The Double‑Stuff Illusion in Retirement Planning

The Double‑Stuff Illusion in Retirement Planning

February 27, 2026 · 28 min

About this episode

Tim Wood discusses the impact of taxes on retirement savings and the importance of planning ahead.

That million‑dollar nest egg may not be as big as you think once taxes enter the picture. This episode uses a simple Double Stuff Oreo analogy to explain why retirement accounts can create false expectations around what’s actually yours. Tim Wood breaks down how required minimum distributions, Social Security taxation, Medicare premiums, and ordinary income taxes affect retirees, and why planning ahead matters long before withdrawals begin. The conversation also explores Roth conversions, gua...

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Host: Tim Wood

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Organizations: Social Security, Medicare

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