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Mastering Roth IRA conversions: Your guide to smart retirement planning

By: Yogesh Prasad, CFA, CAIA

Are you looking to supercharge your retirement savings and outsmart Uncle Sam? If so, a Roth IRA conversion might be your secret weapon. But before you dive in, let’s break down this powerful financial strategy and see if it’s the right move for your future.

Understanding Roth IRA conversions: The basics

Imagine you’re at your favorite coffee shop, faced with a choice: pay for your latte now or later. Paying upfront might sting a bit, but you’ll sip your drink worry-free. That’s the essence of a Roth IRA conversion – you pay taxes on your retirement savings now, so you can enjoy tax-free withdrawals later.

But unlike your morning coffee, this decision can have a monumental impact on your financial future.

What exactly is a Roth IRA conversion?

A Roth IRA conversion allows you to transfer funds from a traditional IRA into a Roth IRA. The key difference lies in the tax treatment:

Traditional IRA: You get a tax break on contributions, but withdrawals are taxed in retirement.

Roth IRA: You contribute after-tax dollars, but qualified withdrawals in retirement are completely tax-free.

Here’s a handy comparison to illustrate the differences:

Feature
Traditional IRA
Roth IRA
Contributions
Tax-deductible
After-tax
Growth
Tax-deferred
Tax-free
Withdrawals
Taxable
Tax-free (if qualified)
RMDs
Required at age 73
Not required for original owner

When does a Roth conversion make financial sense?

1. You're in a lower tax bracket now

If you expect to be in a higher tax bracket during retirement, converting now could result in significant long-term savings. For example, if you’re early in your career or taking a sabbatical, your current lower income might make this the perfect time to convert.

Tax rate
Single filers
Married individuals filing joint returns
Heads of households
10%
$0 to $11,925
$0 to $23,850
$0 to $17,000
12%
$11,925 to $48,475
$23,850 to $96,950
$17,000 to $64,850
22%
$48,475 to $103,350
$96,950 to $206,700
$64,850 to $103,350
24%
$103,350 to $197,300
$206,700 to $394,600
$103,350 to $197,300
32%
$197,300 to $250,525
$394,600 to $501,050
$197,300 to $250,500
35%
$250,525 to $626,350
$501,050 to $751,600
$250,500 to $626,350
37%
$626,350 or more
$751,600 or more
$626,350 or more

Source: www.irs.gov

2. You want tax diversification

Having both traditional and Roth accounts gives you more flexibility in managing your tax liability in retirement. This strategy, often called “tax diversification,” allows you to draw from different accounts strategically based on your tax situation each year.

3. You're concerned about future tax rates

If you believe tax rates will increase in the future (which, given historical trends and current national debt, isn’t unreasonable), locking in today’s rates through a conversion could be a smart move.

4. You Want to Leave a Tax-Free Inheritance

Roth IRAs can be excellent wealth transfer tools. Unlike traditional IRAs, Roth IRAs don’t have required minimum distributions (RMDs) for the original owner, allowing the account to potentially grow tax-free for decades.

Red flags: When to reconsider a Roth conversion

1. You're at your peak earnings

If you’re at the zenith of your career, you might be paying a premium on every dollar converted. For instance, if you’re in the 35% tax bracket now but expect to be in the 24% bracket in retirement, a conversion might not be beneficial.

2. You lack liquid funds to pay conversion taxes

If you can’t pay the conversion taxes without dipping into your IRA, it might not be worth it. Using IRA funds to pay taxes reduces the amount that can grow tax-free, diminishing the benefits of the conversion.

3. Retirement is just around the corner

If you’re planning to retire soon and will need to tap into your IRA funds, the benefits of conversion might not have enough time to materialize. The break-even point for many conversions is often 10-15 years.

4. It could affect your social security or medicare

A conversion could increase your taxable income, potentially affecting your Social Security benefits or Medicare premiums. This is particularly important for those nearing or in retirement.

Pro tips for a successful Roth conversion

1. Start small with partial conversions

You don’t have to convert your entire IRA at once. Consider a series of partial conversions over several years to spread out the tax hit. This strategy, often called “bracket filling,” involves converting just enough to “fill up” your current tax bracket each year.

2. Mind your tax brackets

Calculate how much you can convert without pushing yourself into a higher tax bracket. 

3. Use non-IRA funds to pay taxes

Paying taxes from your IRA reduces the amount that can grow tax-free. If possible, use funds from a taxable account to cover the conversion taxes.

4. Plan ahead and consider the five-year rule

Conversions are irreversible, so make sure you’ve considered all angles before proceeding. Also, be aware of the five-year rule: you must wait five years after a conversion before you can withdraw the converted amount penalty-free if you’re under 59½.

Amount of Roth IRA contributions that you can make for 2024

If your filing status is...
An your modified AGI is...
Then you can contribute...
married filing jointly or qualifying surviving spouse
$229,999 or less
up to the limit
married filing jointly or qualifying surviving spouse
$230,000 to $239,999
a reduced amount
married filing jointly or qualifying surviving spouse
$240,000 or more
zero
married filing separately & you lived with a spouse anytime during the year
$9,999 or less
a reduced amount
married filing separately & you lived with a spouse anytime during the year
$10,000 or more
zero
single/head of household/married filing separately & you didn't live with a spouse anytime in the year
$145,999 or less
up to the limit
single/head of household/married filing separately & you didn't live with a spouse anytime in the year
$146,000 to $160,999
a reduced amount
single/head of household/married filing separately & you didn't live with a spouse anytime in the year
$161,000 or more
zero

Source: www.irs.gov

The bottom line: Is a Roth conversion right for you?

A Roth IRA conversion can be a powerful tool in your retirement planning arsenal, but it’s not one-size-fits-all. Like a bespoke suit, your financial strategy should be tailored to your unique situation.

While the prospect of tax-free withdrawals in retirement is alluring, the upfront tax bill can be substantial. As the old adage goes, there’s no such thing as a free lunch – or in this case, a tax-free retirement.

Before making any moves, consult with a qualified financial advisor or tax professional. They can help you run the numbers and determine if a Roth conversion aligns with your long-term financial goals. After all, the ultimate objective isn’t just to save on taxes – it’s to build a retirement that’s as rich and satisfying as that perfect cup of coffee you’ve been dreaming about.

Remember, the key to a successful retirement strategy is not just about maximizing returns, but also about minimizing risks and optimizing your tax situation. A well-executed Roth conversion strategy could be the difference between a good retirement and a great one. So,

take the time to understand your options, crunch the numbers, and make an informed decision that sets you up for a brighter financial future.

References