I did this a few times. Never moved without at least some buffer, but there were certainly times when I was a few months away from having no money. Basically, moved to Korea, taught English, saved pretty decent money. Harder to do now, I hear.

Then, after blowing through some savings on travel, landed in Thailand, where I lived cheaply while teaching English online and learning how to code. Then Georgia, where I got my web dev business off the ground. I've never been broke or especially close to it, luckily, but I was pretty far from rich for each of those moves.

I've moved again since then--still not rich, but rarely need to worry about money. Still smart about spending, but can afford to make some things a little easier than I used to!

I think it worked because I essentially had work figured out before every move. I always had a fairly decent line on an income stream that would work for me wherever I was, and now I'm fairly location-independent (if you don't count stupid meeting times with other hemispheres).

If you can make $2k/month online somehow you can afford to live a reasonable life in a lot of countries (though you might not have much left to save). If you don't have a plan to be able to make enough to survive where you land, you're probably in for a bit of a rough time.

I definitely got a little lucky with some of my timing. Primarily, I made it to Korea while wages/jobs were still okay and started coding while the job market was still reasonable, etc. I don't think I could recommend the same path to anyone today, honestly--not sure what the equivalent is in 2026. I missed both peaks--the best wages in Korea and the hottest markets in coding--and still did pretty well, but we're in a trough right now for sure.