Okay, a weird thing about the pass-thru “Section 199A deduction” created by the new tax law. Section 199A changes retirement planning for some small business owners.

Some entrepreneurs should consider abandoning, temporarily, traditional retirement accounts like 401(k)s and IRAs.

Confusingly, other business owners may want to do just the opposite and boost their use of traditional retirement accounts.

Still another group of business owners probably want to sharpen their pencils and look seriously at a multi-year Roth conversion strategy.

If you own a business, therefore, you want to learn the gritty details of new law. And consider carefully how it changes taxation of an individual business owner’s income.

Note: This blog post’s information has been updated for the final Section 199A regulations which appeared on January 18, 2019.

Section 199A Deduction Substitute for IRA or 401(k)

A first technique some small business owners in states without income taxes may want to consider? Using their Section 199A deduction as a substitute for a traditional IRA or 401(k) retirement account.

But let me explain this technique using a simple example.

Suppose you run a successful sole proprietorship earning $100,000 a year. Further say you’re married and will use in 2018 the new $24,000 standard deduction.

Your taxable income in this case equals $76,000 before the Section 199A deduction.

The Section 199A deduction in this case, however, adds another deduction to your return. That deduction equals 20% of the $76,000 of taxable income, or $15,200, which drops your taxable income another $15,200 down to $60,800.

And so here’s where Section 199A changes retirement planning…

In this situation, if you operate your business and live in a state without income tax, you have little reason to use a tax-deferred retirement account. You may as well use the tax-sheltered income and the savings created by the $15,200  Section 199A deduction for retirement savings.

Note: Seven states don’t tax income: Alaska, Florida, Nevada, South Dakota, Texas, Washington and Wyoming.

Rather than contribute, say, $5,500 to your IRA and possibly your spouse’s IRA, you may just want to contribute that money to a potentially taxable account.

How Tax Accounting Works

No, wait, I know that sounds counter-intuitive. But consider how the tax accounting works in a situation like this.

First, you don’t need to contribute to an IRA or 401(k) to get a tax deduction that helps fund your retirement savings.

For example, you don’t need a $5,500 IRA contribution to put a $5,500 tax deduction on your tax return. You actually get an automatic $15,200 tax deduction simply because you own a profitable business.

Second, the new Section 199A tax deduction itself shelters investment income that you might have paid federal income tax on prior to Section 199A.

At the income level described here, the Section 199A deduction pushes the household taxable income down well into the new 12% tax bracket which means that roughly $17,000 of your qualified dividend income and long-term capital gain income will be subject to a 0% tax rate.

Note: To learn where the 12% tax rate bracket ends for other filing statuses, you can look at Oblivious Investor’s web post here.

That $17,000 of “breathing room” maybe doesn’t sound like that much space. But you might actually be able to have nearly $1,000,000 in a stock market index fund before you pay taxes on qualified dividends and long-term capital gains.

Note: Qualified dividends from the Vanguard total stock market index fund run about 2%.

IRA Deduction May Reduce Sec. 199A Deduction

Now, yes, you are absolutely correct that contributing $5,500 to a traditional IRA or 401(k) gets that taxpayer another $5,500 of annual tax deduction. That deduction annually saves her or him perhaps another $660 of taxes in a situation like that described here. But maybe those savings aren’t that compelling.

Do note someone further reduces their taxable income with an IRA or 401(k) contribution and that that reduction also reduces their Section 199A deduction. (In the example given here, that reduction in the Section 199A deduction “costs” about $130 of lost Section 199A tax savings.)

Now we’re talking not $660 of lost annual tax savings but maybe $530 of lost savings.

And then look at the big picture where someone foregoes those annual tax savings by using a taxable account. Over 35 years, she or he accumulates roughly $500,000 in real dollar terms (if they earn five percent annually and contribute $5,500 each year). The taxpayer will have paid $18,000 to $19,000 in income taxes over those 35 years. Which is a lot. But she or he then draws down that money without paying income taxes.

That seems a reasonable choice for some taxpayers living and working in or planning to retire to states with no or very low state income taxes…

Other Disadvantages of IRA and 401(k) Accounts

You know what else to remember? Remember you lose some other subtle benefits by putting money into an IRA or 401(k) account.

Often we don’t think much about these other lost benefits, but they become more significant in a example like that described here.

Consider, for example, these drawbacks of an IRA or 401(k) plan as compared to a taxable account that isn’t actually taxable:

• IRA or 401(k) accounts convert tax-free and preferentially taxed qualified dividends income and long-term capital gains (due to the 0% tax bracket and the 15% tax bracket) into ordinary taxable income.
• IRA or 401(k) accounts eventually subject you to required minimum distributions in retirement, which may force you to realize income and liquidate your portfolio even if you don’t need the money.
• With an IRA or 401(k) account, you may find yourself paying early withdrawal penalties or subject to more complicated withdrawal math if you retire or draw money before reaching  age 59 and 1/2.
• IRA or 401(k) accounts conceivably limit your investment choices. Direct real estate investment and small business ownership become pretty impractical inside a tax-deferred investment account, for example.
• Taxable accounts may provide additional tax saving opportunities during the years you accumulate in the form of foreign tax credits, tax loss harvesting and non-cash charitable contributions.
• Taxable accounts provide some taxpayers with meaningful estate planning benefits. The ability to gift stocks to heirs without income tax consequences, for example. And the Sec. 1014 step-up in basis when a shareholder passes away (which means heirs such as a spouse avoid capital gains taxes).

The long and short of it? For some self-employed middle-class taxpayers in states with no or low state income tax, the IRA or 401(k) option has lost some or even much of its luster.

Section 199A Deduction Substitute for Roth Account

Once you understand the tax accounting reviewed in the preceding paragraphs, another actionable insight may come into focus… For some self-employed taxpayers, especially those living in states with either no state income taxes or very low state income taxes, Roth-IRAs and Roth-401(k) options lose much or even all of their attraction.

A Roth-style account, as you probably know if you’re reading this, doesn’t give you a immediate tax savings. (In the preceding paragraphs’ example, this tax savings runs $500 to $600 per $5,500 contribution.)

But even so, a Roth-style account offers benefits: You escape income taxes on the investment income earned inside the account. You don’t have to take required minimum distributions (though your heirs will.) And neither you nor your heirs pay income taxes on the money drawn from the account.

These benefits, however, lose their attraction for a small business owner enjoying a generous Section 199A deduction and paying a 0% qualified dividends and 0% long-term capital gains federal tax rate because of that Section 199A deduction.

In essence, Section 199A gives these self-employed taxpayers in states without a state income tax the same tax accounting–except without the extra complexity and restrictions of a Roth.

Taxpayers in states with very low state income tax rates get nearly the same accounting–but again without the extra complexity and restrictions of a Roth.

Section 199A Roth Conversions

Another connection between Section 199A and Roth accounts: Business owners with significant tax-deferred retirement account balances should look at the option of using the Section 199A deduction to avoid paying income taxes on Roth conversions.

In other words, a business owner with a $20,000 or $40,000 or $60,000 Section 199A deduction might in effect use that deduction to shelter $20,000 or $40,000 or $60,000 of “Roth Conversion” income from federal taxes.

Just so you know? I am not a hardcore fan of Roth-style accounts (something I’ve chattered lots about in blog posts before, such as Are Roth-IRAs and Roth-401(k)s Really a Good Idea.)

But federal income tax rates are noticeably lower for middle class and upper class taxpayers for at least the next few years even before the Section 199A deduction.

Maybe, given those already low rates, business owners should not piddle away the tax savings from Section 199A. Maybe, instead, they should use the Section 199A loophole to restructure their retirement savings for the long run.

Over the next few years, some business owners might easily move a few hundred thousand dollars from tax-deferred retirement accounts to Roth-style accounts without (in one sense) paying additional income taxes.

Escape Section 199A Disqualification with Pension

One other wrinkle related to the interplay of Section 199A and retirement planning for high income taxpayers. You may be able to escape Section 199A disqualification by ratcheting up your pension contributions.

I know. Confusing, right? But let’s dig into the details.

Okay, so as noted in earlier paragraphs, some middle-class and even upper-middle-class small business owners may need to reassess their use of IRAs and 401(k) accounts and possibly dial down their contributions.

A few folks may also want to get aggressive about Roth conversions over the next few years due to Section 199A.

However, some high income taxpayers may need to look at dialing up their contributions to tax deferred retirement accounts (and dialing down any Roth conversions) in order to get the Section 199A deduction.

Here’s why: A single taxpayer with a taxable income in excess of $207,500 or a married taxpayer with taxable income in excess of $415,000 loses the Section 199A deduction if she or he earns that income in a “specified service trade or business,”  such as white-collar profession… or if he or she runs a business that doesn’t have employees with W-2 wages or depreciable assets.

This disqualification and limitation stuff gets complicated quick. (I discuss the rules on specified service business disqualification in more detail here: Sec. 199A Pass-thru Entity Deduction and the Principal Asset Disqualification. And I cover the W-2 wages and depreciable assets limitations in detail here: Sec. 199A Deduction Phase-out Calculations.)

But the basic rule goes like this: In order to not lose the Section 199A deduction due to W-2 wages or depreciable assets limitations or due to being a specified service business, you need to have taxable income of $157,500 or less if single and taxable income of $315,000 or less if married.

A taxpayer subject to these “income-based” eligibility requirements, therefore, may want to arrange for larger pension contributions that push down their income to a level that allows them to take the Section 199A deduction.

For example, suppose you are a single taxpayer who enjoys $207,500 of taxable income from a successful small business sole proprietorship. Also suppose your operation requires no W-2 employees and employs no depreciable assets.

With this profile, you get no Section 199A deduction. Zero.

Requalifying for Section 199A with a Pension

However, if you set up a pension plan with a large contribution that pushes your income below the threshold amount, you regain the ability to use the Section 199A deduction. For example, if you set up a one-person 401(k) plan and use that to make a $50,000 pension fund contribution, that contribution lowers your taxable income to $157,500.

With a taxable income equal to $157,500 you don’t need to worry about W-2 wages or depreciable assets (or about being in a specified service business for that matter) to get the 20% Section 199A deduction.

The 20% Section 199A deduction, by the way, equals $31,500 if your taxable income equals $157,500.

In the example described here, then, a $50,000 pension fund contribution may mean you add a $50,000 pension contribution to your federal and state tax returns as well as a $31,500 Sec. 199A deduction to your federal tax return.

Note: The pension fund contribution will probably appear on both your federal and state income tax returns. The Section 199A deduction will probably only appear on your federal income tax return.

This snowballing of the deductions adds incentives for the business owner to “go big” with their pensions.

Here’s another example: Suppose instead you are married and earn $415,000 in taxable income in a specified service business operated as a one-person operation: A locum tenens physician or a management consultant or a performing artist.

At $415,000 in taxable income, sorry, you don’t get the Section 199A deduction.

If, however, you setup a defined benefit pension plan that requires a $100,000 pension fund contribution, that drops your income to $315,000 and gives you a $63,000 additional deduction.

If you’ve considered a defined benefit pension plan before but passed on the idea due to the cost, that extra $63,000 of deductions may provide the extra financial incentive you need in order to make the move.

Final Comments about How Section 199A Changes Retirement Planning

Let me close with two quick closing comments about the interplay of Section 199A with your retirement plan.

First comment: Clearly, Section 199A changes retirement planning for some small business owners. Most business owners need to reexamine their retirement plans. You may choose to stay with your current approach. But the landscape has changed. Make sure your plans shouldn’t change in response.

Second comment: The Section 199A statute runs from 2018 through 2025. Then, per the current law, the deduction goes away. As a result, business owners may want to act quickly in order to get as many years of Section 199A benefits as they can. And then, unfortunately, that 2025 sunset means in 2026 things will change again and you may need to update your retirement plan once more.

Additional Section 199A Information

If you want to learn more about Section 199A, this blog also discusses other key elements of the Section 199A in these posts:

199A Deduction: Calculating Your Tax Savings

Real estate investor Section 199A Deductions

S Corporation Shareholder Salaries and Sec. 199A Deduction

Section 199A Deduction Phase-out Calculations

Section 199A S Corporation Dissolution

Finally, if you’re a tax practitioner or other professional who needs to really understand how Sec. 199A works in order to serve clients, consider purchasing and downloading our Maximizing Section 199A Deductions monograph.