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

What is the "Curse of the Dow" and is your portfolio at risk?

30 Jun 2026 · 1 min

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1:01

In this segment of Mike Milligan’s YouTube video, he uses Serena Williams as a vivid illustration of a uniquely designed financial plan that preserves optionality. He highlights that Williams, despite being financially secure and having a Hall of Fame tennis career, chose to return to the court after a four‑year hiatus because her life‑plan included the flexibility to do so. Milligan stresses that a one‑of‑a‑kind financial plan isn’t about conventional retirement at 65, but about maintaining the freedom to pursue unexpected, passion‑driven opportunities later in life. He reiterates that the content is purely educational, not investment advice, and prompts viewers to self‑evaluate whether their own financial plans provide similar optionality, encouraging them to begin building such flexibility if it’s lacking.

Chapters

Serena Williams does not need to play tennis for money. She's one of the wealthiest athletes of her generation. She owns a venture capital firm. She owns a clothing line. She has a Hall of Fame career and 4 years of distance from competition. She walked back on the court anyway because she wanted to, because she could, because she wanted her kids to see her play, because the plan she built for the rest of her life Included the option to do exactly this one-of-a-kind thing. That is what a one-of-a-kind financial plan is for. It is not about retiring at 65 to play golf. It's about the optionality to walk back onto the court in the future if that's what's calling you. Again, educational only, not a recommendation, but ask yourself this question. Does your plan give you the option to do the things that call you? If the answer is not yet, that is not a failure. It's time to get started.