5 unspoken truths about becoming digital nomads (most never tell)

When people hear my story of becoming one of many digital nomads to work and travel anywhere in the world, they almost always tell me that they too would love to pack up their current life to be a digital nomad. They’d even get specific with an idyllic image of lounging under a shaded canopy on a pristine-white sandy beach in Thailand.

I’d nod and lightly encourage the dream, patiently answering their questions about how I became a digital nomad and sustained the lifestyle for years. But lately, I’ve started to have reservations about the way we talk about digital nomads. And it’s time I came clean with my own digital nomad experiences.

You “don’t regret it”? My bullshit detector just went haywire.

There are thousands of articles on becoming a digital nomad on Google (exhibit A above). I know because I’ve read (and have written) many of them.

But what many of these articles WON’T acknowledge is the inauthentic, bullshit, double-rainbow portrayal and fetishization of digital nomads (and their travels in general). Some of us scream into our GoPros and jump off a waterfall, thinking we’re defying convention. But take a good, hard look: We digital nomads actually are…

…the new hipster.

Digital nomadism has become another form of counterculture that’s been absorbed into the mainstream. We think we’ve got it all figured out. That we’ve bent all the rules and have “hacked life,” but in reality we have really turned into a novelty-chasing culture tending toward the commoditization of this lifestyle. Just look at Remote Year, for example. You can pay money to be a digital nomad for a year, like you’re just going on a goddamn cruise (which, by the way, exists too…).

Look, I say these things because I am 100% guilty.

Over the last three years, I have had the highly coveted privilege and ability to work remotely from seven different countries for months at a time.

Here’s a snapshot of me pretend-working in my tiny, 150-square-foot studio in Paris:

Stephanie becomes one with digital nomads in Paris

And here’s me pretend-being-Zen in Oahu:

digital nomads tend to like nature

OK, one more of me pretend-contemplating the virtues of living a life off the beaten path in Utsunomiya, Japan:

digital nomads also tend to like park benches

Who wouldn’t be in awe of this?!

But there’s just one giant, misleading problem: I’m tired. So damn tired.

Tired of the expectations that people somehow have of me to keep up this lifestyle for their own voyeuristic pleasures…

Tired of the way people either put me on a pedestal or make me feel alienated upon learning how I choose to live…

Tired of having to say goodbye to people I had just started to bond with over and over again…

But most of all, I’m tired of the things most digital nomads won’t tell you beyond those videos of them scuba diving in the Maldives or zip lining through the Costa Rican jungle.

Why? Because so many of them are doing a damn good job hiding the fact that they’re not as happy or fulfilled as people think they are. That being a digital nomad doesn’t change you fundamentally. It’s your life … but over there. And when you get back (and you will), your problems don’t go anywhere.

And it’s for five key reasons I wish people had been real with me about when I started:

  1. Becoming a digital nomad isn’t possible for everyone
  2. Making money while traveling  can be a trap
  3. Researching will never properly prepare you to be a digital nomad
  4. Being a digital nomad strains relationships
  5. Easily losing sight of why you became a digital nomad


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1. Become a digital nomad isn’t possible for everyone

I have since hit the brakes on my nomadic lifestyle, but when people catch a whiff of what I do they usually ask to “pick my brain” (shudder) on how they can also make money while traveling to all the exotic locations on their bucket list.

Each and every time, I give this oft-disappointing advice: Well, that depends.

Save that follow-your-dreams stuff for a Disney movie script. Because “how do I become a digital nomad?” isn’t the right question.

The right question is actually: Do my immediate personal circumstances align with all the things required to be a digital nomad?

In other words, are you…

  • Single without dependents or any familial obligations? (Or do you have a family situation that allows you all to live this lifestyle together?)
  • Free from financial obligations such as credit card debt, a mortgage, student loans, etc.?
  • Capable of earning consistent income that allows you to set up life anywhere you go?
  • Comfortable with instability (mental, emotional, environmental, stomach)?
  • In this for the long haul (because, sure, anyone can travel long term on a budget for a while)?
  • OK with being alone and a perpetual foreigner (unless you’re lucky to be traveling with a companion/buddies)?

I’m in a privileged position because no matter what Facebook ad or a course promises you, not everyone can do this.

The jump to a working life on the road was not a spur-of-the-moment decision that I had made willy-nilly. It wasn’t some brazen act of rebellion. It had been heavily calculated, as if I was planning the first 15 moves in a game of chess. The decision was made slightly easier, however, because my own professional and personal circumstances were just right.

Professionally, I had spent over a decade writing, teaching others how to do what I do through guest posting, and strengthening my business acumen. I had actively built the right relationships and reputation that provided me with avenues for steady income. Then on the personal front, I had no family of my own to look after, had paid off any major outstanding debt, had accumulated enough savings to keep me comfortable for a year or two, set up all of my bills to be paid automatically, forwarded my physical mail to the right places, and made sure I didn’t burn any bridges.

Basically, I was clear to depart whenever without having to worry about coming back to the otherwise smoldering remains of the previous life that I could have neglected. I tell you these things because, as you can now imagine, the steps I laid out are a far cry from the messages of those short-sighted gunslingers who shout, “It’ll all work out in the end. Just follow your dreams!”image3 4

Nah, son.

Pragmatism is extremely important to consider. A lifestyle is something that you can enjoy and sustain, after all. Screaming #YOLO and buying a one-way ticket to Amsterdam as a way to escape the realities of your current situation aren’t that.

I’ve seen some young, strapping digital nomads start out optimistically only to run themselves into the ground and return home jaded, emotionally tattered, and (sometimes) in a terrible financial situation. Here is an account of someone who started out strong, but packed it home:

Big ups to Eva for being so open here.


These are the people who think being a digital nomad is this bold choice that helps them shed their old life and problems. But returning home is a big reminder: wherever you go, there you are.

The stakes can be high and they require you to think more deeply about this decision than “eff it, it’ll work!”

2. Making money while traveling can be a trap

In our age of the internet, smart, sustainable digital nomadism (this is a thing now) isn’t impossible. But if you want to build a business, surprise — being a digital nomad with a viable business means you still have to nail down the unsexy basics of building a business, day in and day out. Doing your taxes by the beach is still doing your taxes. When you’re constantly on the move as a nomad, however, building a business gets complicated when your discipline and focus are constantly waylaid by distrac — ohh, look at that pretty waterfall!

If you don’t run your own online business or already have regular clients, websites like Remote.co, Upwork, and Fiverr are specifically designed to help you find freelance work that can earn you some scratch while you’re in — wherever.

But there’s a catch.

Many of these gigs don’t pay that well for the time you may have to spend on them — certainly not enough to sustainably support a lavish nomadic lifestyle. This could lead you to a different, simply bigger hamster wheel, leaving you running endlessly after underpaid gig to underpaid gig.

And soon you become too busy to enjoy the sights and too far away to quickly build a network in your field.

So unless you can become highly specialized and land higher-paying, consistent clients, sporadic gigs here and there may not generate the income you need or want. Even if you’re smart about budgeting and are staying in a low-cost area, the stress of constantly trying to make ends meet can eventually run its toll on you mentally and emotionally, leading to burnout and possibly getting you stuck in places.

3. Researching will never properly prepare you for the life of digital nomads

There are a few unspoken truths about digital nomadism. Chief among them: we are not meant to be nomadic. It’s not mentally healthy.

Sure, at first the idea of going with the wind can feel like a cheap roller coaster thrill on infinite loop.

Until you eventually realize that you need to come down from that thrill and just feel normal.

Some of my friends used to complain to me about the drudgery of their daily routine, and I’d nod along in solidarity. But after constantly needing to reconstruct my days and weeks in every new environment, I found myself envying their routines. It’s odd how you don’t realize the valueof having a routine until you no longer have one. Every little decision and question, even the mundane everyday things like where to get my groceries or if a coffee shop has Wi-Fi, threw a wrench in my day.

I missed and craved that normalcy of working out in the same gym or grabbing coffee from the same coffee shop where people knew me by name … and dare I say, the feeling of having a set place I could call home.

My constant cycle of setting up and dismantling my temporary home was not home. Because just as I started to feel comfortable, I’d have to pack up and set up camp all over again. It messed with my head of where home even was. And that, too, was draining, as these other digital nomads can attest to:

TheTravelHack talking about choosing not to be a digital nomad


travel hack talks about the plights of digital nomads

This couple talking about settling down on


The reality is that being a nomad doesn’t wrest you from your life. It’s still your life, but in country X now. And any problems and baggage you have will still be there (or sometimes even manifest in new, unpredictable ways!).

4. Being digital nomads strains relationships

Most people can’t fully comprehend this idea of living life off the grid. In a sense, it’s just so much easier to say “yep, I’m an accountant!” as your dinner partner nods and pokes at their salad.

My flexibility allows me to go all over the globe to build new friendships, rekindle old ones, and reconnect with long-lost family members (largely in part due to the many essential apps that help you work from anywhere). That is incredibly precious and amazing! Until … I have to leave. Leaving people over and over again was so emotionally taxing, like a slow and steady erosion of your grip with relationships, but these days I’ve adopted the mindset of “It’s not ‘goodbye.’ It’s ‘see you later.’”

If you can pull it off, going to destinations that have a built-in community is ideal. Or the even better scenario is to invite and coordinate with friends and have everyone meet you at a certain destination. For example, one Thanksgiving holiday, I’d spent time in Costa Rica with a group of friends that was made up mostly of entrepreneurs (but of course). There were over 30 of us that had dropped by and passed through, and it was wonderful seeing so many familiar and new faces, even if briefly.

5. Easily losing sight of why you started the path of digital nomads in the first place

In a way, becoming a digital nomad has become somewhat of a capitalistic command. According to copywriters, you should “screw the 9 to 5 life” and “follow your passion.”

The implication is clear: you’re a sucker for being “trapped” in a full-time job that keeps you in the rat race. But here’s the kicker: becoming a digital nomad, ironically, becomes its own sort of rat race. In other words, how many of us digital nomads can outdo each other in novelty?

Who can travel to and live in the greatest number of countries?

Who can build the biggest social media audience talking about all the cool shit we’ve been doing?

Who can get to the most remote place (that still has internet) and act like the most untethered, I’ve-got-it-all-figured-out lone wolf?

They say that travel is a powerful form of personal development, though not from all those WOW, LOOK, IT’S MACHU PICCHU IN THE BACKGROUND moments. Yet so many of us digital nomads have twisted the virtues of exploring new countries, cultures, and people, and turned these lessons learned from traveling into vain, surface-level fodder for YouTube and Instagram.

Initially, I thought that I was doing this digital nomad thing for the love of travel and worldly and self-discovery. But as I went from one place to another, I realized that I had been traveling for the wrong reasons. No longer was I interested in traveling for … travel. To my dismay, I was getting high off of chasing novelty. I’d gone down a disingenuous path, where the only way for me to feel like I was doing something of worth was going to the next destination that would bring comments on social media like, “Wow, you’re so lucky to be there!”

Indeed, I was, but please tell me more about it so I can feel validated. (Of course, that may just be me.)

It took some time before I learned that the raw traveling and nomadic experience is a slow, painful process (like anything) of blowing yourself to bits and pieces when you first arrive at a destination; and then somehow putting yourself back together one frustrating, difficult, or delightful experience at a time.

Being a digital nomad was totally worth it — both the highs and lows of the experience. There have definitely been many moments that gave me pause and made me breathlessly tell myself, “Holy shit, this is my life.” 

And yes, holy shit, this is my life, and I am so grateful that I get to live it.

But I just want you to know one important thing: Most digital nomads don’t have life figured out any more than anyone else who claims to have life figured out.

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