I read articles about people who quit their jobs, sold everything and traveled. And it's always "the best decision they ever made." Have you ever seen a story that didn't turn out so well?

Not traveling, but we did move.

We quit our jobs and moved to a $5000 shack in The Philippines which we happened to have built for my mother-in-law. Spent two years planning, lots of money moving, sold my car, packed up all my stuff and left it with my parents.

Didn't work out due to noise, pollution, the overwhelming threat of crime, ambiguous property rights, higher prices than expected for utilities and food, and generally being poor and uncomfortable in an already poor country. We planned to have almost twice as much income as we ended up leaving with and spent the first month fighting for that via long distance calls, and it wasn't sustainable. We never even got to the point of asking my folks for the money they'd promised to buy a house.

We did have fun for a while riding our bikes around, exploring, going to beaches and meeting new people, got a dog, took up spear fishing. I intended to spend the money I got from selling my car to buy a catamaran to sail around and between the islands, but we never got that far.

We came back to the US, spent even more to move half our junk back, left the rest behind and had to replace a lot of things, got our jobs back, moved into an apartment, paid off our new debts, took us three years to buy another car, and here we sit in temperate clime first world happiness or whatever with no intention of ever trying that again, probably.

I still think, with enough money and wherewithal (the latter of which I have a negative amount), it'd be cool to live and travel to different countries, stay in rental houses, not hotels or shacks, for weeks or months. I am thinking about taking a vacation soon once I'm settled into my new job.

/r/AskReddit Thread