Retirement isn't good enough. By the time you retire you are in your 60s, which is too late for me.
The default outcome for startup founders is not "filthy rich" but rather "older and poorer".
If you try to break out and get thrown in solitary then sure, I guess you're worse off, but either way you're still trapped. What's really funny is that when your attempt fails it's the other prisoners who want to cut you down for trying & want to see you punished the most.
nxc18 offered pretty good advice, I'm not sure what your alternative is?
I like work because it has me doing stuff that's similar to what I want to do in my free time, but provides the necessary incentives to actually do it each day.
My job isn't perfect, but it has me doing productive, rewarding, mostly-interesting stuff with a bunch of smart people whom I like and can learn from.
It's worse than my dream life for my dream self, but it's better than my dream life for my actual self. I may not be behind, but I still like to feel like I'm moving forward, and work does that for me.
On the other hand, I did quite enjoy my ~1 month of working four-hour days a few years back, so there's probably a better balance than I have right now.
Meaningful work and a sense of accomplishment doesn't seem like it's caused by a culture of shame. I can get that from a hobby (painting, writing, programming, carpentry), or I can get it from a job (painting, writing, programming, carpentry). In either case, it seems normal beyond the boundaries of culture to derive satisfaction from this.
It might be a lot harder to derive satisfaction from hobbies with no "productive" output (my long bike ride, hiking in the woods) due to a culture insisting on productivity, but I don't think it's true that the productive ones would be valued less than non-productive ones if not for enculturation.
What I don't like is the routine, having to be at work at 8:00 AM M-F or otherwise losing my livelihood.
It's the requirement and forced interaction that bothers me.
Agreed.
The number of twenty (or even thirty) -somethings I've met who have been trying to make it in the bay area for years and still don't have more than a few month's worth of expenses saved up worries me. Y'all are in an incredibly vulnerable position, and it's not going to get easier to make wages the older you get.
The great thing about living frugally is you can actually have a great lifestyle while doing it. For example, I could re-create a fancy $10 breakfast sandwich from a local coffee shop in 10 minutes and for less than $1 per sandwich. You can eat like a king for a fraction of what eating out costs, and you'll probably get better quality.
If you're in the bay area, you should probably get out unless you're being paid enough to make it worth it (most aren't).
In ten years you can have far more security, money, and free time than the average person can even think of. And its really not that hard. For a techie, living paycheck to paycheck is very much a choice.