Why Timing Matters More Than Taxes Alone

Why Timing Matters More Than Taxes Alone

March 20, 2026 · 29 min

About this episode

Tim Wood discusses the importance of timing in tax decisions for retirement and highlights common pitfalls in retirement planning.

The wrong tax move at the wrong time can quietly reshape retirement. In this episode, Tim Wood breaks down when Roth conversions make sense, why timing matters more than rules of thumb, and how partial conversions can offer flexibility as tax brackets shift. The conversation also explores common retirement blind spots—guessing instead of planning, spending too much too early, overlooking healthcare costs, and assuming you’ll always be able to work. Tim explains why focusing on income first he...

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