Reasonably Happy

Reasonably Happy

Where were you at 30?

I was in the Moat of Low Status

Paul Ollinger's avatar
Paul Ollinger
May 06, 2026

I recently met up with two business school pals for dinner. As we waited for our table and enjoyed a cocktail in the bar, we started talking to a couple of younger guys.

Oh to have more hair than money…

They were recent Kellogg MBA grads who worked for a very large online retailer. (I won’t say which one, but it’s as big as a South American river.)

Friendly and respectfully curious, they asked us about our career paths. They were duly impressed with my accomplished classmates—a hedge fund manager and former start-up executive who has rung the bell a few times. I’ve done all right myself.

Then one of the guys asked an excellent question: “Where were you at 30?”

I laughed, pointed to the software leader, and said, “When I was 30, I was deep in debt, sharing a two-bedroom, one-bathroom walk-up with this guy, and working in an industry that was unravelling violently.”

The young men smiled at my unimpressive answer. I elaborated.

On my 31st birthday in March 2000, the stock market was in free fall. The Nasdaq Composite index lost 1/3 of its value in four weeks, on its way to shedding 80% over 18 months.

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