I was overpaying for a run-down, tiny room in a bad Brooklyn neighborhood with sporadic hot water and a roommate who forgot to flush. Overnight — literally, overnight—I was renting a gorgeous room in Florence, Italy from a friendly art teacher who loved to share her cooking, and a balcony that overlooked the city’s legendary cathedral (the same one that helped kickstart the Renaissance).

And I was paying half as much on rent and living expenses.

Freelancing is all about the perks: making your own hours, working wherever you want, and sidestepping the doldrum cubicle life. But taking the plunge into becoming a digital nomad, the ultimate perk, is a scary one that often goes unexplored.

Becoming a digital nomad isn’t easy. But it is so much easier than everyone thinks! What often scares people off is the laundry list of obstacles that seem to be in your way, namely:

  • Working without the security of a steady paycheck or the camaraderie of your colleagues
  • Leaving behind friends and family
  • Abandoning your comfort zone
  • Language barriers
  • Meeting new people (the “I’m shy” myth)
  • What to do with all your stuff
  • Irrational fears like: “what if I lose my passport?” or “isn’t is dangerous to live abroad?”
Fierce traveler logo
It can be scary to take the first step to becoming digital nomad, but there is a fierce traveler in you just waiting to come out! Fierce Traveler logo by pmo

These obstacles are much are scarier in your head than in reality. When you focus on everything that could go wrong, you forget all the amazing things that could go right. Sure, sometimes the language barrier will cause trouble and, sure, sometimes you’ll get homesick. But sometimes you’ll also have magical experiences with fascinating people that will make it all worth it.

When I started freelancing, it took three years of navigating horrible housing situations and exorbitant living costs before I worked up the courage to do what I really wanted to do: buy that first plane ticket and a gigantic backpack and head overseas. Twelve countries and five continents later, it was the best decision of my life. No question about it.

Remote jobs are steadily on the rise, but that doesn’t make the thought of traveling to, and working in, a foreign country any less scary. Here, I share what I learned along the way so you can avoid making the same mistakes I did.

Get paid in Belgrade

cartoon of a home office by Odius.
For a home office, both “home” and “office” can be relative. Illustration by Odius

First things first, you need a source of income independent of location. I’m a content creator for digital marketers, which is a fancy way to say that I’m a pro blogger. But digital nomads come from a variety of different industries, although most tend to revolve around the internet. Some common remote jobs are:

  • Graphic designers
  • Programmers
  • Videographers
  • Social media professionals
  • Editors and proofreaders
  • Ecommerce proprietors
  • Customer service representatives
  • Virtual assistants
  • IT technicians
  • Business owners

A lot of these positions are client-based, but don’t think you have to find clients in the country you’re visiting. As long as you’re happy with a 3-month tourist visa (see the Visa section below), you can continue finding clients from your home country.

One thing to be aware of is the late-night business call. Considering the time zone differences, I regularly attend phone meetings with American clients at midnight or later. As a night person, I don’t necessarily mind this — in fact, it’s a bit of a thrill to talk business in the alley next to a bar or with a special someone waiting for you in bed. But even if you’re a bit rigid on this, I’ve noticed my clients are more than willing to shift their schedules to find a time that suits us both. In all my years of doing this, scheduling a business call has never been a problem.

If none of the jobs above appeal to you, or if you want to avoid the hassle of learning a new skill, there’s always one golden-ticket job that anyone from anywhere can pursue: language teacher

I taught for a couple years in Milan before I got into pro blogging. Teaching English is a risk-free way to earn a long-term visa, and it streamlines meeting new people and making friends. However, you’re glued into a school/city for however long your contract is, so it’s not for the rapid traveler.

If you’re a native English speaker, you have your pick of countries as an EFL teacher (although competition is worse in some cities). But regardless of your mother tongue, someone, somewhere, will pay you to teach it to them. Getting a teaching certificate is fairly cheap and easy, too, so you can’t use “I’ll never find work” as an excuse not to become a digital nomad!

Manage money in New Delhi

Buildings for multiple banks.
Citibank, HSBC, and many other banks have branches all around the world, so that’s one less thing to worry about. via Pexels

Keep in mind, you’ll still need to pay taxes in your home country if you’re traveling under tourist visas. I use my father’s address for my taxes, and as long as the IRS gets their check, they’re happy.

If you’re not using a tourist visa, i.e., you have an actual job in the country you’re visiting, then obviously the rules are different. Each country handles taxes their own way, but you should be able to ask any questions you have before signing your documents. If an employer is willing to hire you, they’ll be willing to explain how taxes work.

As for banking, I use my U.S. Citibank account with minimal drawbacks. They’re pretty popular internationally, and I can use at least 80% of ATMs around the world. My biggest complaint is sometimes they’ll freeze my card because they see activity in a new country. Of course, I usually forget to tell customer service where I’m headed. A more responsible nomad won’t have this problem.

My goal is to get an HSBC account. Of all the banks in the world, HSBC is the one I see most frequently in different countries, and it seems to cater to travelers. Check out NerdWallet’s Best Banks for International Travel 2017 for more useful information about banking overseas.

Stay a while in São Paulo

Choosing where to go on a map.
Anyone who said “it’s the journey, not the destination” never spent a 9-hour flight in the middle seat between two snorers. via Pexels

When choosing where to set up your digital nomad headquarters the world is literally your oyster. I tend to go for places with warm and open cultures (it makes it easier to forge friendships), cities on the smaller side, and those that are known for being affordable. But if you want to check off all the world-famous tourist destinations or live in a shack in the Australian outback, I won’t stop you.

Figuring out what neighborhood to live in can be a bit trickier. I usually take the advice of people who’ve been there before about where the good bar scenes are or which areas to avoid at night. If I don’t have a personal reference, I just poke around online until my questions are answered. Although I try to distance myself from the tourists on Trip Advisor, I can’t deny that their forums come in handy when learning about a place. When scoping out areas to live in, make sure that the neighborhood has what you need, and that you can afford it. I always look into the coffee shop scene beforehand and try to rent rooms in areas that have wifi cafes for work.

As for the how, I usually use Airbnb. It’s convenient, and I like the guarantee (you’ll soon learn the world is full of swindlers who prey on out-of-towners). I book the first 30 days through Airbnb because there’s usually a price break for a month. Then, if I like the place, I rent the additional months directly from the host to avoid the site’s fee. The hosts prefer this too, especially if you pay in cash.

If you know someone in the area before you go, they can usually help you find a place, too. Friends of friends have invited me to Facebook groups that exchange sublets and those tend to be cheapest. I’ve also heard good things about Couchsurfing, but have never tried it myself as I’d rather pay extra for more privacy.

Make friends in the Netherlands

Illustration of friends for a social net website by WolfBell.
Strangers are just friends who haven’t added you on Facebook yet. Social net website by WolfBell

Making friends seems to be what causes the most fear in the prospective nomad—and for good reason. I’m not going to sugar-coat it: lonely periods are par for the course for digital nomads, lasting weeks or even months, but if you hang in there, you’ll cultivate two essential life skills: thriving in solitude learning how to make friends in any situation.

Making new friends is a muscle that gets strengthened with use, but there are some tips that can help to make the process a bit easier:

1. Make the first move.

I was shy for most of my life, but traveling has trained me to be much more outgoing. It’s now second nature to start a conversation with a stranger. So much of traveling is learning about who you are and pushing yourself to become a better person. With practice you can turn your weaknesses into strengths.

From personal experience, I know how excruciating making new friends can be at first, especially since a lot of work-at-home positions attract the introverted type. But the good news is, it gets easier every time you do it. So start practicing today—right now, in fact! If you begin talking to people you don’t know now, by the time you’re ready to leave you’ll be a lot more confident.

On top of that, the country’s culture will determine how easily you can meet the locals. In Italy, all you have to do is step outside your apartment to make friends.

2. Find your niche.

There are meet-ups, activity groups and classes all over the world that can help you meet people, and at the very least there are always bars and clubs. Determine which ways are best for you to meet people.

Language exchange sites like Conversation Exchange have been a huge help for me. Just as it sounds, these sites connect people that want to learn the a country’s native languages. It works well because if you’re in a foreign country, your mother tongue will usually be in demand. You can even start using it today to meet a pen pal in your next location. Just refrain from hitting on anyone—it’s not a dating app! Speaking of dating apps, they can also be a shortcut to making “friends.” I’ll sometimes set up an account in my next city a couple weeks before arriving just to get a head start.

3. Don’t be afraid of being alone.

Inevitably, there will be lonely times, even if just for a night or two. Learn to make the most of it, whether attending an event by yourself, or staying in and watching TV. It will save you a lot of distress if you learn to become comfortable in solitude. That’s not just good advice for traveling, but life in general.

If having travel companions is important to you, you can also join a digital nomad group. There are talks about gangs of digital nomads that travel together gypsy-style around the world. While I like the freedom of going solo (in groups, you don’t always get to choose where you go), I can see the appeal of traveling in groups, especially if you’re new to the whole nomad thing or want to travel to a location that may be a bit sketchy to navigate solo.

Pack in Peking

Luggage print design with famous world destination theme by Prim.
If you were going to a desert island and could only take 66 lbs of luggage, what would you take? Luggage design by Prim for K Chen

Before I did it, the thought of selling and getting rid of my things was horrifying. After I did it, I never felt better in my life.

There’s something so liberating about fitting all your worldly possessions into a single piece of luggage. The act of deciding what to keep and what to let go forces you to examine the role of material possessions in your life. Would you rather hear a captivating tale from a Russian painter in a snowy bar in Moscow or hold on to that second hair-dryer?

In my giant Samsonite, I have a small wardrobe of summer and winter clothes, my laptop and accessories (including all socket adapters), a spare bag for small trips, a handful of art supplies for fun, and backups of a few hard-to-find brands for things like mosquito-repellent and acne cream. I keep everything of sentimental value in two shoeboxes at my dad’s house, and add my new souvenirs to it every time I make the trip back there.

Books are the worst because they’re heavy. I’d recommend investing in a Kindle or just reading off your phone.

You want to get your bag down to less than 30 kg, about 66 lbs. Anything more requires extra fares on airplanes. Unfortunately my bag is up to 33 kg at the moment with souvenirs I haven’t dropped off yet, and it’s frequently an issue during airline check-in.

If you’re struggling with letting go of possessions, I think it’s time you sat down and rewatched Fight Club.

Get a visa in Vancouver

Travel documents for a flight.
The golden rule of visa laws: hope for the best, prepare for the worst. Via Pexels

Visa laws are the bane of my existence. Almost every country permits a 90-day stay on a tourist visa, at least for Americans. I’ve heard the requirements are stricter for citizens of some other countries. My poor Norwegian buddy wants to take his Nepalese girlfriend to meet his family, but they’ve been cutting red tape for months just trying to get her a vacation permit.

Some countries are more relaxed about visa laws than others. In Argentina, I had to pay a fine for overstaying my visa by one day, and missed my boat because the fine could only be paid in a special government building. After a misstep in Japan, true to form, they pulled me aside and politely explained the rules of their visa program. Meanwhile, countries like Nepal encourage multiple returns because they charge per visa and have a large tourism industry.

Some countries turn a blind eye to “visa runs,” where you leave the country for a weekend or so and return with a fresh new 90-day visa. But pulling this off takes thought, so do your research beforehand about how acceptable this practice is in the country you’re visiting. Often, it will come down to the officer you work with at the immigration office. Look for a friendly face.

Be sure to research visa laws online before planning a trip; sometimes you need to buy a visa online before they even let you board the plane.

Bring fido to Hokkaido

A pug dog poses in front of a traditional Japanese building.
Like people, some pets love traveling, while others prefer to stay at home. Via Pexels

My first year as a digital nomad, I took my cat with me. Pets will restrict you in terms of where you go, both in where you can rent a room and which countries you can travel to without quarantines (island nations have the strictest rules). But traveling with your furry companion is doable, if you’re willing to make a few sacrifices.

My cat hated traveling and was not nearly as happy as I was, but luckily my ex offered to take him since they were familiar with each other. If you look hard enough, there’s always an alternative to dumping them in a shelter.

Take the leap!

I’ve said it before and I’ll say it again: becoming a digital nomad was the greatest thing I’ve ever done. When I think about who I was before and who I am now, I feel grateful and humbled that I was lucky enough to have this opportunity. Throughout your journey, you will see your insecurities and bad habits melt away, and you’ll discover new, admirable traits that you never knew you had. It’s clear that some things can only be learned through traveling.

If you want to learn to fly, at some point you have to jump off a cliff.

Do you have questions about becoming a digital nomad? Ask me anything in the comments section now!