Craig Wear, CFP®Craig Wear, CFP® | Expert in Roth Conversions & Tax-Efficient Retirement Strategies for IRA Millionaires

Why IRA Millionaires Shouldn't Listen to This Roth Conversion Advice (and what to do instead)

9 Sept 2026 · 2 min

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1:33

In this video Craig Wear, CFP®, challenges the widely‑circulated advice that Roth conversions should be limited to the top of a taxpayer’s current income tax bracket—or just below the Medicare‑premium trigger—each year. He explains that while this “guardrail” works for modest IRAs (under about $500,000), it can be costly for high‑net‑worth accounts of $1 million or more. Wear walks through two illustrative scenarios: (1) converting each year up to the 22 % bracket, which after nine years yields roughly $7.4 million for the family (about $400 k more than doing nothing); and (2) a calibrated, multi‑year conversion plan that looks ahead 30 years, varying conversion amounts based on the family’s long‑term cash‑flow needs. This second approach produces about $8.1 million—over $700 k more than the fixed‑bracket method—and reduces lifetime taxes to $443 k. The key insight is that paying a bit more tax now, deliberately, can dramatically shrink future required minimum distribution (RMD) streams, turning a large future tax hit into a modest, manageable one. Wear frames the smarter plan as “what does the family need over the next 30 years?” rather than “what bracket am I in this year?”

Chapters

The common advice is to convert right to the top of your current tax bracket and stop there, or right until you have to start paying extra Medicare premiums and stay there. Stay under the line. Don't pay a penny more than you have to this year. And I understand that line feels like a safe guardrail. And if that's your plan, you're in good company. It's what almost everybody gets told to do. I won't say that your advisor is wrong to say that, but this just isn't the thing that they do every day. And if your IRA is sitting under $500,000, that advice may serve you just fine. In fact, it's probably correct. If you should do conversions, conversions at all. But it's when the dam has $1 million or more in it that it starts costing you. And let me compare the 2 scenarios real quickly for you. The first converts to the top of the 22% bracket every year. 9 years later, the whole IRA migrates and the family ends up with about $7.4 million. That beats doing nothing by about $400,000. Here's what a smart plan does. It stops asking what bracket am I in this year and starts asking what does this family need to keep over the next 30 years? The conversions aren't the same every year. Some years you go higher, some years you pull back, depending on what the math says across the whole timeline. That plan lands at $8,100,000, over $700,000 more, and the lifetime taxes drop to $443,000. And that's the part that surprises everybody. The better plan actually asks you to go higher, pay more tax now on purpose, so the future RMD flow becomes just a trickle. For most people, it feels wrong, but it's the difference between a plan that feels smart and a plan that actually works.