What’s Your Biggest Missed Opportunity You Considered at the Time?
A recent chat with friends who are edging toward retirement sparked a fun, reflective conversation about the opportunities that slipped through our fingers. We all have stories about “the one that got away,” and, in hindsight, we find humor in how life unfolded. I’d love to hear yours as well.
A couple of my own coming-to-grips moments:
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The forgotten Bitcoin era: I had an old computer that mined roughly 500 BTC. Back then, there wasn’t much you could do with them, so I repurposed the machine for a FreeNAS experiment and didn’t bother backing up the BTC. It’s one of those “oops” memory lapses that sticks with you.
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A car that shaped a financial decision: In 2010 I bought a Tesla Roadster Sport and grew to love the car. Later, I traded it in for a Model S, which then led to another trade. The sentiment was strong enough to consider placing a substantial investment (~$140k) into the newly IPO’d company. I debated carefully, chose to stay emotionally neutral, and ended up investing in a broad index (VTSAX) instead. Another “oops.”
From my friends, the standout missed opportunity was turning down an offer to join a startup as non-founding engineer #1, holding about 3% equity. That startup has since evolved into a company valued at tens of billions of dollars.
What about you? What’s your biggest missed opportunity, one you realistically weighed at the time but ultimately didn’t act on? Share the story, the moment, and what you learned—plus any hindsight you’d offer to others navigating similar crossroads.
