Tag Archives: Solo401(k)

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. 

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. 

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. 

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. 

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.

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.