In this edition of our Motley Fool Conversations series, Fool personal finance expert Dayana Yochim and retirement planning analyst Dan Caplinger discuss whether converting traditional IRAs and 401(k) plans to their Roth counterparts is a smart move. Although you pay taxes up front on a conversion, the payoff is that you never have to pay taxes on your Roth assets again -- even when you take withdrawals during retirement.

Dan and Dayana go through the pros and cons of doing a Roth conversion with some specific ideas on helping you make the right decision for your own personal financial situation. In addition, Dan points out how you can take advantage of special "do-over" provisions of Roth IRA conversions in order to maximize your returns in stocks facing big binary events that will make or break their futures. Overall, whether converting makes sense depends on what your current tax rates are compared to what you expect they'll be when you retire.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.