Luck and Striking it Rich

February 14, 2021

Saw this thread on twitter about career paths and payoffs that caught my attention:

Threadreader link

If you want to extract the maximum amount of payoff from your tech career path, that is probably quite a profitable path.


What’s missing from this discussion is the role that luck plays in this game. Sure, joining fast-growing companies early is a grand strategy, but how do you spot one of those? And what if you’re wrong? Would you accept years of minimum salary and worthless stock options?

For most people, following the S-curve and sticking to working at established companies, all the while collecting an increasing salary and benefits package, while building a technical and team-building reputation is probably the right risk-reward balance.

“It takes money to make money”, the saying goes, and it’s true here as well. If you can’t afford to forgo years of potential earnings down several dead-end ventures (i.e. the most likely outcome), you’re not going to see the day your startup goes exponential.

It’s one thing for someone who has had the good luck to strike it rich to describe how they got there; it’s quite another to bet your future years on uncertain ventures if you don’t have reserves to fall back on.

Their past glory is your future risk.

Good luck.

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