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

How Much Should You Roth Convert?

14 Oct 2026 · 2 min

Watch on YouTube

1:35

In this conversational YouTube segment, Craig Wear, CFP®, challenges the common advice of only converting enough to fill the current tax bracket when doing Roth IRA conversions. He argues that for clients with over $1 million in traditional IRAs, a strategy that pushes conversions above the current bracket can better protect their families in the long term. Wear critiques the typical CPA mindset of focusing on one‑year tax windows, emphasizing the need for a far‑reaching, future‑proof plan. He illustrates the point with the story of a client named Nancy, who waited until age 70 to act after following her CPA’s limited advice; the delayed conversion cost her significantly more than if she had acted at 65. The discussion highlights the tension between short‑term tax minimization and long‑term wealth preservation for high‑net‑worth retirees.

Question is, how much should you convert?
Well, the standard advice is to fill whatever room is left in your current tax bracket and stop right there. Sadly, this usually doesn't work as well for people with over $1 million in their IRAs. If you want a plan that actually protects your family in the future, you're most likely going to have conversions that push you above your current bracket.
There's a lot of people and even CPAs out there who won't like that idea, don't like that idea, and will never like that idea.
True, but look, the idea of paying higher taxes and and the implications it can bring in the short term feels counterintuitive. And most CPAs are great at their job, which is to look one year at a time, maybe the next year, but a future-proof strategy requires looking a lot further out. In fact, it reminds me of a client named Nancy. You remember the story about Nancy?
I definitely remember her story. She was 70 when she came to us and still had over $1 million in her IRAs. 5 years earlier, she'd asked her CPA about converting, but he told her to convert just enough to reach the top of bracket and stopped there. She said that something about it didn't sit right with her. But, you know, since he was the expert, he's the CPA, she went along with it. You know, by the time she called, required distributions were about to start and the window she needed had already closed right behind her. I mean, we still built her a plan. It just cost a great deal more to start it at 70 than it would have at 65.
Unfortunately, we see a lot of those circumstances, but that's such a great question to ask anyone when making a plan this big.