The internet is full of people promising to show you how to throw off the shackles of adult life and become a digital nomad.

Soon you’ll become a nubile 22-year-old who owns nothing but a backpack and works 4 hours a week while lying on the beach and getting endless notifications from your adoring fans. You’ll never have to answer to anyone or do boring paperwork again. And the money will just pile up in your bank account.

Sure, good luck with that.

It’d be easy to think only 20-somethings without any responsibilities can be digital nomads. Most people are confusing being a digital nomad with the current incarnation of those kids who take under the table bartending jobs and become surf instructors for a little while after college. Most of them go back to the “real world,” while others find ways to make it work and spend their whole lives in some tropical paradise without ever having a 9-5.

That’s all well and good, but what about those of us who want to own nice furniture, aren’t in perfect health, and want to save for retirement? How can we be digital nomads?

You can be a digital nomad and still own a home Click To Tweet

white guy with a fedora pretending to work on a laptop while in a hammock on the beach

If this is your image of what being a digital nomad is like, you’re in for a rude awakening.

Adjust your expectations

If you’re sipping cocktails on the beach and only spending a few minutes looking at your emails while your bank account fills up, you are:

  • At the top of a pyramid scheme
  • Running a scam
  • A retired business owner
  • Being supported by your parents
  • Living off your trust fund
  • A kept man/woman

People who are making money off of their websites are starting a business like any other. The first few years include a lot of hard work, none of which is guaranteed to pay off. Being a business owner is full of risk. We hear a lot about successful online business owners, while the many more who fail don’t make headlines.

Being a digital nomad is more likely to mean working a pretty regular job while changing your location every few weeks, months, or years. Some careers give you the flexibility to work part time or bunch your time off, but just because a job is “online” doesn’t mean you’ll be making bank without doing work.

stereotypes of a digital nomad: dorky white guy with a backpack and a laptop on the beach

This guy lives in his mom’s basement. Which is totally fine when you’re 19 and traveling the world. But what happens when you’re 30 and overdue to start saving for retirement?

Decide how you want to travel

Do you want to be on the road 365 days a year? Do you want to maintain a home base? How many cities do you want to visit in a year?

Maybe you want to sublet your condo and spend two months in Portugal every year.

Maybe you want to be on the move constantly for a year or two or longer.

Maybe you want to spend a month abroad and a month at home.

Knowing what your ideal way to travel the world is will make it easier for you to live the life you want, while still paying your mortgage.

The easiest way to actually work full time while traveling is to travel slow. Spending a few weeks (or months) in one place means you can see the sights and get to know it at your leisure, rather than in a few packed days.

Trying to get work done (or dial in to a conference call) from the airport sucks. It does not feel like living the dream.

BANGKOK - FEB 22: Unidentified people use laptops in a cafe at Bangkok Art and Culture Centre (BACC) on Feb, 2012 in Bangkok, Thailand. BACC is a popular work place for 'digital nomads' and students.

1000 Words / Shutterstock.com

Figure out your career

Quitting your job to become a digital nomad is for kids who can move back in with their parents. For those of us who are financially independent, keeping your current job is almost always the best choice.

Transitioning to remote work

Could you perform the majority of your work without being physically in your office? Many companies will allow you to work remotely, even if they aren’t open to hiring someone remotely or don’t have a specific policy.

A company that isn’t comfortable agreeing to let you work remotely full time may allow you to work remotely for a few weeks a year to allow you to travel.

If you work for a company with offices around the world, they may allow you to work from a different city temporarily or for a few months a year. This is one of the easiest ways to get a work permit.

Don't quit your job to become a digital nomad Click To Tweet

Getting a job abroad

If keeping your current job means staying in one place, there are lots of other options.

Most careers will allow you to travel. Many jobs are designed to be temporary or actually require you to live in different locations around the world.

  • Nurses can travel around the country or the world working in different medical centers
  • Professors can get visiting lecturer posts or funding for conducting research abroad
  • Business consultants can take contracts internationally
  • Diplomatic posts often require time living abroad
  • Enlisting in the military virtually guarantees you’ll be spending time abroad

Other opportunities to live and work abroad are open to young people. These programs are typically for people under 30 or 35.

Other programs are open to professionals of any age.

  • Teach English abroad
  • Join the Peace Corps
  • Volunteer with different service organizations

Find (or make) a remote position

If none of those are the right option for you, there are plenty of sites to connect you with distributed companies hiring for remote roles.

You can also create your own role by joining the ranks of the gig economy. If you do, I’d advise you to make sure you have plenty of money saved up to support yourself as you get off the ground. Don’t quit your job and then set up an Etsy store or start looking for freelance clients, since it’ll probably be a slow first couple months.


Make it legal

Work permits are not optional. Neither are taxes. Quite a few digital nomads are skirting both of these right now and seem to be getting away with it, but I do my best to follow laws and international treaties. If you have assets that are worth seizing, you probably would like to follow the rules, too.

Being away for an entire year does not make you a non-resident for tax purposes. If you’re a US citizen and haven’t established residency in another country, you’re on the hook to pay taxes like anyone else. If you establish tax residency in another country, you’ll still have to file taxes in the US, although tax treaties save you from double taxation.

Some countries will allow you to work remotely on a tourist visa. Others don’t. Quite a few countries don’t make their policies for remote workers clear. Remote workers can get permission to live in a country legally with programs like self-employment visas, artist visas, research visas, and non-earning visas. Don’t just show up at the border and assume things will work out, unless you have a very flexible backup plan.

If you’re a US citizen, you have plenty of options for living abroad, legally.


728x90 HealthTap

Figure out housing

There’s this idea that being a digital nomad means quitting your job and selling everything you own. That’s totally optional.

If you rent, it’s easy to give up your lease. You can sell things, donate things, and put the rest in storage.

But owning a home — and wanting to keep it — doesn’t have to stop you from living abroad.

If you’re keeping your place

If you know people in the military, you probably know a few small time landlords. Families will buy a house each time they’re stationed somewhere and rent it out to other military families when they’re moved to their next spot. It’s a great way to build wealth and diversify your income. Managing a real estate portfolio across multiple countries is probably more of a logistical hassle than it’s worth, but there are times when it’s worth owning several homes in one or two countries.

If the math works out, it’s probably worth keeping your home, especially if you might move back after a few years. This depends on how much you could get for rent, what the carrying costs are, the rate of appreciation, and the tax implications of being a landlord.

Depending on where you live, finding someone to rent your home is usually fairly simple. Be clear about what maintenance you expect your subletters to do — are they taking the trash out, mowing the lawn, caring for your prize cactus, and watching your dog? Mention that in the ad and put clear instructions in writing.

If you’re a renter or have a homeowners association, check your lease, association rules, and local laws to see what the requirements are for subletting your apartment.

find a home to stay in with a home office

Finding a place to stay abroad

I have gotten requests on CouchSurfing from people hoping to stay with me for free for a few months. Don’t be that guy. That guy’s not successful.

If you want to live in a bubble of 20-something kids, you can join a coworking community that will take care of all the housing details for you. If you loved staying in hostels when you backpacked Europe, but want a more comfortable bed and privacy, this is probably a fit for you.

You can book an AirBnB for a month and pump up the local economy. It’s easy and probably more comfortable than staying in a hotel for months.

If you’re planning on being in one place for more than a month, your best bet is likely arranging a temporary place to stay and finding an apartment once you arrive. Word of mouth, expat meetups, Facebook groups, CouchSurfing groups, and the local version of Craigslist are all great places to learn the ropes for finding an apartment.

The ideal way to arrange accommodations is to set up home swaps. If you’re interested in spending a summer abroad, it’s fairly easy to find teachers and families eager to swap homes for two weeks or the whole summer.

It can be a challenge to arrange trades for long terms outside of summer holidays, but it’s certainly possible. Home swapping keeps things simple in that you pay the same amount for housing as you always do and your guests are covered under your insurance policy. There’s something magical about the true sharing economy — all sorts of laws and expectations are triggered when money changes hands.

Know what your ideal work environment is. Do you need an office area where you’re staying? Are you okay working at a kitchen table? Do you prefer coworking spaces? Are you happy working at coffee shops? Will you camp out at the local library? Keep this in mind when choosing a place to stay — and make sure there’s a backup if something goes wrong.


Make sure you’re protected

Before you leave, think about all the things that could go wrong. Your basement could flood. Do you have a handyman to call in and someone to take care of your tenants? You could get into a car accident. Does your health insurance cover you abroad? Who would have to pay for damage to the car?

The longer you’re away, the more likely it is that something will go wrong. Once you have an idea of how to take care of potential emergencies, you can enjoy your travels without worrying.

  • Health insurance
  • Travel insurance
  • Homeowners insurance
  • Emergency contacts

You might be surprised by some of the perks that come with your credit cards or your existing insurance. There’s no need to pay for duplicate coverage.

Take care of the details

The most important thing for working remotely is fast, reliable internet. Make sure wherever you’re staying has wifi. Know places nearby you could work if there were an issue. You might look into buying a mifi.

You’re going to need access to money as you travel. Make sure your bank won’t hit you with outrageous charges when you withdraw money from an ATM. Get a credit card without foreign transaction fees. Set your bills to autopay, get paperless statements, and don’t forget to review your bills for suspicious charges.

Using your phone internationally can be an expensive nightmare, but it doesn’t have to be. Set up a plan to make sure your phone will work abroad. You can’t give your clients and coworkers a new phone number every time you switch locations.

It’s surprisingly difficult to eliminate the need for paper mail entirely. You can have a friend take care of it or sign up for a service to collect your mail and send you a scan.

There’s always some detail that will be forgotten or something that will come up, but the more prepared you are, the easier things will be.

 

Pin It on Pinterest

Share This