Forest Hill's Jeff Judge in Kiplinger: The Roth conversion advice nobody qualifies

By Jeff Judge, CFP®, AEP®, ChFC®, CLU®, Managing Partner, Chesapeake Financial Planners, Forest Hill, MD.

Roth conversions get treated like a rule everyone should follow: pay the tax now, enjoy tax-free growth later. It's good advice often enough that it's become a reflex, and reflexes are where mistakes hide.

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I wrote a piece for Kiplinger on five situations where converting is actually the wrong call. Converting in a year your income is already high can push you into a bracket you didn't need to enter. Needing that money again inside five years costs you the penalty-free window. A conversion can also trigger a Medicare premium surcharge two years down the road, long after the decision is made and forgotten.

For families in Bel Air and Fallston, and for commuters heading into Towson every day who are trying to plan retirement around a schedule that doesn't leave time to research this stuff, the lesson isn't that Roth conversions are bad. It's that the question is never yes or no. It's whether this conversion, in this year, at your numbers, actually works.

The takeaway for Harford County retirees and pre-retirees: run the numbers before you convert, not after. A decision that looks smart in isolation can create a tax problem that shows up two years later, when it's too late to undo.

This piece builds on "Think a Roth Conversion Is Always Smart? Here Are 5 Times It Could Cost You," in Kiplinger (September 2026).

Jeff Judge, CFP®, AEP®, ChFC®, CLU®, is Managing Partner at Chesapeake Financial Planners in Forest Hill, MD. Book an intro call.