The only thing harder about moving to another country is deciding on where. You can read guidebooks and forums all day but you’ll never be absolutely certain that recommended places fit you best. You need to go there to find out for yourself.
Let’s start with the first two steps…
Step 1: Compile a long list of cities and countries that you want to visit. Categorize those by continent and see if it’s obvious that you should visit one continent before all others. For me that was the case for South America, though Eastern Europe was a close second.
Step 2: Plan out a logical route for your first ambitious trip abroad. Fill the spaces in between with cities you are curious about and others that help chop up long trips. Consult guidebooks to see about train or bus times between cities along with ballpark lodging numbers that help you calculate a rough budget. Giving you a budget estimate is useless without knowledge of your travel style and tastes, so ask those who are similar to you for an idea. (You can also use sites like One World to plan around-the-world trips via airplane.)
For me travel has two modes: research and living, with some overlap in between. I generally like to visit a city first before committing an extended period of time there. My first trip to South America was mostly research, hopping around and taking notes on the cities I liked. Out of the 30 or so I visited, I discovered two that I wanted to return to: Cordoba and Rio. I did stay in both cities longer than I planned, but not long enough to where I felt like I was a resident instead of a tourist. Understand that to find a city you love, you may have to visit a lot of cities you dislike. It’s a process that takes time.
My current trip is heavy on the living side. I stayed in Medellin for six months, with research side-trips to Bogota, Cali, and Santa Marta. I’m now in Rio de Janerio after researching the north of Brazil. If I like any of these research cities I’ll stay up to a week and consider returning in the future for a longer time. For example Pipa is a beach town that I would definitely live for a summer, something that I would not have known unless I visited. While I value other people’s opinions of places, I won’t know for sure unless I go there and have a look.
I don’t really see the point of doing only research, which is the Western way of travel, assuming the Westerner is not merely going to a Caribbean resort. There will most likely be foreign cities that make you happier than your own, and visiting them without having the option of staying longer to feel it out seems a bit torturous to me. If you’ll never be able to move to a city that you love, I’m wondering if it’s best not to travel in the first place, because you’ll be stuck in your crappy city knowing for sure that there is something better.
Step 3: Figure out money and work logistics. This is where guys start with the excuses that they “can’t,” but to me that says they don’t want it bad enough. Fine, stay where you’re at it and live vicariously through others, but I get emails from guys all the time that are working their asses off just for a month away, and that’s usually how it starts: a decent-sized trip that a guy figures out how to lengthen in future years. My first trip away was only a week long.
Step 4: Enjoy your trip. I strongly urge you to integrate yourself into the cultures you visit by learning the language and avoiding other gringos. How will you know if a city is good or not for a medium or long-term stay if you don’t mix with the people who live there? If you’re coming to South America, learn Spanish or Portuguese. Don’t be lazy. With just a few hundred words you’ll be able to do so much more and be more motivated to talk to locals and begin to understand how they’re like. It’s okay to stay in hostels but every now and then spring for a roach motel to get away from English and general comfort. Push yourself a little more than you’re used to.
Step 5: Reflect after your trip is over. Is there a city you fell in love with? If you visited at least a dozen, chances are one of them will be worthy of a lengthy return. How can you make that happen? You’re probably going to have to figure out a different way of making money, perhaps your own internet or freelance business. Talk to other guys who have what you want and figure out how they did it. While it will be hard to duplicate someone else’s success, there will be lessons you can learn. I know it’s not easy to figure out a new way of making money, but I’ve met a ton of guys doing it. You can as well if you have slightly above-average intelligence, and if you’re reading this right now then chances are you do.
Step 6: Live abroad. Book a one way ticket with money in the bank and some passive income coming in on the side. Once there rent a room and spend a couple hours a day working, a couple hours a day learning the local language, and the rest on your own pet projects. Hang out at a local university, explore the nightlife, make friends, sleep with the local women, enjoy life, and eventually return home a better man. What more can you ask for?
And thankfully while living in a city your expenses will be significantly lower than when traveling through.
After my current trip in South America, I plan on coming back to D.C. to recharge for several months and then maybe do a tame trip through parts of Europe. That’s my master plan, research and living, research and living, until there’s not a whole lot of research left to do and I build roots in a place that I love.