Due to some lucky events I was able to maintain some fairly large custom ERP system. After few inital years all the big problems were fixed and I was keeping eye on it for next 10 years. In reality it meant about 1 or 2 hours of work every (other) month and I was paid enough to be confortable, not that much, but enough to live the life I wanted. Kind of universal income reality.
What do you think? Did I missed going to the office? Was I depressed because I haven't been climbing corporate ladder? Nah, it was awesome.
I spent few years traveling, I worked on more then 50 projects (SW and HW), I tried to launch few startups and helped couple VC funded companies, I've even bought farm and and was fortunate to spend a few years with my newly born kids without constantly thinking about some deadlines that was not imposed by me. I never felt like I was wasting my life, quite oposite: I had so much time for exploring various projects and learn new skill and I didn't need to think about will-that-make-it-me-some-money type of questions.
I am currently working normal job (well, it remote and 4-days a week, but still) writing software for banks, telcos and other corporations and it just didn't filled me with purpose or self-actualisation.