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Ask an Advisor: Help Me Understand the ‘Best Way’ to Manage an IRA. Is It Better to Pay Taxes Now or in Retirement?


 Which is the best way to handle an individual retirement account (IRA)? Let it sit and earn money, then pay taxes on the withdrawals in retirement? Or roll it over to a Roth IRA? Should I pay the taxes now and get tax-free money later? And can I have the taxes due on the rollover taken from the rollover account itself?


When you’re thinking about whether to convert a traditional IRA to a Roth IRA, you have more to consider than the immediate tax hit.

While taxes play a big part here, they aren’t the only factor at play. So you’ll want to look at the full picture as you figure out whether a Roth conversion makes sense for your current and future finances. (And it makes sense to consult a financial advisor or tax advisor before you make this move to ensure it’s all done correctly.)

Traditional vs. Roth IRAs

An advisor answers tax and retirement questions.

Before we dive into conversion factors, let’s briefly talk about the differences between traditional and Roth IRAs. Again, most people focus on the tax effects, but there are several other factors that separate the two types of retirement accounts. Those differences make Roth IRAs a winning choice for many people.

Some key differences between traditional and Roth IRAs include:

Tax timing: Traditional IRA contributions are (generally) tax-deductible when they’re made, and all withdrawals are taxed when they’re taken. Roth IRA contributions are not tax-deductible, and all withdrawals are tax-free when taken (as long as you follow the rules). That means earnings in a Roth IRA are never taxed.

Easier access to your money: Traditional IRA withdrawals taken before retirement age are subject to 10% penalties on top of the income tax hit. Roth IRA contributions – but not earnings – can be withdrawn at any time without penalty since you’ve already paid tax on them, so you can access your money when you need to (once you pass the five-year conversion anniversary).

Required minimum distributions (RMDs): With traditional IRAs, you’re required to begin taking RMDs once you hit age 73. With Roth IRAs, you never have to take distributions if you don’t want to.

Reduced taxable income: Traditional IRA withdrawals are subject to regular income taxes, increasing your taxable income. Roth IRA withdrawals are not taxable and not included in taxable income. Lower taxable income can keep you in a lower tax bracket. As an added bonus, it can help you avoid paying income tax on Social Security benefits in retirement.

Tax-free inheritance: Your heirs will pay taxes on withdrawals from inherited traditional IRAs. Heirs taking withdrawals from inherited Roth IRAs won’t pay any income taxes as long as the five-year rule has been met.

For these reasons, many people can benefit long-term from converting a traditional IRA to a Roth IRA. But before you race to make this move, consider the best way to manage it, so you don’t end up in financial difficulty.

When to Convert to a Roth IRA

An advisor answers tax and retirement questions. Since you will face a bigger tax bill when you convert a traditional IRA to a Roth IRA, you’ll want to do this strategically. If you have fluctuating income, it makes sense to convert more during a lower-income year and avoid conversions in a higher-income year.

You can also convert your traditional IRA in blocks rather than doing it all at once. You’ll need to track multiple five-year anniversaries, but you’ll be able to spread out the current income tax burden over several years rather than having to come up with an enormous lump sum all at once.

As for timing, the further away you are from retirement, the better the conversion will serve you. The tax-free earnings in the Roth will have more time to accumulate and accelerate, leaving you with a bigger tax-free nest egg for the future.

When a Roth IRA Conversion Doesn’t Make Sense

There are also situations where a Roth conversion doesn’t make sense.

For example, if you’re almost ready or already receiving Social Security and Medicare benefits, doing a Roth conversion will increase your taxable income, potentially resulting in taxable Social Security and increased Medicare premiums.

Or if you’re already retired and using the funds in your traditional IRA to cover your living expenses, the current tax hit could make it harder to pay your bills. Another reason to skip this strategy: You don’t have enough nonretirement funds available to pay the taxes, which can make the conversion a losing proposition.

The 5-Year Rule for Roth Conversions 

Roth IRA conversions come with a special restriction: You can’t take penalty-free withdrawals from the Roth IRA before the five-year anniversary of the conversion. And that applies to every conversion separately if you spread it over multiple tax years.

The five-year clock starts at the beginning of the tax year during which you converted the IRA. So, for example, if you converted $25,000 from a traditional IRA to a Roth on Nov. 15, 2022, the clock starts on Jan. 1, 2022. That means you could start taking penalty-free withdrawals after Jan. 1, 2027 – less than five full years from the actual conversion date.

This rule prevents people from doing an end run around the 10% tax penalty for early withdrawals from a traditional IRA. So don’t count on taking tax-free withdrawals on your Roth conversion right away.

Dealing With Roth Conversion Taxes

It’s tempting to use a portion of the rollover funds to pay the taxes on your Roth conversion – but that would be a huge mistake.

Make sure you have enough in regular savings to pay the full tax bill on your conversion.

Any amount you take out of the traditional IRA that doesn’t go into the new Roth IRA counts as an early withdrawal. That means, in addition to the regular income tax owed, that money will also be subject to the 10% early withdrawal penalty.

For example, say you want to convert $20,000 from a traditional to a Roth IRA. You estimate the income taxes on the conversion will be $2,000 (or 10% of the total). If you withhold $2,000 from the rollover amount, your Roth conversion will only be $18,000.

The other $2,000 will be considered an early withdrawal … and you’ll end up owing an additional $200 in IRS penalties. Plus, your Roth will have less money in it to start, and that means lower tax-free earnings over time.

Bottom Line

Don’t use part of the conversion funds to pay the taxes. It will cost you penalties now and earnings growth over the long run.

Michele Cagan, CPA, is a SmartAsset financial planning columnist and answers reader questions on personal finance and tax topics. Got a question you’d like answered? Email and your question may be answered in a future column.

Please note that Michele is not a participant in the SmartAdvisor Match platform.

Investing and Retirement Planning Tips

  • Consider working with a financial advisor for guidance on how to handle retirement accounts. Finding a qualified financial advisor doesn’t have to be hard. SmartAsset’s free tool matches you with up to three financial advisors in your area, and you can interview your advisor matches at no cost to decide which one is right for you. If you’re ready to find an advisor who can help you achieve your financial goals, get started now.
  • As you plan for income in retirement, keep an eye on Social Security. Use SmartAsset’s Social Security calculator to get an idea of what your benefits could look like in retirement.

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