Tag Archives: Roth versus Traditional

Can You Find the Hidden Roth IRA?

Perhaps you have a Hidden Roth IRA.

You might be thinking “No way. I did not lose track of a Roth IRA!”

The Hidden Roth IRA is not a lost retirement account. 

Rather, the Hidden Roth IRA is a Roth IRA that hides inside traditional IRAs and traditional 401(k)s. 

How can a Roth IRA hide in a traditional retirement account? It turns out tax free distributions (essentially, a Roth IRA) from traditional retirement accounts occur more often than you would think.

This article searches for Hidden Roth IRAs. You’ll be surprised how often retirees can benefit from the Hidden Roth IRA.

The Standard Deduction and the Hidden Roth IRA

We live in an era of a rapidly growing standard deduction. 

The standard deduction is to the Hidden Roth IRA what the flux capacitor is to time travel. 

The standard deduction makes the Hidden Roth IRA possible!

Increasing the standard deduction, as the One Big Beautiful Bill did, greatly expanded the Hidden Roth IRA. 

It gets even better. Through 2028, the senior deduction expands the Hidden Roth IRA for many age 65 and older. The new nonitemizers’ charitable deduction effectively increases the standard deduction by $1,000 per person for Americans with some charitable inclinations. 

Senator Cory Booker has recently proposed a significant increase in the standard deduction which would help many retirees enjoy the benefits of the Hidden Roth IRA.

Golden Years Hidden Roth IRAs

The “prime time” of the Hidden Roth IRA is one’s mid-to-late 60s, particularly the 66th through 69th birthday years.

In today’s environment, a married couple in their mid-to-late 60s could take more than $45,000 annually from traditional IRAs and have the “taxable” income fully offset by the available standard deduction, additional standard deduction, senior deduction, and potentially the nonitemizers’ charitable deduction. 

During the Golden Years, there are no required minimum distributions (RMDs). There’s no Premium Tax Credit on the table, so controlling income for PTC optimization is not a consideration. Further, Social Security can be delayed until age 70, resulting in increased annual payments, potentially reducing volatility in one’s 70s and 80s. 

Yes, the Golden Years Hidden Roth IRA mostly or fully goes away once the couple claims Social Security. Social Security benefits are ordinary income that soak up the standard deduction and senior deduction, reducing or fully eliminating their ability to shield traditional IRA/401(k) distributions from federal income taxation. Nevertheless, for multiple years of one’s retirement well into five figures can come out of traditional IRAs as a tax free Hidden Roth IRA. 

The Golden Years Hidden Roth IRA is the best Hidden Roth IRA, in my opinion. But it’s not the only Hidden Roth IRA. 

72(t) Payment Plans and the Hidden Roth IRA

Some retirees will get a jump start on the Hidden Roth IRA. Early retirees starting a 72(t) payment plan naturally tend to get the benefit of the Hidden Roth IRA.

Prior to the One Big Beautiful Bill, I did a YouTube video about this concept using the then-current 2025 numbers. Even prior to the OBBB expansion of the standard deduction, a married couple on a 72(t) payment plan could have more than $25,000 a year in a Hidden Roth IRA.

72(t) payment planning naturally marries with the Hidden Roth IRA. In most cases, I strongly favor mostly or fully spending down taxable account assets prior to initiating a 72(t) payment plan. Having spent down the taxable assets, it’s difficult for early retirees to incur significant income other than the 72(t) payment itself. 

This naturally clears the path for the 72(t) payment to enjoy the benefit of the Hidden Roth IRA. Those benefits can last for the better part of two decades in an extreme case such as the one posited in this YouTube video. 

Married Couples Taking RMDs

In today’s environment, many taking RMDs will enjoy the Hidden Roth IRA. Why?

Most 70-something and 80-something’s main sources of income are Social Security and retirement account distributions. 

Let’s consider average and median wealth and income statistics. The average monthly Social Security benefit, as of January 2026, is $2,071. Multiply that by 12 months and 2 spouses and you get $49,704 in Social Security per year. 

Median retirement account balances for those 75 and older as of 2022 was just $130,000.

Let’s round up those numbers for an 80 year old couple, Sal and Sophia. Assume $70,000 in total Social Security, $2,000 of interest from an online savings account, and $24,752 in RMDs from $500,000 in traditional IRAs. That’s a retired couple well above Social Security average benefits and median retirement account balances. 

Does this above-the-median married couple enjoy the benefits of the Hidden Roth IRA while taking RMDs?

You betcha!

How much? 

Of that $24,752 RMD, $24,410 is a Hidden Roth IRA!

This YouTube video demonstrates how Sal and Sophia, with a half million traditional IRA, can have all or almost all of their RMD be tax free. That demonstrates the power of the Hidden Roth IRA. 

I’ve found that it’s possible that a married couple taking RMDs on a $1 million traditional IRA could enjoy the benefit of a Hidden Roth IRA to a small degree in 2026. See this YouTube video for some numbers. 

The Hidden Roth IRA is a real phenomenon for many Americans taking RMDs. Based on the Social Security and retirement account statistics, it is very possible the majority of married couples taking RMDs can benefit from the Hidden Roth IRA.

Singles and Widows Taking RMDs

The benefits of the Hidden Roth IRA are not reserved only for married retirees. Singles and widows can also benefit. This is true even for many single/widowed retirees with above average Social Security income and above median retirement account balances.

On my YouTube channel I discussed an 80 year old single person with a half million traditional IRA and $40,000 of annual Social Security income. She enjoyed the benefit of an $8,660 Hidden Roth IRA. 

Yes, singles and widows tend to enjoy much less when it comes to the Hidden Roth IRA. But even those widows with above average Social Security and above median retirement account balances can enjoy a degree of Hidden Roth IRA benefits.

Inherited Traditional IRAs and the Hidden Roth IRA

One thing people fear is the taxes on inherited IRAs. The 10 year payout rule is viewed as a detriment to leaving heirs traditional IRAs. At first blush, taxing a large traditional IRA within 10 years seems to create a huge tax problem.

But will it really be a problem?

Consider many inheritors of large traditional IRAs. They themselves might already be retired or might decide to retire because of the large inheritance.

I ran through one such scenario on my YouTube channel. It may be the case that even a $2 million inherited traditional IRA could enjoy significant Hidden Roth IRA benefits for some or all of the 10 year payout window.

Implications of the Hidden Roth IRA

The Hidden Roth IRA has several important implications for financial planning. 

All of the below tactics and considerations are offered as educational insights. They are not offered as advice for you or any other individual’s situation. There are times when retirees would wisely want to avoid the below tactics. 

But, if all else is equal, in a general sense the Hidden Roth IRA makes the below tactics more appealing. 

Spend Down Taxable Accounts First

The first is that spending down taxable accounts first in retirement is very attractive, particularly for the early retiree. Part of the reason the Hidden Roth IRA can be so significant is the lack of other income hitting one’s annual tax return. 

Spending down taxable assets first has several advantages, including potentially setting up years of enjoying the Hidden Roth IRA later in retirement. 

Limit Ordinary Income in Retirement

A second implication is it is desirable to limit ordinary income hitting tax returns in retirement. There are various ways to achieve this. For example, holding bonds in traditional retirement accounts takes bond interest income off our tax returns. Consideration should be given to rolling pensions into IRAs to reduce annual ordinary income payouts earlier in retirement. 

Delay Social Security

Delaying claiming Social Security increases future monthly benefits. It also keeps Social Security income off one’s tax returns in their 60s, increasing the runway available to the Hidden Roth IRA.

RMDs are Not Harmful for Many Retirees

Consider Sal and Sophia. They are required to take a $24,752 RMD, almost all of which is tax free. A forced tax free distribution in one’s 70s or 80s is not harmful. Many Americans will enjoy the benefit of the Hidden Roth IRA on a portion of their RMDs. 

Yes, many affluent retirees taking RMDs will not get the benefit of the Hidden Roth IRA. Even for them, RMDs tend not to be all that harmful. 

Why would a couple like Sal and Sophia ever do a Roth conversion if most, if not all, of their RMDs while they are both alive benefit from the Hidden Roth IRA? 

Resource

I’m aware of only one book that discusses the phenomenon of the Hidden Roth IRA. In Tax Planning To and Through Early Retirement, Cody Garrett and I discuss the Hidden Roth IRA in the context of drawdown planning. 

Conclusion

Do you like Roths? If so, one of the best ways to have a Roth is to contribute to a traditional 401(k) at work. In retirement, some of that account may be distributed tax free as a Hidden Roth IRA. 

Many Americans will enjoy the benefit of the Hidden Roth IRA. The Hidden Roth IRA hides inside “taxable” traditional retirement accounts such as IRAs and 401(k)s. 

Planning such as spending taxable accounts first in retirement and reducing ordinary income hitting one’s tax return can increase the benefits of the Hidden Roth IRA.

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

Follow me on LinkedIn: @SeanWMullaney

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 ask the question: should I contribute to a Roth 401(k) or contribute to a Roth IRA? Below I discuss why, in the vast majority of cases, I strongly favor Roth IRA contributions over Roth 401(k) contributions. 

Roth Accounts

Who does not love tax free accounts? The Roth, properly distributed, can create tax free income.

The Roth is becoming particularly attractive for the early retiree trying to optimize Premium Tax Credits. Yes, you can potentially fund pre-65 retirement expenses from traditional retirement accounts or sales of taxable account assets. But (with uncommon exceptions) both trigger taxable income, increasing the possibility of going over the 400 percent of federal poverty level cliff. 

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 $168,000 (single) or $252,000 (married filing joint) of modified adjusted gross income (2026 numbers). 

The maximum annual contribution to a Roth IRA is $7,500 (if under age 50) or $8,600 (if age 50 or older) (2026 numbers). 

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, particularly during one’s working years. 

Roth 401(k)s

Roth 401(k)s are a workplace retirement plan. Contributions can be made through payroll withholding. 

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 2026, the annual Roth 401(k) contribution limit is $24,500 (under age 50). Those aged 50 and older by year end qualify for additional catch-up contributions. 

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 workers 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 35, 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 $110,000. They have approximately $2,000 of annual interest and dividend income. They claim the standard deduction of $32,200 in 2026. 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 ($7,500 each) and contribute to a traditional 401(k) ($24,500 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 $24,500 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). 

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 $7,500 annual Roth IRA contribution. 

For Stephen and Becky, the idea is to Pay Tax When You Pay Less Tax. As I’ve explored on my YouTube channel, it’s frequently the case that retirees are lightly taxed. The odds are that Stephen and Becky will pay the most tax when they are working. Thus, the better path is likely to be to take the tax deduction (the traditional 401(k) contribution) during their working years and then pay tax on traditional retirement accounts in retirement.  

Trade Off Profile

The trade off profile of the traditional 401(k) versus Roth 401(k) tilts towards the traditional 401(k) contribution.

Every dollar contributed to a Roth 401(k) is a dollar that could not have been tax deducted into a traditional 401(k).

The opposite is true when it comes to IRAs. Every dollar contributed to a Roth IRA is not a dollar that could have been deducted into a traditional IRA in many cases due to the relatively low income limits many face on the ability to deduct a traditional IRA contribution.

If I’m going to do Roth, don’t I want to do the Roth that does not sacrifice a tax deduction? 

Situations Where the Roth 401(k) Contributions Make Sense

Generally there are four situations where choosing to contribute to a Roth 401(k) makes sense. In these situations, the tax rate arbitrage play available to Stephen and Becky isn’t available. 

In the first three 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 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?

End of career wind downs where one reduces workload, and thus, taxable income, can be a great time to switch to the Roth 401(k) for retirement contributions. 

Transition years are a great time to make Roth 401(k) contributions instead of traditional 401(k) contributions. 

Mini-Retirements

Taking a year-long mini-retirement beginning February 1st? January 401(k) contributions might be best made to the Roth 401(k) instead of the traditional 401(k).

No Hope

Picture a charismatic franchise NFL quarterback. He’s got a $50M 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).

High Earners’ Catch-Up Contributions

This isn’t a question of “traditional versus Roth” preference. It’s a question of the tax law.

Starting in 2026, those making more than $150,000 in prior-year W-2 wages from an employer cannot make catch-up contributions to a traditional 401(k). Their catch-up contributions must be made to the Roth 401(k). 

Sure, this rule takes away a valuable tax deduction. But having Roth money going into retirement is not a bad thing. Those high earners with cash flow sufficient to make Roth catch-up contributions should consider doing so. 

Additional Resource

Cody Garrett and I did a deep dive on all things retirement planning, including Roth retirement accounts, in Tax Planning To and Through Early Retirement, available on Amazon and many other online sources. 

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

Follow me on LinkedIn: @SeanWMullaney

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. 

Five Phases of Retirement: Sean’s Presentation at the 2025 Bogleheads Conference

I presented Tax Planning for the Five Phases of Retirement at the October 2025 Bogleheads Conference in San Antonio, Texas.

Highlights of the presentation include, but are not limited to, the following:

Tailored Taxable Roth Conversions (TTRCs) 7:48

The Hidden Roth IRA 13:20

Might Half Your Income Be Tax Free in Retirement? 19:43

7 Ways to Mitigate RMDs 25:09

The Widow’s Tax Trap 28:43

The Real Job of a Retirement Account 33:20

Airplane! and Tax Planning 42:38

HSA PUQME Planning 47:57

I hope you enjoy it!

If you like this sort of analysis, there’s a whole bunch more in the book Tax Planning To and Through Early Retirement, which Cody Garrett, CFP(R) and I wrote in 2025.

Please let me know what you think about the presentation in the comments.

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

Follow me on LinkedIn: @SeanWMullaney

This post and the presentation (including Q&A) in the YouTube 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.

The Widow’s Tax Trap and RMDs

People worry about taxation in retirement. In particular, they worry about the taxation of required minimum distributions (RMDs), especially after the death of a spouse. Widows find themselves in the single tax brackets after decades of enjoying the more favorable married filing jointly tax brackets. 

Widows and widowers finding themselves as single taxpayers is often referred to as the Widow’s Tax Trap. 

RMDs require taxable withdrawals from traditional retirement accounts such as IRAs and 401(k)s. But just how bad are they when a widow or widower is in the Widow’s Tax Trap?

Let’s unpack just how bad the combination of the Widow’s Tax Trap and RMDs is for an 81 year-old widow with a very tax inefficient structure: almost $3.7 million of her approximately $4.5 million of financial wealth in a traditional IRA.

My experience tells me many financial planners and gurus will tell you this is a terrible outcome. That $3.7 million traditional IRA is infested with taxes!

But is it really?

81 Year-Old Widow in the Widow’s Tax Trap

I put together an analysis of an affluent widow in the Widow’s Tax Trap. Let’s call her Jane. Her traditional IRA causes her to have an RMD of almost $190,000. Wow!

Grab the tax analysis file here!

To be fair, most Americans will never have a $3.7 million traditional IRA and/or a $190K RMD. But I analyze them to demonstrate “what if the widow is highly inefficient from a tax perspective?”

What are the federal income tax rates on that feared RMD? 

Isn’t it remarkable that an 81 year-old widow with almost $3.7 million in a traditional IRA has more of her RMD taxed in the 12 percent tax bracket than in the 32 percent tax bracket?

Despite all the fear of taxation of RMDs, that’s the reality when it comes to a very affluent, very inefficient 81 year-old widow. 

Some might say “but what about IRMAA?” “What about the net investment income tax?”

Yes, Jane pays IRMAA of approximately $6,500 in two years because of her RMDs. And yes, the RMDs trigger approximately $500 of net investment income tax.

But do either of these have any impact on Jane’s lived experience and financial success?

Absolutely not!

The government scores some Garbage Time Touchdowns on Jane by collecting some IRMAA, some net investment income tax, and some income tax in the 32 percent bracket. 

A Garbage Time Touchdown is a late in the game touchdown scored by a team that will lose the game regardless of the touchdown. As a New York Jets fan, sadly I’m an expert in Garbage Time Touchdowns.

Jane has some tax inefficiencies that are just Garbage Time Touchdowns.

Think about the lifetime arc of Jane’s taxes in today’s tax planning world:

  • As a single individual, Jane likely deducted workplace retirement plan contributions at a 22, 24, or 32 percent rate. Win versus the IRS!
  • As a married couple, Jane and her husband likely deduct into workplace retirement plans at a 22 or 24 percent rate. Win versus the IRS!
  • In early retirement, they live off taxable accounts and do not do Roth conversions. They may pay nothing in federal income tax! Win versus the IRS!
  • Once taxable accounts are depleted, traditional retirement account distributions could have benefitted from the Hidden Roth IRA. Win versus the IRS!
  • Even RMDs are likely subject to the 12 percent and 22 percent brackets while they are both alive. Win versus the IRS!
  • As a widow, the relatively minor tax inefficiencies creep in. These are Garbage Time Touchdowns. 

This arc, which eschewed Roth 401(k) contributions and taxable Roth conversions, screams “Jane wins a blow out victory over the IRS” over the course of her lifetime. 

Sure, at the end Jane gave up some Garbage Time Touchdowns to the IRS, but not after decades of defeating the IRS. 

What’s more important than winning the spreadsheet is lived experience. Notice that Jane paying 32 percent on about six percent of her RMD has $200K of after-tax cash flow? 

In order for the Widow’s Tax Trap to bite hard, the widow generally has to have about $200K or more of after-tax cash flow.

The taxes bite when widows can most afford them!

Watch me break down the tax analysis of our 81 year-old widow on YouTube.

Roth Conversions to Avoid the Widow’s Tax Trap

Should Jane and her husband have done taxable Roth Conversions in retirement to avoid the widow paying 32 percent federal income tax on some of her RMDs?

Here vocabulary becomes very important. Yes, some taxable Roth conversions taxed at 22 percent or 24 percent could have been beneficial. But they were hardly necessary.

Outside of cases where taxable Roth conversions create enough required income to qualify for a Premium Tax Credit, taxable Roth conversions are not necessary. 

Yes, there are times where large taxable Roth conversions can be beneficial in that they mitigate harmful effects of the Widow’s Tax Trap. But the analysis above shows that the harmful effects of the Widow’s Tax Trap aren’t all that harmful for the vast, vast, vast majority of Americans. This is true even those with most of their financial wealth in traditional retirement accounts. 

Why would Jane and her husband prioritize large scale taxable Roth conversions to avoid having six percent of her RMDs as a widow being subject to the 32 percent tax bracket? 

Further Reading

The tax planning landscape has changed. One resource that puts aside the fear and realistically tackles today’s tax and retirement planning landscape is Tax Planning To and Through Early Retirement, a book I’m proud to have co-authored with Cody Garrett. 

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

Follow me on LinkedIn: @SeanWMullaney

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.

2025 Year-End Tax Planning

It’s that time of year again. The air is cool and the New York Jets season is over. 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. 

Taxable Roth Conversions

Before we talk about taxable Roth conversion timing, we must talk about taxable Roth conversion desirability. Taxable Roth conversion desirability has significantly declined in recent years. Many commentators have not caught up to the new reality.

Fortunately, Mike Piper knows what time it is. At the 2024 Bogleheads conference, he said “[Roth conversions] don’t usually improve financial security in retirement.” Cody Garrett and I also acknowledge and tackle the changed landscape in our new book Tax Planning To and Through Early Retirement. 

Yes, there can be some taxable Roth conversions that are highly advantageous. But they tend to be much more limited in scope and scale than most commentators acknowledge. In our book, Cody and I detail the sorts of taxable Roth conversions that tend to be beneficial.  

Back to timing. For a Roth conversion to count as being for 2025, it must be done before January 1, 2026. 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 (hopefully done with up-to-date thinking) 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 2025. 

For those age 65 or older by year-end, the Roth conversion calculus should consider the new senior deduction.

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

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 2025, the appreciated stock must be received by the donor advised fund prior to January 1, 2026. This deadline is no different than the normal charitable contribution deadline.

2025 is a great time to make a donor advised fund contribution. Why? Because of the new 0.5% of income haircut on itemized charitable deductions starting in 2026. Assuming one has high income in both years, 2025 might be more desirable than 2026. I walked through an example of how the new haircut reduces itemized charitable deductions with Brad Barrett on the ChooseFI podcast. 

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 2025. Donor advised fund planning should be attended to sooner rather than later. 

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 2024 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 2025. If you do, don’t forget to reassess your workplace withholdings for 2026 early in the year.

One great way to make up for underwithholding, particularly for retirees, 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 2025 is not December 31st, as I will discuss below. But if you have already completed a Backdoor Roth IRA for 2025, the deadline to get to a zero balance in all traditional IRAs, SEP IRAs, and SIMPLE IRAs is December 31, 2025. 

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 federal 0% long-term capital gains tax bracket and with an asset in a taxable account with a built-in gain, tax gain harvesting prior to December 31, 2025 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 federal 0% long-term capital gains 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 2025 is December 31, 2025. 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, 2025. 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. 

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 2025 is April 15, 2026. 

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 2025 tax year is April 15, 2026. Those doing the Backdoor Roth IRA for 2025 and doing the Roth conversion step in 2026 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 2025 is April 15, 2026. 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 2025 is April 16, 2026. 

2026 Tax Planning at the End of 2025

ACA, HDHP, and HSA Open Enrollment

It’s open enrollment season at work and November 1st starts ACA medical insurance open enrollment for 2026. 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).

New for 2026! All Bronze and Catastrophic ACA plans will qualify as HDHPs! This opens the door for many self-employed and early retired individuals covered by these plans to make deductible HSA contributions. These deductible contributions can increase Premium Tax Credits and lower income taxes. 

As I write this in mid-October 2025, the Premium Tax Credit is in flux. I do think many early retirees and self-employed individuals will benefit from considering a Bronze or Catastrophic plan. As I’ve said before, Bronze is Gold!

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 2025 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 LinkedIn at @SeanWMullaney

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

Tax Planning To and Through Early Retirement Launch Day

It’s finally here! Tax Planning To and Through Early Retirement launches today, September 23rd. It’s available at Amazon and other online retailers.

To mark the occasion, we discussed the book on yesterday’s episode of the ChooseFI podcast and today’s episode of the BiggerPockets Money podcast.

We will be on several more podcasts in the coming weeks and months discussing the book and its concepts. 

One I’m particularly excited about is this Friday’s BiggerPockets Money podcast episode where we discuss tax planning for the five phases of retirement drawdown. You can find that episode on September 26th on the BiggerPockets Money YouTube channel and on podcast players.

I have also put two special YouTube videos on my YouTube channel discussing concepts from the book. 

  • Today I posted a video discussing just how much tax a retired married couple might pay on a $40,700 Roth conversion using an example from the book. You might be very pleasantly surprised by the result.

A Favor Request

I speak for both Cody and myself when I say we are grateful for all of the support we have received for this project.

If you have purchased the book and read it, we humbly for one more favor. Please write an honest and objective review of the book on Amazon. The number and quality of reviews is vital to the book remaining one that Amazon recommends to its customers. 

We want to get word out about Tax Planning To and Through Early Retirement. You can help us do that with an Amazon review! 

Thank you for considering our request.

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

Follow me on LinkedIn: @SeanWMullaney

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 Planning World Has Changed

The tax planning world has changed. Have I and my fellow advisors caught up?

Below I discuss three changes in the past three years. These recent changes make a big impact on retiree taxation. Most commentators and gurus have largely ignored these changes.

The world has changed. It’s time for financial planners and tax advisors to adjust their advice accordingly.

No RMDs Until Age 75

In September 2022 required minimum distributions (“RMDs”) began at age 72. RMDs make traditional retirement account balances in retirement accounts less desirable, since they require taxable distributions.

In December 2022, SECURE 2.0 became law. For those born in 1960 and later, it delayed the onset of RMDs until age 75. SECURE 2.0 moved the needle when it comes to the desirability of traditional retirement accounts since it cancelled the three most likely to occur RMDs.

How long do we expect people to live beyond age 75? Take a look at the most recent Social Security Trustees Report actuarial table. For the vast majority of Americans, RMDs will now impact a very small proportionate share of their lifetime. 

It’s time for advisors to question prioritizing a planning concern, RMDs, that now impacts a very small slice of most Americans’ lives. 

Permanently Extended Lower Tax Brackets and Higher Standard Deduction

In 2022, advisors were on alert.

Better do those Roth conversions before lower tax rates sunset in 2026 was the common refrain. To be fair, in 2022 the Internal Revenue Code stated that the lower tax rates and the higher standard deduction expired on New Year’s Day 2026. 

Since 2022, both the world and the Internal Revenue Code have changed.

The sunset never happened! In July 2025, the One Big Beautiful Bill permanently extended the previously “temporary” lower tax brackets and the higher standard deduction. In fact, the new bill slightly increased the higher standard deduction ($750 for singles, $1,500 for those married filing jointly).

Let’s think about what that means for taxes in retirement. RMDs that would have been taxed at 15%, 25%, and/or 28% will now be taxed at 12%, 22%, and 24%. That makes a big difference in planning, as the taxation of RMDs becomes less harmful. 

It gets better! Less of most Americans’ RMDs will be taxed in a taxpayer’s highest bracket, thanks to the higher standard deduction. The higher standard deduction drags taxable income down in retirement, decreasing the amount of an RMD subject to the taxpayer’s highest marginal tax bracket. 

Senior Deduction

New for 2025 is the senior deduction. It is up to $6,000 per person for those 65 or older by year end. Yes, it is subject to modified adjusted gross income (“MAGI”) phaseouts between $75,000 and $175,000 for singles and $150,000 to $250,000 for those married filing jointly. But those income phase outs still allow many rather affluent retirees to claim some or all of the senior deduction.

Many affluent retired couples will not show $150,000 of MAGI, especially prior to claiming Social Security. Even those with $200,000 of MAGI, a very limited cohort of affluent retired couples, get $6,000 of the potential $12,000 deduction. While the senior deduction may be more limited for affluent single retirees, many will be able to control income so as to qualify for some of the senior deduction.

The senior deduction helps with several retirement tax planning tactics and objectives. For some, the senior deduction opens the door wider for significant tax free taxable Roth conversions prior to collecting Social Security. For others, it will open the door to very significant Hidden Roth IRA distributions prior to collecting Social Security. The senior deduction also reduces the tax hit on RMDs, since it lowers the amount of the RMD subject to the taxpayer’s highest marginal tax rate. 

2025 Increased Deduction: Consider a married couple both turning 65 in 2025. On New Year’s Day, their 2025 standard deduction was $33,200. Pretty good. With the increased standard deduction and the new senior deduction, assuming their MAGI is $150,000 or less, their total combined 2025 “standard” deduction is now $46,700. Yes, the tax planning world has changed!

Senior Deduction Uncertainty

Some worry: doesn’t the senior deduction vanish in 2029?

Aren’t we back to the “temporary” tax cuts that lowered the tax brackets and increased the standard deduction? 

“Temporary” was simply the weigh station to “permanent” in that case. I strongly suspect something similar will happen with the senior deduction.

Let’s play out the politics. If Congress does nothing, in 2029, the senior deduction, the new deduction for tipped income, and the new deduction for overtime income all vanish overnight. Is it politically wise for Congress to allow seniors, waiters, waitresses, and many blue collar workers to face tax hikes? 

Congress tends to act in its own best interests. While there are no guarantees, the politics are well aligned for the senior deduction to be extended into 2029 and beyond. 

Tax Planning Impact

Fewer RMDs. Lower tax rates and a higher standard deduction. The senior deduction.

Three big changes in three years change tax planning.

We’ve heard commentators push for Roth 401(k) contributions during the working years and aggressive Roth conversions during the early part of retirement. Both tactics optimize for taxes in the later part of retirement. But we’ve just seen three changes in three years that significantly lower taxes later in retirement. 

If the goal is to pay tax when you pay less tax, it’s time to adjust our thinking. 

This is particularly true when it comes to Roth 401(k) contributions. These contributions, for most taxpayers, tend to cost a tax deduction at the taxpayer’s highest lifetime marginal tax rate. In a changed world where retiree taxation has been significantly reduced, that’s not likely to be good planning for most Americans. 

My view is that the new tax planning environment reduces the desirability of significant Roth conversions prior to collecting Social Security. As Mike Piper stated, one of the main benefits of Roth conversions is to reduce tax drag caused by RMDs. The new tax laws significantly reduce that tax drag. Thus, accelerating income tax through Roth conversions becomes much less desirable.

Tax Planning Resource For a Changed World

Cody Garrett, CFP(R), and I created a resource for the new tax planning landscape. 

Tax Planning To and Through Early Retirement is a book that tackles the new realities of tax planning, including deep dives into accumulation planning, drawdown tactics, taxable Roth conversions, RMDs, the Widow’s Tax Trap, and the senior deduction. 

We also have an entire chapter titled Planning for Uncertainty. In that chapter we tackle the “What about future tax hikes?” question using history, logic, and reason. 

Conclusion

In football and in tax planning, the game changes. The recommendations advisors made four years ago may have been the right recommendations then. But big changes in the retirement tax landscape require advisors to reevaluate their strategies and tactics when it comes to tax planning. 

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

Follow me on LinkedIn: @SeanWMullaney

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.

2026 401(k) Catch-Up Contributions and the Quorum Clause

Starting in 2026, those with significant prior year W-2 incomes must make catch-up contributions to 401(k)s and other workplace retirement plans as Roth contributions. 

Mandatory Roth catch-up contributions deny many workers 50 and older a valuable tax deduction. 

The new rule originates with SECURE 2.0, a component of the Omnibus bill passed in December 2022.

The validity of the Omnibus bill has been questioned. In 2023, the Attorney General of the State of Texas sued the Department of Justice claiming that the House of Representatives did not have a sufficient quorum under the Quorum Clause to enact legislation when the Omnibus was passed. I share the Attorney General’s concern and have written to the government expressing that concern. 

Were the Omnibus were to be invalidated on Quorum Clause grounds, the rule requiring mandatory Roth catch-up contributions could not be sustained.

Judicial Results to Date

In the federal courts in Texas, four federal judges have weighed in. Two have opined that the Omnibus was passed in a Constitutionally qualified manner consistent with the Quorum Clause. Two have opined that the Omnibus was not passed in a Constitutionally qualified manner since the House did not have a sufficient quorum at the time of the Omnibus’s purported passage.

First, in February 2024 a federal district court judge determined that the Omnibus was not passed in a Constitutionally qualified manner. In August 2025, that opinion was overturned 2 to 1 by a three judge panel of the Fifth Circuit. 

SECURE 2.0 Lay of the Land in September 2025

Here is how I assess where we are in September 2025. 

First, it is likely that SECURE 2.0 will never be overturned. While I cannot say that definitively, I feel rather confident that it will survive, and I would plan around that outcome.

Let’s play out the future. As of this writing, I do not know if Ken Paxton, the Attorney General of the State of Texas, will appeal the August decision to an en banc panel of the Fifth Circuit and/or to the Supreme Court. But assuming it goes to the Supreme Court, just for analytical purposes, I suspect at least two of the institutionalist bloc of Justices Roberts, Kavanaugh, and Barrett would side with both the Biden and Trump Departments of Justice against overturning the Omnibus on Quorum Clause grounds.

From a planning perspective, it’s time for higher income W-2 workers to understand that they must make any 401(k) or other workplace retirement plan catch-up contributions as Roth contributions in 2026. The IRS confirmed this in recent guidance. 

The threshold to be considered high income for this purpose is likely to be slightly more than $145,000 of W-2 wages from that employer in 2025. I suspect that in October the IRS will come out with the exact threshold 2025 W-2 wage threshold amount applicable in 2026 (this is adjusted based on inflation). 

In late 2025, those subject to this potential restriction may want to prioritize W-2 income reduction planning opportunities such as making remaining 2025 401(k) contributions as traditional contributions to potentially fit under the 2026 threshold. 

Silver Lining: Required Minimum Distributions

There’s a silver lining to SECURE 2.0 likely surviving Quorum Clause concerns: delayed RMDs. For those born in 1960 or later, SECURE 2.0 delays the onset of required minimum distributions (“RMDs”) from age 72 to age 75. 

This delay requires all of us to step back from the inchoate fears about taxes in retirement and reassess RMDs and their impact.

Conclusion

While the final path of the Omnibus Quorum Clause litigation is not certain, it’s tilting heavily towards the Omnibus, and thus SECURE 2.0, surviving concerns about the House of Representatives’ use of proxies to establish a quorum in December 2022.

From a financial planning perspective, it is time to plan for higher income workers being required to make 401(k) catch-up contributions as Roth contributions. Further, it’s quite reasonable for those born in 1960 and later to plan on RMDs beginning at age 75.

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

Follow me on LinkedIn: @SeanWMullaney

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.

One Big Beautiful Bill Passes

On July 4th, President Trump signed into law the reconciliation bill, commonly referred to as the One Big Beautiful Bill.

The Bill will drive a significant amount of my content creation this summer.

On my YouTube channel, I will devote my Saturday videos to discussions of how the One Big Beautiful Bill impacts financial planning and retirement planning. Already I did a video stating that the One Big Beautiful Bill ought to have us questioning our thinking about the future, and a video about how One Big Beautiful Bill changes the tax planning landscape for charitable giving.

Separately, I am working with Cody Garrett, CFP(R), to put the finishing touches on our forthcoming book, Tax Planning To and Through Early Retirement, which we anticipate publishing later this year. The book will devote significant space to how the new law changes retirement planning.

To find out when we are publishing the book, please sign up for an email alert here.

Two One Big Beautiful Bill resources:

The bill text: https://www.congress.gov/bill/119th-congress/house-bill/1/text

Jeff Levine’s X thread on the bill: https://x.com/CPAPlanner/status/1940856699872858202

Follow me on YouTube: SeanMullaneyVideos

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.

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The Middle Class Trap

I have said the tax laws want you to retire early. 

Counter to that point, the BiggerPockets Money podcast has warned that the tax laws are an effective bar to many retiring prior to age 59 ½.

So who is right? The FI Tax Guy or Scott Trench and Mindy Jensen of the BiggerPockets Money podcast?

This isn’t just a discussion in my mind or a late night debate at the Waffle House. It’s become a debate in the financial independence space. Just last week, the Middle Class Trap was the topic of the ChooseFI podcast. 

We will return to that episode of ChooseFI later. For now, I want to start by defining the Middle Class Trap and providing the two reasons I don’t believe the Middle Class Trap is a trap. Then I will move onto several numerical examples, including four Mindy Jensen provided on ChooseFI. 

The Middle Class Trap Defined

Scott Trench and Mindy Jensen walk through their definition of the Middle Class Trap from in this YouTube video. I encourage you to watch it.

Boiled down, the argument is that primary residence wealth is trapped and traditional retirement accounts are trapped until age 59 ½. Thus, many in the middle class have trapped wealth and cannot retire prior to age 59 ½ despite good numbers on paper.

There are two problems with their argument. First, primary residence wealth isn’t the owner’s wealth as we ordinarily conceive and define it. Second, traditional retirement accounts are not trapped prior to age 59 ½. 

The Primary Residence Question

Too often we think of primary residences as investments. They are not, as Douglas Boneparth observes. They are a form of consumption.

People say “I have a million dollars in home equity so I am a millionaire.” 

No, you are not.

I can prove it.

Peter has a $500 checking account, a car, clothes, and a $1 million home with no mortgage. He sells the home for $1 million. He immediately must get a hotel room to sleep in tonight.

John has a $500 checking account, a car, clothes, rents an apartment, and has $1 million in VTSAX in a taxable account. He sells $10,000 of VTSAX for cash. He now has a pile of cash and need not make any adjustments to have a bed for the night. 

Is Peter’s home equity really his wealth when accessing causes significant life adjustments? John’s VTSAX is his wealth. His accessing it requires no life adjustments. 

So what then is market driven appreciation in home equity? It’s growth in asset value that primarily benefits three classes of people:

  1. The next generation
  2. Owners willing to change geographies or willing to significantly downsize
  3. Owners needing long-term care at the end of life

Market driven increases in home equity are not a trap. Rather, they are wealth that, in many cases, someone else gets to enjoy.

Imagine I’m writing a blog post and the doorbell rings. I answer and the delivery man says, “Mr. Mullaney, congratulations! You won a contest. The prize is $1,000 of Blippi toys!”

Those Blippi toys are my wealth that my toddler Goddaughter gets to enjoy. 

It’s no different with market driven increases in home equity. It’s wealth that shows up on your doorstep that most likely will be enjoyed by the next generation. 

In no way do those Blippi toys trap me. Same with market driven increases in home equity. 

The 10% Early Withdrawal Penalty is No Bar to Early Retirement

I’ve written about the myriad ways to fund retirement prior to 59 ½ without incurring the 10 percent early withdrawal penalty. I’ve spoken about it on two episodes of the ChooseFI podcast (475 and 491).

But until now, I have never explicitly said the following:

Those 50 and older with sufficient assets are in no way barred from early retirement due to the 10 percent early withdrawal penalty even if all of their financial asset wealth is in traditional retirement accounts. 

While 72(t) payment plans are not the ideal retirement plan, they are more than adequate enough to use to retire in the year one turns age 50 or later. Those 50 or older, with a simple spreadsheet and some diligence, are in no way barred from early retirement due to the 10 percent early withdrawal penalty. 

What about those under age 50? 

Few under age 50 will be able to retire on traditional retirement accounts alone because of sufficiency concerns. Tax concerns are not the problem when thinking about retiring prior to age 50 – it’s all about sufficiency!

Fortunately, the profile tends to resolve itself. To have enough financial wealth to retire in one’s 40s, the prospective early retiree most likely contributed to some combination of Roth accounts or taxable accounts prior to retirement. While not insignificant, traditional retirement account contribution limits are such that for many, it will be difficult to rely on them exclusively to build up sufficient assets for retirement prior to January 1st of the year of one’s 50th birthday. The 40-something early retiree can start their early retirement distributions from Roth accounts, taxable accounts, or a combination of both, obviously without penalty. 

Summed up, when assessing the Middle Class Trap, for those under 50, their profile itself usually resolves the issue. For those 50 and older, the 72(t) payment plan rules are so advantageous (due to a major change in 2022) that a spreadsheet requiring one amortization calculation, some coordination with a financial institution, and a bit of ongoing additional diligence resolves the issue. 

For both age cohorts, there is no tax trap. 

Does this mean the 10 percent early withdrawal penalty has been, in effect, repealed? Hardly! If someone like me, in their late 40s, wants to take $20,000 from a traditional 401(k) to fly round-trip in a suite, I will pay a hefty 10 percent early withdrawal penalty. The penalty is still effective to discourage impulsive onetime withdrawals before retirement. But the penalty is not effective to prevent early retirements with a systematic, sustainable withdrawal plan. That’s the obvious intention behind the series of substantially equal periodic payments exception.  

Examples from Mindy Jensen on ChooseFI Episode 543

Last week’s episode of the ChooseFI podcast, featuring host Brad Barrett, Mindy Jensen, and Can I Retire Yet blog author Chris Mamula was a great contribution to the FI space. 

During the ChooseFI episode, Mindy offered some numerical examples to argue for her case. That is a very legitimate tactic, and I personally love examples. Unfortunately, using numerical examples ran up against a limitation of the audio podcast format, since it can be difficult for participants and listeners to fully process multiple numbers while listening to an episode.

Mindy started sharing numerical examples around 25:00 in the podcast. I went back to the YouTube video and put Mindy’s numbers in the below table. I then added a row totaling financial assets and two rows laying out theoretically possible annual withdrawal rates. 

AmountPerson APerson BPerson CPerson D
Primary Residence Value or EquityNot givenNot given$3,000,000$800,000
Traditional Retirement Accounts$268,000$36,000$1,200,000$234,000
Roth Retirement Accounts$18,000$143,000$0$0
Taxable Brokerage Accounts$187,000$306,000$0$60,000
Cash$106,000$119,000$225,000$69,000
HSA$0$0$35,000$0
Total Financial Assets$579,000$604,000$1,460,000$363,000
Morningstar Annual SWR (3.7%)$21,423$22,348$54,020$13,431
Six Percent Annual Withdrawal Rate$34,740$36,240$87,600$21,780

Let’s use a range of withdrawal rates just for illustrative purposes. On the low end, we’ll use Morningstar at 3.7 percent, which can be fairly considered to be conservative. On the high end, let’s roll the dice a bit and use 6 percent.

Notice that the problem in the examples is not that the person has everything locked up in traditional accounts. The problem is sufficiency! Aside from Person C, it does not matter if all of the financial wealth is in Roth accounts, taxable accounts, or split between the two of them. 

Persons A, B, and D are not in the Middle Class Trap. Rather, they are in a situation where they need to work longer unless their annual spending is incredibly modest, even by financial independence standards. 

I believe that Person C could consider living on cash and later starting a 72(t) payment plan, but we really can’t tell without knowing much more information, including their age and their annual spending level in retirement. 

Middle Class Trap 72(t) Payment Plan Examples

In one podcast episode, Mindy and Scott put the parameters of the Middle Class Trap at $1M to $1.5M of trapped wealth (see 3:19 of this video). How bad is the federal income tax result if we assume practically all of that wealth is in traditional deferred retirement accounts?

Using the old Four Percent Rule of Thumb for our 72(t) annual payment at both ends of the spectrum, and assuming a $40,000 taxable savings account and 5 percent interest on it and on the annual 72(t) payment taken at the beginning of the year and spent evenly during the year, here’s the 2025 federal income tax result by my estimation.

Single $1MSingle $1.5MMarried $1MMarried $1.5M
Interest Income$3,000$3,500$3,000$3,500
72(t) Payment$40,000$60,000$40,000$60,000
AGI$43,000$63,500$43,000$63,500
Standard Deduction$15,000$15,000$30,000$30,000
Taxable Income$28,000$48,500$13,000$33,500
Federal Income Tax$3,122$5,584$1,300$3,543
72(t) Payment Funding for Expenses Other Than Federal Income Tax$36,878$54,416$38,700$56,457
Effective Federal Income Tax Rate7.26%8.79%3.02%5.58%
AGI as a Percent of 2025 Federal Poverty Level274.76%405.75%203.31%300.24%

I believe this table strongly supports my contention that the tax laws want you to retire early. Look how light the taxation is on 72(t) payments! 

You may ask “I thought federal tax rates started at 10 percent – how do these people pay effective rates less than that?” The answer is the standard deduction, which loves early retirees. Because of the standard deduction, all four taxpayers enjoy what I refer to as the Hidden Roth IRA. They take some amounts from their traditional IRAs and pay 0 percent federal income tax on them.

Is the 72(t) payment plan outcome perfect? No. Those on a 72(t) payment plan have to abide by the restrictions of the 72(t) payment plan rules. But those rules are not that bad, and allow for techniques to potentially increase or decrease the annual payment.

I will note two things. First, I am not arguing anyone should simply plan on getting to an early retirement age and have every last penny in traditional retirement accounts. I am arguing that it is hardly a trap if someone gets to age 50, has every penny in traditional retirement accounts, and wants to retire using a reasonable withdrawal rate.  

Second, managing for Premium Tax Credit can be a concern. At the high end of Mindy and Scott’s Middle Class Trap range, a single taxpayer would be shut out of a Premium Tax Credit (having gone a bit over the 400 percent of FPL cliff) if they were on an ACA medical insurance plan in 2026, unless later tax law changes in 2025 amend Section 36B. This person could turn on Premium Tax Credits by electing a slightly lower initial 72(t) annual payment. 

Sufficiency Is The Real Problem

We should spend more time on the real problem: retirement sufficiency. According to UBS, median adult wealth in the United States in 2023 was just $112,157. Even considering that older Americans are likely to have greater wealth than younger adults, the median wealth statistic means many Americans of all ages are significantly behind in retirement savings. The best way to catch up is by making traditional retirement account contributions. 

Update May 1, 2025

Thank you to Mindy Jensen who wrote a thoughtful response to this blog post. You can read it over at BiggerPockets.

Stay Tuned

This won’t be the last time you hear from me on this topic. Cody Garrett and I are currently writing Tax Planning To and Through Early Retirement, a book we hope to publish later this year. We will address all sorts of issues when it comes to accessing wealth and tax planning for those retiring prior to turning 59 ½.

What questions do you have about retiring prior to 59 ½? Let us know in the comments below and we might just answer your questions in Tax Planning To and Through Early Retirement!

Sign up for updates about Tax Planning To and Through Early Retirement here: https://www.measuretwicemoney.com/book 

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

Follow my YouTube Channel at @SeanMullaneyVideos

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.