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

5 Strategies for Retirees to Control the Uncontrollable

15 Jan 2026 · 1 min

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In this segment, Mike Milligan warns retirees and those nearing retirement about the dangers of investor overconfidence, citing CFA Institute research that most investors overestimate their ability to beat the market. He explains how overconfidence leads to excessive trading, concentrated holdings, and neglect of downside protection, which can jeopardize a retiree’s ability to fund living expenses. Milligan emphasizes the fundamental principle that market movements are cyclical—what rises will fall and vice‑versa—and stresses that a well‑diversified portfolio is the most reliable way for retirees to preserve capital, reduce emotional decision‑making, and ensure they can sleep at night without fearing a major loss.

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Overconfidence, the silent killer, Mike. Research from the CFA Institute shows that many investors believe they can outperform the market, but very few actually do. And overconfidence, it just leads to excessive trading, concentrated positions, and really neglecting downside protection. Guys, what goes up is going to come down, right? What goes down is going to go up. And that is just basic advice. What we need to make sure though is that your money especially those who retired or approach retirement, we got to make sure that a major loss doesn't impact your ability to live. And so it's important to realize that you are— that having a well-diversified portfolio gives you the best chance to sleep at night and not making overly emotional decisions.