An Acknowledgement and Appreciation of Luck

I’ve been reflecting on the last ~4 years of my career, and i keep thinking about how easy it is to underestimate luck.

At 28, I was making ~125k and lined up for a promotion to ~160k. It depended on my boss getting promoted first. She didn’t so everything stalled.

I randomly applied elsewhere and got an offer for ~180k.

The day I gave notice, my boss told me she was leaving. If I had waited a few weeks, her role would’ve opened anyway.

New job:

- ~2 months in, a C‑suite leader leaves. My boss gets promoted but keeps managing me.

- They open her old role. The internal candidate doesn’t get it and leaves. That opens up his role.

- I raise my hand and get it (~200k), even with ~2 months of paternity leave coming up.

- ~10 months later, my boss pulls me into long term incentive program + bumps my comp (~290k).

- ~1 year after that, the company gets acquired. Two weeks before the deal is announced, my counterpart at the acquiring company quits. They hold the role for me and give me a $100k retention bonus to wait.

- Post close, my titles get bumped (VP to an SVP) and comp lands a bit over 400k.

I’m not saying this was all luck. I worked hard, took risks, and generally did well.

But it’s impossible to ignore how much of this came down to timing and randomness. If even a couple of those events don’t break my way, my trajectory looks very different.

I think it’s easy to attribute outcomes mostly to skill, strategy, or hustle. Those matter a lot. But I think we collectively underweight how much luck shapes careers.