[jskdvsksnb]

One anecdote: I had a very cushy position at a post-IPO startup that was taking off. My initial RSUs had appreciated by 5x by the time I left. Every time they vested I took the money off the table.

My colleagues loved me, I got great performance reviews, but I didn't feel like I was learning or growing. I was severely burnt out after working on a couple projects that exploded due to organizational problems. I went through 3 managers in a year because of reorgs and departures. Ultimately I left that job because I tortured myself - what was I doing, what value did I add? How would I get a job after this when my skills were out of date?

Meanwhile the company's stock has tripled since I left. Even if I had sold every time my stock vested I would be a millionaire by now. I grew up poor, and the security of having that money in the bank would be life-changing. Instead I'm at a new startup where I'm not any happier, but I also don't get a million dollars.

[bumby]

>new startup where I'm not any happier

The post reads like you left for one reason (fear if complacency) but your unhappiness is rooted in something completely different (financials).

Both may still be wrong way to get happy, but it’s hard to expect a job to provide that if you aren’t consistent about what you should be shooting to improve

[jskdvsksnb]

People can be unhappy about more than one thing.

My point is that the "value experience over comp and comfort" perspective was drilled into me when I was starting out, and it definitely contributed to what I now think was a mistake.