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I have lived this lifestyle, it is ok, with some caveats.

If you do extended travel, learn how to be outgoing. My first long trip was to Japan. Being shy and quiet made the first 3 months a nightmare. Luckily, at the time I was young and still reasonably good looking so women would ask me out. But it would have been more fun and easier if I hadn't had such social anxiety. I did some extreme personality modification afterwards and when I went other places I had a much better time.

It is very important to nail #1, figure out a career that you love, or at least LIKE. It isn't as though you come back, return to work, and your work anxiety is alleviated by your fond travel memories. In fact, your travel experience makes it much worse because you are just thinking "fuck I could be on the beach in Thailand right now instead of rebooting these servers at 4 in the morning."

Safety net is sort of important. You don't want to return and then be stuck taking the first job that comes along. Note that safety net doesn't necessarily mean having a bunch of cash. It could mean having a friend or family with an extra room where you can stay in the area where you want to work. In my case it sucked, because most of my friends were bums like me who live in studio apartments, and most of my family lives in the extreme middle of nowhere. Trying to find a job in Palo Alto while you are in the Yukon is not easy or fun.

Also, figure out what you really want. Travel is easy. You just need money for a plane ticket. You can go almost anytime. I didn't realize until after I traveled that what I really wanted was financial and career independence. I probably missed out on 5 prime career building years by bumming around doing the travel/slacker thing. Now I have to compete with Google Ycombinator braniacs. Back in the day, I only would have had to be as smart as the guys who made BlueMountain.com or geocities...



> I did some extreme personality modification afterwards and when I went other places I had a much better time.

I'd love to hear more about this. Usually when I go to a party I talk to a few people and have an OK time. However, the few times I've talked to everyone at a party, I've had a memorable blast. It's definitely not natural and I feel I have to be warmed up socially.


Well, I am crazy. Around my friends I am outrageous and will say anything for a laugh. Around people I don't know I clam up and hide in the corner. I just decided to act the same way around strangers as I do around close friends.




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