Craig Wear, CFP® advises a systematic approach to Roth IRA conversions throughout the year rather than trying to time the market. He recommends maintaining regular conversions and accelerating or adding larger conversions when a market correction (e.g., 10–12%) occurs, since that may present especially attractive opportunities to convert.
The whole game plan is, look, if I don't know, I don't have a crystal ball whether the market's going up or down, then what you're trying to do is get some conversions happening systematically throughout the year. Now, remember, if you go with that hedger timing, if you do have a market correction of 10, 12% like we normally do during the course of a year, man, boom, jump on it. That's the time to really start throwing in. Maybe you do a couple quarters at once, or maybe you just do the rest of it for the whole year, thinking, gosh, I may not have a better opportunity than that.
