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

Don't Time the Market with your Roth Conversion

17 Jun 2026 · 1 min

Watch on YouTube

1:05

In this segment Craig Wear, CFP®, explains why a solid retirement tax plan alone cannot guarantee optimal Roth IRA conversion timing because market movements are unpredictable. He highlights that many high‑net‑worth IRA owners miss conversion windows when market dips align with their personal tax and retirement thresholds. To solve this, Wear introduces the client‑focused tool “Roth Radar,” which continuously monitors market conditions against an individual’s tax brackets, Medicare income limits, and survivor tax considerations. When the market dip coincides with the client’s optimal conversion point, the tool alerts the client and quantifies the exact amount to convert, turning a market decline into a strategic opportunity to improve long‑term tax positioning.

Chapters

So a solid plan can tell you how much room you have to convert and help you avoid unnecessary tax brackets, Medicare thresholds, and survivor tax problems. But the market doesn't move on your schedule. So when the opportunity suddenly appears, all you can see is how much water is being squeezed out in the jug, and by the time most people realize what happened, the market's already on its way back up. That's why most IRA millionaires miss out on these opportunities, because even a strong tax plan can't predict the window. It can only help you recognize what to do when that window opens. That's what a tool we give our clients does. It's called Roth Radar. Because you shouldn't have to spend your early retirement constantly keeping an eye on the market, we do that for you. And it's not just watching whether the market is up or down. The market being down is not enough. Roth Radar watches for the moment where the market lines up with your actual retirement plan. That way you don't miss the window of opportunity and you know exactly how much to convert. So with the right plan in place and a system watching for the right moment, What feels like a market collapse to everyone else becomes your shining opportunity. You get to move money out of your IRA into a better long-term tax position.