Bootstrapping overseas as an American

Am I allowed to work there?

No, not really.

But they’re not checking. Places like Southeast Asia are chock full of expats living there, doing silly things like “visa runs” to the next country and back every couple months to remain a tourist for years on end.

Even in Europe, where you wouldn’t be able to get a self-employment working visa (if such a thing existed) with less than six months effort and a good lawyer, you’ll find that they’re really a lot more interested in keeping the various people coming in from the South from doing so than they are in messing with you. Given the level of effort required to find somebody at the Santander ferry port to even stamp your passport, it’s unlikely that anybody is conducting a multi-month surveillance of your AirBnB “office” up in the hills above the Cote de Azur.

Uh, what? No. Don't do this. Just because you might be able to get away with it in certain Southeast Asian countries doesn't mean you can get away with it in Europe. Sure, you might be "fine" for a couple months after your Schengen visa expires, but good luck if you ever need to, say, fly back to the US for a few days, or even hop over to the UK. When you try to get back in, you will almost definitely face consequences.[1]

(EDIT: It's worth noting that you don't even have to attempt to re-enter to risk getting caught. Even a routine traffic stop can get you in trouble. In addition, they check your passport at most airports before boarding a flight that leaves the Schengen zone.)

Yes, self-employment visas do exist (though admittedly only in some EU countries), and no, they do not require "six months effort and a good lawyer". In Germany for instance, a freelance visa is a pretty straightforward process, and the vast majority of people who apply for it do so without hiring a lawyer or even spending much money.

If you're going to work in a foreign country, at least try to do so legitimately. You might find that it's not as difficult as you think, and you won't have to live with the vague fear of serious legal action hanging over your head.

OP, please don't recommend this to people.

[1] http://travel.stackexchange.com/a/13697

That was an odd piece. I'll start with the provably wrong statement: "Even in Europe, where you wouldn’t be able to get a self-employment working visa (if such a thing existed) with less than six months effort and a good lawyer"

It took me about 2 months to get a self-employment residency permit for Sweden. While I looked around for lawyers to help, I couldn't find any, and ended up writing it myself. It seems very few people do that option.

YMMV of course. Which is my point.

But as for the other parts, it depends on the type of person you are and what you want. I did the 3-month-at-a-time tourist visa option for a bit over a year. (It's not quite a 'visa run' because it wasn't a cross over the border and back thing.) It got tiresome to start make friends and then leave them, then come back, only to leave again.

On the other hand, there are people who do that for decades, and love it.

While I sell software, my customers are businesses, in a market where most contacts start by meeting people and word-of-mouth. Most of the people who might buy are in the US or Europe, and that's also where most of the conferences are held. It's much more expensive to send my bundle of atoms from South Africa (one of the places I considered living) than from Sweden.

Again, this isn't true of everyone. There's a big difference between "and start bringing in a few hundred bucks a month from paying customers" and my software, which sells for a few tens of thousands.

It also becomes harder if you want to have access to a local user's group (I co-founded the local Python user's group) or makerspace.

So if your interests are surfing, rock climbing, Swedish women, and beaches, and you are selling direct to customers who expect no personal connection, etc. then certainly living overseas can be a great idea.

I do believe that living or even just a multi-month travel overseas is a good thing to do at least once. Just bear in mind that it's not always as rosy as this author paints.

I did this with a few differences. It was 2004, so a few services from these days were not as "available" from a quality perspective -- particularly, VoIP. I left to France with a PSTN phone device that answered calls to my business number, and forwarded them to a French PSTN fixed phone number -- all at international rates, which were a bit more expensive back then. I did later move to a VoIP service, when the quality was reasonably acceptable.

Time differences in Asia would be different than France - maybe a few hours too many for me. I particularity loved the time difference between France and the US (~8 hours). Everyday, there was a whole day of work before my clients in the US would wake up. If needed, I could make a few calls before I had dinner and went out.

I had a 3 year established list of clients when I moved there, so that helped. A fairly stressful aspect of living abroad was that all my clients came in "locally" by way of local google advertising. And as it happens, when someone picks up the phone and calls a number that seems local to them, they tend to assume they're talking to someone who is physically present in their city.

Many clients were turned off after realizing that I was working abroad -- and not telling them (which I tried a couple times) was very strange as well -- it's just a balancing act. So my suggestion would be to get into a borderless niche business, if you can -- something like doing "websites for x" -- where a company would much rather work with someone with niche products and expertise, rather than someone local. Then the subject of where you physically are never really comes up, or makes sense. SAAS would work in that way too, of course.

A few notes based on my experiences:

1. Decide who you want to be in your new country, and be that person from absolute day one. Changes of setting are one of the most effective ways to end bad habits and start new ones. Want to wake up for sunrise and jog on the beach every day? Start the habit from day one.

2. 'Visa-Runs,' do work many places outside of N. America/Europe, but they must be done religiously. Miss one, and you could face massive penalties.

3. Go with a business to maintain, not a business idea to build, and be sure to have a strong support team in the U.S., and at least a handful of well-enough connected friends in the country you choose.

4. It's really tough to choose an International Health Insurance plan, but don't let the vast array of options deter you from doing so. Sure, health costs are low in many places, but a plan with MedEvac benefits included can really provide added peace of mind.

5. Make friends with motorcycle or taxi drivers, and pay them very well. These guys are the eyes and ears of the city you have made home, and being on their good side is very beneficial, and enjoyable.

6. Compensate for time differences with prompt and reliable communication. People learn not to expect responses from you right away, but if you can establish a system where clients and partners know there will be a response in their inbox by the time they wake up, the distance is less noticeable.

7. It's not easy, but can be an incredible lifestyle for those who go 'all in.'

I'm doing this in Vietnam. Not necessarily by choice at this point (got married, having a kid, need to stay now).

The FEI thing only applies if you are paying taxes in your "host" country. Thankfully, you can minimize the burden in a few different ways. State taxes are another matter though. I was a resident of NYC, but became a resident of Nevada before I left.

The visa situation in Vietnam is fucked right now. I was doing the tourist 3 month multiple entry, which you can reup 3 times in country for a year total, but now you can't do that. Getting the fiancé temporary residency, but you wouldn't believe how Kafka-esque that whole process is here. Though it wasn't as bad, or as expensive, as getting a marriage license. That required a shit ton of coffee money.

It was fun for the first two years, but now I can't wait to get the hell out of this place.