Craig Wear, CFP® explains a practical, systematic approach to Roth IRA conversions called the "hedge your bet strategy." The method recommends dividing the total intended annual conversion into equal amounts and executing each portion at the beginning of every calendar quarter to reduce timing risk when market direction is uncertain.
Plan B is. I'll just call it the hedge your bet strategy, which is basically you saying, look, I really don't know whether the market's going to go up or down. I just know I got to get these conversions done, but I want to do it. So in that case, you want to go toward a more systematic conversion plan. Most people opt for a calendar quarter. So at the beginning of every calendar quarter, you divide what your total conversion is going to be by the appropriate amount, and that's the amount that you convert on that calendar quarter. The whole game plan is, look, if I don't know, if 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.
