You call your CPA in March and ask about converting part of your IRA to a Roth. The answer comes back fast. That’s a big tax bill this year, so don’t do it.
Then you ask us the same question. We tell you to convert as much as you reasonably can.
Both answers come from people who want the best for you. So why don’t they match? Most of the time it isn’t because one of us is wrong. It’s because we’re answering two different questions.
Two professionals, two different jobs
Your CPA’s job is to get this year’s return right and keep this year’s tax bill as low as the law allows. That work has a deadline and a scorecard, and both are measured inside a single tax year.
Our job is different (although we have the advantage of being both a CPA and a financial advisor). We’re trying to make your money last for the rest of your life, which could be another thirty years. Sometimes the smartest thirty-year move is to pay more tax today.
Neither view is wrong. They’re looking at the same issue through different windows.
The bill you see today isn’t the only one
Suppose you skip a Roth conversion at 64 to keep this year’s taxes down. That money stays in your traditional IRA, and it keeps growing.
Eventually the withdrawals stop being optional. The IRS requires you to start taking withdrawals at 73, and those withdrawals count as taxable income.
The conversion you skipped at 64 can come back as a bigger required withdrawal at 75. The tax didn’t disappear. It moved, and it grew while it waited.
Income affects more than your tax bracket
Your income also sets what you pay for Medicare. Cross a line and your Part B and drug premiums go up.
The rule includes a built-in delay. Social Security sets your 2026 premium using your 2024 tax return.
That lag catches people. One high-income year can raise your premiums two years later, long after your CPA has closed the file on that return. A good plan looks at both effects before you act, not after.
Some decisions can’t be taken back
A Roth conversion is permanent. The IRS is clear that a conversion made in 2018 or later cannot be undone. There’s no reversal if the market falls or your income lands higher than you expected.
That’s a reason to slow down and get both professionals talking before you sign anything. It isn’t a reason to avoid conversions altogether.
They agree more often than you’d think
Here’s a case where both views line up.
If you’re 70 1/2 or older and you give to charity, you can send money straight from your IRA to a qualified charity. The gift counts toward your required withdrawal, and the amount stays off the taxable line of your return. For 2026 you can give up to $111,000 this way.
Your CPA likes it because it lowers this year’s taxable income. We like it because it shrinks the account that drives your future withdrawals. Same move, two good reasons, no argument.
Know what each person owes you
It helps to understand the ground rules.
Under federal law, an investment adviser is a fiduciary. The adviser has to serve your best interest, can’t put its own interests ahead of yours, and owes you that duty across the whole relationship rather than at one moment in it.
Your CPA also works under professional standards. The engagement is usually built around the specific work you hired them to do, which is often preparing and filing your state and federal tax returns.
How to break the tie
When the two answers conflict, resist the urge to pick the one you like better. Try this instead.
Ask each person what time period they’re solving for. This year, or the next thirty?
Ask what each one assumes about your future income and your future tax rates.
Ask to see the math over ten or twenty years, not just this April.
Then get everyone on the same call.
Most disagreements shrink fast once both professionals can see the whole picture instead of their own corner of it.
The short answer
Listen to both of them.
Your CPA is telling you the truth about this year. We’re telling you the truth about the next thirty. You need both answers, and you need them in the same conversation, which is there’s a benefit to having a financial advisor who is also a CPA.
