What You Should Know If You Want to Work Remotely and Travel the World

A digital nomad is basically a remote worker, independent contractor, freelancer: anyone who can get stuff done from anywhere. And if you’re not a remote worker, you could even convince your boss to let you work from home if you’re up for the challenge!

“Digital nomad” has kind of become an obnoxious buzz phrase, but it’s an accurate way to describe this type of lifestyle. Freelancing is a more common way to earn a living, and remote work is an option for more full-time employees than ever before. If that describes your situation, you might have an opportunity to pick and choose where you want to work day in, day out. If you’re lucky enough to work from anywhere, you can take advantage of your freedom and work while you travel.


It sounds really exciting to be able to take your laptop and work from Central Park or Tokyo or wherever your desires take you. Of course, it’s not always that easy in practice. You may have obligations to your pets, your children, your extended family, your home, or a partner. If you do, you’ll have to consider them in your plans. However, even if you don’t have those obligations—let’s say you’re a single renter with no pets or children—coming up with a plan still requires a fair amount of preparation.


Digital “nomad” isn’t entirely accurate. You still need a home base. Maybe it’s your parents’ house; maybe it’s your own home. Either way, your bill providers, employers, and banks probably require a physical address to set up your accounts. Plus, you need an address to receive mail.


The Postal Service has a couple of options that can help keep your mail under control while you’re away. You could hold your mail for up to 30 days, for example. If you’re back around that time, you’ll get all your held mail delivered at once. For longer stints, use their Premium Forwarding Service to temporarily forward mail to your new address. Just keep in mind that if you move around, you need to update your forwarding address every time you move.

Of course, if someone lives at your home base, they could just hold the mail for you (and open anything important so you’ll know what’s going on!)


It’s one thing to visit a foreign place for a week or two, but there are some cultural considerations to make if you’re going to be there for a while: the language, for example. It may be easy to get around with tourist-level fluency if you just need to ask where the bathroom is and where to get good food. When you’re there for a while, though, you might need to ask more complicated questions.


There’s also the matter of health insurance. Your overseas health insurance coverage varies, and you can check your Explanation of Benefits to see exactly what’s covered and what isn’t. Still, you want to check with your provider to make sure you’re indeed covered. And if you’re not, or if you want coverage beyond emergencies, you have a few options.


While there are different lodging options, from extended stay hotels to hostels, Airbnb is the go-to option for many travelers. And it’s super convenient…but not for everyone.  If you’re working remotely, that probably means you need Internet access. If you’re visiting an area where Wi-Fi isn’t readily available, you might consider a mobile hotspot or router so you have online access wherever you go.


Beyond the technical stuff, you want to establish a routine and boundaries. You’re in a new place, and it’s tempting to just forget about everything and go explore. On the flip side, you might get so stuck on work that you never make time to leave your temporary home, defeating the entire purpose of being a digital nomad.


You’re presumably in a different timezone than your colleagues back home, so that’s another thing to build into your schedule. Overall, you want to come up with a work schedule and then optimize it based on your time zone. Front loading your work is key. You want to be courteous of your coworkers, too.


Even when you front load your work, you’ll inevitably have to communicate with them, and you want to avoid texting or emailing them in the wee hours of the morning, even though it might be prime time in your area. Tech can help with this. Most email clients allow you to schedule your messages so you can write them now but they’ll send later (Boomerang for Gmail does this, too). You can also snooze your own incoming email messages so you protect your quiet hours in your own time zone.


Of course, the cost of renting a place month-to-month is going to be your biggest expense. It may or may not be more expensive than renting a place in your home city. Airbnb prices vary, too, with significantly higher prices during peak tourist season, or around major events.


If you’re a freelance blogger who regularly writes about travel, you might be able to get away with writing off some of your digital nomad expenses. If you’re a freelance web designer, on the other hand, you’ll probably have a harder time justifying the need for travel. Either way, you’re still entitled to a home office deduction like any other remote worker.

The rules get complicated quickly, though. Generally, if you’re a U.S. resident, you’ll have to pay taxes on your worldwide income. You’re also not subject to income tax in most other countries if you don’t become a resident, but that could change if you stay in a country for too long.