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My wife and I would like to work remotely (I'm in CS and she's in accounting). Our idea is to travel in about two-month increments from country to country. We have NO idea what kind of restrictions we're going to face. We are U.S. citizens, we'll have U.S. jobs that are remote.

We want to keep our house in Oregon, but move freely about the world, doing our jobs remotely. We would like to return to the U.S. at least once a year.

So a typical cycle might be: Canada, Japan, U.K., Germany, Mexico, U.S. @ 2 months in each place.

What kind of issues (if any) am I going to hit and how do I get past them? This could be taxes, U.S. citizenship issues, Duration of Stay, etc... I am 100% new to this idea so any good links or advice would be greatly appreciated.

adipro
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Mike
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    Your major problem is likely to be gaining admission to the UK and possibly other countries. You are not allowed to support yourself in the UK by working remotely for a foreign employer. If you admit to this, you won't be allowed in, and if you don't admit to it, but they find you out, they'll probably give you a ban for lying. – phoog Apr 14 '16 at 07:00
  • Thank you for that info. I had no idea there were rules like that. Where would you go to find info like that? Or better yet, info like that for a global search? Are there countries friendly to the idea of working remotely? – Mike Apr 14 '16 at 15:52
  • I don't know whether there are countries friendly to the idea. I think one reason the law hasn't caught up with reality is that it's so easy to just go somewhere and work remotely without telling anyone. The UK is particularly strict about making sure travelers can support themselves without working; I don't know about other countries. You can find episodes of "UK Border Force" or the like on YouTube in which people including Americans and Australians are refused entry because they intend to work in the UK. I can't say more than that it's risky, which is why I'm not posting an answer. – phoog Apr 14 '16 at 15:58
  • You won't have any citizenship issues. Atleast not U.S. citizenship issues. As long as you file your taxes and maintain the U.S. address, no problems there either (remember that you might have to pay state taxes). Every country will have its own rules and cultural attitudes. You will have to be more specific. – ouflak Apr 14 '16 at 18:15

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