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.

And the same person can be unhappy for different reasons no matter what choices they make. After a few of those, one starts to distrust almost any decision-making framework :)

If it helps (and it probably doesn’t, much) try not to beat yourself up too much. It’s hard to know which big decisions are mistakes and which are great, except in hindsight. I’ve made a few that turned out well; a few that turned out poorly; some that were terrible except for a twist of fate that made them great; and some that were great except for a twist that ruined them.

There’s a lot of rand() going on in life, after all.

I didn’t mean to imply you can only have one goal. But I do think sometimes people are not always aware of what would make them happy and instead default to what values hate been “drilled into” them rather than defining them for themselves

My value is "I want to have enough money to provide for my family". One way of achieving that is by getting a big lump sum payout, at the risk of future employability. The other is switching jobs frequently to stay on top of things and remain employable. I think your tone is a little condescending.

My point is that I overweighted the risk of future employability from staying a few years at a shitty place. Lots of people on HN will tell you that's a death sentence and they would never hire you with a period like that on your resume. But in retrospect I don't think it would have had nearly the impact I imagined.

Employers usually look at the last few roles on the CV, many times they don't even read the entire resumé. After a period of stagnation it's always a possiblity to take a trendier role for less pay - if the previous job offsets this relative pay cut, the engineer still won.