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

DON'T Roth Convert in December

26 Jun 2026 · 1 min

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1:12

In this segment, Craig Wear, CFP®, argues that converting a traditional IRA to a Roth at the end of the year—when many people wait to assess their annual income—is a missed opportunity. Using a 2022 market drop of about 30% as a case study, he illustrates how “Tom” froze his conversions during the downturn, paying higher taxes later and forfeiting tax‑free growth. Wear explains that converting when a holding’s value is low reduces the taxable amount and, if the asset later recovers inside the Roth, all subsequent gains are tax‑free forever. He emphasizes that a market correction within an IRA should be seen as the optimal conversion window, not a reason to pause.

Chapters

So Tom converts every December, same time, same approach. And look, it feels organized. You wait till the end of the year, see where all your income is, check with your CPA or your TurboTax program, but it ignores the single biggest advantage available. So like in 2022, for example, the market dropped about 30%. Tom's growth holdings lost nearly a third of its value. And Tom did what most people do when things get shaky. He froze. He paused and didn't do conversions. He waited because, man, if it's going to fall this far, maybe it'll fall further again. And I mean, it felt responsible and who wants to convert when things are really low is kind of where a lot of people's attitudes are. And it's actually the most expensive decision that Tom made that year. See, when a holding drops in value and you convert it at a lower price, you pay taxes on the lower amount. That's a straight tax savings right there. But here's the bigger part, the recovery, when that holding climbs back up and beyond, if that happens inside the Roth, all of that growth is tax-free permanently. So Tom didn't just pay more tax than he needed by waiting. He also missed out on tax-free growth that he's never going to get back. A market correction inside your IRA isn't a reason to pause. It's actually the best conversion opportunity that you get.