I'm kind of in this situation now, and it doesn't feel super great to be sort of trapped in a golden handcuffs kind of situation. The effect would be less intense if it weren't an entirely mental exercise.

I have two thoughts:

1) I generally take the higher paying gigs but mostly so I can accelerate retirement 2) Even in the crappiness of high paying jobs (I often think I'm essentially being bribed to put up with all the BS) I can generally maneuver myself into doing interesting work. It takes about 1.5 years of concerted effort, but once I understand how stuff works, I can generally start nudging stuff in the right direction, and can eventually find some form of fulfillment amongst the BS.

I'm only commenting on 1, not on the rest of your comment:

> I generally take the higher paying gigs but mostly so I can accelerate retirement

My problem with this outlook is that sacrificing my current well-being for increased future well-being is risky. I don't know how long I will live or what my health will be like. I have to make the best of the time I have now (without sacrificing too much future well-being, of course!)

Not that I don't do the same, just, it feels risky, on its own. I think the rest of your comment is super important for this reason.

It's a tricky balance to strike. I used to think that you should just work if it's available to you, but now I'm much more inclined to work so you can afford to not work in the near-term rather than only at the hypothetical end. If you can afford to be laid off or quit and just willingly chill and do whatever for a while, that's a good option to take.

Absolutely. I’m painfully aware that I didn’t offer any solution either, because it is a balance that everyone must find for themselves. The main thing I was trying to get across is that sacrificing now for a reward in the possibly distant (relatively speaking) future is too risky for me since I don’t know what the future holds (and given how many people I know who have died young makes me reluctant to take for granted that I would reach retirement age (even early))

The sentiment is certainly shared.

Having worked in startups for most of my career, I see a lot of engineers who yo-yo between high paid, boring jobs in FAANG-esque companies and burnout-inducing early stage gigs.

I love working at startups and hated working at a large company. You learn 10x more in a fast paced environment where you get a chance to work on a little bit of everything and talking to partners and investors compared to a large scale company where you’re tweaking a small area of the company. Startups are obviously not for everyone and I know plenty of people that prefer the corporate environment either because they like the stability, hours, or the salary.

Which is a really weird situation when you think about it! This gives credence to the theory I've heard that corporate jobs are "unsustainable" in that they will only hire "smart" people, but actively make their employees dumber.

Whether that's the particular mechanism or not, I think this bears investigation.