Edition 06 · November 3, 2026

Seven Financial Mistakes I Watched Smart People Make During My Nearly Forty Years in Corporate Finance, Part 2: The Transition-Specific Mistakes

Mistakes 5 to 7. The habits that matter most in the years surrounding the transition out of corporate life.

Last month, I shared the first four financial mistakes I watched smart, capable people make during nearly forty years in corporate finance: not capturing the full 401(k) match, carrying credit card debt, accepting the thirty-year mortgage as inevitable, and treating health as separate from wealth. Those are the foundational habits, the ones that matter no matter where you are in your career.

This month, I want to share the remaining three: the mistakes that surface specifically in the years surrounding the transition out of corporate life.

Mistake 5: Taking Social Security Too Early

The temptation to claim Social Security benefits at sixty-two is understandable. It feels like money you have earned and are finally receiving. But claiming early permanently reduces your monthly benefit, and that reduction can affect your financial security for decades.

The full edition, including all three transition mistakes and the household strategy behind them, publishes November 3.

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