Did almost exactly this for all of 2014 (part of 2015). With a US citizenship, and visited 10 countries for a month+.
Working remotely for a foreign corporation generally isn't against the terms of a tourist visa (consult the specific country you're visiting). All officials I asked had no problem with it, from South America/Asia/Europe (Germany will actually let you stay longer, up to 2 years, if you're a remote worker/freelancer). You do need a work visa if you're planning to do work for a company that exists locally (competing with the locals, etc).
It was hugely income tax advantageous. There's a huge US tax credit if you aren't living in the US (your first $95-120k tax free), and I wasn't staying long enough in any country to meet their reporting requirements.
Mostly Airbnb's, an occasional hostel/hotel if I didn't plan ahead.
My routine when arriving in a new country would be to quickly find a place to stay and a coworking space, then explore the city/country when I wasn't working.
There are several countries that will offer you citizenship by investment, including some with visa-free entry to US and Canada. Of course there is no guarantee this will last or that you personally will be able to travel (see Roger Ver).
I'd remain a citizen of the US, so I'd still owe taxes to the US. Then, use a family member's address as a home address for official documents.
Visas would take some planning for countries requiring a visa for your passport. Many cities have consulates that you can go to. For example, if you were in Tokyo and wanted to go to Bankok next and needed a visa for Thailand, you'd head over to the Thai consulate near Meguro station to complete the formalities.
I suppose I may be skirting local employment laws in some places, on the other hand, my employer is not likely based in that country and would therefore have no tax reporting obligations.
This is actually the big lie of being a Digital Nomad. It's not legal.
As a US citizen there are only a handful of countries/territories that you can work legally without any sort of paperwork (Puerto Rico, USVI, Samoa) and a handful more that have official working holiday schemes:
- Singapore
- New Zealand
- Australia
- South Korea
- Ireland
If you are in the EU citizen you can work freely within the EU.
However most folks aren't writing about working holiday visas or working within the EU. They are writing about South East Asia and Central/South America. Neither of which allow people to go and work without permits.
People are breaking the law and being way too public about it.
"What kind of activities are not considered to be “work”?
An activity which does not really ‘take away’ from opportunities for Canadians or permanent residents to gain employment or experience in the workplace is not “work” for the purposes of the definition."
Working for my own US company isn't competitive to local workers.
Every country I've visited has a similar definition, though I can't say for sure if every country does, so it's best to check before attempting to go.
It's problematic that most countries immigration websites don't explicitly point out that working for a company abroad or for yourself is not permitted on visitor visas, but if you write to their respective embassies then you will find this to be the case.
I've always gotten the answer from officials "if you aren't competing with local workers, you're fine". As always, depends on the country. Further down the source I just cited:
"Examples of activities for which a person would not normally be remunerated or which would not compete directly with Canadian citizens or Permanent Residents in the Canadian labour market and which would normally be part-time or incidental to the reason that the person is in Canada include, but are not limited to:
long distance (by telephone or internet) work done by a temporary resident whose employer is outside Canada and who is remunerated from outside Canada;"
It's the definition of "work", whether you're competing with locals, and whether you're being paid by a Canadian company.
Many countries don't have this clearly documented, as until very recently (last 10-15 years), the only real "work" was competitive with local citizens/residents. All work visa documentation is written with this implied definition. Many countries are starting to call this out as an exception (like Canada above, Thailand recently, etc, etc).
Until it's clear for a particular country, it's best to talk to an official.
Awesome that Canada has clarified that. The first I've seen.
Thailand's laws however explicitly don't. Work is defined very broadly. I've never seen it clarified beyond the report from Chiang Mai a couple of years back. Unfortunately the guy didn't have the authority to make the statement.
If the employer is in the country you are visiting, you are correct. But if the employer is in a different country also (that is my thinking), then I'd expect there is no visa issue because the employer has no tax obligation to that country. It would be the same as if I vacationed in a different country, but responded to work e-mail for my US employer.
Working remotely for a foreign corporation generally isn't against the terms of a tourist visa (consult the specific country you're visiting). All officials I asked had no problem with it, from South America/Asia/Europe (Germany will actually let you stay longer, up to 2 years, if you're a remote worker/freelancer). You do need a work visa if you're planning to do work for a company that exists locally (competing with the locals, etc).
It was hugely income tax advantageous. There's a huge US tax credit if you aren't living in the US (your first $95-120k tax free), and I wasn't staying long enough in any country to meet their reporting requirements.