Are most digital nomads self employed or remote employees?

#1

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Summary

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#2

I’m currently interviewing for positions which are 100% remote, so I don’t have a lot of insight into how to ask your current employer to allow you to work outside of the country, but in general the concerns US employers have is your being available to work and collaborate during business hours in the United States. I’d suggest offering to overlap your work schedule with the home office (at least 50% of the time? 75%? 100%?). Traveling through South America makes this pretty easy. And you should be prepared to attend some meetings at odd hours. Suggesting it as a trial run for six months might make them more comfortable as well. I don’t particularly see why your employer should care where you’re working from; it’s up to you to comply with the laws of wherever you end up, not them. The only exceptions would be if your job requires working with data that can’t be legally accessed from outside the United States, or something similar.

As for traveling around, many countries grant US citizens an automatic tourist visa at the border. Whether you’re comfortable working on a tourist visa is up to you, but as long as you don’t tell the border officials that’s what you’re planning on doing it’s very unlikely you’ll be refused entry.

#4

In most cases you wouldn’t be working illegally but that may depend on the country. When I first started working remote outside of the US for my US employer I asked the Colombian and Argentina embassies if I can stay on a tourist visa for tourism purposes—of course—while I work remote and they said it’s not a problem. It’s a difficult concept for people to grasp. In many countries you may find you must pay tax depending on your duration of stay. In Colombia it was more than six months depending on your visa. If you’re there for tourism purposes you should be good. If you’re there to stay forever or conduct business in that country then that’s different. In Europe last summer I was asked about staying for the complete 90 days and if I work. I said my employer is in the US and that I can work from anywhere and they didn’t have further questions.

Time zones, I just overlap my work time with my coworkers in the states. I’ve been doing it for nearly three years now from all over the world. In Asia I work 3 am to 11 am and then explore the rest of the day. In Europe I work 10 am to 6 pm.

Brian