Making the nomadic lifestyle work. Or making me work for it. Or something.
October 20, 2010 8:12 AM   Subscribe

Can this freelance developer make this nomadic lifestyle thing work (tax and visa questions about Asia especially)?

So I finally broached the subject with my incredibly flexible and awesome boss yesterday about shifting from working here in the office as a part-time dev to working as a contractor remotely. Uh, really remotely: we are in the Northeast of the U.S. and I told him I want to be working remotely from Asia. But he agreed to it—we'll work out the details regarding meeting regularly, working hours, etc. etc. I imagine getting paid is going to be slightly tricky (I assume they can send checks to my parents who can deposit them, if I can't do direct deposit, but if anyone has a more clever idea I'm all ears) but I'll work it out.

What I'm more concerned about is where to live and how long. I'm going to give this "have barely any possessions" thing a shot, and I want to be spending my time, for now, in Asia. Japan is a top pick—I imagine I can tolerate living in a gaijin house or whatever for three months or so. I also would love to spend time in Thailand, Malaysia, South Korea, Hong Kong...etc. I want to explore Asia. I figure if I'm frugal I can do this pretty cheaply, bounce around using local airlines (although I know Japan is expensive to fly in and out of and not serviced by the budget airlines, so no need to tell me...unless I'm wrong about this!), even staying in cheaper countries (Thailand, say) when I need to sock some money away.

The two things I'm most concerned about are visas and taxes. Is it going to be a problem for me to bounce around on tourist visas for three to six month periods but actually be working wherever I go? That is, will immigration officers in Thailand (say) be looking at me askance if I've been in Thailand for three months, then Japan, then a few weeks in Singapore, then back in Thailand...

Also, say I decide I want to spend more time in a country like Japan; is there a way to get a working visa if I'm not actually working for a Japanese employer (and any information on how this is in any random Asian country would be welcome)? Or can I do the weekend trip to South Korea thing and just get another three months on my tourist visa? I imagine this would be a problem after a while but for a few times is it okay?

And of course taxes; I know there is this ~$80000 upper bound on income for U.S. citizens living abroad, so I figure I can safely ignore taxes (other than to be responsible about filing) but am I being too lackadaisical about this? If I come back to the U.S. for a month or two here and there, will I have to just pay fed/state taxes for the months I was living in the U.S.?

Finally: health insurance!? I want to make sure I can be taken care of if I get hit by a bus, but otherwise I'm in really good shape (for a mid-30s guy).

I'm looking for "don't forget about this thing, it can really bite you in the ass if you're not careful" kinds of advice. And I know I'm being a bit vague about exactly where I want to go, but I also welcome stuff like "you should look into country X 'cause it's cheap and internet is plentiful..." kinds of advice too.

In any case whatever you can tell me will be great. Thanks people!!
posted by innocuous_sockpuppet to Work & Money (6 answers total) 12 users marked this as a favorite
Best answer: You cannot ignore taxes unless you are out of the country for more than 330 days of the year, or you have a residency (and have proof of paying taxes) in the country you are traveling to. So if you visit the US for more than about five weeks, you have to pay taxes, and not just for those five weeks, but for the whole year. I have lived like you are planning for the past four years. Work for a company in the US, come and go on tourist visas. But I have never yet been able to claim the Foreign Income Exclusion.

It is really hard to get a visa (beyond tourist) most places as a self-employed or remotely-employed person. Almost all visa paths involve family reunification, school, or having a local employer to vouch for you. I'm sure someone else can answer your question about the rules for qualifying for another three month period in Japan. In Senegal, crossing the border is enough. In Europe, you have a maximum of 3 out of any six months, so you need to leave for a significant amount of time. It really depends on the country.

when I was in Africa I bought evacuation insurance and maintained my US coverage. In Europe I bought a long term travel insurance policy. Right now I am just winging it with my US coverage, which pays 75% in overseas medical bills.
posted by Nothing at 8:26 AM on October 20, 2010

Best answer: Oh, also check your state tax rules, because they are very different. When I was a California resident, my residency basically suspended if I was out of the country for six months, and I owed no state taxes after that. In Virginia they count you as a resident until you establish residency in another US state - so if you leave the country from Virginia, you will always owe state taxes.

I love the time difference, which allows me to get five or six hours of work done without the distraction of emails coming it from my US colleagues. I have a friend deposit my paychecks. That works fine.

Figure out some solution for your mail in general. That's easy to forget.
posted by Nothing at 8:32 AM on October 20, 2010

Oh, and a Skype number is nice to have too. Maybe Google Voice is even better now? I have an account but haven't really used it. But having a US number to give to people is very useful.
posted by Nothing at 9:23 AM on October 20, 2010

Best answer: Sounds like you something that might work is a long term multiple entry business visa for wherever you're going to base yourself, and tourist visas for other places.

Maybe look at South Korea as the base (a quick google suggests they do a 5 year multiple entry business visa for US citizens with maximum stays on each visit of up to 3 months), and then you're typically looking at 2-3 month tourist visas for much of SE Asia.

If you can get your current boss to verify that you're on business for them, it would be immensely helpful.
posted by Ahab at 9:41 AM on October 20, 2010

Best answer: The 4-Hour Workweek and The Practical Nomad are chock-full of helpful information and pointers to specific resources.
posted by Jacqueline at 12:40 PM on October 20, 2010

Response by poster: Well, looks like this question has stalled out and is unlikely to get much more activity. However, quality counts more than quantity, and all of you gave me some really solid stuff to think about. In fact, Nothing, I could use your comments as almost a complete template for how I'm going to do this—sincerely, thank you very much! Ahab, I hadn't considered the multiple-entry visa, and South Korea could be a good location, so I'll look into that. And Jacqueline, I've been meaning to get ahold of the 4-Hour Workweek for some time now, so you reminded me I need to get off my butt and do that.

Thank you all! Very helpful!
posted by innocuous_sockpuppet at 7:53 AM on October 21, 2010

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