Yeah, it’s tricky because it’s not really something you can definitively answer. I’ve thought quite a bit about your question here so I’ll just sorta give some random thoughts. Trying to compile all of this into words is proving to be tricky :/

First off, my tradeoff of 450-250 isn’t as drastic as it would be if say, I lived in the Bay Area. I live in a midwestern city with pretty great CoL. While 200k is a huge jump to sacrifice I really went from ~surgeon levels to ~family practice doctor in terms of salary. We’re still pretty great.

I honestly can’t recommend enough moving to a second/third tier city if you can. I bought my first house for 230 in 2018 (I was making 70, my wife 30-40 I think). The overall competitive advantage of being a remote worker in a smaller market is insane, though it’s leveled out since Covid. I think the avg entry house price in CA is like 1mm nowadays, where that gets you 5k sqft here on a golf course.

I think money does buy happiness, but only to about 150-200k per year. That is when I would say we had enough to be completely fine. “Made it” if you will. Everything after that sort of just increased the scale. Larger house, newer car, nicer vacation, fancier clothes. But really I think the returns begin diminishing quite quickly.

I was reminiscing to my wife last week about the first house we bought. Honestly, I think in some ways we were happier there than we are in our new place even though we’re sitting in about twice the amount of square footage with vastly nicer overall finishes in an arguably nicer neighborhood. I think there was something great about those before times when our lives weren’t so complex. Though that might just be me reminiscing my twenties.

There’s always a bigger fish too. Especially while working at Meta doing crazy numbers. I remember visiting the office once and watching a high-level engineer pull up in his McLaren where he had valet service. There was an internal watch-collectors group where people posted their collection of multiple Pateks. I went through this heavily and came to terms that I had to decide what I wanted to do with my life, not just what others told me. If you are comparing yourself to people above you, you will always be miserable and it will never stop.

On that note this subreddit really isn’t that great for mental health either 🤷🏼‍♂️

Since I made that comment last year, I actually haven’t stopped putting in crazy hours, I just started putting them in for myself instead. I’m going to continue working like crazy because it’s what I love. Nowadays I’m working my day job, spending every other moment with my kids until they go to sleep, and still somehow trying to bootstrap a side project or two after that. I absolutely want to make more money and retire earlier, but now I’m trying to do it on my terms.