A short YouTube talk by Craig Wear, CFP® about Roth conversions that focuses on common perceived risks—especially market timing and selling assets to pay conversion taxes—and argues these fears are often overstated because conversions are typically done as a planned, multi-step strategy rather than a one-time event.
So there are a few risks that people bring up about doing Roth conversions, and they're not, they're not wrong. They just are, I think, a little bit over sensitive. The biggest one that people are afraid of is that they do a conversion today and the stock market's really high and they have to sell assets to pay the tax on the conversion, and now the balance is lower and they're afraid that today the balance is up here. I do the conversions, pay the taxes, and now the balance is here and the stock market goes down. Rarely happens that way because rarely is a one and done conversion strategy the right strategy for you.
