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.
All of that _is_ work, just in a different form.
In my case when somebody asked me and I haven't have had much going on I did it, but I haven't chased anything.
I enjoy my current job, but it's still a job. I have people to answer to, politics to deal with, work that I dislike that I have to do in order to do the work that I do like, frustrating people who I have to work with sometimes... the usual.
If that just went away, and I could choose what to do with every moment of my time, and associate with who I wanted, and focus on passions rather than work I don't care about... that would be the best.
I took four months off last year and it was absolutely incredible. Even to the point where when I was (very rarely) bored, I even enjoyed being bored. Sure, four months isn't a year, or ten years, or 40 years, but it just felt like the right way to live. In a weird way it actually felt more structured; I actually planned things with friends (or by myself) at particular times, stuck to the things I'd committed to, exercised more, cooked more, and just felt so unhurried and relaxed all the time.
We'll see, I guess.