Retirement planning involves complex rules, and you rarely get a second chance if you goof up. But in converting a Roth IRA, the opportunity to recharacterize your conversion essentially gives you a do-over opportunity that you can use to boost your total retirement assets.

In the following video, Dan Caplinger, The Motley Fool's director of investment planning, goes through Roth IRA recharacterizations and how they work. Dan notes that when you convert an IRA, you can later recharacterize it, essentially undoing the entire conversion. That can be especially lucrative if your investments drop in value, as it prevents you from having to pay taxes on a higher amount. But Dan also goes through strategies that let divide your IRA into two parts, retaining the option to recharacterize either part. In his example, by taking high-flying consumer discretionary stocks General Motors (GM -0.17%) and Best Buy (BBY 0.20%) in one pot and lagging telecoms AT&T (T 1.10%), Windstream (WINMQ), and CenturyLink (LUMN -0.76%) in another, you can choose to keep whichever half outperforms the other while recharacterizing the underperforming portfolio.

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