Roth conversions in your sixties: the four-question filter I use before I touch one.

Half the Roth-conversion advice on the internet is built for the wrong client. Before you convert a single dollar, here are the four questions that decide whether the math actually works for you.

Roth conversions are one of the most talked-about planning moves in the pre-retirement years, and one of the most misapplied.

The basic premise is simple: convert traditional IRA money to Roth now, pay ordinary income tax today, enjoy tax-free growth and withdrawals later. In the right scenario, this is genuinely powerful. In the wrong scenario, you’ve accelerated a significant tax bill for no real benefit.

Half the Roth conversion advice on the internet is built for the wrong client. Running through these four questions before you touch anything tells you which side of that line you’re on.

What You Need to Know Before You Convert a Dollar

According to the IRS, there is no statutory cap on how much you can convert from a traditional IRA to a Roth IRA in a given year. You could convert your entire traditional balance at once if you wanted to. Whether you should is a different question entirely, and the answer depends almost entirely on how the four factors below line up for your specific situation.

The Four-Question Filter Jeff Uses Before Every Roth Conversion

Question 1: What’s your current marginal rate versus your likely retirement rate?

This is the foundational question. If you’re in the 22% bracket now and expect to be in the 12% bracket in retirement, the math probably doesn’t favor conversion. You’d pay more today than you’d save later.

If the situation is reversed, the case for conversion gets considerably stronger. The scenario where conversions make the most sense: you’ve retired but haven’t yet started taking Social Security or required minimum distributions. Income is lower, the bracket is lower, and there’s still a long runway for tax-free compounding.

Jeff calls the window between retirement and age 73 (when required minimum distributions must begin, per the IRS) the “sweet spot” for conversions. Income drops, the bracket drops, and the clock is still running. Most people who have the ideal conditions for a Roth conversion are sitting right in that window and don’t fully realize it.

Question 2: Do you have funds outside the IRA to pay the tax?

This is the make-or-break question most people skip. If you pay the conversion tax from the IRA itself, you’ve reduced the converted amount and defeated part of the math. The conversion only makes full sense when you can pay the tax bill from a taxable account, keeping the entire converted amount working inside the Roth.

Paying from the IRA is better than not converting at all in some cases. But it’s materially worse than paying from outside. Run the numbers on both scenarios before you decide.

Question 3: How long is your runway?

Tax-free compounding needs time to overcome the upfront cost. Converting at 68 and expecting to need the money by 73 may not give the math enough room. Converting at 62 with a 20-year spending horizon is a different calculation.

A rough benchmark: a conversion typically needs 7 to 10 years of tax-free growth to break even against the alternative of leaving the money in a traditional IRA, depending on the tax rate difference and the assumed growth rate. If your runway is shorter than that, conversion may not be the right move, regardless of how your rates compare.

Question 4: What does this do to your Medicare premiums?

Conversions add to your modified adjusted gross income. A large conversion in year N triggers IRMAA surcharges in year N+2. Medicare uses a two-year income lookback to set Part B and Part D premiums, which means a large 2026 conversion raises your Medicare costs starting in 2028.

This is a real and consistently underestimated cost. For a married couple at certain income thresholds, IRMAA surcharges can add several thousand dollars per year in Medicare premiums. Running the numbers before the conversion, not after, is the only way to account for this correctly.

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How to Use the Filter in Practice

Work through all four questions before converting anything. The conditions that make conversion worth modeling seriously:

Your current bracket is lower than your projected retirement bracket
You have taxable assets to cover the tax bill outside the IRA
You have at least 7 to 10 years before you expect to need the converted funds
The conversion won’t push your income into a higher IRMAA tier

If any of those conditions flip, the math changes. That doesn’t mean conversion is wrong, but it means the case is weaker and deserves a closer look before you move.

Jeff runs this filter with clients in their early-to-mid 60s every year, not just once. The variables shift. Brackets change. Retirement timelines move. The right answer in year one isn’t always the right answer in year three.

What This Filter Won’t Tell You

The four questions will tell you whether conversion is worth pursuing. They won’t tell you the optimal conversion amount. That’s a function of your specific brackets, your state tax situation, your Social Security timing, and how IRMAA thresholds interact with your income across each year of the conversion window.

That math is worth doing carefully, and it changes every time Congress adjusts the brackets or the Social Security Administration updates the thresholds.

The Right Answer Is Almost Always “It Depends”

Roth conversions aren’t universally good or universally bad. They’re good for the right person, in the right year, at the right amount. The four questions tell you which of those you are.

If you’re in or approaching the gap years between retirement and age 73, this planning is time-sensitive. That window closes on its own schedule. Schedule a no-obligation call with Jeff to run through the filter for your specific situation.

The information provided is for educational purposes only and should not be construed as investment advice. Investment strategies should be tailored to individual circumstances, risk tolerance, and goals. Past performance doesn’t guarantee future results. Consult with qualified financial professionals regarding your specific situation.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Great Valley Advisor Group, a registered investment advisor and separate entity from LPL Financial.