Introduction to the Digital Nomad

David Powell
min read


The Alpha and Omega of Google search results, Wikipedia, defines the phrase “Digital Nomads” as:

“Individuals who leverage telecommunications technologies to perform their work duties, and more generally conduct their lifestyle in a nomadic manner.”

— Wikipedia

People like us explain the moniker a little more personally and emotionally, though. A digital nomad lives life on his or her own terms, doing things they love, and daily turning their dreams into realities.

If you’re like me, you might even have a few friends who are living this seemingly ideal lifestyle. Maybe they’re other startup founders or successful freelancers who moved to Bangkok or Kuala Lumpur and started living like royalty while working part-time. Real people are doing this — not just as kids with backpacks hitchhiking from town to town and party to party, but as professionals who have made a commitment to dreaming, exploring, and living in many different cultures.

I followed these entrepreneurs and freelancers via their blogs, podcasts, and Instagram accounts, pining for the day I could join them. More than anything, I wanted it, but I felt like I had valid reasons to stay:

  • I was a Dean’s List Student with a hefty scholarship at a growing university.
  • My latest internship was with a startup boasting serious funding, powerful founders, and huge potential — the words “full-time when you graduate” were said within my first two weeks.
  • My business connections, friends, family, and girlfriend were all in my home city.
  • Dropping everything to freelance and roam the earth scared the shit out of me.

You’ve probably written a similar mental list of reasons why you could never “drop everything and travel the world.” Some of those reasons are valid, but the truth is that when faced with a drastic change to our routines, most of us are just cowards. Things suddenly seem too good to leave, and our fantasies of exploring the beaches of Mexico with a drink in our hand and a beautiful chica on our arm become unrealistic, childish ideas. We shuffle back in line and sheepishly accept another period of monotony.

And then we realize again why we wanted out. Familiarity breeds contempt.

For me, contempt tasted something like this:

  • Attending a University where tuition was $45k and climbing each year only to watch helplessly as programs in my department evaporated while forced to take statistics classes (rated the number 2 most useless skill in the world) from a professor who didn’t know what year it was.
  • Working 16–18 hour days trying to keep up with freelancing, an internship, and classes — then getting drunk enough to forget my problems on the weekends and calling this living.
  • Realizing that this routine was the start of my career and adulthood, and this lifestyle may very well be the template for the rest of my time in the world.

This story, these factors — they’re not special. Tim Ferriss, Mark Manson, and countless other internet entrepreneurs found themselves in similar situations, despairing that their life might become an insipid 9–5 grind for 30–40 years before they either retired or committed suicide.

This wasn’t the lifestyle I wanted, but I didn’t know how to leave or if I even should. I kept thinking of Ferriss’ line at the beginning of the fabled, stereotyped, life-changing The 4-Hour Workweek:

“Life doesn’t have to be so damn hard.”

— Tim Ferriss, The 4-Hour Work Week

Or did it?

Sound like a familiar struggle to anyone?

What will you wish you’d done ten years from now?

Enter Ben Dolgoff

Ben is a successful tech entrepreneur with a history in app development that got his company a write-up in TechCrunch. Beginning his career in a corporate finance job and then partnering with a buddy on nights and weekends to develop an app, Ben made the jump to startup co-founder with grace few first-time CEOs could match. After selling his first app, creating two others that generated passive income, launching side projects, and consulting other startups, he was making great money for someone whose office was a coffee shop.

And after spending three years in Nashville, Tennessee, Ben had made several friends and created a life for himself. At the beginning of 2015, Ben jumped ship to spend a few months abroad and then moved to Costa Rica.

Now, he spends his time at the beach, working out, practicing Spanish with locals, running his businesses, and loving every minute of the Central American sunshine. Each morning, Ben wakes up to his ideal day.

Leaving his life in Nashville behind seems like the obvious choice from this side of the adventure, but no one could have predicted what would happen once Ben departed to live la pura vida. He assumed no small amount of risk.

When I asked him about it, he told me his thought process was simple.

“You’ve got to think to yourself, ‘What will I wish I’d done ten years from now?’”

— Ben Dolgoff

Is that a trite expression? Hell yes.

Honestly stopping and thinking about it made a successful, intelligent businessman move across the world, though.

And it made me move to Eastern Europe.

Location Independence

When you acquire customers, communicate with employees, send invoices, and run your entire business online, the sky’s the limit — so long as you can get wifi up there.

Tweet: When you run your business online, the sky’s the limit — so long as you can get wifi up there.

As a web content writer, I don’t need a permanent city or even country. I am a location independent worker, which isn’t just something I like — it’s my number one qualifier for the method by which I generate income.

The Zelda-loving 10 year old would be proud of all the castles I’ve explored in my travels.

Because when you’re the type of person who would rather work for yourself and build your own business, you’re the generally the type of person who isn’t content for very long. My ambition to be successful in business directly flows into my ambition to keep having larger, more exciting experiences. The sense of risk and adventure that cause me to raise prices, to find more clients, and to put systems in place to make my freelance business run more smoothly are the same feelings that make me stir crazy when I’m in one place too long.

Before your brain starts moving too fast, and you begin to believe that feeling this way is utterly narcissistic and of no benefit to the world as a whole, let me share a quote from Chris Guillebeau’s The Art of Nonconformity, a book I read while debating my own journey not long ago.

“Some people call this selfishness, but I tend to believe the answer is more complicated — without the energy I derive from being by myself, I know that I wouldn’t be of much use to anyone else later on. Your dreams and big ideas belong to no one but you, and you never need to apologize for or justify them to anyone.”

— Chris Guillebeau, The Art of Nonconformity

If you’re reading this, you probably feel the same way. You’re already a digital nomad in your mind, and you’re a step away from living the dream.

What Being A Digital Nomad Is Not

If you’ve had experience with Workaway, WWOOFing or TEFL opportunities, you know they can be fantastic options for the budget traveler looking for something long-term in a foreign country. As an employee or volunteer in these programs, you can further immerse yourself in the culture of the country you choose to visit, and employers generally provide your meals and lodging.

It’s a great gig, because most of these are only part-time positions, and you get a built-in friend group in the form of your co-workers.

For a digital nomad, though, this is an inhibiting lifestyle. Not only is this method of travel unnecessary for us, it’s also counter-productive. For one thing, in most places you visit, getting lodging, food, and a built-in network of other travelers can be had for the price of a bunk in a hostel — which most freelancers, no matter their experience or skill, can earn in less than an hour.

Unless you really love manual labor, then you’ll probably grow to resent being tied to a place for a period of time volunteering when you could be exploring or working for your (paying) clients. With part-time volunteer work and at least part-time work on your business, you don’t have much time for sightseeing, meeting locals, or dancing in clubs.

Programs like this help you save money, but as an entrepreneur, you can create money as you travel. Remember, becoming a digital nomad is adopting a lifestyle, not just extending your vacation time. As you travel, you’ll actually be building your career freelancing or managing your startup.

What The Digital Nomad Lifestyle Is

Architecting your life

The lifestyle of the digital nomad is just that: a lifestyle. You’ll be developing habits and routines and probably even regular work hours. This isn’t a bad thing, because now you’re in control, and you decide when and how everything changes.

The popularity of “lifestyle design” which our polarized hero Tim Ferriss introduced in 4HWW exploded the way it did because people like the idea of architecting their ideal day and then actually being able to make that their routine. For me, an ideal life is one where, at a moment’s notice, I can go somewhere across the globe and still have my business. It means if I want to stay out until 6 AM each night and wake up at noon each day, I can (but I don’t recommend it to anyone else).

When you commit to being a digital nomad, you make the rules.

This isn’t a freedom from responsibility but rather an assumption of greater responsibility on our parts.

Since we don’t have the structure of a consistent place of residence, group of friends, or time zone, we have to make our own rules. Without regular runs, bodyweight exercises, and even yoga, life abroad can destroy your body (I’m speaking from experience).

The other travelers I’ve met who have been gone for 8 months or more cook for themselves more often than they go out, sleep regular hours, and limit how much they drink on weekdays.

Surprisingly, it can be done.

This doesn’t last forever

Something you should probably understand before jumping into this head-first is that it probably won’t last forever. Skipping town every three weeks and moving from adventure to adventure is beautiful — doing it while making money and improving your life is something many people dismiss as pure fantasy.

Eventually, though, we burn out on this. I haven’t yet, but I’m not speaking from my own experience. While he still travels, even Tim Ferriss has a permanent address (I remember when I noticed his location on his Twitter profile no longer read “Global” but instead “San Francisco”).

And the traveler’s patron saint, Jack Kerouac, took long breaks between his time “On the Road”.

This adventure can extend as you want, though. As often as you want to travel, you can. Therein lies the beauty.

If you’re still on the fence about the lifestyle of a digital nomad, I’ll leave you with a slightly more eloquent version of what Ben told me about leaving everything and moving to Central America.

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover. ”

— Mark Twain

In my next post

Why are you leaving? — Expectations and goals for world travel

  • What are you running from?
  • How travel changes you (and how it doesn’t)
  • How to set realistic goals for your journey

Making mistakes so you don’t have to,


Further Reading

Note: These aren’t affiliate links. It’s not that we don’t like making money (we do) but because I want you to trust that I’m not just writing this to make a commission. These are all legitimately blogs and books I read and find value in. Take a look.



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