A Detroit listener named Dave put a sharper question to financial advisor Wes Moss than most people bother to ask: if Roth conversions are so universally praised, why does the math not work for everyone? Moss’s answer, delivered on the Clark Howard Podcast’s “Ask An Advisor” segment on March 31, 2026, cut through a topic that usually generates only cheerleading.
“The Roth conversion has taken on its own virality. It’s like, whoa, you got to do a Roth conversion. Everybody needs to do a Roth conversion or else you’re crazy. That’s not true at all,” Moss said. He is right. The reason comes down to one question most people never ask before converting: what tax rate am I paying today, and what rate will I actually face in retirement?
The Tax Rate Spread Is the Only Number That Matters
A Roth conversion is a tax prepayment. You pull money from a traditional IRA, add it to your taxable income for the year, pay ordinary income tax on it now, and the money grows tax-free going forward. The conversion wins if your current tax rate is lower than your future rate. It loses if your current rate is higher. That single comparison is the entire analysis.
Moss walked through the core scenario directly: “If you’re going to convert IRA money to a Roth and pay 20% to do it or 25% to do it, but you know, in retirement, you’re going to be in the 15% bracket federally and your state tax may end up at zero, then why would you pay 25% to get money out of an IRA and put it in a Roth when you’re only going to be paying 15% in the future?”
That spread, 25% today versus a lower rate later, means every converted dollar carries an embedded penalty. On a $100,000 conversion, a 10-point rate mismatch costs $10,000 in unnecessary taxes. That is the price of following advice that did not fit the situation. One more hidden trap: Moss revisited the topic on the May 12, 2026 episode of the same podcast, warning that conversions produce a sudden tax bill that people quickly regret. “When the tax bill comes due 3 months later, 6 months later, a year later, people forget all the glory of Clark Howard talking about the Roth,” he told Howard. “And you know what they remember? $12,000 tax bill.”
It is also worth noting that one of the most common arguments for accelerating Roth conversions has lost its urgency. For years, advisors warned that the lower rates from the 2017 Tax Cuts and Jobs Act would expire after 2025, making now the time to convert. The One Big Beautiful Bill Act, signed in July 2025, permanently extended those rates. The seven-bracket structure, with rates of 10%, 12%, 22%, 24%, 32%, 35%, and 37%, is now the permanent law. The sunset argument for rushing conversions no longer applies.
Dave’s Actual Strategy Deserves a Serious Look
Dave described himself as someone with two-thirds of his money in a traditional IRA, and he proposed an alternative: spend down the traditional IRA in lower-tax years and delay Social Security until 70 rather than converting. The strategy has genuine merit.
Assume Dave is 63, has $900,000 total, with $600,000 in a traditional IRA and $300,000 in taxable accounts, and plans to retire at 65. Between 65 and 70, he has five years with no Social Security income and no wages. His taxable income is entirely within his control during that window. Drawing $50,000 per year from the traditional IRA during those years would likely keep him inside the 12% federal bracket for a single filer, which covers taxable income up to $50,400 in 2026. Many states also exempt IRA withdrawals from state income tax after a certain age. He pays a low rate on money he would have had to take out anyway once required minimum distributions begin at 73, and he earns a permanently higher Social Security benefit that is inflation-adjusted for life.
A Roth conversion during his working years, when income is higher, could easily push him into the 22% or 24% bracket. Paying a higher rate now to avoid paying a lower rate later is not a plan. It is an expensive mistake dressed up as one.
When Conversion Actually Makes Sense
The profile where Roth conversions deliver real value is specific. A retiree who left the workforce early, has a gap before RMDs or Social Security begin, sits in the 12% bracket during that window, and expects large RMDs to force them into the 22% bracket or higher later is a genuine candidate. Consider a retiree at 60 with $1.5 million in a traditional IRA and no other income. RMDs starting at 73 could force $80,000 or more per year into taxable income, potentially triggering higher Medicare premiums through IRMAA surcharges on top of the direct tax hit.
IRMAA operates as a cliff system. For 2026, the standard Medicare Part B premium is $202.90 per month. Once a single filer’s Modified Adjusted Gross Income exceeds $109,000, surcharges kick in and the total Part B premium can reach $689.90 per month at the highest income tier. Every dollar of a large RMD counts toward that MAGI figure, as does every dollar converted to a Roth. The surcharge is calculated based on income from two years prior, so a conversion done today affects Medicare premiums two years later, making the true cost easy to underestimate.
Converting $50,000 to $75,000 per year during a low-income window at 12% can genuinely reduce lifetime tax burden when the spread runs in the right direction: a low rate today, a higher rate forced later. That is when the math works.
Dave’s situation runs in the opposite direction, and Moss gave him the honest answer: “Don’t feel as though you’re crazy because it doesn’t make sense to you, because it doesn’t make sense for a lot of people.”
The One Step That Clarifies Everything
Before converting a single dollar, estimate your retirement tax rate with specificity. Add up expected Social Security income, any pension, and the RMD you would face at 73 based on your projected IRA balance. Compare that total to your current marginal rate. If retirement income pushes you into a lower bracket, skip the conversion and spend down the traditional IRA in low-income years instead. If RMDs threaten to push you well above your current rate, gradual conversions during the gap years can pay off.
The IRS’s RMD tables and the Social Security Administration’s benefit estimator at SSA.gov provide the key inputs. The math is not complicated. What is complicated is the persistent cultural pressure to convert regardless of individual circumstances, and Moss’s willingness to push back on it directly is rarer than it should be.
Editor’s note: This update added context from the May 12, 2026 Clark Howard Podcast episode in which Moss described the “$12,000 tax bill” retirees remember long after conversion enthusiasm fades, noted that the One Big Beautiful Bill Act permanently extended TCJA tax rates, removing the sunset-driven urgency often cited for accelerating conversions, and refreshed the IRMAA section with 2026 figures including the $202.90 standard Part B premium, the $109,000 single-filer threshold for surcharges, and the $689.90 top-tier monthly premium.
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