The first time I did it the startup I was working for was drying up and blowing away so I decided that was a good time to start my own startup. I figured it wou

The first time I did it the startup I was working for was drying up and blowing away so I decided that was a good time to start my own startup. I figured it would take a couple months. That was a spectacular failure where I realized that most of my mental models were either explicitly broken or the Fischer Price version of the actual model. I learned an outrageous amount. By the end I was glad I did it and wondered if I would do it again. I found it easy to get a new job. Quitting and working on my own project was probably the best career move that I had made up to that point. I took the next job and realized that I no longer enjoyed working for other people. I had seen too much. Office politics now seemed extra goofy too. It's just hard to take seriously. So I reloaded my savings and then after a while quit again and I'm back to working on my own projects. I learned a lot since last time but I'm sure I still have a lot to learn. Learning has always been the fun part for me. This time rather than working on just one thing I wanted to experiment with a bunch of different projects which is proving to be fun and already yielding more traction. I'll tell you what the not fun part of the whole thing is, part of this is just the part of the world I live in and people I hang out with. People hate it! Boy do they hate it. Did you remember the part in pulp fiction where Jules is telling Vincent "I'm just gonna walk the earth, like Caine" and Vincent is going "No, Jules you're gonna be a god damn bum". Most conversations I have seem to have that undertone. Not having a boss, especially before you reach success seems to make people really uncomfortable and sometimes upset. On the other hand not everyone reacts that way and I feel like it can shine a light on who your best friends are so thats cool. It's a weird path, but I've enjoyed it quite a lot so far. I'm also sort of a weird person so I don't think it would work for everyone. I don't have any kids. I'm not really into material things so my expenses are extremely low. I usually work for longer than this but I've done the math and I'm pretty sure I could cover 1 year of expenses with 1 month of work. It's a good ratio. I've also thought about doing this in SEA or Eastern Europe to cut expenses more. The idea of being a "digital nomad" (if thats what they still call it) seems super fun.