Technically speaking, it's easier than ever before to live on the road. Just about the whole world is wired, and there's no shortage of companies offering all sorts of services and support to make it simpler and more enjoyable to be a digital nomad.

But just because combining work and travel is easier now than it once was, that doesn't make it easy overall. There's still a daunting range of logistical and personal considerations you need to take into account before packing your bags and getting started on the nomadic lifestyle.

What are they? Lifehacker's Kristin Wong, a veteran traveler herself, interviewed Stephanie Lee, who just returned from a nine-month stint as a digital nomad, in order to lay out all the basics you need to consider for a helpful in-depth article. Here in brief are the five points you need to think about before packing up your laptop and hitting the road.

1. Where's your home base?

Yes, the whole point of the digital nomad lifestyle is that you can work from anywhere, but even when you're wandering the globe you still need to maintain a home base for logistical reasons.

"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," points out the article.

2. What are you doing about health insurance?

People get sick and injured everywhere, so no matter where you're going, you need to think about what will happen if you fall ill. Check with your health insurance provider to see what they will cover you for outside the U.S. (if you have Medicare or Medicaid they cover nothing).

If you discover you're not adequately covered, there are a number of options, according to Wong, including short-term travel health insurance, U.S.-based international healthcare coverage (which is pricey), or international health insurance that doesn't cover the U.S. at all.

3. What will your work routine look like?

Obviously, to get stuff done while you're on the road, you're going to need a good wifi connection but, as Wong notes, a mobile hotspot or router should take care of that if your accommodation doesn't provide what you need. But beyond getting yourself plugged in, you also need to consider how you plan to balance travel and work.

"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," she writes, so think about your most productive hours, as well as time difference issues and when your colleagues will be online, and get planning.

4. What about taxes?

If you're a freelancer, can you write off your travel expenses? That depends, Wong says. "In order to write off expenses, the IRS says they need to be 'ordinary and necessary,'" she explains. Which means in order for something to be deductible it has to be mandatory for your work, not an optional lifestyle choice.

Therefore, "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," she concludes, offering more details from a tax strategist if you're interested in a deeper dive.

5. Have you considered all the hidden costs?

Your housing might be cheaper in many international locales, but don't forget that you're going to be living on the road and that means additional expenses you wouldn't incur at home. "Even though you're not exactly a tourist, you'll probably still spend more money on, say, going out to eat, than you would back home," for instance.

Will you join a coworking space? How much are you going to spend on intra-country transportation? How many lattes are you going to buy working in coffee shops? Make sure you factor these sort of expenses into your budget.

This informational really only scratches the surface of what Wong has to offer, so if you're seriously thinking of ditching your desk for an international adventure, definitely check out all her advice in the complete post.

Are you a digital nomad? Do you have any other tips to share?

Published on: Nov 29, 2016
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