> Coming at it from a different perspective, I did something similar to this by saving money on a US salary and then moving to a low cost of living country. I spent years at a time not working or even thinking about how to make money. I think almost everyone has felt the pain of financial and social obligation, but very few people have experience a total lack of such obligations for years at a time which leads to things like fantasizing about FU money.

While I haven't fantasized much about that, I'd say the past half decade has been very similar to what you describe.

> I can tell you that for me personally I don't think it was ideal. Yes, at first the freedom is exhilarating, but it doesn't last forever. There were two big problems. One is that you feel disconnected from society. This is hard to explain but being outside of normal social structures you lose a sense of context and meaning to your actions.

Thanks a ton for putting that into words and making me feel less isolated about having similar feelings! In my interactions with family and friends, I often felt guilty somehow about not sharing their day-to-day concerns. I was relatively frugal generally, but I'd just buy whatever I wanted. Going to a supermarket with them was frustrating and somewhat embarrassing, because they'd hunt for the cheap stuff. Or sometimes they'd 'indulge' and their indulgence was something that just wouldn't register for me as anything noteworthy if I'd be shopping by myself.

We'd talk about future prospects (a number of them working in the 'service industry') and I would hide the fact that for me these issues were not on my mind at all. Not because I'm rich by any means, but because I get messages and calls from recruiters on a weekly basis, and could potentially make more in three months than they would in a year.

> Second is that when you don't have any social or financial pressures it's hard to avoid the path of least resistance. It's very easy to fall into bad habits, just watching youtube, reading reddit, bad diet, etc.

My 'saving grace', I suppose, has been a constant desire to keep learning and an anxiety-driven need to 'stay up to date in my field'. But I definitely lost a lot of my 'fire' and self-improvement and goal-setting once I was good enough to just get work without even looking for it.

> I would assess myself as someone who would be less susceptible to these problems. I consider myself a fairly self-motivated person and definitely an introvert. But after several years it starts to weigh on you.

Same here. I've had an unusual life and had an unusual amount of freedom to be an auto-didact and develop skills that will probably allow me to be 'okay' no matter what (barring life's usual curve-balls). As much as I don't want to complain about that luxury, there's a weird feeling of isolation that results from it. A sort of "what's the point when nobody around me shares my (privileged?) concerns?" as well as a sense of "I feel I have an obligation to use this unique privilege for good but I don't know how". In my case, anyways.

> Today I work in an office. There are often times when it's hard and I have to deal with things I don't want to. But I still think it's better than when I wasn't working. I think if I never had the experience of not working I would probably only see the downsides of office life as the upside is quite abstract and hard for me to articulate. I don't think this is something unique to me, I think it's human nature to want social structure and this naturally comes with social obligations. But for most people not being constrained to social structures was never an option anyway so they underestimate how much it affects their happiness.

Not putting your choice down at all; it's often entered my mind, I can't help but feel like somehow that would be a kind of defeat. Sure, lots of it is probably good, but maybe there's a creative way to get all that without the downsides? Is that maybe the challenge to face?

Again, no judgment. I've never been less happy than I've been since I reached my situation of 'freedom' and the guilt over not feeling really happy and content about it. I have often considered just getting a 'regular' job again.