Couple years back I walked away from a company that IPO’ed, cashed out enough to not worry about rent or food for the next 20–30 years. I swore off jobs, told myself I’d build something of my own. But I haven’t built anything. Haven’t even tried applying anywhere, too stubborn for that. Most days I just circle around ideas, start, stop, drop. Repeat. Money isn’t the problem—it’s this gnawing restlessness, this sense that I’m wasting what could have been momentum. I don’t know what I’m building, and that not-knowing is eating me more than anything else.
Most people underappreciate how tough it is to get yourself motivated & creating anything when the structure of a job falls away. Its fine to go take a job, just for the structure/mental stimulation it provides.
If you do take a job, I wouldn't be surprised if you eventually find a passion project that'll make everything fall into place. Its ok that it takes time to discover that passion.
(I took 2 years off for an entrepreneurial project. Finished it in the first year, bummed around purposeless for the next one. Went back to work early. 15 years later, beginning to get curious/driven again.)
It’s not like I haven’t considered getting a job — I’ve gone through this exact cycle so many times I’ve lost count. The job hunt feels dismaying, so I default to chasing ideas. It feels right for a while… until I’m back at the same question: is a job what I needed all along? My better self honestly craves structure, waking up with a clear, singular goal.
