Mike MilliganFounder and CEO, 1.oak Financial · Founder and CEO, 1.oak Financial

The 3 Biggest "Punches" Retirement Brings

22 Jan 2026 · 1 min

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In this segment, Mike Milligan warns that the most dangerous early blow to retirees is akin to a Mike Tyson uppercut: retiring just before a market decline. He explains that withdrawing money from investment accounts for living expenses while the portfolio is shrinking locks in losses that are hard to recover from. This phenomenon is called sequence‑of‑return risk, and it occurs when retirees walk into a market downturn with their “hands down,” exposing them to irreversible financial damage.

Chapters

Well, the most dangerous early hit in retirement is similar to a Mike Tyson uppercut. It's retiring right before the market goes down. See, we're talking about taking money out of your investment accounts as income to live on while your investment balances are shrinking, locking in losses you can't recover from. We call, this would be equivalent of an uppercut, it's called sequence of return risk. Mm-hmm. You're just not being hit, you're walking into it with your hands down.