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Brem: I haven’t used the phrase ‘best’, but I’d say the emphasis is on finding the ‘right’ country. Why? Because I’d rather not pick the wrong country and be miserable for six months. Also, there are plenty of countries which (to cite the old maxim) I’d like to visit, but would never want to live there.

Lastly, how many times are we going to do this? A half dozen? So, in that vein, I’d like to pick one of the top six ‘most right’ countries for us.

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Sorry to be a bit snarky, but that’s the second time you’ve alluded that “America” doesn’t include Canada, when literally it should. I don’t deny that US citizens might be called Americans by themselves and everyone else, and I can’t really speak to the average Canadian’s relationship with the word “America,” and I suppose that anything that titles itself with “America” is US-centric or worse, exclusively about the US, and I don’t have a degree in geography. Yet, any use of the word America that assumes America==US is illogical and sounds incongruous to me.

Back to the original topic: from somebody who moved to the island of Kauai to start a business with 1 year in savings, didn’t get very far, and now works at his old tech writing job remotely, I have mixed advice. I think it is an admirable goal, and I’d love to be a working nomad, but I think there are valid reasons more people in our field are not doing it (artists/musicians, healers, and surfers seem to do it quite well).

My first reaction was that working and/or running a tech business from overseas may sound like no big deal, but the reality is much different. I think that it will take you 1-3 months just to be operational, from getting through bureaucracies, to mundane things like getting DSL and reliable phone (go cellular/mobile) up and running. You can throw money at the problem, ie rent a furnished suite/house with an established connection (but then you’re risking the expat enclave unless you’re in a first-world country), and I assume you will run your business clandestinely out of your dwelling, so that maybe you can minimize the setup time.

Another issue I struggle with is the tug between sitting down and getting to work, and wanting to explore this fascinating new place. You’ve travelled and worked abroad much already, so I assume you know yourself well enough to avoid this. But don’t underestimate the drag of having to work when it’s sunny outside and exotic scents and sounds waft in through an open window. Also, be prepared to deal with the time zone difference (which is one advantage of Central/South America).

Personally, I would love to do what you’re planning, except I would try to not be employed during that time. Maybe you are planning on making your accounts dormant or sustain them with minimal maintenance, but you’d need an excellent rapport with your customers. It might reassure them to fly home and meet them after 3 months, and you may need to do it anyways to get around visa restrictions. You might want to be flexible in the duration as well, keep it month to month in any services you buy. For example, you might find you need to move back home after 3 months, or maybe you’ll find yourself so well established that you’ll want to stay 9 or 12 months to explore some more.

There’s also a difficult social barrier to just moving around. People are friendly everywhere, but they don’t just open themselves up to new friendships with everyone who comes along–especially if they know those people won’t stay (although maybe that only applies to touristy places like Kauai that have a high turnover). You’ll want to become culturally integrated, at a minimum learn to speak the local language, but 6 months just won’t be long enough–you’ll be scratching the surface and you’ll know enough to know that you are. And trust me, after 6 months away from your old friends, you start having a different relationship with them. There are always the true friends who will welcome you back, but even for them you will be slightly out of touch.

As for the destination, I would choose something that is close to many weekend destinations–assuming you’ll be working full weekdays. Being on Malta and flying to North Africa/Italy/Greece/etc seems like too much trouble, and while Malta has much to see, you might be frustrated by being confined there. Then again, you might be willing to spend more than I, so a 3-day weekend to see the museums of Cairo with upscale lodging might be possible for you.

Alternatively, you could focus on a small area or an island such as Malta and not do any trips afar. Try to see all the corners the tourists don’t see, experience the local ways of life.

Since this sounds like the first of several work/travel experiences, I do suggest you start with someplace easy, say France/Spain/Italy or a Scandinavian country in the summer. That’ll give you experience in running your business from afar, and make finding the right accomodations not too difficult. Then land transportation by train or rented car is easy even for 2-day weekends, and you’ll feel like you got to see a lot. I suggest you target smaller cities hosting universities, those are generally connected and still quaint, happening yet still walkable. If you like mountains, I suggest Grenoble in France (I lived there for 6 years, both as a student and tech worker) or Graz in Austria (my wife grew up near there–it has the advantage of being closer to Central Europe/Croatia if you’re so inclined).

To summarize, it’s a cool endeavor, but expect things to be not as you expect them–if that’s not illogical.

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Gregg: Indeed, I must add one of those to the hall.

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