When Converting a Roth I.R.A. Back to a Traditional One Makes Sense Michael E. Goodman, of Wealthstream Advisors, has a client whose charitable donations offset some of the tax bill from converting a traditional I.R.A. to a Roth. WHEN it comes to making financial decisions to save on taxes, you don't usually get a do-over. Just ask all those people who rushed to make large tax-free gifts to family members at the end of last year before a historically high exemption was set to expire. Not only did the exemption not end, but it was increased for 2013. And there was no way to get those tax-driven gifts back. One exception to the no-do-over rule involves the Roth I.R.A. When people move money from a tax-deferred I.R.A. to a tax-free Roth, they pay income taxes on the amount they transfer. Because the move has huge tax implications, the federal government gives people a chance each year to change their minds if they do it within a certain period of time. Over the last three years, planners pushed the conversion idea especially hard with clients because of certain tax advantages. And some people might have been pushed harder than they should have been. Those who made the conversion to Roth - and now regret it - will have until Oct. 15 to change their minds and get back the taxes they paid. But undoing it, even if it makes financial sense, may be hard for some people to even consider. For many tax-driven investors, it probably took a lot of convincing from accountants and advisers to get comfortable with paying up to 35 percent of the account value in federal taxes. With the deadline to "recharacterize" a Roth, to use industry jargon, fast approaching, I wanted to take a look at some of the questions surrounding Roths before and after Oct. 15. Should anyone have second thoughts, if retirement investing is the ultimate in long-term planning, or should a conversion be seen as just another financial strategy? Are there risks to undoing a transfer? And now that income tax rates have risen, are Roth conversions less attractive going forward? THE ROTH RUSH To understand why voluntarily paying a large tax bill on retirement savings was attractive last year, you have to first understand the difference in how money put into and taken out of traditional and Roth I.R.A."s is treated. In a traditional individual retirement account, money is put in before taxes are paid; when it is withdrawn after a person turns 59 ½, it is taxed as income. Those who do not need the money in their 60s can wait until they are 70 ½, at which point there is an annual required minimum distribution that is calculated based on life expectancy. But that will make the withdrawals bigger and the tax rate higher. If that I.R.A. is passed on to heirs, they still have to pay income tax on the withdrawals and the account will be considered part of the estate. In a Roth I.R.A., money is put in after taxes are paid and is later withdrawn tax-free. There are no required distributions. It is also included in an estate, but when it passes to heirs they can make withdrawals free of income tax. Therefore, to convert from a traditional I.R.A. to a Roth I.R.A., you need to pay the income taxes you did not pay when that money was originally put in. The amounts can be large and can put people into a higher tax bracket for the year. The certainty of higher income tax rates in 2013 made the conversion attractive last year: high earners, in particular, could pay federal tax at 35 percent instead of the current 39.6 percent. They also owed state taxes, but the amount depended on their state. "It takes a client who understands the importance of converting something from tax-deferred to tax-free and paying the taxes upfront," said Winnie Sun, managing director of Sun Group Wealth Partners. It's a pretty prudent client who understands that it's better to convert your I.R.A. and pay the taxes now. CHANGING YOUR MIND Yet even though proponents say there are people for whom such a conversion makes a lot sense, there are others who did not think it through fully. People who should not undo their Roth conversion - and may want to consider additional conversions if they can stomach the tax - generally fall into three categories: They have other investments to live on. When they are forced to take distributions, they will end up paying tax at a higher rate on money they do not need. Or, ultimately, they would like to leave their retirement account to their heirs. There is a subset that could temporarily be in a low tax bracket, and a conversion for heirs might make sense. John Napolitano, chief executive of U.S. Wealth Management, gave the example of an executive who retires at 64 and has a few years of deferred compensation being paid to him. "Once they're done taking out their deferred compensation, their tax bracket is pretty low," he said. If they go from 40 percent to 28 percent, I'd recommend a partial Roth conversion and they pay taxes at a lower rate than they're used to.