Financial planner Craig Wear argues that waiting for a lower tax bracket to convert to a Roth is a trap. The traditional IRA keeps growing while you wait, creating a larger tax bill later. He's never seen the math work out where delaying conversion beats converting sooner, even at a higher rate.
A truth that I've learned over a decade and a half of really focusing in on Roth conversions is that you simply must convert at a higher tax bracket than you're probably comfortable with. And if you wait or go small or go slow, your IRA is going to grow into a much bigger tax bomb for whoever, whether it's your spouse or the other. Waiting sounds like a good answer because it feels safe, but it's actually a trap. Every year you delay, that IRA is going to grow and that tax problem is going to get worse. And I have never seen a circumstance where the math proves that waiting waiting even for a potential lower tax bracket will make up for the added tax of the growth in that timeframe to get there, whether it's 1 year or 5 years.
