The paradox of life on the road as a “Digital Nomad”

When everywhere is home, nowhere is home.. But some of the best stories couldn’t be discovered without getting lost

Fantasy vs. Reality

The panphlet for being a nomad is nothing short of vocational porno for the average wagie, but I want to shine a light on the unfiltered reality of what its really like. Challenging, never-boring, even liberating, but not without the metric tonnes of ballache and the logistical shitstorm that comes along for the ride.

A lot of people think that digital nomads have it easy, the ideal lifestyle, “working” on the beach, the flashy snaps of a laptop with a beer in view, endless changes of scenery, and always in good company. But the truth is not always as it seems, sure it is a desirable lifestyle rife with thrill and novelty, but it is also a challenging and taxing way to live that grinds you down over time. But before we get into all that, lets look at all the pretty photos:

Photo by Anastasia Nelen https://unsplash.com/@mnelen

Is that really the best place you can find to work or are you homeless?

The reality looks much more like this:

Buried under a mountain of scrap papers somewhere in eastern europe, espresso and cigarettes, beat up laptops that should’ve given up years ago, patchy Wi-Fi and a dodgy power outlet that gradually turns your CPU into a small thermo-nuclear-reactor. But to me, this is still 100 times better than a modern progressive officespace with its quotas and manadatory corporate diversity and inclusion indoctrination retraining.

Behind every fake beach pic is a mammoth chunk of admin that went into being there, behind every team call taken in the sun there is a palpable level of stress and loneliness. When the basic assumptions of life like accomodation and security are in constant flux, life does become more complicated, and when you arent bound to any particular place or people at any time – theres bound to be a feeling of longing that develops. Constraints exist for a reason and in the end monotony is just another word for security and comfort.

But the perks absolutely cannot be ignored. No two days have been the same since I started and I havent felt profoundly bored with work-life in years. If you get the opportunity to manage yourself and it suits you, you should ride the wave as long as you can. Its not a lifestyle I would soon trade in for a regular 9-5, because above all it is about complete autonomy over your time and space, and ultimately freedom.

Unspoken Challenges – The never ending skirmish with Logistics..

You learn a lot living on the road but no qualities develop more so than resilience and relentless optimism. As with anything complicated in life, there are times you get it wrong and things shit the bed, but in your normal home life there is always multiple crutches, family and safety nets to prop you back up when things go awry.

Fortunately or unfortunately as a nomad you lose all of that and find most of the time you can only really count on yourself, its not your fault the taxi broke down and you missed your connection but nonetheless it is you who will sit in Bogota airport for the next 28 hours and Barbara from Avianca customer service (despite what she says) is not really on your side either. Your friends and family are sick of hearing about how much fun you’ve had in South America, and besides they’re asleep now. So you dive into the one reliable thing that keeps on providing and sustaining you on this hedonistic journey, paradoxically – its work.

The war with logistics is on-going and feels like it will never end, because it wont. On a standard holiday you need to make sure you can stumble back to your accomodation, avoid the barrio and try not to lose your passport, thats about it. As a nomad at all times you need to ensure you have a valid visa, health insurance, multiple bank accounts, a 5g mobile unlimited data plan, everything thats needed for normal life, your flights and accommodation for the next 2 locations, (a shell company or three), additionally, where are you going to keep your stuff? You really shouldn’t have gotten that Maine Coon.. Or the 30″ OLED.. and what happens with the Volkswagen you left in Madeira?

When everything is in flux all the time you have to be 3 steps ahead of where you are going to be next and sometimes the ballache is overwhelming. While most people are wondering what kind of pasta they want in their bolognese, you are sweating in the Budapest airport wondering if your photoshopped K-ETA will get you into Seoul or put in Korean prison. It doesn’t seem like it but this is a huge amount of work to stay on top of, if you let it slip (like some people) you find yourself up immigration-shit-creek without a proverbial paddle and a harsh conversation at the border. Thankfully I’ve always been white lucky and never had too much trouble (its satire guys, chill).

Financial Considerations & Material Solutions

With everything said in the above, there is one cure all for the endless logistical nightmare and that is cash. With enough gold doublons you can solve any accomodation mishaps, transportation failures, you can even straight up buy your way to citizenship in most countries (pay to win). It isnt common knowledge but you can truly live wherever you want if you have the dough to back it up. Even the strictest countries on immigration usually sellout in this regard. Throw enough money at just about any logistical problem and you can solve it. Money isnt everything blahblahblah its a lovely bumper sticker, but there is no denying one thing: it solve problems.

For material problems, there are material solutions. In the end, if you can afford not to have massive headaches then its wiser to spend the coin and live in peace. Sometimes that means paying the lawyer to take care of all your paperwork, sometimes that means flying business class for that last leg of the journey back home. Because yes, sometimes a good nights sleep really is worth a thousand dollars. And if you know you just know.

When you can afford the luxury its nice to have and when you cant, you spend the whole flight wedged between a snorer and a former sumo trying to dream up new ways to make more money.

Loneliness and Social Life

Without a doubt if you travel more, you meet more humans, and if you dont then you just arent doing it properly. You greet a new culture through its people and even for introverts it can be hugely rewarding (despite the discomfort) to be perpetually thrust into constant social interactions.

Contrary to the last section, this is why travelling on a shoestring budget is so much more fun. You dont make friends with the Duke of Amman from the rooftop of the Fairmont… (oh wait maybe you do.. Bad example). But you get what I mean. Its nice to have the option to robe-up and hibernate with room service after Macchu Picchu but primarily you want to spend your time on the ground, where the life is.

One paradox though is that all these connections (however brilliant they might be) are short lived. Often times barely longer than a meal, or even a single moment, you laugh and carry on grateful to have crossed paths but its all very fleeting. I could go on and say that the nature of it wears you down over time but the truth is that it doesnt really, not everything needs to last forever in the end. Being memorable isn’t a necessary pre-requisite to fulfillment and if you write it down you’ll remember that moment just the same.

But there is an undeniable transient nature to the social aspect of always moving around, you find those few rough gems around the place and keep them stored away, the far-flung friends in different cities that always deliver barrells of laughter and good fun even when the longest time has passed. They’re always close but far away. You have the voice notes and the memories of them along with your family but often no physical nature of familiarity, sometimes you just want to flick them in the ear, wrestle, or give them a hug.

Deeper relationships go the same way whether or not anyone cares to admit it, the only person that can really love a nomad is another nomad. Otherwise its too much pressure to keep them in one place, either you feel you’re sacrificing your whole life for this person, or they feel they’ve clipped your wings and are holding you back. Its common to end up with a “bird in every nest” but it isn’t any kind of situation conducive to settling down and starting a family. Eventually you meet one you say you’ll give it up for, but the backpack calls, and when it calls its always answered, especially when you peer into the reality of common mundanity and uncover whats really expected of you..

The Paradox of Exclusivity

There is an emerging trend for digital nomad “coliving” environments where a bunch of people who want to travel “without their friends” but still have the convenience of “having friends” all join together, its cool and all but it ends up being pretty much as you can imagine. A lot of organised fun and big hiking trip group photos full of “best friends” who probably never even see each other again. A lot of this stuff leans into the real paradox of exclusivity which is not something we really have time to unpack but in a nutshell:

If the barrier to enter a group is 0 then by definition the value of the group membership is 0. If Harvard suddenly opened its doors to every single person who applied the value of admittance would drop to 0. The exclusivity and barrier of entry into a given collective defines the value of inclusion on an individual level. So if you can simply be dropped into an automatic friends group without having to do any of the social filtering and spadework then… You see what I mean. The outcome is pretty much as you expect it.. All quite fleeting and mostly transient in nature.

Motivation and actually doing the work

You have to work for yourself as if you were your own boss, but also be kind to yourself like you are your best friend. But they also say never go into business with a friend.. So right away we are starting on the backfoot.. If you were someone who struggled in school with any kind of group project unless you could be the boss (definitely me) then you are probably the kind of person who fits the bill for self-management.

If you cant concentrate on anything that someone else has told you to do but go into multiple day long frenzies of hyperfocus when you have your own project to work on then also similarly, it would seem the lifestyle appeals to your personality.

Lets be honest and summarise it appropriately: if you are a very driven person but a bit of an asshole to deal with then you are well cut out for being a nomad.

Wavey Productivity

Self motivation and ass-kicking is part of the gig and never been really something I’ve struggled with since I’m a natural born nerd and I love what I do. But productivity definitely comes and goes in waves, 3 weeks you are sprinting for a deadline (or even just to prove to yourself that you can) solve a problem / deliver a product. Then next fortnight you’re in a temple training at Taekwondowon barely checking your phone, because theres a chance you were meant for the UFC all along, and a perfect sidekick is the golden ticket..

The traditional setup of a corporate line manager and an externally enforced schedule does have its perks though, you can relax knowing that you’ve done your hours and its someone elses fault if that doesnt amount to the desired output. Being managed means you can sleep better and relax into your role by just falling in line, again it is the constraints that provide the comfort.

The main thing I’ve realised over the last few years in my professional life is that a task will generally always take the amount of time that is allotted to it. Even just setting a timer on your desk with the estimated time you think it will need generally ends up resulting in it being completed in the same time or less simply because you’re aware of the timer. Its purely psychological and in this example you’ve just outsourced the duty of your superior to the digital timer.

The way I see it deadlines do push things forward in the end and the threat of unemployment/homelessness is a pretty damn good motivator for most people. But if you despise being told what to do (and you love what you do) then you might just be able to manage without all that noise. Although its not a path you can easily come back from, the idea of having someone sit on my shoulders now gives me the willies, I couldnt do it.

Daily Adventure and Stress

Without blowing the trumpet too hard I have to say this way of living is an adventure that is like a hard open-world videogame that you just cant stop playing. Every week offers some kind of new experience or challenge and the daily navigations of exploring a new place, planning a new trip, fumbling awkwardly around a new language are highly addictive. You get hooked on the stress just as much as the excitement, you grow in resilience when things go haywire, and as with the videogame, as you uncover more of the map and its characters your love for the world deepens too.

The big existential questions like “what am I doing with my life” rarely occur when you’re on top of a mountain or napping beside a lake. The stresses of “so-and-so they shouldn’t have said or done xyz to me” rarely linger when you’re wandering through an old germanic cathedral with enormous stained glass windows or typing away in the corner of a Japanese cat cafe.

There is an element of “you’re just running away” that people can quite validly throw at your feet once in a while but to that the response is always “everyones running to something, I’m just going in a different direction”.

In the end of July marks the 8th year of living out of a backpack (with some stopovers in between sure). I know it cant hold up forever, and there come a day when the cows come home to roost (is that a saying?) and its time to lay down some roots and finally stop being a dickhead. But for now this is what works and keeps me engaged and moving forward with life.

Regardless of what the future holds, we’ll all have sacrificed many doors which closed so that others could open, we’ll all have different regrets, missed opportunities and varying weights to our pots of gold. But I know given the type of person I am that I will not regret having bought the ticket all those years ago.

Conclusion

The truth is that the lifestyle is a trade-off between constant novelty and increased stress, and also comfort for challenge. It’s not for everyone, but I do think those with the desire should try and run in it in production for at least a little while sometime in their lives. I know nomads get a bad rap, people throw around buzzwords like gentrification and colonialism and they’re probably right.

But in the end they’re probably no better in their own ways too buying gizmos and drinking coca-cola. Nomads are not taking jobs, they bring external cash into a local economy and the ones that arent completely insufferable generally have a good story or two up their sleeve they’re willing to share.

Every new place offers lessons and opportunities for growth, but no place is perfect permanently, at some point you will run out of novelty and move on, but the moving on cannot continue forever either. You’ll see your friends with committed relationships and kids saying “man I see the pictures and I reckon you’ve got it made, I’m living it vicariously through you” and the funny thing is that you could look back and say the exact same thing to them. Ultimately, every lifestyle has its pros and cons, everything has a tradeoff, you should draw inspiration where you can but always take the hype with a pinch of salt.

Leave a Reply

Your email address will not be published. Required fields are marked *