@brydanger, 22 years ago, after a divorce, feeling adrift, and thinking "money is no longer that important to me in the grand scheme of things," I quit my job at a law firm, sold everything, and set off on an open-ended adventure, hoping it might help me figure out what I wanted to do with my life. I thought I might travel the world, but I didn't get farther than Central America and a bit of the Caribbean. I had enough in savings that I could go for a year without a job if I had to when I came back to civilization, which was the plan to do at some then-indefinite point.
But, unlike you, after a year of wandering, and not having had the great epiphany about what I wanted to do with my life, I chickened out. I came back to the US and my old profession, albeit in a reduced-responsibility role--I never again chased the almighty dollar, and I took loads of time off to travel. I just couldn't see myself doing either the full-time nomadic life OR the full-time suit-and-tie life and, unlike you, I did not have or develop skills to do anything else to earn money--not really. As you can imagine, I met plenty of people who had done it, but I never met anyone whose lifestyle really appealed to me. There were those who had taken odd jobs such as bartending, and some who had even bought the bar, a few with boats who had run out of money, those who adopted a sort of hippie lifestyle making handicrafts, and then there were the scuba instructors and English teachers .... But I never ran across anyone who seemed to have made it work quite like you have. Granted, if I did the same thing today I imagine I would run across digital nomads and travel bloggers/influencers--things that didn't really exist back when the Internet was young. I recall having to go find an "Internet cafe" to check email every week or two and let the people back home know I was still alive.
It seems to me that you have a wonderful combination of attitude and abilities. It seems that you: (1) are not afraid of taking big risks, (2) had a safety net back home in the form of real estate, and (3) had or were able to develop useful, in-demand skills--beyond the sort of commonplace skills I mentioned (bartending, etc). My impression is that this third facet--the development of useful skills, including a knack for starting businesses--is really what separates you from most who attempt this sort of thing. Can you tell I am envious? I have never been a risk taker, I didn't have much of a safety net back home, and I have no entrepreneurial instincts whatsoever. Some people have a "can-do" attitude; I have a "can't-do"--I'll find every reason in the world why attempting something would be futile. And the last thing I would ever do is buy a Bust Out Another Thousand, though I do recall fondly hitching rides as crew on others' boats.
Still, taking even just a year off and traveling, even though it sort of wrecked my career trajectory, was the best thing I ever did. I am so impressed to see that someone was able to make a real go of the nomadic life and not just eke out a life on the fringes of society.
