12 For 12: Realities Of Living As A Digital Nomad

Cue the music. Let’s do this.

Remotely Interesting: 12 For 12 is a series of a dozen articles covering everything I learned during my time in Remote Year. For my final entry in the series, I’m getting real about this whole remote work phenomenon. Thank you for following the series, and feel free to catch any entries you missed here.

When I told the people in my life that I was going to travel the world while keeping my full-time job, responses ranged from “It’ll be a year-long vacation” to “I’m giving your bedroom to the family dog.”

Travelling with Remote Year was a lot of things. The term “social experiment” was thrown around a lot, and I understand why — there were a lot of untested variables at play. But there were also a lot of surprises and straight up falsehoods surrounding the basic idea of working remotely, and if anyone is considering taking the plunge, it’s best that they have all the facts beforehand.

(And my Mom gave my bedroom back to me once I returned home. I’m not sure how the dog feels about that.)

Dramatization: May not have happened.

1. You Are Captain Of The SS Privilege

Let’s just get this out of the way right now.

If you have a stable enough employment situation at a job that can be done remotely, and also have the finances and infrastructure (if I had a dollar for every MacBook Pro my friends were travelling with, I could afford a down payment on a MacBook pro) to do that job reliably from anywhere on Earth, you are essentially a fraction of a fraction of the world’s population.

If you’re feeling an impulse to get defensive, put a pin in it. The presence of privilege doesn’t invalidate all the hard work and sacrifice you may have experienced to get to this point. It’s just an even-handed analysis of the external circumstances that allowed you to have this opportunity.

Speaking of real talk.

2. Your Life Will Seem Petty As Hell

Complaining about the wi-fi strength in a cafe in Cambodia is a surreal moment. Suddenly, you’ve injected First World Problems into the developing world. It can be a very humbling #douchebag thing to realize about yourself, but it will probably happen to you in some way or another.

Even though you’re living it up in a foreign country, your daily grind is still completely rooted in the culture and vibe of your workplace (and life) back home. So even though you’re technically working from South America, you’re not. Because if you were actually working in Bolivia, you’d be looking at an average annual salary of around $400.

But hey, social impact. One of the amazing benefits of being a digital nomad is your ability to really give back to your host country. Right?

Dropping those hard personal truths all day.

3. You Are Not Giving Back To Your Host Country

I never paid income tax to any of the 11 countries I lived in over the course of a year.

Thanks to grey market competitors like Uber and Airbnb, I never paid any significant amount into local taxi or hotel businesses.

My rent and travel expenses were covered by my Remote Year fee, so I’m not sure what taxes, if any, were being paid out there.

On multiple occasions, I saw a high-speed internet line being installed into a workspace to be used exclusively by members of RY. The list goes on and on, and I’m not sure if the final tally adds up to anything better than glorified voluntourism (without the volunteering).

Countries around the world are moving quickly to accommodate digital nomads, but I don’t know if any of the open concept offices or unlimited wi-fi packages are trickling down to benefit locals in a meaningful way. Especially if we continue to insist that developing nations present us with a work situation that’s identical to the one we’ve known back home.

4. Stop Trying To Make “Digital Nomad” Happen

I remember the first time I realized I was a “Millennial,” and how useless and vague that descriptor seemed at the time. Subsequent years of every Boomer columnist within reach of a keyboard proceeding to refer to Millennials as one homogenous generation (that was also responsible for all of society’s ills) certainly didn’t help the situation. Sloppy labels suck.

Which brings us to “Digital Nomads,” a phrase that is simultaneously offensively vague and vaguely offensive.

Do you have a home to return to? Do you have citizenship in any recognized nation on Earth? If you ran out of money or got laid off today, would you have a place to stay?

If you answered yes to any of those questions, congratulations!

You are not a nomad. So stop throwing the term around.

Please refer to entry #1 above. We’re already ridiculously lucky enough for the experience as is; do we really need to fabricate a super special title for ourselves?

Are we all so unified in our beliefs, goals, and personalities that we should be seen as one giant global tribe?

Search your feelings; you know it to be true.

5. You Are Not Part Of A Giant Global Tribe

Remote Year is most likely the most well-known (and well-funded) company getting into the digital nomad business, but it’s an increasingly crowded marketplace. With every new competitor that appears, one thing becomes immediately clear: No one knows what remote workers stand for.

Are we a group of travel-minded professionals who see the world as one multicultural networking event? Are we trying to test the effects of functional alcoholism on our job productivity? Are we just bored and horny? There’s no consensus.

That’s why any company that tries to create a grand unifying theory behind why people are driven to become digital nomads is setting itself up to fail. I love my Remote Year tramily like a family, but the only thing we all truly have in common is that we paid the deposit for the program and hopped on a plane. Everything beyond that is a variable.

6. It’s Business

When people ask me about my year, I have some excellent stories all queued up in my brain: The day I spent with elephants, the time I food poisoned myself by drinking mysterious tea out of a plastic bag on the Bolivia-Peru border, the time I was in an ATV accident and went sand-sledding immediately afterwards.

All of those stories took place on weekends, because my weekdays were spent working at a laptop. My biggest, dirtiest secret from Remote Year is that I was boring and basic as hell because I needed that money to, you know, survive.

But sometimes I wish people would ask me more about the business/survival side of RY — I’ve got stories there, too. Like the time I stress-ate four hot dogs in Buenos Aires while struggling to finish a freelancing contract, or the time I dropped my laptop and politely asked it to come back to life from the Blue Screen Of Death (and it did, somehow).

Remember when Disney created the perfect man?

7. But It’s Also REALLY Personal

You don’t uproot your life to travel with a group of 70+ strangers under the control of a relatively untested startup unless you’ve got some shit going on, you know?

We weren’t all tragically flawed characters running from our collective past — this isn’t LOST. But the more you got to know someone on Remote Year, the more you’d start to understand what they were struggling with before you met them.

“But Mike,” you say, “Isn’t that how all friendships work? Literally all of them?” And you’d be correct. And kind of rude, interrupting my flow like that. But yes, the friendships you form as a digital nomad operate like any other, but the context is different.

Want to see the old stereotype of travel changing someone? Meet them in South America, travel with them through Europe and Asia, and pay attention to who they are when you say goodbye. Everyone grows, everyone is better for the experience, and at least some of the people you’ve been around literally had their dreams come true in your vicinity. It makes your life back home look like a holding pattern.

8. Time Loses Meaning

When your days are literally numbered, you treat them differently. Weekends go from “A safe space to eat chips and watch Netflix” to “The setting of my next great adventure.”

Seasons are relative when you can start your day with a Peruvian winter and end it with London in the summer.

You find yourself completely willing to move in with someone after only knowing them for five months. (Or maybe that’s just me.)

I wish I could bottle the momentum and mastery of time I had while working abroad, but it really seems to come with the territory. As amazing as he was, Southeast Asia Mike (in all of his tank top glory) cannot function in Toronto.

But that doesn’t mean everything returns to normal if and when you go back to being a non-remote worker.

Oh, Doctor Who GIFs. I’ll miss you the most.

9. Time Gains Value

I’m done Remote Year now. I’m back at home. And my days feel so much tighter than they ever did abroad. Despite having less exploring and adventures packed into my schedule, I feel like I’m always cutting a corner somewhere in my day to make time for something else.

Then I did the math.

While abroad, I would work an 8-hour day. No more, no less (unless the situation demanded it). I would either work from home or from a workspace within walking distance.

Back home, when factoring in the distractions and lost productivity time that are part of working in an office, plus the hour-plus commuting time (both ways) I face to get to the city, my entire work day is more like 10–11 hours.

That’s 15 hours a week I’ve lost in transition. No wonder I feel sluggish and trapped at the same time. And I don’t know how to fix it; that’s just how time works here.

10. You Learn To Live Simply (But Expensively)

After a year of living out of a couple of bags, it can be jarring to come back home to an apartment (or a home, or a storage container) full of so much useless shit.

Remote Year teaches you to live with what you can carry. (Or what a gigantic airplane can carry in a cargo hold, but it’s basically the same thing.) After a while, this becomes your norm, and anything more seems superfluous. Why can’t everyone live so simply and cheaply?

Slow your roll there, Into The Wild. Living small and living cheap are not the same thing.

If anything were to happen to my expensive laptop, that would have been it for my ability to do my job, and by extension keep travelling as part of Remote Year. The grand majority of all the money I earned this past year went to my RY fees as well. I’ve minimized what I need in my life to be happy, but that doesn’t mean I can survive with a backpack and a smile.


11. This May Not Be Sustainable

I have serious doubts about the long-term viability of the digital nomad lifestyle. For starters, check out the previous 10 points. But it’s not just that.

First off, the majority of jobs just aren’t remote-compatible. Anything requiring manual labour or a skilled trade is out. Same goes for anything that requires in-person interactions with customers or clients.

Now we need to account for employers and workplaces that aren’t willing or able to let an employee work abroad. I’m not a salaried employee at my job, and if I were, I think there would be insurance liability reasons preventing them from letting me galavant around the world while on their benefits plan.

At this point, remote-capable employees comprise a small slice of the global workforce; not quite enough to inspire a new age of workplace culture.

But you can’t work remotely without a country willing to host you. As the number of remote working programs increases, countries will be forced to take notice of the increasing amounts of foreign visitors essentially working full-time while sinking most of their money back into grey market businesses.

How will those governments choose to deal with the hotels, apartments, and workspaces that these digital nomad culture companies will continually rent out in perpetuity? At what point does a grey market startup go from filling a niche to exploiting a loophole?

I don’t have the answers to these questions, but I can’t be the only one asking them.

Oh, #KanyeShrug. I’ll miss YOU the most.

12. It Will Violently Change Your Life

Change is good, right? Well, it depends.

Remote Year can end up feeling like living under quarantine. Not only are you cut off from your old life and a lot of the pressures of the outside world, but you’re way more likely to catch something from someone in your group.

(No, not like that.)

The amount of apps, startups, and side projects that are created within each Remote Year group is amazing, and a direct result of being in close proximity to inspirational people with great ideas. That’s a big win for you.

Know who probably won’t feel as enthused? Your employer back home, who didn’t sign up for you to return home all starry-eyed and ready to pursue projects outside of the company.

I have no way of proving this, but I think there’s a chance that employers of digital nomads will see huge numbers of them opting to spread their wings and chase their dreams (by quitting their jobs).

I am 100% on Team Dreamchaser, but remember what I said earlier about employers ultimately having the final say on whether an employee can go remote or not? If word of mouth says that everyone who works remotely returns with a strong desire to quit their job within a month, I can’t see why bosses would keep saying yes.

Does this point to a huge flaw in how many societies treat office culture and the manager-employee relationship? Absolutely.

Can it be changed? Nothing is impossible, and I think millions of people could be living and working happier if some tenets of workplace management culture were flipped upside-down.

But if someone tells you that you’re part of a social experiment, there’s always the chance that you’re really just part of a social trend. I want the idea of remote work to become a world standard, but I understand that I could just end up being part of the lucky generation that got to experience all of this before the door closed behind me.

Damn ungrateful millennial digital nomads, amirite?

Cue the music, and thanks for reading.