Episode 6: Should You Do Roth Conversions Before Retirement?

The years between your last paycheck and your first Social Security check may be the single best tax planning window of your life. Roth conversions in that window can save you significantly — but only if you do them strategically.

In this episode, I explain why pre-retirement Roth conversions are such a powerful move, who benefits most, and how to approach them without accidentally bumping into a higher tax bracket.

In this episode:

▸ What a Roth conversion is and how it works

▸ Why the pre-retirement window is often the best time to convert

▸ How to identify your conversion target each year

▸ The tax traps to watch for — Medicare surcharges, bracket creep, and more

Before Social Security starts and before RMDs kick in, many pre-retirees find themselves in the lowest tax bracket they'll see for the rest of their lives. That window is the ideal time to convert traditional IRA or 401(k) money into a Roth, paying tax now at a lower rate to avoid higher taxes later. The strategy works, but the execution requires precision. Convert too much in a single year and you can trigger IRMAA Medicare surcharges, push into a higher bracket, or make more of your future Social Security taxable. The goal is filling your bracket deliberately, not crossing it.

Episode 6 of the Retirement Transition Series — 12 short episodes for people who are 5–10 years from retirement.

▶ Next: Episode 7 — The Biggest Risk in Early Retirement

▶ Watch Episode 5 →How Retirement Income Is Taxed — What Most People Don't Know

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