement plan creates the oddity that a $10,000 deduction (the traditional Solo 401(k) contribution) reduces taxable income by only $8,000.

QBI has thus created a new class of deductions – what I call “80% deductions.” These deductions reduce QBI and thus (in total effect) are deductible at only 80 percent of their gross amount.

As applied to small business retirement plans, 80% deductions are particularly troublesome. Recall Mike put $10,000 into his Solo 401(k), netting him an $8,000 federal tax deduction. When Mike goes to take the $10,000 (and its growth) out of the Solo 401(k), all of it will be taxable.

Matching 80% deductions with 100% inclusions is usually not smart tax planning.

I’ve written more about this phenomenon (what I call the Solo 401(k) Trap) here.

Planning Options

In cases where taxpayers are below the taxable income limitations of Section 199A ($163,300 and $326,600 (MFJ) for 2020), taxpayers will have to weigh the benefit of the 80 percent deduction for a traditional contribution to a small business retirement plan versus other options. Some of those other options include (if eligible):

  1. Make employee contributions to a Roth IRA, Roth Solo 401(k), and/or after-tax contributions to a Solo 401(k)
  2. Make contributions to a health savings account (a “HSA”)
  3. Make contributions to a traditional IRA
  4. Invest the earnings in taxable accounts and/or pay off existing debt.

Roth Contributions

Roth versus traditional receives much Internet discussion, particularly in the FI community. All agree that a taxpayer’s current marginal tax rate is vitally important. 80% deductions lower marginal tax rates. Take Mike, who with his retirement plan contributions lowered his 2018 taxable income to $39,174. As a married filing joint taxpayer, his marginal federal income tax rate is 12 percent. However, the marginal rate on the $10,000 retirement plan traditional contribution is only 9.6 percent (80 percent of 12 percent). In order for the traditional contribution to be advisable, Mike better be pretty sure he can pull the money out of the Solo 401(k) at a marginal federal tax rate below 9.6 percent. Being that the lowest marginal tax rate is 10 percent today, that does not seem very likely.

In Mike’s case, he would have been much better advised to leave his taxable income at $47,174 and made the Solo 401(k) contribution a Roth Solo 401(k) contribution.

HSAs/IRAs/Small Business Retirement Plans

Many small business owners are looking for current tax deductions, and many are in marginal tax brackets much above the 12 percent bracket. The interaction between Section 199A and small business retirement plans creates a new pecking order for self-employed individuals looking to reduce taxable income through plan contributions. That order is as follows:

  1. HSA Contributions (if eligible)
  2. Deductible Traditional IRA Contributions (if eligible)
  3. Traditional Small Business Retirement Plan Contributions

HSA Contributions

I’ve written about my fondness for HSAs here. What’s important for this purpose is that contributions to HSAs do not reduce QBI. Thus, contributions to HSAs are “100 percent deductions” and not 80% deductions. In addition to all their other advantageous tax attributes, HSA contributions should be prioritized over small business retirement plan traditional contributions from a Section 199A perspective.

Deductible Traditional IRA Contributions

Deductible contributions to traditional IRAs (for those who qualify) also should be prioritized over traditional contributions to small business plans from a Section 199A perspective.

In the previous version of this post, I expressed the concern that deductible traditional IRA contributions might reduce QBI. Fortunately, there is nothing the IRS and Treasury has provided (including the instructions to the new Form 8995) indicating that the government believes deductible traditional IRA contributions reduce QBI. Based on my understanding of the tax law, which has been reinforced by IRS and Treasury silence on the matter, I am comfortable that deductible traditional IRA contributions should not reduce QBI.

Taxable Accounts

There is no requirement to contribute to small business retirement plans. You can simply take profits and invest them in taxable accounts. Considering that traditional small business retirement plans contributions are now 80% deductions that must later create 100% income, you may opt to simply not make plan contributions and keep profits in taxable accounts. That may be very sensible if either or both the following are true: 1) you are currently in a very low marginal federal tax bracket and 2) you anticipate being in a much higher marginal federal tax bracket in the future.

S Corporation Owners

For S corporation owners, only the operating income after the owner’s W-2 salary is eligible for the Section 199A deduction. Small business retirement plan contributions are 80% deductions for the S corporation owner just as they are for the sole proprietor and for partners of partnerships with flow-through QBI.

Consideration should be given to employee versus employer contributions. To my mind, the new Section 199A deduction does not necessarily impact whether to make an employee contribution to a Solo 401(k) as a W-2 employee of your business. Yes, your salary is an 80% deduction. But what you from there with your salary (take it home, put it into a traditional Solo 401(k), or put it into a Roth Solo 401(k)) does not increase or decrease your qualified business income (though it could impact the taxable income limitations).

But an employer contribution to a Solo 401(k) (which must be a traditional contribution) does reduce your QBI. Employer contributions to Solo 401(k) plans often fall into the Solo 401(k) Trap.

In many cases, if you qualify for the QBI deduction you should give strong consideration to foregoing the employer contribution. Planning in this regard can benefit from professional consultations.

Your Employees

If you have employees, offering a SIMPLE IRA plan does not change the Section 199A result with respect to their salary. Normal operating expenses (including salaries) of QBI-generating businesses do create 80% deductions, but there is only so much that can be done about that. Unlike your own retirement plan contributions, which are (almost) entirely discretionary, operating expenses are necessary for the conduct of the business. Giving your employees the option of deferring some of their salaries through a SIMPLE IRA does not change the math on the Section 199A deduction, since employees’ salaries reduce QBI regardless of whether the employees contribute some of their salary to a SIMPLE IRA.

The relatively small mandatory employer contribution to employees’ SIMPLE IRAs are 80% deductions, making them a bit more expensive for the business owner (assuming the owner qualifies to claim the QBI deduction).

The Section 199A QBI deduction makes SEP IRA contributions more expensive for most self-employed business owners. In order to make contributions to his/her own SEP IRA, the owner must also make contributions (in an equal percentage of compensation) to the employees, and now those deductions are only 80% deductions (assuming the owner qualifies to claim the QBI deduction).

Upper Income Taxpayers

For some taxpayers, Section 199A will make their small business retirement plan contributions more, not less, valuable. In a previous post, I gave the example of Jackie, a sole proprietor lawyer whose 2020 taxable income (pre-retirement plan contributions) of $215,848 left him unable to claim any Section 199A QBI deduction. Maximum employer and employee traditional contributions of $57,000 to a Solo 401(k) lowered his taxable income such that he was able to qualify for a $31,770 QBI deduction (a 100% deduction) in addition to the $57,000 traditional retirement plan contribution deduction (an 80% deduction).

This interaction turned the $57,000 deduction into an effective $77,370 deduction (80 percent of $57,000 plus $31,770). In this case, Jackie’s retirement plan contributions are 136% deductions!

For upper income taxpayers near the QBI taxable income limitations, small business retirement plans may be a very powerful tool, and unlike those with more modest incomes, these upper income business owners may have an opportunity to maximize their Section 199A deduction by contributing to retirement plans.

Conclusion

The combination of Section 199A and small business retirement plans creates tax planning opportunities and challenges. Many small business owners will benefit from professional advice to determine the best path forward considering the new law, opportunities, and challenges.

FI Tax Guy can be your financial advisor! FI Tax Guy can prepare your tax return! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters.

Small Business Retirement Plans

If you are self-employed or have a side hustle, you have great opportunities for tax-advantaged savings. Small business retirement planning has been an area of significant confusion due to the multitude of plans available and the different qualification rules for each.

Below I describe the three most important plans for most small businesses to consider, provide the qualification requirements, and discuss when each plan is the best option.

Fortunately, for roughly 90 percent of small businesses, there are only three options worth considering: the Solo 401(k), the SIMPLE IRA, and the SEP IRA. In many cases, one of the three options quickly becomes the advantageous option.

After I discuss the three main small business retirement plans, I will provide some commentary on other available plans, but for most small businesses, the playbook consists of these three plans.

The administrative burdens (forms, paperwork, fees to financial institutions) of all three of these programs are relatively light these days, though all three plans do have some forms that must be properly completed, signed, and filed.

Before we begin, three quick notes. First, on limitations. Below I provide (in a general sense) the upper annual limits on contributions to the plans. It is important to note that contributions can be made in a manner below the limits – the plans are flexible in this regard. Second, generally you can contribute to a small business retirement plan and to a Roth and/or traditional IRA. Having access to a small business retirement plan does not prohibit a contribution to a Roth IRA or a traditional IRA. Third, before implementing a plan it is best to discuss your business and needs with the plan provider. Providers can have rules that are different from (and/or in addition to) the applicable tax rules.

Solo 401(k)

The Basics: A Solo 401(k) (sometimes referred to as an “Individual 401(k)”) is a 401(k) plan established by a self-employed individual for only their own benefit. Solo 401(k)s can be established by self-employed individuals in their own name and by corporations (usually S corporations in this context). Self-employment for this purpose includes a sole proprietorship, limited liability company (“LLC”), or other entity treated as disregarded from their single owner and reported on a Schedule C on their tax return.

The main advantage of the Solo 401(k) is that it allows annual contributions by the self-employed individual in his/her role as the “employee” and annual contributions by the self-employed individual (or S corporation) in his/her role as “employer.”

Employee contributions are limited to the lesser of earned income or $19,500 ($26,000 if 50 or older) in 2020. Employer contributions are limited to either 20 percent of self-employment income or 25 percent of W-2 wages (if the self-employed individual is paid through a corporation, including S corporations). Total employee and employer contributions are limited to $57,000 ($63,500 if age 50 or above) in 2020.

Today, many financial institutions (including Fidelity, Schwab, and Vanguard) offer low-cost Solo 401(k) options.

If eligible, the Solo 401(k) is almost always the best option for the self-employed individual. It offers the greatest potential for tax savings of the self-employed plans and it is relatively easy to administer.

An important note on the Solo 401(k) vis-a-vis the SIMPLE IRA and the SEP IRA: the Solo 401(k) is the only small business plan that allows Roth “employee” contributions. This allows self-employed individuals the ability to put away up to $19,500 ($26,000 if 50 or older) annually that will grow tax free. For all three plans, the “employer” contribution is always a traditional contribution (i.e., tax deductible today, taxable upon withdrawal). Note, however, that not all financial institutions offer the Roth employee contribution option in their Solo 401(k) plan, so it is important to check with the provider before signing up if the ability to make a Roth contribution is important to you.

Spouses employed by the self-employed individual (or their corporation) can also participate in the Solo 401(k) (only to the extent of their earnings from the business and subject to the above stated limitations), increasing the tax benefits of the plan.

Eligibility: In order to establish a Solo 401(k) plan, a person must have self-employment income, and must not have employees other than their spouse. For this purpose, an employee is anyone who works 1,000 hours during the year for the business. Starting in 2024, an employee also includes anyone who has worked 500 hours in each of 3 consecutive years.

Different plans have different rules on other employees. Some Solo 401(k) plans do not allow you to have any non-owner/non-spousal employees (regardless of the numbers of hours worked).

To have a Solo 401(k) in any tax year, the plan must be established by the deadline for the tax return, including extensions. That deadline also applies to employer contributions.

Generally, employee deferrals to a Solo 401(k) must be made by the end of the calendar year. There is an exception: if the Solo 401(k) is for a self-employed person (reporting self-employment income on Schedule C), the employee deferral must be formally designated by year-end, but then can be paid into the Solo 401(k) before the tax filing deadline (including extensions if the taxpayer extends his/her Form 1040).

Ideal for: Solo 401(k)s are ideal for anyone who is self-employed and does not have employees (other than a spouse).

SIMPLE IRA

The Basics: The SIMPLE IRA works in a manner somewhat similar to a 401(k) plan. It allows employees (including self-employed owners of the business) to defer up to $13,500 ($16,500 if 50 or older) of earnings in 2020 through traditional employee contributions. The SIMPLE IRA also has relatively modest required employer contributions to each eligible employee’s account (described below).

Today, many financial institutions (including Fidelity, Schwab, and Vanguard) offer low-cost SIMPLE IRA options.  

In order to have a SIMPLE IRA for the year, the employer must establish the SIMPLE IRA by October 1st of the year. One narrow exception is when the business is established after October 1st, in which case the plan must be established when administratively feasible.

The SIMPLE IRA has two main advantages over the SEP IRA. First, it gives the self-employed owner and any employees a valuable option – the option to make traditional contributions to the SIMPLE IRA account. By contrast, the SEP IRA (discussed below) does not allow for employee contributions. Second, the required employer contribution is relatively low. Employers must make either matching contributions of 3 percent of salary (in 2 out of every 5 years that percentage can be reduced to 1 percent) or automatic annual contributions of 2 percent of salary to each employee’s SIMPLE IRA. Thus, the SIMPLE IRA can give the self-employed owner(s) the option to defer up to $13,500 ($16,500 if 50 or over) of earnings in a relatively affordable manner.

Eligibility: In order to be eligible for a SIMPLE IRA, the employer must have no other retirement plan and must have 100 or fewer employers during the year.

Ideal for: Self-employed individuals that are not eligible for a Solo 401(k) and are looking to provide themselves and their employees the option to defer some taxable income at a relatively low cost to the employer. Partnerships where two or more owners (non-spouses) work in the business and/or small businesses with employees are good candidates for a SIMPLE IRA.

SEP IRA

The Basics: A SEP IRA is allows only employer contributions. Generally, the employer can make annual contributions of up to 25 percent of eligible compensation (20 percent of a sole proprietor’s self-employment income), limited to $57,000 of contributions (in 2020).

Today, many financial institutions (including Fidelity, Schwab, and Vanguard) offer low-cost SEP IRA options.  

The SEP IRA has two important advantages. First, it allows the employer to elect each year whether to make contributions. The employer can elect to forego contributions or reduce the contribution each year. Second, the SEP IRA has the latest deadlines of all the plans. A SEP IRA can be established for a tax year by the deadline for filing that tax year’s tax return, including extensions.

The main disadvantage of a SEP IRA is that it generally requires equal percentage contributions to all eligible employees. Said differently, in order for the self-employed owner of the business to make an employer contribution to his/her own account, the business must make the same percentage contribution to all eligible employees. This makes the SEP IRA an expensive way to save for your own retirement if you are self-employed and have employees. SEP IRAs are also subject to “top heavy” rules whereby the employer may be required to put in additional contributions to the rank-and-file employees’ SEP IRAs if the owners’ and executives’ SEP IRA balances are too high vis-a-vis the rest of the employees’ SEP IRA balances.

Eligibility: An employer (a sole proprietor, partnership, or corporation, including S corporations) can establish a SEP IRA program. Employees that are 21 years old, earn $600, and have worked for three of the previous five years for the employer must be allowed to participate.

Ideal for: There are three situations in which a SEP IRA can be highly advantageous. The first is for a side hustlers that maximize their 401(k)/403(b)/TSP contributions to their W-2 employer’s plan. The SEP IRA provides a mechanism for these side hustlers to defer more income. Note, however, that this can also be accomplished through a Solo 401(k), and in most cases the Solo 401(k) is preferable to the SEP IRA (if a taxpayer is eligible for both).

The second situation is when a self-employed person has not established a self-employed retirement plan by year-end. In such cases, the taxpayer can establish and fund a SEP IRA for the prior year before their tax return deadline (including extensions).

Third, a SEP IRA can be helpful in situations where a small business has a small number of employees, all or most of which are very important to the business. The SEP IRA provides a way to give highly valued employees a significant benefit.

Side Hustlers

For most side hustlers, the question becomes: are you covered by a retirement plan (such as a 401(k)) at your W-2 job? If you are not, the Solo 401(k) in most instances is likely your best option.

If you are covered by a workplace retirement plan, such as a 401(k), then the SEP IRA may be your best option, since you can defer up to the lesser of 20 percent of your side-hustle income or $57,000 (in 2020) while you can take advantage of your $19,500 ($26,000 if 50 or older) employee contributions through your workplace plan. While the “employer” contribution calculation is the same for a SEP IRA and a Solo 401(k), the administrative cost of the SEP IRA (including IRS filings) tends to be lighter than that of the Solo 401(k).

In some situations, side hustlers might want to forego a SEP IRA and use a Solo 401(k) (instead of a workplace 401(k)) for some or all of their annual employee contributions. That would be true if you want to make Roth employee contributions and your workplace plan does not allow them and/or you believe the investment options in your Solo 401(k) plan are better than the options in your employer’s plan. However, in all cases consideration should also be given to ensuring you at least get the full match in your employer’s 401(k) plan.

One important consideration for side hustlers and all self-employed individuals is what I call the Solo 401(k) Trap. Because of the new Section 199A deduction, many will want to forego deducting retirement plan contributions to self-employment retirement accounts (i.e., traditional employee contributions to Solo 401(k)s and employer contributions to Solo 401(k)s and SEP IRAs) and instead make Roth employee contributions to Solo 401(k)s.

Note that there is no benefit to having both a Solo 401(k) and a SEP IRA for your side hustle, because contributions to both plans count against the relevant limitations (i.e., having two separate plans does not increase a taxpayer’s contribution limitations).

Other Plans

There are other options available to small businesses. All (with the exception of the SIMPLE 401(k)) of them involve significantly more administrative burden and costs than the Solo 401(k), the SIMPLE IRA, and the SEP IRA. Often these plans are not feasible for small businesses and these plans are rarely feasible for side hustlers.

SIMPLE 401(k)s

SIMPLE 401(k)s are very similar to SIMPLE IRAs, with some differences on the margins not worth mentioning here. Most financial institutions offer SIMPLE IRAs instead of SIMPLE 401(k)s.

Keoghs

Keoghs come in both defined contribution and defined benefit (i.e., pension) models. Keoghs involve significant additional administrative burdens when compared to Solo 401(k)s, SIMPLE IRAs, and SEP IRAs.

401(k)s

There is nothing stopping a small business from establishing a 401(k) plan just like the largest employers. However, as a practical matter, it is difficult for most small businesses to do so. First, they involve significant set-up and maintenance costs. Second, 401(k)s are subject to discrimination testing to prevent business owners and high compensated employees from enjoying the benefits of the plan to a much greater degree than rank-and-file employees. This testing can lead to either reversals of previous contributions to the plan or additional employer contributions to rank-and-file employees.

Defined Benefit Pension Plans

A defined benefit plan (where the employee receives a stated benefit during retirement years and the employer funds the plan during the employee’s working years) is another option. These plans require significant compliance costs, including actuarial calculations. Further, if you have employees, these plans can be quite expensive for the self-employed business owner. In addition, these plans often work against the financial independence model in that they tie up assets until the account owner reaches a certain retirement age. However, given the right set of circumstances (usually older, highly compensated earners), these plans can be advantageous and create large current tax deductions.

Conclusion

Small businesses have a great opportunity to create tax advantaged retirement savings. For those eligible for a Solo 401(k), in most cases significant consideration should be given to establishing one. Depending on your circumstances, the SIMPLE IRA or the SEP IRA might be a great solution.

My hope is that this post has given you some working knowledge of the three main options for small businesses. Small business owners will often benefit from obtaining professional advice regarding their retirement planning and the programs they ought to establish.

Next Week

Next week’s post (click here) explores small business retirement plans in light of the new Section 199A qualified business income deduction and how the two concepts interact.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters.


Tax Efficient Estate Planning

THIS POST HAS NOT BEEN UPDATED FOR THE SECURE ACT, WHICH WAS ENACTED IN LATE 2019.

If you have significant assets, you need an estate plan. A good estate plan makes handling the financial aspects of your death much easier for your loved ones and creates the opportunity for multiple generation wealth creation.

For most, the need for good estate plan is not about the estate tax. Very few Americans, particularly very few actively seeking financial independence, will be subject to the federal estate tax, as there is now (as of 2019) a $11.4 million estate tax exemption. Thus, only the very largest of estates will pay the federal estate tax. For purposes of this post, assume that all estates are below this threshold.

If you are aren’t subject to the estate tax, why do you need to make a tax efficient estate plan? The answer is the income tax considerations of your heirs and beneficiaries. Some assets cause your heirs and beneficiaries to have very little or no additional income tax. Other assets can cause a significant increase in the income tax burdens of your heirs and beneficiaries. Below I analyze each of the tax baskets and discuss the estate planning considerations for each one.

Being that the FI community generally aims to build up significant assets to achieve financial independence, good estate planning is particularly important if you are on the road to (or have achieved) financial independence.

A quick caveat at the beginning – tax is only one consideration in estate planning. There are many others, including the needs of spouses, children, and other potential heirs, and the desires of the donor. Below I offer thoughts on tax optimal estate planning — of course the tax considerations need to be balanced with other estate planning objectives.

Spouses

A quick note on leaving assets to spouses. Generally speaking, the tax laws favor leaving assets to spouses. A spouse is a tax-preferred heir in most situations (the main exception being leaving retirement accounts to younger beneficiaries with low RMDs). As the focus of this post is passing wealth to the second generation efficiently, most of the discussion, other than a few asides, will not address the tax consequences when leaving an asset to a spouse.

Tax Baskets

Below are the four main tax baskets (tax categories in which individuals can hold assets):

  1. Traditional (a/k/a Deductible) Retirement Accounts: These include workplace plans such as the 401(k), the 403(b), the 457, and the TSP, and IRAs. Under ideal conditions, the contributions, when earned, are not taxed but the contributions and earnings are taxed when later withdrawn.
  2. Roth Retirement Accounts: These include workplace plans such as the Roth 401(k), the Roth 403(b), and the Roth TSP, and Roth IRAs. Under ideal conditions, the contributions, when earned, are taxed but the contributions and earnings are tax-free when later withdrawn.
  3. Health Savings Accounts: HSAs are tax-advantaged accounts only available to you if you have a high deductible health plan (a “HDHP”) as your health insurance. Under ideal conditions, the contributions, when earned, are not taxed and the contributions and earnings are tax-free when later withdrawn.
  4. Taxable Accounts: Holding financial assets in your own name or otherwise not in a tax-advantaged account (tax baskets 1 through 3). The basic concept is taxable in, taxable on “realized” earnings (rental income, business income, dividends, interest, etc.) while in the account, and partially taxable (value less “tax basis”) on the way out.

Baskets 1 through 3 require “ideal conditions” (i.e., compliance with the related tax rules) to operate as outlined above. Let’s assume for purposes of this post that no errors are made with respect to the account in question.

Traditional Accounts

Of the four tax baskets, traditional accounts are often (from a tax perspective) the worst kind to leave to a spouse and the third worst to leave to non-spouse heirs. Why? Because traditional accounts, through required minimum distributions (“RMDs”), are eventually going to be entirely taxable to your beneficiaries and/or their beneficiaries. Non-spouse beneficiaries generally must take RMDs in the year following the donor’s death.

When passing traditional accounts to the next generation(s), a general rule of thumb is younger beneficiaries are better for such accounts, because the younger the beneficiary, the smaller their earlier RMDs, and thus the lower the tax hit of the RMD and the longer the tax-deferred growth.  

Spousal beneficiaries, unlike non-spouse beneficiaries, have the option to delay RMDs until the year they turn 70 ½. However, once they turn 70 ½ they will be required to take taxable RMDs, increasing their taxable income.

For charitably inclined, traditional accounts (or portions thereof) are a great asset to leave to charity. As you will see, your individual beneficiaries would prefer to inherit Roth accounts (and in most cases will prefer to inherit taxable accounts), but the charity is generally indifferent to the tax basket of an asset, because charities pay no income tax. So all other things being equal, if you have money in traditional accounts, Roth accounts, and taxable accounts, the first money you should leave to a charity should be from your traditional accounts.

Lastly, whatever your plans, you are well advised to ensure that all your traditional, Roth, and HSA accounts have valid beneficiary designation forms on file with the employer plan or financial institution.

Roth Accounts

Roth accounts are fantastic accounts to inherit for both spouses and non-spouses. While non-spouses must take RMDs from the inherited Roth account in the year following death, the RMD is non-taxable to them. All beneficiaries benefit from tax-free growth of assets while they are in an inherited Roth account. This makes spouses (able to defer RMDs until age 70 ½) and younger beneficiaries ideal (from a tax perspective) to inherit Roth accounts.

Roth conversions are a potential strategy to save your heirs income tax. If you believe your heirs will have a higher marginal income tax rate than you do, and you do not need the tax on the Roth conversion, you can convert amounts in traditional accounts to Roth accounts, pay the tax, and lower the overall tax burden incurred by you and your family.

Health Savings Accounts

There are two, and only two, ideal people to leave an HSA to – your spouse or a charity. Spouses and charities are the only ones who do not pay tax immediately on an HSA in the year of death.

Unfortunately for non-spouse, non-charity beneficiaries, the entire account becomes taxable income to the beneficiary in the year of death and loses its status as an HSA. This can cause a significant one-time spike in marginal tax rates and cause the beneficiary to lose (to federal and state income taxes) a significant amount of the HSA. This makes the HSA the worst tax basket to leave to non-spouse, non-charitable beneficiaries.

Spouses are allowed to continue the HSA as their own HSA, and thus can use it to grow tax-free wealth that can cover (or reimburse) qualified medical expenses.

If you are charitably inclined and unmarried, the HSA should be the first account you consider leaving some or all of to charity.

Taxable Accounts

Taxable accounts, including real estate and securities, are generally good assets to leave to beneficiaries because of the so-called “step-up” in basis. As a general matter, when a person dies, their heirs inherit assets in taxable accounts with a “stepped-up” basis. This gives the heirs a basis of the fair market value of the property on the date of death.

As a result, a beneficiary can generally sell inherited assets shortly after receiving them and incur relatively little, if any, capital gains tax.

A couple of additional notes. First, leaving appreciated taxable assets at death to heirs is much better than gifting such assets to heirs during your life. A quick example: William lives in a house he purchased in 1970 for $50,000. In 2019 the house is worth $950,000. If William gifts the house to his son Alan in 2019, Alan’s basis in the house is $50,000. However, if William leaves the house to Alan at William’s death, Alan’s basis in the house will be the fair market value of the house at William’s death.

Second, the step-up in basis at death benefits spouses in both “common law” states and community property states. In all states, separately held property receives a full step up in basis when inherited by a spouse. For residents of common law states, jointly held property receives a half step-up – the deceased spouse’s portion is receives a step-up in basis while the surviving spouse’s half does not. For residents in community property states, the entirety of community property receives a full basis step-up at the death of one spouse.

Conclusion

Generally speaking, in most cases spouses will prefer to inherit assets in the following order:

  1. Roth
  2. HSA
  3. Taxable
  4. Traditional

In most cases, non-spouses will prefer to inherit assets in the following order:

  1. Roth
  2. Taxable
  3. Traditional
  4. HSA

The best two tax baskets to leave to charities are HSAs and traditional accounts.

You can obtain significant tax benefits for your heirs by being intentional regarding which tax baskets you leave to which beneficiaries. Some relatively simple estate planning can save your heirs a significant amount of federal and state income tax.

FI Tax Guy can be your financial advisor! FI Tax Guy can prepare your tax return! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters.

Section 199A Examples and Lessons

Introduction

As this is being re-published (January 2021), we are in the third filing season of the new Section 199A qualified business income deduction. It is an area of the tax law that practitioners are still digesting.

I have previously written on the basics of the Section 199A deduction. This post builds on that introductory post. It provides analysis on rules from the IRS and Treasury and gives examples of how the deduction works in specific situations.

Takeaways

  • Deductions such as the deduction for one-half of self-employment taxes paid and the deduction for self-employed retirement plan contributions reduce the qualified business income (“QBI”) qualifying for the Section 199A deduction.
  • In many cases, Section 199A reduces the tax savings on traditional retirement plan contributions. Taxpayers may want to consider Roth employee contributions instead of traditional employee contributions to retirement plans because of this change.
  • Some taxpayers may want to prioritize contributions to traditional IRAs and HSAs instead of contributions to self-employed and small business retirement plans to maximize their Section 199A deduction.
  • Potentially powerful tax planning opportunities exist whereby taxpayers can reduce their taxable incomes such that they can go from no Section 199A deduction to a significant deduction. See Managing Taxable Income below for one example.
  • Many small businesses (including many sole proprietorships and S corporations) should not make charitable contributions, since these reduce qualified business income deduction. Rather, the owners of these small businesses should make charitable contributions in their own names.
  • The IRS and Treasury have provided a safe harbor under which rental real estate activities can qualify for the Section 199A deduction.
  • Dividends received from mutual funds and ETFs investing in domestic REITs can qualify for the Section 199A deduction.

Below are examples and commentary addressing Section 199A.

Side Hustler

Mike works a full-time job. His W-2 for 2018 reports $90,000 of wages. Mike also receives $1,000 of qualified dividend income (“QDI”) in his taxable account. Mike has a side hustle where he nets $10,000 in Schedule C profit. Mike pays $1,413 in self-employment tax on that profit. Mike claims the standard deduction.

Recall that the Section 199A deduction is the lesser of:

  1. 20 percent of your taxable income less your “net capital gain” which is generally your capital gains plus your QDI; or,
  2. 20 percent of your qualified business income (“QBI”).

The deduction for one-half of self-employment taxes is factored into the determination of QBI. Thus, in Mike’s case, his Section 199A deduction is the lesser of:

  • 20% of Taxable Income: 20% times ($90,000 plus $10,000 plus $1,000 less $707 less $1,000 less $12,000 = $87,293) = $17,459; or,
  • 20% of QBI: 20% times ($10,000 less $707 = $9,293) = $1,859

In this case, Mike’s Section 199A deduction is $1,859.

Mike’s taxable income is determined by deducting, for adjusted gross income, one-half of the self-employment taxes ($707) he pays with respect to his side hustle income. However, that deduction for half of his self-employment tax must also be subtracted in determining his QBI.

Note further that the Section 199A deduction does not reduce self-employment taxes. The Section 199A deduction is only an income tax deduction. It does not reduce the amount subject to self-employment taxes (in Mike’s case, $10,000).

Sole Proprietor with a Solo 401(k)

Lisa owns a sole-proprietorship that generates $100,000 of business income in 2020 as reported on Schedule C. Lisa pays $14,130 in self-employment taxes. Lisa contributed $19,500 to her traditional Solo 401(k), and makes an employer contribution to her traditional Solo 401(k) of $18,587. Lisa is married to Joe who makes $75,000 in W-2 wages. Lisa and Joe claim the standard deduction.

The deduction for retirement plan contributions is factored into the determination of QBI. Thus, in Lisa’s case, her Section 199A deduction is the lesser of:

  • 20% of Taxable Income: 20% times ($100,000 plus $75,000 less $7,065 less $19,500 less $18,587 less $24,800 = $105,048) = $21,010; or,
  • 20% of QBI: 20% times ($100,000 less $7,065 less $19,500 less $18,587 = $54,848) = $10,970

In this case, Lisa’s Section 199A deduction is $10,970.

QBI has the effect of making certain income “80% income.” What I mean by that term is that only 80% of the income is subject to income tax. This has a flip side – some deductions become only “80% deductions,” meaning that only 80% of the deduction generates a tax break.

Notice that the Solo 401(k) contributions reduce the QBI deduction. Thus, Solo 401(k) contributions are now “80% deductions” due to the QBI regime. For example, if your marginal tax rate is 22 percent, the marginal tax rate savings on your traditional 401(k) employee contribution is only 17.6 percent. But years later, when you withdraw the money from the Solo 401(k) the money will be “100% income.” You will not get a QBI deduction for those withdrawals.

I blogged more about the 80% deduction phenomenon here.

This will cause many sole proprietors to consider Roth Solo 401(k) employee contributions instead of traditional Solo 401(k) employee contributions, since the the tax savings on traditional self-employed employee contributions is reduced as a result of the QBI deduction.

Note further that for the Solo 401(k) employer contribution there is no choice to be made because there is no option to make a Roth employer contribution. All employer contributions must be traditional contributions.

Another observation: If Lisa and Joe had a low enough adjusted gross income (under $105,000) and Lisa made a deductible $6,000 contribution to a traditional IRA, that contribution would not have counted against her QBI. A contribution to a health savings account would also not have lowered her QBI.

For taxpayers whose Section 199A deduction is limited by 20% of QBI, contributions to traditional IRAs and HSAs should be favored over self-employment retirement plan contributions, since the IRA and HSA deductions are 100% deductions while the self-employment retirement plan contributions are 80% deductions. Hat tip to Jeff Levine who made the retirement plan contribution prioritization point on Twitter.

For taxpayers whose Section 199A deduction is limited by 20% of taxable income, contributions to traditional IRAs, HSAs, and self-employment retirement plans are all 80% deductions, and thus Section 199A normally does not factor into determining how to prioritize these contributions. However, all of these are tools taxpayers may be able to use to lower taxable income to qualify for a Section 199A deduction, as discussed in the Managing Taxable Income section below.

S Corporation

Assume the facts are the same as the previous example, except for the following differences. Lisa operates her business as a wholly-owned S corporation instead of as sole proprietorship. Before any sort of compensation, the S corporation makes $100,000. Assume that in this case, the S corporation pays Lisa $50,000 of W-2 wages, which is further assumed to be reasonable. Lisa makes employee contributions of $19,500 to her traditional Solo 401(k) from those wages. The S corporation makes the maximum employer contribution of $12,500 (computed as $30,500 of Box 1 W-2 wages plus $19,500 of elective deferrals times 25 percent). Thus, Lisa will have flow-through income from the S corporation (reported to her on a Schedule K-1) of $33,675 ($50,000 less $12,500 less $3,825 — the employer portion of the payroll tax).

Thus, in Lisa’s case, her Section 199A deduction is the lesser of:

  • 20% of Taxable Income: 20% times ($50,000 plus $33,675 plus $75,000 less $19,500 less $24,800 = $114,375) = $22,875; or,
  • 20% of QBI: 20% times ($33,675 — the QBI) = $6,735

In this case, Lisa’s Section 199A deduction is $6,735 because in the S corporation structure, the business income is split between a salary the S corporation pays her (which is not QBI) and the flow through profit of the S corporation, which is QBI (assuming it is domestic trade or business income).

The S corporation has various pros and cons from a tax perspective. Lower employment (payroll) taxes are a significant benefit, while lower maximum employer retirement plan contributions and lower Section 199A deductions are drawbacks.

Managing Taxable Income

Jackie is a lawyer operating as a sole proprietor. Law is one of several specified service trade or businesses (“SSTBs”) where the benefits of Section 199A are completely phased out if your taxable income exceeds $213,300 ($426,600 for married filing joint taxpayers using 2020 numbers). In 2020 Jackie has $240,000 of Schedule C income from the business. His self-employment taxes are $17,075 in Social Security taxes and $6,428 in Medicare taxes, for a total of $23,503 reported on Schedule SE. Jackie takes the standard deduction.

Jackie’s taxable income is thus $215,848 ($240,000 less $11,752 less $12,400). Because Jackie’s QBI is from an SSTB and his taxable income is above $213,300, he cannot claim any Section 199A deduction.

Now let’s add some tax planning to the scenario. Imagine that early in 2020 Jackie realizes he won’t qualify for the Section 199A deduction based on his numbers. He decides to open a Solo 401(k), which he can make an $19,500 employee traditional contribution to, and he can make an employer contribution of $37,500 for total contributions of $57,000 (the maximum allowed). This radically changes his Section 199A math, since (as will be demonstrated) his taxable income is now below $163,300. Once your income is below $163,300, you qualify for the Section 199A deduction only subject to the computational limits. Thus, in Jackie’s case, his Section 199A deduction is the lesser of:

  • 20% of Taxable Income: 20% times ($240,000 less $11,752 less $12,400 less $57,000 = $158,848) = $31,770; or,
  • 20% of QBI: 20% times ($240,000 less $11,752 less $57,000 = $171,248) = $34,250

Thus, Jackie’s Section 199A deduction is now $31,770! By managing his taxable income (by maximizing retirement savings), Jackie turned a $57,000 deduction into a more than $88,000 of deductions. Sure, the $57,000 deduction for retirement plan contributions is an “80% deduction,” but it creates the additional $31,770 of a Section 199A deduction (which is itself a “100 percent” deduction).

Jackie also lowered his marginal federal income tax rate from 35 percent to 24 percent and reduced his taxable income from $215,848 to $127,078!

Note that contributions to a health savings account would be another tool to deploy to lower your taxable income if you are concerned about Section 199A’s taxable income limitations.

Taxpayers bumping up against Section 199A taxable income limitations will likely need to prioritize traditional employee contributions to Solo 401(k) plans over Roth employee contributions. In addition, self-employed taxpayers bumping up against the taxable income limits in 2021 may want to establish 2021 Solo 401(k)s (if they are eligible to do so) to lower taxable income in order to qualify for the Section 199A deduction.

It will be wise for taxpayers to consult with tax advisors to run the numbers on Section 199A and other tax planning considering the complexity of the rules and the potential benefits of successful planning.

Charitable Contributions

The IRS gave us a bit of a head-scratcher in the instructions to the new Form 8995. The Form 8995 is used (starting with 2019 tax returns) to compute the QBI deduction. In the instructions, it states that charitable contributions reduce QBI.

Here is an example of how that rule would play out:

Cosmo is the sole shareholder of Acme Industries, an S corporation. In 2019, Acme reports QBI operating income of $100,000 to Cosmo on his Form K-1. It also reports $1,000 of charitable contributions made by Acme during 2019. The total QBI Cosmo can claim from Acme Industries is only $99,000, as the charitable contribution reduces QBI, according to the IRS. This is true even if Cosmo claims the standard deduction and thus has no use for the charitable contribution on his 2019 tax return.

Personally, I believe the IRS is on questionable ground in claiming charitable contributions reduce qualified business income. However, with some rather simple tax planning (which I generally believe to be prudent), you can avoid this issue altogether. If you want to make a charitable contribution, simply do so in your own name. Do not have your business — whether an S corporation, a small partnership, or a sole proprietorship, make the charitable contribution.

Rental Real Estate

The IRS and Treasury issued Notice 2019-7 and Revenue Procedure 2019-38 providing a safe harbor under which rental real estate activity can qualify for the Section 199A deduction. A safe harbor is a set of requirements, which, if satisfied, automatically qualify a taxpayer for a particular benefit. Stated differently, a safe harbor is a sufficient, but not necessary condition, to receive a benefit.

While rental activities that constitute a trade or business can still qualify for the deduction if they do not meet the requirements of the safe harbor, as a practical matter it will be much easier to sustain the deduction if you can qualify for the safe harbor.

Requirements

The requirements to satisfy the safe harbor with respect to any “rental real estate enterprise”  (a “RREE”) are as follows:

  • Separate books and records documenting the income and expenses of the RREE must be maintained.
  • At least 250 hours per year of qualifying activity must be done with respect to the RREE.
  • Starting in 2020, detailed records documenting the time spent on the RREE must be maintained (see Revenue Procedure 2019-38).
  • A statement electing the application of the safe harbor must be attached to the tax return.

Multiple Rental Properties

Rental property can be combined for purposes of determining if you have an RREE. However, residential and commercial real estate cannot be aggregated and must be kept separate. Thus, at a minimum if you own both commercial and residential property, you have two RREEs, and you must apply the tests to each separately to determine if each RREE qualifies for the safe harbor.

Qualifying Activities

In a bit of good news, the 250 hours can be done by the owner, agents, employees, and/or independent contractors. However, many activities do not count toward the 250 hours, including building and long-term redevelopment, finding properties to rent, and arranging financing. Qualifying activities include collecting rent, daily operation of property, negotiating leases, screening tenants, and maintenance and repairs.

Triple Net Leases

Triple net leases do not qualify for the safe harbor. For purposes of the rule, these include “a lease agreement that requires the tenant or lessee to pay taxes, fees, and insurance, and to be responsible for maintenance activities for a property in addition to rent and utilities.”

House Hacking

For those using house hacking to pursue financial independence, there are several considerations. If you house hack by renting spare bedrooms in your primary residence (tenants, Airbnb, etc.), then you do not qualify for the safe harbor with respect to the rent generated by your primary residence. However, if your house hack consists of renting out separate units in a single building, the rental income could qualify for the safe harbor if (i) those other units are separate residences and not your own residence for any part of the year and (ii) you otherwise satisfy the requirements of the safe harbor.

REIT Mutual Fund Dividends

Dividends from REITs and REIT mutual funds can qualify for the QBI deduction. Generally, box 5 of Form 1099-DIV will indicate those REIT dividends which qualify as Section 199A dividends.

Example

In 2018 Luke makes $50,000 from his W-2 job. He operates a sole proprietorship that generates a $4,000 taxable loss (which would have been QBI had it been net income). Luke also receives $3,000 of dividends from the Acme Real Estate Mutual Fund, which he holds in a taxable account. Acme’s Form 1099-DIV provided to Luke indicates in box 5 that $2,400 of the dividends are Section 199A dividends. Luke claims the standard deduction. In Luke’s case, his Section 199A deduction is the lesser of:

  • 20% of Taxable Income: 20% times ($50,000 less $4,000 plus $3,000 less $12,000 = $37,000) = $7,400; or,
  • 20% of REIT Dividends: 20% times $2,400 = $480

Thus, Luke’s Section 199A deduction is $480. He gets this deduction even though the dividend was paid by a mutual fund and even though he had a QBI loss. His QBI loss will carryover to 2019, and will reduce his 2019 QBI that potentially qualifies for the Section 199A deduction.

Lastly, note that if Luke held the Acme mutual fund shares in a retirement account (traditional and/or Roth IRA/401(k), etc.) or a health savings account, the REIT dividend would not have qualified for the Section 199A deduction.

Conclusion

Even as of January 2021, taxpayers and practitioners are learning new wrinkles in the Section 199A QBI deduction. For taxpayers with side hustles and small businesses, it can represent a significant income tax break. Some taxpayers will need professional help to determine how best to maximize the deduction.

Further Reading

I have written several blog posts addressing the Section 199A QBI deduction. Here are the links below:

Introductory Post

Section 199A and Retirement Plans

Read why the Section 199A QBI deduction may mean a Solo 401(k) is better than a SEP IRA

For the self-employed, the Section 199A QBI deduction may present an opportunity to do more efficient Roth IRA conversions.

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Cosmo Kramer and Financial Independence

I’m not aware that there’s ever been a television show or movie about a financially independent character. However, one particular character strikes me as embodying, if inadvertently, many aspects of FI – Cosmo Kramer of the hit comedy Seinfeld.

Two introductory points. First, I’m an avid fan of Seinfeld, but I’m no expert. I’m sure I’ll miss pertinent information in this post – please feel free to add relevant Seinfeld/Kramer info in the comments.

Second, financial independence is not Cosmo Kramer’s lodestar. Quirkiness is. Many things influenced the character, but none more so than his overwhelming quirkiness, which led to many laughs on the show.

Kramer’s Origin

Cosmo Kramer is based on Larry David’s former real life neighbor, Kenny Kramer. Actor Michael Richards put his own spin on the character. The first episodes feature a shut-in motiff for Kramer, but quickly the character became much more social and confident. Kramer believes he’s smarter than everyone else, but he does not brag about it. He simply presents his version of the world as if it is everyone else’s (it’s not).

Kramer does not have a job. In an early episode, The Truth, Kramer claims to not pay taxes. Jerry responds that it is easy not to pay taxes when you don’t have income. 

Kramer’s Finances

In The Visa, George gives some insight into Kramer’s financial situation. According to George, Kramer’s life is sort of like a fantasy camp, and he reveals the following nuggets about Kramer’s financial life: “Do nothing, fall ass-backwards into money, mooch food off your neighbors.”

Kramer may not be a millionaire. There’s no indication that Kramer simply sold a lucrative business and is now living off the proceeds. Kramer claims not to be a millionaire when he discovers Calvin Klein is selling a perfume called “The Ocean.” Kramer previously pitched a cologne named “The Beach” to Calvin Klein, and complains to Jerry that “I could’ve been a millionaire! I could’ve been a fragrance millionaire, Jerry!” when he believes Calvin Klein stole his idea.

Later, in The Van Buren Boys, Kramer sells his life stories to J. Peterman for $750 and hosts a get-together to celebrate his financial upturn. Even in the 1990’s, few thousandaires (much less millionaires) would assemble their friends to celebrate a $750 score, but Kramer is quirky enough to do it.

Kramer never seems very anxious financially, but on two occasions he doesn’t appear to have the liquidity to pay unexpected bills. In The Diplomat’s Club Kramer runs up a $3,200 debt gambling on airplane arrivals and departures. He calls Newman to provide a unique piece of U.S. Postal Service memorabilia as collateral so he can make one more bet. In The Seven, Jerry bills Kramer for all his mooching. In order to pay the bill, Kramer sells Newman a bicycle for $50. Perhaps when you have trouble covering an unexpected bill for $50 it’s normal to celebrate a $750 financial upturn . . .

Kramer did have a gambling addiction, but it generally appears to be under control throughout the series. During its rare flare-ups, Kramer either gambles with Jerry’s money or uses Newman’s most valuable asset as collateral.

While the show never uses “FI” to describe Kramer, it once featured the character retiring early to Florida. In The Wizard, Kramer retires (from what, the other characters have no idea) to Del Boca Vista after having sold the movie rights to his coffee table book about coffee tables. Sure enough, Florida living doesn’t agree with Kramer, and he moves back to New York. In the next episode, The Burning, Kramer has a part-time job as an actor portraying diseased patients for medical school students.

Kramer’s Professional Background

Little is known about Kramer from prior to the start of the Seinfeld series. He appears to have little particular business knowledge or training. In The Package, Kramer acknowledges that he does not know what a “write off” is. Assessing Kramer’s work product in The Bizarro Jerry, Mr. Leland surmises that Kramer has “no business training at all.”

Kramer worked at Brandt Leland

Kramer’s Lifestyle

Kramer is known for mooching off his neighbor Jerry. In The Dealership, he test drives a new car Jerry is considering. Kramer wants to know how long the car can run with the gas gauge on “E,” since he doesn’t “want to be the one responsible for purchasing costly gasoline” when borrowing Jerry’s car. Kramer frequently helps himself to Jerry’s food and beverages, thus keeping his grocery bill low.

Kramer appears to live a relatively low cost lifestyle. He wears vintage clothes and drives older cars. In The Nap he swims in the East River for exercise.

Kramer is not immune from frivolous and/or luxury purchases. He purchases a hot tub for his living room. He enjoys Cuban cigars, though he never pays cash for them. Initially, he obtains them from George (who received them as a gift from Mr. Ross). Later, Kramer barters with the Cuban consulate to obtain cigars in exchange for clothing.

One defining Kramer characteristic is that he’s always up for making some additional income. In The Beard he gladly accepts $50 to pose in a police lineup. In The Rye he drives a friend’s hansom cab in order to make $250 a day. In The Bookstore, Kramer and Newman attempt to operate a rickshaw business in New York. Kramer and Morty Seinfeld sell vintage raincoats in The Raincoats. 

Kramer frequently does odd jobs with his friend Mickey Abbott. In The Race, Kramer works as a Coleman’s department store Santa, with Mickey as his elf. In The Burning he and Mickey portray diseased patients for medical school students. In The Stand In he and Mickey work as stand-ins on All My Children. Mickey hooks Kramer up with a seat-filler job at the Tony Awards in The Summer of George.

Kramer is also an arbitrager. In The Bottle Deposit he and Newman collect bottles and cans in New York (where the refund is 5 cents a bottle and can) and plan to drive them to Michigan to collect a 10 cent refund per bottle and can. They joyfully sing “at ten cents a bottle and ten cents a can we’re pulling in $500 a man!!!”

None of these pursuits are what we would call a side-hustle. They are very “one-off” and do not create a consistent stream of income. To my mind, a great modern Seinfeld episode plot would be Kramer offering his services on Fiverr – that would give him odd jobs where hilarity would ensue.

Kramer at His Most FI

The Keys and The Trip (Parts 1 and 2)

In a three episode arc spanning from the end of Season 3 to the beginning of Season 4, Kramer moves to Los Angeles to pursue a Hollywood career. His motivation appears to be two-fold. He’s angry with Jerry over a dispute regarding spare keys, and he is genuinely interested in becoming an actor and producer. Kramer hitch hikes (after his car breaks down) and lives in a rather dilapidated apartment. He certainly isn’t flush with money in California, but he’s willing to sacrifice to pursue his Hollywood dream. Kramer’s is able to follow his dream because he is so financially independent. 

The Voice

In The Voice, Kramer establishes a corporation (Kramerica Industries), hires an intern, and earnestly attempts to invent a bladder system for tankers to prevent oil spills. He and his intern Darren even do some ill-fated research and development on the concept. When the idea fails, Kramer suggests an alternative invention – a bottle that dispenses both ketchup and mustard.

The Strike

Kramer’s back to work!

The Strike, known most for its Festivus angle, is where Kramer is at his most and at his least FI. Kramer receives a call that the strike is over. Apparently, he was an employee of H&H Bagels. Over a decade ago Kramer went on strike for $5.35 an hour. Since the minimum wage recently increased to $5.35 an hour, Kramer ends his strike and goes back to work. It’s the rare occasion where Kramer puts work ahead of his everyday quirky life, and his mindlessly going to work just because they now pay $5.35 an hour strikes me as very un-FI.

Later that episode, Kramer acts in a more FI manner. He strikes when his boss won’t let him take off to celebrate Festivus. Prioritizing Festivus over work is very FI (although obviously it’s much more quirky than it is FI). That said, simply leaving the job, instead of staging a strike and picketing, is the more FI path. Kramer eventually ends his strike, but not because of financial concerns. He caved because he really had to go to the bathroom.

How Did Kramer Achieve His Version of FI

It’s hard to understand why Kramer does not need to have a steady job and yet is quite comfortable. He certainly does not seem to have had a lucrative career, and he’s too young to be a pensioner. One would think the show would have mentioned it if he won the lottery. In The Maestro, Jerry tells Kramer that he’s surprised Kramer is “so litigious.” That quote seemingly rules out Kramer being the beneficiary of a lawsuit judgment or large settlement.

My best guess is that Kramer is the beneficiary of a trust, perhaps established by his father, an aunt or an uncle, or a grandparent. He has access to money, but his difficulty with coming up with money in a pinch in The Diplomat’s Club and The Seven indicates that perhaps he receives income to support himself but does not have access to significant assets. Thus, my best working theory is that Kramer is the beneficiary of a trust or otherwise has access to a stream of income, one that is sufficient but not overly generous. In terms of assets and liabilities, it appears that Kramer probably has a relatively modest amount of assets and little in the way of liabilities. 

Do you agree that Kramer embodies many aspects of FI? Are there other fictional characters that are financially independent?

Photo of Michael Richards by Alan Light

Tax Gain Harvesting

Last week’s post addressed the concept of tax loss harvesting – selling stock or securities (in a taxable account) to create a beneficial tax loss. This post addresses tax gain harvesting – selling stock or securities (in a taxable account) to create a beneficial tax gain.

Beneficial tax gain? How could it be good to create a taxable gain?

Fortunately, not all taxable gains create federal income tax. Below I discuss two scenarios where incurring a taxable gain may not increase a taxpayer’s current tax liability and would have other favorable consequences.

0% Capital Gains Tax

Under current law, some taxpayers pay a 0% federal income tax rate on long-term capital gains. Based on the new tax numbers effective after tax reform, more and more taxpayers will find themselves in relatively low marginal tax brackets.

Single taxpayers with a taxable income of $39,475 or less and married filing joint (“MFJ”) taxpayers with a taxable income of $78,950 are currently (using 2019 numbers) subject to a 0 percent federal long-term capital gains tax rate. Because the calculation is based on taxable income and not adjusted gross income, taxpayers get the benefit of the standard deduction (or itemized deductions, if greater). Thus, single taxpayers with adjusted gross income of $51,675 (including a standard deduction of $12,200) or less and MFJ taxpayers with an adjusted gross income of $103,350 (including the $24,400 standard deduction) or less qualify for the 0% federal capital gains.

This presents a great planning opportunity if the taxpayer has an appreciated security (such as a stock, bond, mutual fund, or ETF). Here is an illustrative example:

Example 1: Joe and Mary file their 2019 tax return MFJ. In 2019 Joe and Mary will together have $81,000 of W-2 wages. They have $1,000 of interest and dividends. They take the standard deduction (which is $24,400 for MFJ in 2019). Thus, their 2019 taxable income is $57,600 ($81,000 plus $1,000 less $24,400). Assume Joe and Mary own 100 shares of Acme Corp., which they purchased five years ago for $10 per share ($1,000 total). Assume further that the stock is worth $11,000 on December 1, 2019. Joe and Mary could sell the stock on December 1st, realize a taxable gain of $10,000 ($11,000 less $1,000 cost basis), thus increasing their taxable income to $67,600.

Since their taxable income is still $78,950 or less, the entire $10,000 capital gain is subject to the 0 percent federal capital gains tax. This result obtains regardless of whether Joe and Mary purchase 100 Acme shares two days later for $11,000. Unlike tax loss harvesting, which is subject to the wash sale rules, there are no wash sale rules as applied to taxable gains.

Why might Joe and Mary sell at a tax-free gain and then repurchase? While they don’t pay tax, they don’t save on their 2019 taxes. However, the sale/repurchase significantly increases their tax basis and decreases the taxable gain they will have on a future sale of Acme stock. There’s no way to know if a future sale of Acme stock will be subject to a 0 percent federal capital gains tax rate. By tax gain harvesting, Joe and Mary have dramatically increased their basis in the Acme stock from $1,000 to $11,000 tax-free. Thus, a future taxable sale will incur much less tax.

If, alternatively, Joe and Mary decide that they want to exit their Acme stock holding (thinking that perhaps its meteoric rise has concluded), tax gain harvesting provides them with a tax-free exit. Tax gain harvesting, if you qualify for a 0 percent capital gains tax rate, provides a way to reallocate your portfolio’s holdings without paying federal capital gains tax on appreciated holdings.

Caveats

Three caveats about tax gain harvesting are worth mentioning. First, the determination of whether your taxable income is low enough to qualify for the 0 percent capital gains rate includes the gain itself. Referencing Joe and Mary, if instead of $81,000 of W-2 wages, they had $100,000 of W-2 wages, their tax gain harvesting opportunity is dramatically decreased. In this case, their taxable income before the gain ($76,700 – computed as $100,000 plus $1,000 less $24,400)) appears to qualify for the 0 percent capital gains rate, once you add the $10,000 gain, the taxable income is $86,600, and the gain no longer qualifies for the 0 percent capital gains tax rate.

Second, the gain causes your “adjusted gross income” and “modified adjusted gross income” to increase, and thus have negative consequences on other preferential tax items, including deductions, credits, and qualifying for certain tax benefits. In some cases it may be worth it to run the numbers through a tax forecasting program and/or consult with a professional advisor before pulling the trigger to help understand the impacts on other parts of your tax picture.

Third, state income taxes must always be considered when tax gain harvesting. There are some states that impose no income tax, and thus there’s no problem. But in most states there is an income tax, and there’s no preferential rate for capital gains. States generally tax capital gains like any other type of income. Thus, there can be a (usually small) state income tax on capital gains triggered through tax gain harvesting.

Depending on the state, the tax rate on the harvested gain might be small enough to make tax gain harvesting still well worth it. In any event, it is always advisable to consider what the state income tax effects of potential tax gain harvesting will be before pulling the trigger.

Offsetting Losses

Another time it may be worth it to tax gain harvest is when you already have incurred a significant taxable loss during the taxable year. Here is an illustrative example:

Example 2: In March 2019, Eileen sold shares of the XYZ Mutual Fund and realized a $13,000 capital loss. She has no other capital gains or losses in 2019. If she does nothing else, she will be able to deduct $3,000 of the loss against her ordinary income and carryforward $10,000 of the capital loss to 2019. If Eileen owns shares in the ABC Mutual Fund with a $10,000 built-in gain, she could sell those shares in December 2019, incur no marginal federal or state income tax, and still claim a $3,000 capital loss on her 2019 federal income tax return.

Eileen is now positioned to realize the benefits of tax gain harvesting. She can either restructure her portfolio in 2019 with no additional tax cost on the ABC Mutual Fund gain, or can repurchase ABC Mutual Fund shares shortly after the sale and increase her basis by $10,000.

It is worthwhile to note that by tax gain harvesting here, Eileen does cost herself in tax in the future, since she won’t have the $10,000 capital loss carryforward to use to offset future capital gains (and up to $3,000 in ordinary income) in 2020 and beyond. Thus, tax gain harvesting to offset current year capital losses involves tradeoffs, and taxpayers considering it are often well advised to run the numbers through a tax forecasting program and/or consult with a professional advisor before pulling the trigger.

Conclusion

Those with appreciated assets in taxable accounts should consider tax gain harvesting. One or both of the following need to be true: the taxpayer is in a relatively low tax bracket or has a capital loss in the current taxable year. If either or both are true, there may be an opportunity to save on future capital gains taxes and/or restructure a portfolio at no or low tax cost. As always, it is best to run the numbers and/or consult with a professional advisor before pulling the trigger.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Tax Loss Harvesting

If you have individual stocks or other securities that have a loss in them, you may have a tax planning opportunity: tax loss harvesting.

First off, it is important to keep in mind that tax loss harvesting only applies to assets (such as stocks, bonds, mutual funds, ETFs, etc.) in taxable accounts. It does not apply to assets in retirement accounts and health savings accounts.

If you have assets in taxable accounts that have declined in value relative to your purchase price, you have an opportunity to tax loss harvest. Here’s a basic example:

Example 1: Mark purchased 100 shares of Kramerica stock two years ago for $100 a share ($10,000 total). Based on a disappointing test of an oil-tanker bladder system, Kramerica’s stock is now worth $70 per share. If Mark sells all 100 shares for $70, his total basis in the stock ($10,000) exceeds the amount he realizes on the sale ($7,000) by $3,000.

In Mark’s case, he has a $3,000 capital loss for tax purposes. Capital gains and losses from the sale of property (for most individuals, from securities) are different for tax purposes than other types of income, such as wages, rents, self-employment income, interest, and dividends (collectively, usually referred to as “ordinary income”). Federal income tax law does two things to capital gains and losses. First, it taxes capital gains at a lower tax rate than most other types of income. Second, and most importantly for the purposes of tax loss harvesting, it limits the ability of a capital loss to offset ordinary income.

Capital losses, such as Mark’s loss on Kramerica stock, can offset either capital gains or ordinary income, but only to the extent of $3,000 ($1,500 if the taxpayer files married filing separate) of ordinary income a year.

Thus, tax loss harvesting is a great play in two situations:

  1. A taxpayer has a large capital gain in a taxable year; and,
  2. A taxpayer has ordinary income and can trigger a $3,000 capital loss.

A second example can illustrate the first situation.

Example 2: Lucy sells stock with a historic cost basis of $30,000 for $50,000 in March. Thus, she will have to report a $20,000 capital gain on her tax return. If, however, Lucy has another stock/bond/mutual fund/ETF with a historic cost of $100,000 and a fair market value of $80,000, and she sells it by year-end, she will harvest the $20,000 loss in time to offset the previous $20,000 gain.

Taxpayers with significant capital gains during a year should review their taxable accounts towards year-end to see if there are any opportunities to harvest losses and offset existing capital gains.

For those taxpayers without capital gains, there still can be some opportunity to tax loss harvest.

Example 3: Edward anticipates making approximately $100,000 in 2021 in wages from his employer. If Edward can identify a stock/bond/mutual-fund/ETF with a built-in loss, he can sell the security and reduce his taxable income up to the lesser of the loss or $3,000 in 2021. If Edward owns the XYZ mutual fund with a historic basis of $5,000 and a current value of $2,000, he can sell it before year-end and reduce his taxable ordinary income from approximately $100,000 to approximately $97,000. The capital loss deduction is one taken on the first page of the Form 1040 and is not an “itemized deduction.” Thus, Edward gets the deduction regardless of whether he itemizes his deductions.

Note that Edward is limited in his ability to deduct capital losses in any one taxable year to $3,000. Let’s slightly revise the previous example.

Example 3A: The facts are the same as in Example 3, except the the stock Edward sells has a basis of $10,000. Thus, Edward’s current year capital loss is $8,000 ($10,000 basis less $2,000 sales price) instead of $3,000. However, Edward still can only deduct $3,000 because of the limit on taking capital losses against ordinary income. Thus, Edward’s 2021 taxable income is still approximately $97,000.

Edward can carry forward the excess unused capital loss ($5,000, which is the $8,000 actual loss less the $3,000 used loss) into future tax years. Thus, in 2022, he can offset capital gains and up to $3,000 of ordinary income by the $5,000 capital loss carried forward. If Edward has no capital gains or losses in 2022, he can deduct $3,000 of the $5,000 against his 2022 ordinary income, and then carryforward a $2,000 capital loss into 2023. Edward carries forward the capital loss until it is fully used.

Wash Sales

Tax loss harvesting sounds great, right? But with tax, there’s almost always a catch, and one exists here. The so-called “wash sale” rules.

They are best understood by understanding the concern they address. Say in our first Example Mark sells his 100 shares of Kramerica stock on December 15th to trigger the capital loss. Then on December 16th Mark buys 100 shares of Kramerica stock. Absent the wash sale rules, Mark has had no change in his overall economic position (he still owns 100 shares of Kramerica) yet he’s realized a $3,000 capital loss for tax purposes.

The wash sale rules step in to prevent this sort of gamesmanship. They disallow any loss on the sale of securities when the taxpayer buys the same or similar securities within the period starting 30 days before the loss sale and going through 30 days after the loss sale. The rule applies broadly. It applies to similar securities — for example, selling Vanguard’s S&P 500 index mutual fund at a loss and buying Fidelity’s S&P 500 index mutual fund. It applies to purchases of the same or similar securities by the taxpayer, the taxpayer’s spouse, and by entities controlled by the taxpayer and the taxpayer’s spouse. It can also potentially apply to purchases inside retirement accounts. The wash sale rule also bites to the extent of shares purchased through a dividend reinvestment program where the reinvestment occurs within the 61 day window described above.

Conclusion

Tax loss harvesting provides taxpayers a great opportunity to offset capital gains and possibly up to $3,000 of ordinary income. To work effectively for 2021, taxpayers must sell loss securities by December 31st and must be careful to avoid repurchasing the same or similar securities in a manner that triggers the wash sale rules and disallows the capital loss.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Tax-Efficient Charitable Giving

Introduction

Charitable giving is fantastic! Why not give some of your assets to improve a part of our world? And while you’re at it, why not save a few bucks in income taxes? As is to be expected, this requires some thoughtfulness. For some people, this can drive significant tax savings.

Lay of the Land after Tax Reform

The December 2017 tax reform legislation (often referred to as “tax reform,” the Tax Cuts and Jobs Act, or “TCJA”) significantly altered the landscape for claiming itemized deductions. For 2017, before tax reform became effective, the standard deduction for single taxpayers was $6,350 and $12,700 for married filing joint (“MFJ”) taxpayers. Thus, in order to claim itemized deductions, the taxpayer’s total itemized deductions (such as mortgage interest, state and local taxes, and charitable contributions) had to exceed these thresholds for the 2017 tax year. Many itemized simply because their state tax withholding alone put them in a position to equal or exceed these thresholds. This matters with respect to charitable contributions because if you don’t itemize, you don’t get any tax benefit for your charitable contributions.

Post tax reform, things are different. First, tax reform significantly increased the standard deduction. In 2018 the standard deduction increased to $12,000 for single taxpayers and $24,000 for MFJ taxpayers. Second, the deductible amount of state and local taxes (including individual income and property taxes) is capped at $10,000 per tax return. Thus, for MFJ filers and who paid $10,000 or more in state and local taxes still need $14,001 more in itemized deductions (mostly mortgage interest and charitable contributions) to itemize.

Thus, many will now find that they will take the standard deduction instead of itemizing. The downside is losing the tax benefits of charitable contributions. However, there are several planning opportunities whereby taxpayers can still reap significant income tax benefits of charitable contributions.

Donor Advised Fund (“DAF”)

Ideal for: People (a) with standard deductions very close to their itemized deduction amount or greater and (b) who makes regular, predictable (weekly, monthly, quarterly, or yearly) donations to charities or plan to donate to charities in the future.

How it Works and Tax Benefits: A donor establishes a donor advised fund with a financial institution that has established a charitable institution for the purpose of managing donor advised funds. The donor provides assets to the DAF. Then the donor “advises the fund,” meaning that he or she requests that the fund make disbursements to particular charities in particular amounts. While the institution in control of the DAF could, theoretically, reject the request, as a practical matter as long as the requested charity is a valid, properly registered section 501(c)(3) public charity, the DAF will send money to the charity. There is no explicit time requirement for the DAF to disburse its funds, and thus the DAF can make donations to public charities for several years.

The DAF gives the donor a significant tax benefit in today’s high standard deduction environment. The donor receives an upfront tax deduction for the fair market value of the assets contributed to the DAF in the year of the contribution. It is a way for a donor to bring forward, for tax purposes, the charitable deduction for contributions to a charity or charities occurring over several years. For tax purposes, the DAF aggregates several years’ worth of charitable contributions in a single year without a future tax cost, since the donor is covered by the high standard deduction in the later years when the DAF contributes to the charities.  

Example: Jane and Joe Smith attend Mass every Sunday at St. Joseph’s Catholic Church. Every time they attend Mass they put money in the collection basket as a charitable donation. In November 2018 Jane and Joe add up their projected 2018 itemized deductions (mortgage interest, state taxes, and charitable contributions) and project that they are at $24,000, exactly the same as the standard deduction. They anticipate their itemized deductions in 2019 will only be $18,000. If they make a $5,000 contribution to a DAF in early December 2018, their 2018 itemized deductions will increase to $29,000. Going forward until the DAF is exhausted, the DAF will make disbursements to St. Joseph’s instead of the Smiths making the contributions.

The contribution to the DAF provides the Smiths a significant tax benefit in 2018 ($5,000 reduction to taxable income) and will cost them nothing in 2019, since they will take the standard deduction for 2019 regardless. Forgoing 2019 tax deductions (by accelerating them to 2018 through the DAF contribution) did not cost Jane and Joe Smith any additional tax in 2019 and saved them tax in 2018.

If Jane and Joe were initially at $18,000 in 2018 itemized deductions instead of at $24,000, a $5,000 DAF contribution would not have made sense, because the Smiths would not have enough itemized deductions ($23,000) to exceed the standard deduction.  

Another DAF tax benefit for the donor is that income earned by the DAF (i.e., interest, dividends, and capital gains) is not taxable to the donor. That income increases the charitable impact of the original DAF contribution.

Some caveats: First, a transfer to a donor advised fund is an irrevocable transfer. While the donor retains the right to advise the DAF regarding disbursements to charities, the donor cannot reclaim the funds for him or herself. Second, the institution holding the DAF will charge fees against the DAF assets. Finally, institutions usually require a minimum initial contribution in order to form a DAF.

Donation of Appreciated Stock

Ideal for: Charitably inclined people owning appreciated stock, bonds, ETFs, or mutual funds.

How It Works and Tax Benefits: Donations of appreciated securities to an eligible charity allow the donor to deduct the entire FMV of the stock, up to 30% of adjusted gross income (“AGI”). Alternatively the donor can elect to deduct the basis of the stock, up to 60% of AGI. Further, the donor avoids recognizing the capital gain on the securities on his or her tax return. Thus, this strategy has a benefit from an income perspective (avoids recognition of a gain) and a benefit from a deduction perspective (the itemized charitable deduction).

For those looking to get rid of securities that no longer fit their desired investment portfolio, this can be a very tax efficient manner to do so.

Note that built-in loss securities should not be donated to charities. Rather, they should be sold first in order to trigger the capital loss for tax purposes, and then the proceeds should be donated to the charity.

Hyper Donor Advised Fund

Ideal for: Charitably inclined people owning appreciated stock, bonds, ETFs, or mutual funds that make routine charitable contributions or are interested in making future charitable contributions.

How It Works and Tax Benefits: The “hyper donor advised fund” (my pet name for this technique) simply combines the first two planning techniques.

Here is an example: Sammy owns 100 shares of Kramerica Industries. It is worth $50 per share ($5,000 total) and Sammy paid $5 per share ($500 total). Sammy has determined that he will have $11,000 of itemized deductions in 2018 and is likely to have no more than that in 2019 and 2020. Sammy plans to donate approximately $1,000 to his favorite charity, The Human Fund, annually.

Sammy can transfer the appreciated Kramerica stock to a DAF in December, 2018 and claim $16,000 of itemized deductions on his 2018 tax return without lowering his tax deductions in 2019 and 2020. Sammy also avoids recognizing on a tax return the $4,500 ($5,000 less $500 cost basis) gain he has in the Kramerica stock. The DAF can sell the Kramerica stock, invest the proceeds, and make, at Sammy’s recommendation, annual donations to The Human Fund.

Qualified Charitable Distribution (“QCD”)

Ideal for: (a) those 70 ½ or older and (b) those nearing age 70 ½ who cannot yet do a QCD, but should consider future QCDs when doing current tax planning.

How it Works and Tax Benefits: Donors 70 ½ years old and older can contribute up to $100,000 annually to charity directly from their traditional IRA without the amounts contributed being included in taxable income. The main advantage of this strategy is that the taxpayer’s “required minimum distribution” (“RMD”) can be satisfied by the QCD without a taxable income inclusion to the donor. While the donor does not receive a charitable deduction, that is made up for by excluding the amount of the QCD from taxable income. Given the new higher standard deduction, the taxpayer essentially gets the benefit of a charitable deduction without having to itemize.

While the QCD can satisfy the RMD, it does not have to – if a taxpayer has a RMD of $10,000 for the year but wants to make a $20,000 donation from their IRA to a charity, they can do so and the entire $20,000 amount qualifies for QCD treatment.

QCDs also present a planning opportunity for those not yet 70 ½ years old. Many do Roth Conversions (converting traditional IRAs and other traditional accounts to Roth IRAs) prior to age 70 ½ to reduce future RMDs. Doing so creates current taxable income, but lowers the future balance in the traditional IRA or 401(k) such that in the future RMDs are lower. For those charitably inclined, they may want to limit current Roth Conversions designed to mitigate future RMDs, since future QCDs can be used to eliminate the tax impact of RMDs in the future. Thus, charitably inclined individuals in their 60s may want to leave some amounts in traditional IRAs for future charitable donations. Then, when they turn 70 ½ they can make QCDs to avoid RMD taxable income.

It is important to note that to qualify for QCD treatment, the donor must be 70 ½ or older on the date of the distribution. Second, gifts to private foundations and DAFs do not qualify for QCD treatment. Third, inherited IRAs qualify for QCDs as long as the beneficiary inheriting the IRA is 70 ½ or older at the time of the distribution.

Lastly, the charity should never give any token gift of appreciation for the QCD donation because the receipt of anything in return for the donation disqualifies the distribution from favorable QCD tax treatment.

Bunching Contributions

Ideal for: Charitably inclined people with excess cash at year end.

How it Works and Tax Benefits: For taxpayers at or over the standard deduction threshold near year end, it may be advisable to make next year’s planned charitable donations this year to accelerate the tax deduction and take advantage of the next year’s higher standard deduction. Similar to some of the above techniques, the technique picks a year to itemize deduction and then picks a year (or years) to utilize the standard deduction in a manner the optimizes the total tax deductions taken over a period of time.

Charitable Remainder Trust

Ideal for: Wealthy charitably inclined people looking for a large current tax deduction, often in cases where they have a one-time significant income event, such as the sale of a significant asset or business or a very significant bonus.

How it Works and Tax Benefits: Taxpayers can contribute assets to a trust whereby the donor receives the income from the trust assets for a period of time and a designated charity receives the assets of the trust at the end of a period of years. This technique gives the donor a large upfront one-time deduction based on IRS rules.

This is generally not a strategy very applicable in the FI community, but for certain wealthy taxpayers looking for a significant tax deduction and willing to engage the right legal and tax professionals, it can create significant benefits.

Conclusion

Charitable giving illustrates the need to always consider whether there is a tax angle to a transaction. Contributions, if structured in particular way, can provide significant tax benefits while fulfilling their main purpose — the improvement of society and the advancement of the charity’s eleemosynary cause.  

FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Section 199A for Beginners

Introduction

Tax is a crucial consideration for those with small businesses and side hustles. A new tax provision, Section 199A, passed as part of Tax Reform in December 2017, gives many small business owners and side hustlers a deduction determined with respect to their “qualified business income” (or “QBI”).

So what’s going on? Why would you get a tax deduction for a certain type of income? The short answer is that the Section 199A deduction was needed to help level the playing field for small businesses (especially manufacturers) vis-à-vis large corporations. Tax Reform cut taxes for corporations (generally from 35 percent to 21 percent). To keep small businesses, many of which are taxed on individual tax returns at federal rates up to 37 percent, competitive with larger corporations, Congress enacted a partial deduction for qualified business income. The deduction has the effect of lowering the federal income tax rate on that income.

The QBI deduction also applies to so-called Section 199A dividends. Please see the discussion further below regarding Section 199A dividends.

Do I Qualify for the Section 199A Deduction?

The bad news is that, even for a tax rule, Section 199A is incredibly complex. The much better news is that most of that complexity applies to about 10 percent or less of taxpayers. For 90 plus percent of taxpayers, it isn’t too complicated!

To figure out if it is going to be complicated for you, ask yourself one question (all amounts as applicable for 2021):

Is my taxable income $164,900 or less?

If you’re married filing a joint tax return (“MFJ”), change the question to

Is my taxable income $329,800 or less?

For 2020, apply the above questions with $163,300 for single taxpayers and heads of household, and $326,600 for MFJ taxpayers. For 2021, married filing separate taxpayers use $164,925 as their number.

Remember, the key number is taxable income. Taxable income is your adjusted gross income less your standard deduction ($12,550 in 2021 for singles, $18,800 for heads of householder, and $25,100 for MFJ) or your itemized deductions. So if you take the standard deduction, you’re looking at adjusted gross income of $177,450 for singles, $183,725 for heads of household, and $354,900 for MFJ filers. Those are high thresholds for most Americans and for most of those seeking financial independence).

Section 199A Basic Calculation

If you answered Yes to your bolded question, your Section 199A deduction is computed based on a relatively simple (for tax) calculation. Your Section 199A deduction is the lesser of

  1. 20 percent of your taxable income less your “net capital gain” which is generally your capital gains plus your qualified dividend income (“QDI”) or
  2. 20 percent of your QBI.

Here are two examples to illustrate the calculation (all examples avoid discussing self-employment tax for ease of illustration):

Example 1: Phil has $100,000 of W-2 wage income, $1,000 of QDI from mutual funds owned in taxable accounts, makes $10,000 from a trade or business side hustle reported on Schedule C, and claims the standard deduction on his tax return. Phil’s Section 199A deduction is the lesser of

  1. 20% of Phil’s taxable income less net capital gain ($100,000 of wages, plus $1,000 QDI plus $10,000 of QBI less $12,000 standard deduction less $1,000 “net capital gain” – in this case, his QDI – equals $98,000. $98,000 X 20% = $19,600) or
  2. 20% of Phil’s QBI ($10,000 X 20% = $2,000).

Thus, Phil’s Section 199A deduction is $2,000, fully 20 percent of his side hustle income.

Example 2: Mary owns a sole proprietorship engaged in a domestic trade or business which earned $100,000 this year reported on Schedule C. Mary also earned $1,000 of QDI from mutual funds owned in taxable accounts and claims the standard deduction on her tax return. Mary’s Section 199A deduction is the lesser of

  1. 20% of her taxable income less net capital gain ($100,000 of Schedule C income plus $1,000 QDI less $12,000 standard deduction less $1,000 “net capital gain” – in this case, her QDI – equals $88,000. $88,000 X 20% = $17,600) or
  2. 20% of her QBI ($100,000 X 20% = $20,000).

Thus, Mary’s Section 199A deduction is $17,600, 17.6 percent of her sole proprietorship income.

Section 199A is great news for side hustlers and pretty good news for sole proprietors and other owners of flow-through businesses. Why the slight benefit reduction for our sole proprietor? The answer lies in the benefit of the standard deduction (or itemized deductions, if applicable). Since Mary already had the standard deduction protecting some of her QBI from full taxation, the Section 199A deduction was reduced to account for that benefit.

Note that if Mary had another source of income (other than long-term capital gains or qualified dividend income), such as a Roth conversion amount, or a spouse with income, that income would increase her taxable income limitation and she could qualify for up-to the full 20 percent QDI deduction.

What is QBI?

Now that we have the calculation illustrated, we must ask what is “qualified business income” (“QBI”)? Generally, QBI is domestic income from a trade or business (as defined under normal U.S. tax principles) received by a sole proprietor or by an individual from a “flow-through” business (a partnership, LLC, S-corporation, trust, or estate). Some important considerations:

  • QBI does not include wage income (W-2 income).
  • It is important to maintain documentation supporting that the activity is a trade or business.
  • It is important that the activity not be considered a hobby.
  • Rental income from the active conduct of a rental real estate trade or business is QBI. Income from the renting out of buildings where the owner is not engaged in a real estate trade or business is not QBI. Real estate may become a hot-spot for disputes between the IRS and taxpayers.

High Income Taxpayers

What if you answered No to your question? If you have QBI, you’re likely to need the assistance of a qualified tax professional. The rules get complicated quickly. For those with taxable income above $164,900 ($329,800 for MFJ, $164,925 for MFS), their Section 199A deduction is subject to a limitation and possibly a second additional limitation, as follows:

  1. For taxpayers over the taxable income thresholds, all QBI is subject to a limitation on the Section 199A deduction based on W-2 wages paid by the business and the unadjusted asset basis in the business. The more of these attributes, the greater the Section 199A deduction. Note that unadjusted asset basis is generally the acquisition cost of property. It includes tangible property (including buildings) but does not include land.
  2. Income from a specified service trade or business suffers an additional limitation. The Section 199A deduction for such income is phased out for taxable incomes between $164,900 and $214,900 ($329,800 and $429,800 for MFJ filers) (using 2021 numbers).

The preamble to the proposed regulations states that a “specified service trade or business” is (1) any trade or business involving the performance of services in the fields of health, law, accounting, actuarial science, performing arts, consulting, athletics, financial services, brokerage services, or any trade or business where the principal asset of such trade or business is the reputation or skill of one or more of its employees or owners, and (2) any trade or business that involves the performance of services that consist of investing and investment management, trading, or dealing in securities . . . partnership interests, or commodities.”

The general idea behind the specified service trade or business is that Congress wanted to prevent high earning doctors, lawyers, accountants, etc., from benefiting from Section 199A. Congress intended for the benefits to generally go to manufacturers.  Manufacturers will generally find themselves only subject to the first limitation, and many will have buildings and equipment with tax basis and/or will pay significant W-2 wages to employees and thus will not find the limitation to have much effect.

For those subject to these complex limitations, there can be significant benefits from doing planning and restructuring with the assistance of qualified tax advisors to maximize their Section 199A deduction. Such planning can include planning to increase current year tax deductions (through, for example, increased retirement plan contributions) to reduce taxable income below the relevant testing thresholds.

Section 199A Dividends and Income from Publicly Traded Partnerships

Qualified dividends from real estate investment trusts (“REITs”) (Section 199A dividends) and ordinary income from publicly traded partnerships qualify for the Section 199A deduction. There is no need for the taxpayer to be in a trade or business and there are no limitations based on taxable income. In terms of sheer volume, I expect more returns will claim this Section 199A QBI deduction than the QBI deduction for “normal” qualified business income discussed above.

It is important to note that dividends and other income received in tax advantaged accounts (IRAs, 401(k)s, HSAs, other retirement accounts) does not qualify for the Section 199A deduction.

Tax Reporting

Taxpayers report their QBI deduction on either a Form 8995 or a Form 8995-A (for the 2019 tax year and later). Box 5 of Form 1099-DIV (Section 199A dividends) reports the dividends that qualify for the QBI deduction.

Further Reading

I published a more detailed Section 199A post here. It provides more examples of the application of Section 199A.

I published a post discussing the Section 199A QBI deduction and how the concept interacts with small business retirement plans (click here).

I published a post on a potential planning opportunity available to some self-employed individuals to capitalize on the interplay of self-employed income, Roth conversions, and the Section 199A deduction here.


FI Tax Guy can be your financial advisor! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This posting is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here. 

Thoughts on Trump and Taxes

It happened. The frontrunner for the Presidency said “Sure, . . . why not?” when asked if he would eliminate the income tax on the Joe Rogan podcast. Whoa!!!

Okay, let’s calm down. Let’s not plan on never filing a tax return again just yet.

Tax planning is all about probabilities. Over the 2024 presidential campaign, probabilities have shifted. Below I’ll discuss the changing landscape, what it means for how Americans should approach their own planning (at year-end in 2024 and beyond), and a few thoughts on the future of American taxation.

Trump Tax Promises and Trend

Trump has been quite explicit with three individual income tax cut promises during the campaign:

  • No tax on tips
  • No tax on Social Security
  • No tax on overtime

Trump and his campaign have frequently mentioned these. It’s more than fair for the electorate to hold Trump to these promises.

Separately, Trump has been speaking quite fondly of tariffs. He did so during an interview with Dave Ramsey, which caught my attention.

I saw then what has become even clearer thanks to Donald Trump’s answer Joe Rogan’s question: the Trump Era would, to at least some degree, shift America away from income taxes and towards tariffs. 

I do not view Trump’s answer to Rogan as a promise. It was one line during a 3 hour interview. It should be taken seriously, not literally. Trump briefly stated it in response to Rogan’s question. Importantly, Trump then went into detail not on eliminating income taxes but rather on his fondness of tariffs.  

The above caveats aside, trend here is obvious. Much like with polling, trends matter much more than the top line. I have previously stated that tariffs might become very popular with politicians after Trump’s retirement. Voters don’t file tariff tax returns! That alone indicates future politicians might be more than happy to adopt pro-tariff positions, which could mean less in the way of income taxes. 

What this Means for Americans

Does a Joe Rogan episode radically change financial planning for most Americans? No. But considering the odds, I think it, combined with Trump’s other promises, gives us two insights to consider.

2024 Year-End Roth Conversions

First, there is little reason to rush year-end 2024 Roth conversions, particularly before Election Day. The conventional wisdom had been “better do those Roth conversions before taxes go up in 2026!” That conventional wisdom is now out the window. 

I generally recommend Roth conversions when they make sense for the individual based on the individual’s circumstances. I don’t recommend Roth conversions based on “conventional wisdom” about tax changes in 2026.

Question Paying Tax to Get Into Roth

I have been fond of traditional retirement account contributions. I didn’t think I would get evidence supporting that view from a Joe Rogan episode, but that’s where we are.

If future income taxes are trending down, why not take the deduction while it is valuable? That’s where we are going into the 2024 Election.

Does this mean we should never go Roth? No! But now we must start to question paying tax to get into Roth. 

Please don’t read this to say “oh wow, FI Tax Guy is against Roth.” Far from it! But I must question paying federal income tax in 2024 to get into Roth.

There are times we pay tax to get into a Roth. Contributing to a Roth 401(k) instead of to a traditional 401(k) is paying tax to get into Roth, because we have foregone the tax deduction that we could have received for a traditional 401(k) contribution. Taxable Roth conversions are another time we pay tax to get into a Roth.

There are times we don’t pay tax to get into a Roth. For most people, an annual Roth IRA contribution involves no additional tax, since most Americans do not qualify to deduct contributions to traditional IRAs. Backdoor Roth IRA contributions are the same – there’s no forgone tax deduction. “Taxable” Roth conversions against the standard deduction are another example where there’s no additional federal income tax incurred to get money into a Roth. 

To my mind, these “tax free” ways are the best way to get money into Roth accounts, and in this environment should be favored. 

My Proposal

Many questions and challenges remain regardless of the outcome of the Election. It remains to be seen how much revenue can be raised by tariffs. The 47th President must prioritize significant cuts to federal spending, particularly foreign military spending. Oh, and the federal government has over $35 trillion of accumulated debt.

We are a long way away from axing the individual income tax. But, perhaps a relatively modest measure could get many Americans there. I propose doubling the standard deduction. The IRS just announced the 2025 standard deduction will be $15,000 for singles and $30,000 for married filing joint couples. Why not double it to $30K for singles and $60K for marrieds?

My proposal achieves some great outcomes. Combined with no taxes on Social Security, a doubled standard deduction would eliminate income taxes for most retired Americans. Trump could say he eliminated millions of tax returns with this one change.

Doubling the standard deduction would be a significant tax cut for millions of working Americans. Further, it would greatly reduce the number of Americans claiming itemized deductions, making the tax code easier to administer for the Internal Revenue Service.

Lastly, a government with $35 trillion plus of debt probably shouldn’t stop taxing the Elon Musks of the world. My proposal keeps taxing him and is no tax cut for him at all (assuming he makes more than $30,000 annually in charitable contributions). 

Assuming Congress passes significantly increased tariffs in 2025, I recommend a five year doubling of the standard deduction. That would give the government five years to test out the new system to see if increased tariffs and decreased income taxes, hopefully in concert with significant spending cuts, is successful. 

Conclusion

I will cry no tears if the income tax goes away. However, I don’t think we can plan for its demise.

While the income tax is likely here to stay, the trend is becoming obvious. Tariffs are likely on the way up and income taxes are likely on the way down. That informs retirement and tax planning. There’s little reason to rush Roth conversions, and traditional retirement account contributions are more attractive.

Of course, stay tuned. The Election is not over. There are no guarantees as I write this on October 26, 2024. I promise I’ll have plenty of commentary about year-end planning and more after the Election.

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Using IRAs to Pay Income Taxes In Retirement

It’s the fourth quarter. Now is a great time to check and see if you are on pace to have enough federal and state income tax paid in for 2024.

It happens: people get to the end of the year and see they are severely underwithheld. What do you do in such a situation?

This post explores using IRAs to pay income taxes and explores a novel approach: using a 72(t) payment plan to pay income taxes. 

Income Tax Withholding Requirements

Before we discuss curative tactics, let’s briefly review the requirements. In order to avoid an underpayment penalty for 2024, on must pay in, either through withholding (could be W-2 or 1099-R, we’ll come back to that) or quarterly estimated tax payments, either (or both) 90% of the current year’s tax liability or 100% of the prior year’s tax liability. These are the two so-called “safe harbors.” For those with an adjusted gross income of more than $150,000 in the prior year, that 100% safe harbor increases to 110%.

The 100%/110% safe harbor protects the late-in year lottery winner (among others). As long as he or she has withholding or estimated tax payments that meet 100% or 110% (as applicable) safe harbor, he or she can have millions or billions of dollars in income, meet the safe harbor requirements, avoid the underpayment penalty and pay most of the 2024 tax by April 15, 2025. 

Estimated tax payments are great, but they require early in the year action not possible in the fourth quarter. To meet the safe harbor, generally one quarter of the total amount due under the safe harbor must be paid by April 15th, June 15th, September 15th, and the following January 15th. That’s great, but for those who didn’t make the first three payments going into the fourth quarter, estimated tax payments may not be all that helpful at this point. 

Most states with an income tax have rules that mirror the federal income tax withholding rules, but some states have differences. 

The Retiree’s Secret Weapon for Estimated Tax Payments

Retirees have a secret weapon for making income tax payments, particularly late in the year. IRAs! 

People miss paying taxes during the year. It happens for a variety of reasons. If I were a retiree and I found myself underpaid for either (or both) federal and state income taxes purposes in the fourth quarter, the first place I would look to make an estimated tax payment would be a traditional IRA. 

Why?

Because income tax withheld from a traditional IRA is deemed paid equally to the IRS throughout the year regardless of when the withholding occurs. 

IRA owners can initiate a distribution from their traditional IRA and direct that most of it be directed to the IRS and/or the state taxing authority. That withholding is treated as if it is paid equally throughout the year regardless of whether it occurs on January 5th or December 21st.

That’s pretty good! A late in the year IRA distribution withheld to the IRS can meet either (or both) the 90% safe harbor and/or the 100%/110% safe harbor. 

The downside is that it creates taxable income. In many cases, it turns out retirees are rather lightly taxed. As long as the retiree had a relatively low income tax burden either last year or this year, the taxable withdrawal won’t be a large number, because the applicable required safe harbor withholding will be modest. Thus, the tax hit on the mostly withheld distribution should be rather modest. 

Another advantage of using a traditional IRA to pay income taxes is RMD mitigation. While I believe the concerns around RMDs are wildly overstated, RMD mitigation is a perfectly valid financial planning objective and a good outcome. 

Using an IRA to Pay Income Taxes Under Age 59 ½

You may now be thinking “Sean, that’s a great idea for those over age 59 ½. But what if I’m under age 59 ½? Won’t I be subject to the 10% early withdrawal penalty on the amount I fork over to the IRS?”

That’s an excellent thought! Fortunately, the answer to your questions is “maybe.”

The IRS maintains a list of exceptions to the 10% early withdrawal penalty. Many will not be applicable to most retirees. But there are some options–let’s explore two of them: Inherited IRAs and 72(t) payment plans. 

Inherited IRAs

Beneficiaries of inherited IRAs never pay the 10% early withdrawal penalty with respect to distributions from their “inherited IRAs.” Thus, the inherited IRA is a great place to look to pay taxes from late in the year.

The only downside is the distribution to the IRS or the state taxing authority is itself taxable to the beneficiary. However, the money in the inherited IRA has to come out eventually (usually under the 10 year rule at a minimum), so why not whittle the traditional IRA down by using it to pay income taxes and avoid an underpayment penalty?

72(t) Payment Plan to Pay Income Taxes

Could someone start a 72(t) payment plan to pay required income taxes? Absolutely, in my opinion. It might even be a good idea!

72(t) Payment to Pay Income Taxes Example

Homer and Marge both turned age 56 in the year 2024. They retired early in 2023 and thus had some W-2 income and some investment income in 2023. They had approximately $120K of adjusted gross income in 2023 and thus paid approximately $8,800 of federal income taxes in 2023 (see Form 1040 line 24 less most tax credits — see the comment below) and $2,000 of California income taxes in 2023. 

In 2024 they have ordinary income below the standard deduction and taxable income below the top of the 12% federal income tax bracket. Thus, they owe no federal income tax and a very small amount of California income tax for 2024. They’ve made no estimated tax payments.

In August 2024 they decided to sell their Bay Area home worth $2M to move to a more rural part of California. The sale closed in October 2024 and they had a $500,000 basis in the home. Qualifying for the $500K exclusion, this triggers a $1M taxable long term capital gain to Homer and Marge in 2024. D’oh! 

Very, very roughly, the capital gain creates approximately $175K of federal income tax, $30K of federal net investment income tax, and $100K of California income tax. Note also that the proceeds from the home sale are likely to cause some taxable income in December 2024, but let’s just use the above three tax numbers for illustrative purposes only. 

One of their other assets is a $2M traditional IRA. They have no inherited retirement accounts but they do have some taxable brokerage accounts. To my mind, there are four main ways Homer and Marge can avoid an underpayment penalty.

Option 1: Q4 Estimated Tax Payments

Homer and Marge could make substantial fourth quarter estimated tax payments out of their taxable brokerage accounts by January 15, 2025. They would owe 90% their entire 2024 tax liability at that time and would need to use annualization on the Form 2210 to avoid an underpayment penalty. 

Compared to the other three methods described below, this costs them 3 months of interest on about $275K. In today’s interest rate environment, that is about $2,700 of interest in an online FDIC insured savings account.

Option 2: IRA Regular Distribution

Homer and Marge could, no later than December 31st, trigger a distribution from one of their traditional IRAs, say for $11,100. They could direct the institution to send $8,880 (80%) to the IRS, $2,109 (19%) to the California Franchise Tax Board, and $111 (1%) to themselves (the intuition will likely require they take at least 1% of the distribution). This creates $11,100 more taxable income (taxed at a low federal rate due to income stacking).

The advantage is this qualifies for the safe harbor, meaning Homer and Marge don’t have to pay most of their 2024 income tax until April 15, 2024. The downside to this is it triggers a 10% early withdrawal penalty ($1,110) payable to the IRS and a 2.5% early withdrawal penalty ($278) payable to California. 

Option 3: IRA Regular Distribution and Rollover

This option is the IRA Regular Distribution option plus refunding the $11,100 traditional IRA distribution to the traditional IRA from their taxable accounts within 60 days. This has all the same advantages as the IRA Regular Distribution option plus it reduces 2024 taxable income by $11,100 and avoids the early withdrawal penalties.

Gold, right? My view: I tend to disfavor this tactic. Why? Americans are limited to one 60 day rollover from an IRA to an IRA every 12 months. My personal opinion is that pre-age 59 ½ retirees are usually better served to keep that option on the table. You never know when a significant sum will pop out of a traditional IRA. It will be good to have the option to put that money back into the traditional IRA. If Homer and Marge do the $11,100 IRA Regular Distribution and Rollover, they are locked out from the ability to do a 60 day IRA to IRA rollover for the next 12 months.

Option 4: 72(t) Payment Plan

This option is simply the IRA Regular Distribution option as part of a 72(t) payment plan. The advantage of adding the 72(t) payment plan is avoiding the 10% early withdrawal penalty (federal) and the 2.5% early withdrawal penalty (California). 

Here’s how it works. Before making the $11,100 IRA withdrawal, Homer and Marge do a 72(t) distribution calculation and have their financial institution set up a $172,116.10 72(t) IRA. Here is the 72(t) fixed amortization calculation:

ItemAmountSource
Interest Rate5.00%Notice 2022-6
Single Life Expectancy Years at Age 5630.6IRS Single Life Table
Account Balance$172,116.10
Annual Payment$11,100.00

Homer and Marge then take the distribution from the 72(t) IRA prior to the end of 2024, directing 80% to the IRS and 19% to the Franchise Tax Board.

You say, but wait a minute, now they have $11,100 they have to take annually for each of the following four years. I say, well, okay, they have $2M in tax deferred accounts, why not take some of that without a penalty (perhaps as a form of the “Hidden Roth IRA”) and whittle down future RMDs a bit? 

That said, Homer and Marge can drastically reduce the annual 72(t) payment if they want with a one-time change to the RMD method. Assuming the 72(t) balance on December 31, 2024 is $164,000, here’s what the 2025 taxable RMD from the 72(t) could look like:

ItemAmountSource
Account Balance$164,000
Single Life Expectancy Years at Age 5741.6Notice 2022-6 Uniform Life Table
2025 Payment$3,942.31

One would hardly expect that $4,000 of taxable income would derail Homer and Marge’s tax planning in retirement. Further, they can direct most of that $4,000 to the IRS and Franchise Tax Board to help take care of 2025 tax liabilities, if any. 

Conclusion

For those under age 59 ½, a 72(t) payment plan might be the answer to an underpayment of estimated taxes problem. It is a bit of an “out of the box” solution, but it has several advantages. It allows some taxpayers to delay paying significant amounts of tax until April 15th of the following year by qualifying the taxpayer for the 100% of prior year tax safe harbor. Second, it avoids the 10% early withdrawal penalty. Third, it avoids the once-every-twelve-months 60 day rollover rule. Lastly, a 72(t) payment plan is rather flexible and the required taxable distribution in future years can be significantly reduced by a one-time switch to the RMD method. 

The above said, the first IRA I would look to if I was under age 59 ½ and looking to pay estimated taxes is an inherited IRA. Those are never subject to the early withdrawal penalty and can always be accessed in a flexible manner. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on X: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters.Please also refer to the Disclaimer & Warning section found here.

Inherited Retirement Account Rules Need Radical Reform

My hope is that 2025 ushers in an era of simplification when it comes to all federal laws. Justice Neil Gorsuch co-wrote a book arguing we have far too many laws, and I agree with him. The more numerous the laws, the more corrupt the state.

One area that is insanely and needlessly complicated is the inherited retirement account rules. What happens when someone inherits a traditional IRA, Roth IRA, and/or qualified workplace retirement account? It depends on far too many factors and there are far too many potential outcomes! As just one example, financial planner Jeffrey Levine came up with a flow chart of possible outcomes when a successor beneficiary inherits a retirement account. 

That Mr. Levine could come up with such a flow chart is an absolute disgrace (to the government, not to Mr. Levine). 

Complexity in our tax and retirement account laws shifts power away from ordinary Americans towards lawyers, accountants, advisors (such as me), and the IRS. Let’s shift some power back to ordinary Americans!

It’s time to radically simplify and reform the inherited retirement account rules. 

Current Inherited Retirement Account Rules

Upon the death of the owner of an IRA or qualified plan, the following are potential outcomes in terms of potential inherited retirement account distribution rules:

  • Spousal Rollover
  • Required Minimum Distributions (“RMDs”)
  • 10 Year Rule
  • 10 Year Rule with RMDs
  • 5 Year Rule

Woah! That there are so many possible outcomes, which require significant analysis to determine, is absolutely ridiculous and an unnecessary burden on American taxpayers.

Proposed Inherited Retirement Account Reform

I propose that the current voluminous, complicated inherited retirement account rules be scrapped. They should be replaced by the following simple rules, all effective January 1, 2025 unless otherwise noted.

  1. At the decedent spouse’s death, any retirement account left to a spouse becomes the surviving spouse’s retirement account in the surviving spouse’s own name automatically and immediately upon death.
  1. All other beneficiaries inherit an inherited retirement account which must be emptied within 10 full years following the owner’s death with no RMDs in years 1 through 9. 
  1. The death of a spouse entitles the surviving spouse to a permanent exception to the Section 72(t) 10 percent early withdrawal penalty with respect to distributions from any retirement account.
    • This applies even if the widow/widower remarries.
    • For fairness and simplicity, this applies even if the spouse died prior to 2025. 
  1. Any inherited retirement account a widow or widower treats as an inherited retirement account instead of a spousal rollover account as of the end of 2024 automatically becomes the surviving spouse’s own retirement account in their own name as of January 1, 2025. 
  1. The death of the beneficiary of an inherited retirement account does not change the clock. Successor beneficiaries must empty the inherited retirement account by the end of the 10th full calendar year following the original owner’s death.
  1. Existing inherited retirement accounts (as of the end of 2024) are no longer subject to both the 10 year rule and RMDs. For 2025 and beyond, such accounts are subject to only the 10 year rule.
  1. For fairness and simplicity, any retirement account inherited prior to 2025 subject to a 5 year rule will switch to the 10 year rule (measured as of the owner’s date of death).
  1. Reset Day for Inherited Retirement Accounts Subject to an RMD in 2025: If the original owner died in 2024 or earlier and the inherited retirement account is subject to only an RMD in the year 2025 (under any of the old rules), the inherited account will become subject to the 10 year rule, and no longer be subject to RMDs (both as of 2026), as if the original owner died on December 31, 2025. 
    • The 2025 New Year’s Eve Reset Day applies to both beneficiaries and successor beneficiaries, including those who become successor beneficiaries during 2025.

Simplification

After my proposed reform, there will be two and only two potential treatments for an inherited retirement account: spousal rollovers for spouses and the 10 year rule for everyone else. Note: It takes 8 rules to get to a 2 rule system because in order to get to a 2 rule system there needs to be rules to account for the transition from a very complex system to an understandable system.

Replacing the existing rules with the above 2 rule system would significantly reduce the amount of federal regulations and reduce complexity. Congress stumbled into a great inherited retirement account rule in the SECURE Act: the 10 year rule. It’s time to make that the rule for all inherited retirement accounts except spousal rollovers. 

Rules 4, 7, and 8 are simplification and consistency measures. They logically transition the inherited retirement accounts rules to a single, uniform system with only two outcomes: a spousal rollover or the 10 year rule. 

Rapid Transition

I propose a rapid, though not overnight, transition to a uniform system. Assuming a bill is passed in early to mid-2025, 2025 can be a transition year and then by New Year’s Day 2026 all inherited retirement accounts would be on the new system, meaning all inherited retirement accounts, regardless of when inherited, would be subject to only one of two rules as of New Year’s Day 2026.

Protecting Young Widows and Widowers 

Rule 3 is needed to avoid reform harming pre-age 59 ½ widows and widowers. Under today’s rules, surviving spouses can elect to treat a spouse’s retirement account as an “inherited” account instead of doing a spousal rollover. That inherited treatment avoids the 10 percent early withdrawal penalty on pre-age 59 ½ distributions. 

If pre-age 59 ½ widows/widowers must do a spousal rollover (as I propose), they would be subject to the 10 percent early withdrawal penalty if they took taxable distributions prior to their 59 1/2th birthday. To avoid that outcome, why not make becoming a widow/widower an automatic, permanent exception to the 10 percent early withdrawal penalty?

Transition Entirely to a New Uniform System

Reform should clean the slate of complexity. Without rules 4, 7, and 8, there would be separate systems of rules for retirement accounts inherited prior to 2025 and those inherited in 2025 or later. There’s no need for two separate systems of rules. These three rules make the rules simple for all inherited retirement accounts going forward.

A Small Net Tax Increase

Rule 8 is a modest tax increase, mostly falling on the wealthiest Americans. Considering the hope that 2025 will bring some popular tax cuts, such as eliminating taxes on tips and Social Security, it is good to have at least some logical tax increases in 2025 that would not significantly impact ordinary Americans. Note also that rules 2 and 5 are also likely to be small tax increases while rules 3 and 7 are likely to be small tax cuts. 

Regardless of the likely very modest net tax effect, the simplicity brought by this new system would greatly benefit the administration of the tax rules and ordinary Americans. 

Rule 8 Transition Examples

Rule 8, eliminating inherited retirement account RMDs and switching to a 10 year rule as of 2026, is key to transitioning old inherited retirement accounts to the new, uniform system for taxing inherited retirement accounts. Here are three examples of how it would work.

Example 1: In 2017 Jock died and left his $1M traditional IRA to his son JR. JR, 23 years younger than Jock, turned 40 in 2017. JR started taking traditional IRA RMDs based on the IRS Single Life Table in 2018. In 2022 he redetermined the RMD factor such that by 2025 the factor was 37.8 (start with 44.8 for 2018 theoretically, subtract one annually to get down to 37.8 for 2025). For 2025, JR must take his RMD under the old rules (which still apply) by dividing the inherited traditional IRA 12/31/2024 balance by 37.8 and taking that amount by December 31, 2025. In 2026 JR becomes subject to the 10 year rule by Jock’s deemed death on December 31, 2025. Thus, JR has until the end of 2035 to empty the inherited traditional IRA. He has no RMDs other than in 2035 (the entire remaining balance).

Example 2: In 2022 Huey died and left his $1M traditional IRA to his brother Earl. Earl, two years younger than Huey, turned 66 in 2022. Earl, an “eligible designated beneficiary” under the SECURE Act, started taking inherited traditional IRA RMDs based on the IRS Single Life Table in 2023. For 2025, Earl must take his RMD under the old rules (which still apply) by dividing the inherited traditional IRA 12/31/2024 balance by 19.2 and taking that amount by December 31, 2025. In 2026 Earl becomes subject to the 10 year rule by Huey’s deemed death on December 31, 2025. Thus, Earl has until the end of 2035 to empty the inherited traditional IRA. He has no RMDs other than in 2035 (the entire remaining balance).  

Example 3: In 2017 Al died and left his $1M traditional IRA to his son Barry. Barry has taken RMDs annually. During 2025 Barry dies and Carl becomes the successor beneficiary. In 2026 Carl becomes subject to the 10 year rule (as Al is deemed to have died December 31, 2025) and Carl has until the end of 2035 to empty the inherited traditional IRA. He has no RMDs other than in 2035 (the entire remaining balance).  

Conclusion

The inherited retirement account rules are mindlessly and needlessly complicated. The complexity creates confusion shortly after the death of a loved one. Enough is enough!

It’s time for greatly simplified inherited retirement account rules. That simplifying these rules might help fund popular tax cuts such as eliminating taxes on tips and Social Security is the cherry on top of a great tax reform proposal. 

Follow me on X at @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, legal, investment, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, legal, investment, and tax matters. Please also refer to the Disclaimer & Warning section found here.

Note that a version of this proposal will be posted to the crowd sourced policy website PoliciesforPeople.com. The views reflected in this post are only those of the author, Sean Mullaney, and are not the views of anyone else.

72(t) Payment Plan With a 401(k)

I’ve talked about what I refer to as a “72(t) IRA” both here on the blog and on my YouTube channel.

What I haven’t talked much about, until now, is a 72(t) payment plan coming out of a 401(k). Is it possible? Does it make sense? 

Inspired by a comment on a recent video, I’m breaking down taking 72(t) payments from a 401(k) in this post. As you will see, when compared with the 72(t) IRA, the 72(t) 401(k) has significant disadvantages. 

401(k) Plan Rules

Can you do a 72(t) out of your 401(k)? The answer is “maybe.” Qualified plans, including 401(k)s, have all sorts of unique rules. They vary plan to plan.

There’s no guarantee that you can access partial withdrawals from a 401(k) in accordance with a 72(t) payment plan after a separation from service. 

By contrast, IRAs allow for easily accessible partial withdrawals regardless of age. 

Must Separate From Service

There’s a tax rule to consider: one can only do a 72(t) payment plan from a 401(k) or other qualified plan after a separation from service from the employer.

From a planning perspective, this is not much of an issue. Few would want to do a 72(t) payment plan while still working, as taxable withdrawals from a 401(k) are not ideal if one still has significant W-2 income hitting their tax return. 

72(t) Account Size

According to Notice 2022-6, the 72(t) account balance for the fixed amortization calculation must be determined in a reasonable manner. See Section 3.02(d). The Notice goes on to state that using a balance of the account from December 31st of the prior year through the date of the first 72(t) distribution is reasonable. One should document, usually with an account statement, the balance they are using to have in case the IRS ever examines the 72(t) payment. 

Account size is one area where a 72(t) IRA is generally preferable to a 72(t) 401(k). As Natalie Choate observes in her classic Life and Death Planning for Retirement Benefits (8th Ed. 2019), an IRA can be sliced and diced into two or more IRAs, allowing one to take a 72(t) payment from a smaller IRA and remain flexible, in part through having a non-72(t) IRA as well. This flexibility is generally not possible with a 401(k) or other qualified plan. See Choate, page 595. That means without a transfer to an IRA first, the 401(k) account holder is generally stuck with an account size for the fixed amortization calculation, other than the bit of wiggle room given by Notice 2022-6 Section 3.02(d). Further, the entire account is subject to the locked 72(t) cage. 

72(t) Locked Cage

A 72(t) 401(k) is entirely subject to the many restrictions on 72(t) retirement accounts. When one uses a 72(t) IRA, they often can have a 72(t) IRA and a non-72(t) IRA. This means less of their retirement account portfolio is subject to the 72(t) rules “locking the cage.” For example, the non-72(t) IRA can be used to accept other IRA roll-ins.

72(t) 401(k) Example

An example can illustrate the problems involved in using a 72(t) 401(k) instead of a 72(t) IRA.

Bob wants to retire early in 2024 at age 53. He has some rental real estate that will generate $40,000 of positive cash flow annually and needs $50,000 more annually from his retirement account to support his lifestyle. He has a $2,000,000 401(k) at his current employer. He sets up a 72(t) 401(k) instead of rolling out to a traditional IRA and establishing a non-72(t) IRA and a 72(t) IRA. 

Size: $2,000,000

Life Expectancy: 33.4 (see the IRS Single Life Table)

Payment: $50,000

Solving for interest rate, we get an interest rate of -1.015124%.

Notice that in order to generate a $50K annual payment out of a $2M 401(k), Bob must use a negative interest rate. Bob can’t simply ask his 401(k) administrator to establish two separate 401(k) accounts for him and then use a positive interest rate for the 72(t) payment plan. 

72(t) Negative Interest Rate

This raises an issue: can a taxpayer use a negative interest rate for a 72(t) payment plan under the fixed amortization method? I believe the answer is Yes. Notice 2022-6 Section 3.02(c) allows an interest rate “that is not more than the greater of (i) 5% or (ii) 120% of the federal mid-term rate (determined in accordance with section 1274(d) for either of the two months immediately preceding the month in which the distribution begins)” (emphasis added). 

In my opinion, that wording in no way precludes using a negative interest rate for a 72(t) payment plan. Further, I see no compelling reason for the IRS to be concerned about using a negative interest rate. That said, there is at least some uncertainty around the issue. 

The issue is entirely avoided if Bob rolled out to a traditional IRA and then split that traditional IRA into two IRAs. He could have a 72(t) IRA of about $804K generating an annual $50K payment (using a 5% interest rate) and a non-72(t) IRA of about $1.196M. From a planning perspective, it’s certainly my preference to avoid the issue by using the 72(t) IRA. 

72(t) Structuring Alternative

As a structuring alternative that might be available to Bob (depending on the plan’s rules), Bob could roll the $804K out to a traditional IRA and use that as a 72(t) IRA. He could keep the balance inside his 401(k) and effectively use his 401(k) as what I refer to as the “non-72(t) IRA.” This sort of structuring was discussed on the Forget About Money podcast (timestamped here).

Decreasing the 72(t) Payment

What if Bob wants to reduce his 72(t) 401(k) annual payment (perhaps because he inherits a significant traditional IRA)? Bob can do a one-time change to the RMD method, which is the primary method of reducing the annual taxable 72(t) payment. 

Unfortunately, using a 72(t) 401(k) boxed Bob into a bad corner. Say Bob is age 57 and the 72(t) 401(k) is still worth exactly $2M. He could use the age 57 factor from the Notice 2022-6 Uniform Life Table (41.6) and reduce his annual payment to $48,077. Not much of a reduction from his $50,000 required annual payment.

Had he used a 72(t) IRA/non-72(t) IRA structure instead, and the 72(t) IRA was worth $804K, he could reduce his $50,000 annual payment all the way down to $19,327.

For those looking for protection against significant tax in the event of an inheritance or other income producing event, the 72(t) IRA is preferable to the 72(t) 401(k). 

Increasing the 72(t) Payment

But maybe Bob wants to increase his 72(t) annual payment from $50,000 to $60,000 at age 57. For those with a non-72(t) IRA, this is easy: simply slice and dice that non-72(t) IRA into two IRAs, one of which is a small new 72(t) IRA supporting the additional $10,000 annual 72(t) payment.

What if Bob has a 72(t) 401(k)? I believe that establishing a second 72(t) payment from his 72(t) 401(k) would blow up his existing 72(t) payment plan. The second 72(t) payment would be an impermissible modification of the original 72(t) payment plan, triggering the 10 percent early withdrawal penalty and interest charges with respect to all prior distributions. 

I am uncomfortable with any modification to a 72(t) retirement account unless it is specifically allowed by IRS guidance such as Notice 2022-6, and I see no evidence that a second 72(t) payment plan out of the same retirement account is permissible. Natalie Choate is also of the opinion that taking a second 72(t) payment from an existing 72(t) account is an impermissible modification of the first 72(t) payment plan. See Choate, page 594. See also IRS Q&A 9 (nonbinding), allowing a new 72(t) payment plan from the retirement account only after the taxpayer has blown up their original 72(t) payment plan.  

That said, there is a single 2009 Tax Court case, Benz v. Commissioner, that gives the slightest glimmer of hope. In that case an additional distribution from a 72(t) IRA excepted from the 10% early withdrawal penalty as being for higher education expenses did not blow up an existing 72(t) payment plan, because the additional distribution itself qualified for a 10 percent early withdrawal penalty exception under Section 72(t)(2)(E).

It’s likely a stretch to apply Benz to a second 72(t) payment plan from the same retirement account. That said, I don’t believe it is an impossible outcome. But note that Benz is a single 15 year old court case binding neither on any federal district court nor on any federal appellate court. Further, the IRS never acquiesced to the decision in Benz, meaning they may still disagree with it. Even if the IRS now agrees with Benz they (and more importantly, a court) may not believe the logic of Benz goes so far as to allow a second 72(t) payment plan from the same retirement account. 

Asset Protection

Depending on the circumstances and on the state, it can be true that IRAs offer materially less creditor protection than 401(k)s and other qualified plans. That could be a reason to use a 72(t) 401(k) instead of a 72(t) IRA.

I believe that, as a practical matter, sufficient personal liability umbrella insurance, which tends to be affordable, can adequately fill-in gaps between IRA and 401(k) creditor protection. Of course, everyone needs to do their own analysis, possibly in consultation with their lawyers and/or insurance professionals, as to the adequacy of their creditor protection arrangements.

72(t) Payment Plan Resources

72(t) payment plans are complex. Here are some resources from me and other content creators for your consideration:

Retire on 72(t) Payments

Tax Basketing for 72(t) Payment Plan

IRS 72(t) Questions and Answers

Jeffrey Levine Strategies For Maximizing (Or Minimizing!) Rule 72(t) Early Distribution Payments Using IRS Notice 2022-6

Denise Appleby Watch this before starting a Substantially Equal Periodic Payment – SEPP 72t program

Natalie B. Choate Life and Death Planning for Retirement Benefits (8th Ed. 2019), particularly pages 582 to 605. 

Florida Retirement System 72(t) Calculator (not validated by me).

The 72(t) is far from the only option available for those looking to retire prior to age 59 ½. 

Conclusion

The 72(t) 401(k) is a possibility if one’s 401(k) plan allows it. I usually strongly disfavor doing a 72(t) payment plan out of a 401(k) considering how rigid it is compared to the 72(t) IRA alternative. Further, as discussed above, 72(t) 401(k)s can create situations where the tax law has not, to my knowledge, definitely stated the governing rules. For these reasons, I generally favor using 72(t) IRAs in conjunction with non-72(t) IRAs instead of the more inflexible 72(t) 401(k).

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters.Please also refer to the Disclaimer & Warning section found here.

The Church IRA

“Repay to Caesar what belongs to Caesar and to God what belongs to God.” – Matthew 22:21

What happens with our IRAs and other retirement accounts when we die? Early in our financial journeys, it is incredibly important to plan for our retirement accounts to take care of our loved ones, particularly spouses and younger children. Those concerns should be the primary drivers of the planning for our retirement accounts early on.

But what about later in our lives, when our financial futures are secured and our children are adults? 

I believe it is time to be intentional about the destination of our tax deferred retirement accounts. It’s great to provide for adult children. But how much? And couldn’t retirement accounts help better the world? As discussed below, the Church IRA is a way to give wealth to adult children and to the Church. 

The Origins of an Idea

In August 2023 the combination of a West Coast hurricane and the Podcast Movement conference resulted in my flying to Denver, Colorado on a Saturday to ensure I could attend the conference. As a result, I attended Sunday Mass far from home at St. Gianna Beretta Molla Church in Denver. At that Mass, the homilist, Deacon Steve Stemper, had an idea that spoke to me: treat the Church as one of your children in your estate plans.

The Church IRA

As frequent readers of the blog know, I’m quite interested in tax-advantaged retirement accounts. The idea to treat the Church as one of your children in your estate strikes me as particularly well suited for traditional IRAs.

Let’s illustrate with an example:

Chuck and Joy are married and both are 85 years old. They have a $3M traditional IRA in Chuck’s name, and they have three adult sons: Abe, Barry, and Charlie, in their late 50s and early 60s. 

Obviously, if Chuck dies, Joy needs support. Why not name Joy as the primary beneficiary of the traditional IRA? That leaves a remaining question: who should be the secondary beneficiaries? 

Each of Abe, Barry, and Charlie could be a one-third secondary beneficiary. At the second death, they would get about $1M each. What if instead Chuck names each of Abe, Barry, and Charlie one-quarter secondary beneficiaries (about $750K each) and names his Catholic parish or diocese as a one-quarter secondary beneficiary (also about $750K)?

This is the beginning of what I refer to as the Church IRA.

How much different will Abe, Barry, and Charlie’s lived experience be by inheriting a $750K traditional IRA instead of a $1M traditional IRA?

Further, the “hit” to Abe, Barry, and Charlie is likely to be less than a 25% reduction. Why? Because of taxes!

Each of Abe, Barry, and Charlie will have 10 years to drain the inherited IRA. Odds are they will want to take more than 10% per year from the IRA to manage a potential “Year 10 Tax Time Bomb.” Say Abe is single and otherwise has annual income of $150,000.

If Abe takes 12.5% of the account in the first full year after death, he takes $125,000 if he inherits a $1M traditional IRA. Assuming he takes the standard deduction, Abe will be in the 35% marginal tax bracket. 

If, instead, Abe inherits a $750K traditional IRA, he only takes $93,750 in the first year. With the other $150K of AGI, Abe will find himself in the 32% marginal tax bracket. 

The $31,250 that the Church IRA costs Abe during the year would have been taxed at 32% and 35% federal income tax rates. This illustrates that reducing Abe’s inherited IRA by 25% is not likely to cost him 25% of the after-tax wealth since it is likely he would pay a significantly higher tax rate on those last dollars. 

You could say Chuck and Joy “took” money from Abe, Barry, and Charlie by employing the Church IRA. The money they took from Abe, Barry, and Chuck and gave to the Church is the highest taxed money, making the Church IRA tax efficient. 

The Church IRA and the Owner’s Needs

One of the advantages of the Church IRA is it need not risk the owners’ own retirement sufficiency. Joy has a legitimate interest in her own financial future. The initial Church IRA structure has the advantage of reducing Chuck and Joy’s ability to fund the remainder of their own lives in no way. The Church gets money only after they have both passed. 

Church IRA Implementation

To my mind, the biggest question here is whether to create the Church IRA during our lives or at death. In Chuck and Joy’s case, assuming they want to, at a minimum, employ the Church IRA at death, there are three options:

PATH ONE: Keep everything in a single IRA during their lifetimes. Have the four equal secondary beneficiaries.

PATH TWO: Split the single IRA into four IRAs, each with its own 100% secondary beneficiary (Abe, Barry, Charlie, and the Church IRA)

PATH THREE: Split the single IRA into two IRAs (one worth $2.25M with Abe, Barry, and Charlie as the secondary beneficiaries and a second IRA worth $750K with the Catholic Church as the sole secondary beneficiary).

One of the advantages of the second and third paths is the Church IRA can serve additional purposes. One additional Church IRA purpose is that it be used during Chuck and Joy’s lifetimes to make their routine contributions to the Church (whether that be weekly or monthly). Those contributions can be made through qualified charitable distributions (“QCDs”).

QCDs are a great tax planning tactic during one’s own lifetime for the charitably inclined. They get money out of a traditional IRA tax-free and count against required minimum distributions (“RMDs”). 

Regardless of the chosen path, the Church IRA can also be used during Chuck and Joy’s lifetime to help them fund their own living expenses.

We see that the Church IRA can be simply used at death through beneficiary designation forms. Or the Church IRA can also work during one’s own life to either or both (i) provide for routine lifetime Church donations (preferably through QCDs) and (ii) provide for the owner’s own living expenses. 

Splitting IRAs

IRA owners can work with their financial institution to split an existing IRA into two or more IRAs. This can be done for any reason. Perhaps it’s simply for mental accounting to facilitate a Church IRA like the one in Paths Two and Three described above. 

One does not need to split IRAs to facilitate the Church IRA (see Path One above). But there can be simplicity advantages to having each beneficiary have their own separate and distinct IRA they inherit separate from other siblings and/or the Church. 

RMDs from Split IRAs

Here the tax rules are quite flexible. The tax rules treat all of one’s traditional IRAs as a single traditional IRA for RMD purposes. So Chuck and Joy would have tremendous flexibility in terms of which IRA or IRAs to take their overall RMD for the year from. They could take the RMD from the Church IRA or from one or more of the non-Church IRAs, or they can split it among their various IRAs however they want to. 

Changing Beneficiaries at the First Death

In Chuck and Joy’s situation, there is an important additional consideration. What if Chuck dies first? Joy would inherit the traditional IRA. She would then need to work with the financial institution to appropriately roll the inherited IRA into an IRA into her own IRA.

From there, she should name primary beneficiaries in accord with her Church IRA intention. She has the three paths described above as possibilities for structuring her Church IRA. 

Roth Versus Traditional

Absent incredibly rare circumstances, the Church IRA should be a traditional IRA. Roths are tax-free to individual beneficiaries. Traditional IRAs are taxable to individual beneficiaries. If your adult children are getting some and the Church is getting some, why not leave Roths to the adult children and some or all of the traditional IRAs to the Church? 

The adult children pay income tax and the Church does not. Why waste the tax-free attribute of the Roth on a tax-free entity, the Church? The Church does not benefit from Roth treatment while the adult children do. 

Perhaps the beneficiary designation forms split the Roth IRA only among the adult children and split the traditional IRA among the adult children and the Church, and leave a greater percentage of the traditional IRA to the Church. 

Conclusion

The Church IRA can flexibly leave a share of one’s financial wealth to the Church or other 501(c)(3) charity. It can help us repay to God what is God’s while reducing what is owed to Caesar.

To determine whether the Church IRA is appropriate for us, we need to ask ourselves several questions. How much do my adult children need? Should I leave a significant amount to my Church or other charities? Are there tax-efficient ways to provide for both the Church and my adult children?

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

Follow me on Twitter: @SeanMoneyandTax

This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters. Please also refer to the Disclaimer & Warning section found here.