How to Start Your Journey as a Digital Nomad

David Powell
min read


I spent the first 3 months of this year traveling first across Eastern Europe and then spending some time in California (guess who’d been to Bangkok but never the west coast?). Now I’m back in Nashville for roughly 3 months prepping to leave for Southeast Asia and probably not returning to the U.S. for a really long time. These next few posts will show you how I survived my first digital nomad experiment, how I’m preparing to do this full-time, and what I’ve learned through thousands of mistakes.


A Guide For People Who Hate Guides

When I went to Thailand last summer, I spent maybe a half hour planning and preparing for the trip. It was actually my first time out of the country, but I was going with a non-profit group, and they handled everything from visas to hotel rooms to a translator. I gave them money and packed a suitcase. Besides the Thai translation app I downloaded, I prepped about as much you would for a weekend visit to Chicago, but I had no problems while I was there.

That was great, because I hate planning, and generally I find a high level of prep unnecessary if not detrimental. It was the same with choosing classes at university, the same with moving into my first apartment, and the same with starting my first freelance gig.

I just woke up one day and sort of did it. Things more or less worked out.

Having set a precedent for being completely unprepared, I left for Berlin and my digital nomad experiment earlier this year with no traveler’s insurance, no international phone service, a pathetically thin coat for Eastern European winters, and less than $1,000 in my bank account.

And I got my ass kicked at pretty much every turn.

  • In Berlin, a mounting bracket on my hard drive broke, and while it was a relatively cheap fix, I lost everything on my hard drive and several hours I could’ve been working.
  • In Prague, clients who owed me money didn’t pay on time.
  • In Budapest, I got into a fight with five men and lost. I woke up on the sidewalk with no phone or wallet.
  • In Krakow, I realized that being a productive remote worker in hostel lounges isn’t difficult. It’s impossible.

I still hate planning, but now I see there’s something to be said for being prepared.

Ignorance is bliss until you’re broke and alone in a foreign country. Be prepared.

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I learn most effectively through experience, but I don’t want to project that on you, and you probably don’t want to end up bleeding out your ear on a sidewalk in Budapest in order to learn the value of travel insurance and appropriate times to walk to your hostel alone.

So, at risk of some of your self-realization, I’m writing these next few posts as a guide to preparing yourself for becoming a digital nomad. I made mistakes while I developed systems for making this lifestyle work, and now you can skip some of those and just use what I learned. Great, right?

The Mindset of a Digital Nomad

The first thing most of us need to do is change the way we think about travel. Here are some contrarian thoughts digital nomads have about a lifestyle abroad.

It’s OK to go alone.

I spent the first two weeks of my stint in Eastern Europe with a friend who’s a great, driven individual. He had just graduated university and was taking five weeks to vacation around the hotspots of Europe. He had saved money all summer, didn’t need to work while he traveled, and didn’t plan to work while he traveled.

My remote working situation was different. I had clients who’d be incredibly pissed off if I didn’t meet deadlines. Working was a necessity in order for me to sustain myself while I traveled.

That was my plan, but I couldn’t keep up with changing locations every 4 days and was constantly missing experiences to work or falling behind on projects to have experiences.

Szimpla Pub in Budapest with new friends

My friend and I parted ways in Budapest and I stayed in that city for 6 weeks and actually got things done.

Traveling with a companion isn’t a bad thing, especially if they’re another remote worker who understands your situation of creating a career abroad. I believe solo travel has benefits to the digital nomad, though.

  • You have complete freedom.If you want to spend 6 months in Ho Chi Minh City, you can. If you get sick of the poor air quality or have an aversion to motor scooters, you can leave after your first week without consulting anyone.
  • It forces you to grow socially.Unless you want to be lonely, solo travel will be a catalyst for improving your social skills. It’s sink or swim.
  • You become more self-reliant.When you’re the only person who cares what happens to you, you take control of situations more effectively. Navigating bus systems in Finland and Hungary on my own was enough to make me feel like Jason Bourne, and now when I have problems on the road I solve them quickly and without much stress.
  • No one knows who you are.This allows you to discover who you want to be and change your behavior without anyone bringing up your past or what’s “normal” for you. If you’re in the company of friends, you subconsciously limit yourself based on the pressures and status quo or your previous social experience.

(For more on how being a digital nomad fosters self-improvement see II. Why You Should (And Shouldn’t) Become A Digital Nomad)

Obviously, exceptions exist. I traveled with a friend I met at a hostel for a few weeks after I left Budapest, but if you’re staying in one place for 3–6 months (and I think you should) then you’ll be just as happy going on your own.

Say no to schedules, itineraries, whatever.

This comes down to a fundamental change in your mindset. You’re not a kid on a gap year. You’re not a corporate jockey trying to pack as much as you can into a two-week vacation.

You’re a location independent professional, and travel isn’t a limited luxury; it’s part of your life. In fact, I think you should dispense with the idea of “travel” altogether.

You’re just living your life in many different places.

Also, a major motivator for pursuing this lifestyle is freedom, right? Why create self-imposed boundaries like schedules?

(For more on freedom and location independence see I. Introduction to the Digital Nomad)

Don’t map a route. Pick an airport and go from there.

In September, I’m planning to go to Ho Chi Minh City, where I think I’ll rent an apartment, get a membership at a co-working space, and become a local for 3–4 months.

I’ve never been, though. It might suck. I might hate it.

And if I hate it, I’ll leave. I visited Thailand last summer, and I know I want to be in Southeast Asia, but that might mean Vietnam, Thailand, South Korea, or Cambodia. I’m doing entry-level research (cost of living in a few cities of interest, where I need to apply for visas, etc.), but all I really know is I’m flying into Ho Chi Minh City and figuring the rest out when I get there. And that’s ok.

I think it’s important to have an idea and a starting point, but after that see what happens and take opportunities as they arise.

Take things slow and stick around.

I Skyped my pal Ben Dolgoff towards the end of my time in Budapest. The guy was healthy, happy, and living la pura vida in sunny Costa Rica.

I was freezing my ass off and a little depressed.

The difference between us was that Ben had been in Costa Rica for about three months, settled into living there, made friends, joined a gym, started learning Spanish, and had a daily routine. He was building a healthy lifestyle in another country, participating in local culture, and developing as a person.

I was traveling — always getting ready to leave again, knowing that I had a return flight in a couple of weeks (it was an experimental trip, and at the time I still had a girlfriend in the states).

What Ben was doing is sustainable. Taking 6 months at a time in several different countries and building relationships across the world works (digital nomad lifestyle). Leaving for a new city every couple of days is not sustainable (vacation lifestyle). Aim for slow travel.

(Joel Gascoigne of Buffer has a fantastic post on slow travel: 11 cities in 3 months: The highs and lows of the digital nomad lifestyle)

It’s not that you shouldn’t keep traveling around and visiting new places, but having a base you come back to is important. Like I said, I’ll probably bounce around Southeast Asia for a bit when I first arrive, but I’m planning to settle in somewhere as soon as possible. That’s for both strategic and psychological reasons.

  • I’m not productive and feel I’m missing out on experiences when I blaze through a new city every week.
  • When you’re always on the move you tend to only spend time with other travelers and don’t experience the local culture of a place, making you the worst type of person: a tourist.
  • Having many “single-serving friends” (see Fight Club — but DON’T TALK ABOUT IT) becomes painfully lonely, as you don’t have time to develop real relationships with people. It’s fun to make new friends during a walking tour or over a beer, but eventually you’ll need to be vulnerable with someone, and you probably don’t want to be super open with that Polish girl you met when you both started singing along to “Shake It Off”.
  • It’s harder to be healthy if you’re always on the move. You end up eating more junk, not working out, fucking up your sleep cycles, and neglecting personal improvement practices like reading, meditation, or learning new skills.
  • The most expensive part of travel is the traveling. If you want to make this digital nomad thing sustainable and you didn’t just exit a successful startup, then you probably want to make your way through the world slowly.

Starting Points For Transitions Abroad

Changing your mindset is only half the battle. If you’re still with me on this lifestyle, then here’s some practical steps for choosing where to go and how to get there.

Don’t be afraid to go to less-traveled places.

As an American, I was taught some limiting views about the world. I’m working daily to overpower those ideas, but for years I heard the news in the U.S., the movies in the U.S., and the mothers in the U.S. telling me the same thing: Everyone hates Americans, and they’re out to get you.

I’m not unique. Practically everyone in the world holds some sort of prejudice or a collection of fears towards cultures different from their own.

And most of the time those those fears are irrational and those prejudices are bullshit.

Take “everyone hates Americans” for example. The truth is, most people in the world don’t really give a damn about Americans. They have jobs and spouses and houses and don’t waste much emotional effort developing strong feelings toward an entire country of individuals. They spend even less time thinking of creative ways to target Americans for acts of violence and terror.

While Americans do have a negative reputation in many places,and I do have to start some social interactions by climbing out of the pit George W. Bush, BuzzFeed, and Kanye West dug for me, people are generally as warm and friendly on foreign shores as on my own.

However, what I’ve found and what most other nomads from all countries seem to find is that people across the world evaluate a person by their behavior more than anything else. Shocking, right?

(Still more shocking, they don’t carry concealed weapons around public places just praying a foreigner will walk by so they can abduct and kill them.)

Don’t be an idiot, but don’t write off beautiful, interesting cultures just because they’re unfamiliar.

The world is not out to get you. It’s barely even thinking about you.

Find a region and research cities of interest.

I went to Europe because I had never been, and it seemed interesting. That’s honestly as good a reason as you need to pick a region to travel through. If you’re going to live somewhere for an extended amount of time, though, I recommend doing a higher degree of research or choosing a region you’ve visited before.

After traveling through Thailand last year, I know I love Southeast Asia. It’s unique, it’s warm, and compared to the U.S., most places are inexpensive.

I’ve never been to Vietnam, though, so I’ve studied it a little bit more. Here’s the process I used to select Ho Chi Minh City as my next starting point.

Talk with other digital nomads, listen to their podcasts, and read their blogs.

Nomad List on Medium

Lonely Planet isn’t a bad source for travel information, but it’s for vacationers and kids on gap years, not expats. Part of the reason I’ve chosen Southeast Asia and then narrowed to Ho Chi Minh City was because of social media and blog posts by Pieter Levels, Jason Lengstorf, and John Myers. When Ben visited last year and recommended it, I decided it was at least worth a shot.

If you’re looking for inspiration for your next locality, the Nomad List collection of posts on Medium is a great place to start.

Use Nomad List to estimate costs and potential lifestyle.

Nomad List is the digital nomad’s best friend. From average costs of apartments and co-working spaces to WiFi speeds and venture capital climates, this is the complete rundown. It’s a brainchild of Pieter Levels grown into a collaborative effort by many different nomads. Many of the cities listed have entire eBook guides you can purchase. As soon as you have a region in mind, get on this site and find the best options for your lifestyle and budget.

Ho Chi Minh City on Nomad List

Using Nomad List, I found out Ho Chi Minh City costs a nomad just over $1,100 and an expat less than $1,000/month, and the only real downside is the air quality.

As backups, I checked out Phuket, Seoul, Chiang Mai, and a few others.

I also looked over different Airbnb locations in these cities, but they’re pretty much in line with the averages from Nomad List.

Like I said, I’ll bounce around before I settle in, but now I know roughly how much money I’ll need to do it, what to expect in each place down to the wifi speeds and average co-working space costs.

Get details on visas and travel restrictions.

After I had a list of potential cities and details about each place, I went to the U.S. Bureau of Consular Affairs website to see which places I’d need visas for and how difficult they are to obtain. It’s all there, and luckily most of us can stay at least 3 months in many countries without significant paperwork or problems.

The process of getting a visa might require a number of different items on your part. For example, in Vietnam I don’t need any vaccinations to obtain an entry visa, but I do need $5,000 dollars in my bank account (so no pretending to be Jack Kerouac this time around).

The restrictions and timelines on passport validity vary from country to country, so it’s important to check these pages out before you get too committed to any place.

Small Things That Matter

When I was 11, my mom got me The Worst Case Scenario Survival Handbook. For a boy who threw knives at stumps and tried to start fires with two sticks and dead grass in the backyard, it’s not surprising the small book quickly became my favorite thing.

I doubt I’ll ever have to run across the top of a moving train, fight off a shark, or perform a tracheotomy, but should a scenario arise where any of that is necessary, I could do it (maybe).

And that’s the premise of the book — you hope you never have to use, but if you do you’ll be happy you took some time to get informed.

The introduction to the handbook opens with the Boy Scout motto: “Be prepared.” It then closes with the words, “you just never know.”

When I left for Berlin at the beginning of this year, I was ridiculously unprepared.

And that was stupid.

You honestly can’t plan for all circumstances, and the most effective way to prepare yourself is to decide now that you’ll keep your cool and roll with the punches.

It’s possible to minimize potential damage with a few simple steps, though. Here’s a list of things you should have — not because they’re essential to your time abroad.

But because you just never know.

  • Travel insurance — I met an Aussie in Budapest who fell asleep in a McDonald’s and got robbed. Thanks to his travel insurance, the only real setback he had was losing a SIM card with a picture of him on Abbey Road. I guess he’ll just have to go back and retake it. Anyway, through my research I’ve found World Nomads travel insurance to be among the most recommended. It’s what I’m planning to use when I leave again.
  • Backup credit cards — This is a tip from Jake Jorgovan passed to Ben Dolgoff passed to me. You can easily get your bank and some credit card providers to send you a duplicate of your check card or credit card in case yours in lost or stolen. (There are shitty people out there, and sometimes those shitty people steal your wallet and that sucks.) If you don’t have a credit card that’s exempt from foreign transaction fees, get one of those too. And if you have better credit than a college dropout in their early twenties, check out the Chase Sapphire Preferred for airline rewards.
  • Emergency cash — Hide cash in your shoes, backpack, underwear, whatever. Have a semi-universal and easily exchanged currency (Euros and Dollars are great for this) on you at all times, because you never know when an ATM will run dry (that actually happens) or your card will be declined because you forgot to notify your bank about your weekend visit to Bratislava or you fell victim to those shitty wallet snatchers.
  • Skype/Google Voice Credit — I don’t advocate an international phone plan for anything more than emergencies, because with the glories of WiFi it’s largely unnecessary. Being tied to your mobile device also robs you of the experiences in a foreign culture you came to have. However, the ability to call a bank, a client, or your mom shouldn’t be overlooked. It’s around $0.03/minute for either service, and it’s worth setting up before you go so that you’re not using Facetime Audio with your dad in the U.S. while he holds his phone close enough to his computer so you can verify information with your bank after shitty people took your wallet. (Do I sound bitter about the shitty people? I am.)
  • Someone Who Knows Where You Are — I shouldn’t have to to tell you this. Some of us romanticize running away, though. Some of us also will go from place to place or just visit the closest beach to our new residence while abroad. And that’s fine. You don’t have to check in with your mom or girlfriend or landlord every time you go some place. If you’re in a foreign country alone, though, you need someone to have your back. Sometimes you end up doing stupid things. Sometimes you go to jail (see: The Rum Diary). Again, you just never know.

I can’t tell you everything about being a digital nomad, because I don’t know everything. And I’m pretty sure it’s different for all of us.

I hope this post gave your some places to start, though.

And that’s all this is: a place to start. Believe it or not, I’ve got even more to say.

That’s in the next post, though.

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