In 2013, motivated by the promise of freedom and adventure, I became homeless.
My ‘normal’ life in one of the world’s largest capital cities was starting to feel like a hamster wheel. I was not unhappy, but I was not fulfilled either. I had always questioned (and resisted) society’s promoted life trajectory, but even my relatively unconventional lifestyle was becoming stale.
I started to question whether perhaps the best way to win “the game” I was involved in was to just stop playing it. At least for a while.
I had spent a few weeks in Thailand over the previous couple of years and had met some interesting people who seemed both relaxed and successful. I later found out that they were ‘Location Independent Lifestyle Entrepreneurs’. That’s a smart way of saying ‘Homeless people who sell stuff on the internet’.
They seemed happy and free and inspired, and I dreamed of one day emulating them.
The pivotal moment came when my then landlord informed me that the rent for my tiny studio apartment was going up. I realized that the financial and psychological costs of working just to survive didn’t justify the returns, and I made the choice to take my chances on trying a different type of existence.
What I didn’t sell I gave away, and by the time I was ready to leave everything I owned fit into three pieces of luggage.
I booked a one-way ticket to Thailand. Over the course of the next five years, I never spent more than 6 weeks in any one place, traveling between Africa, Europe, Asia and the US, running my businesses from my laptop.
I had become a ‘Digital Nomad’.
It was an incredibly liberated time in my life and I wouldn’t change it for anything, but it soon became apparent that a lot of the things I’d been sold about the life style were fallacies and half-truths.
The general sales pitch goes something like this: “All you need is a computer, a back-pack and a ticket to a third-world country and before you know it you’ll have a thriving business and an envy-inducing social life, unhindered by the stifling social mores and crushing lifestyle expenses of the modern world.”
And while I actually did grow a successful business and build a worldwide network of wonderful friends, I can tell you that making those things happen from the road wasn’t as easy as the people selling you books and courses on how to do it would have you believe.
Here are the truths I have found on my journey into ‘digital homelessness’.
1. You Will Have To Hustle
“There are ten thousand hustles on the internet.” - Joey ‘Coco’ Diaz
Despite what you might have been told, you will not make enough to thrive, let alone survive by working four hours per week from your laptop in a coffee shop.
And while this lifestyle avoids fixed monthly expenses like car payments and rent, the cost of flights and travel quickly add up.
If you head out hoping to wing it and figure out your business idea while you’re on the road, you will need to have a bankroll saved up. That or a trust fund.
I was lucky enough to have a couple of existing internet businesses and an established reputation as a jiu jitsu instructor BEFORE jumping off into the unknown, which allowed me to earn additional income by teaching seminars and workshops on the road. Without either of those two things the adventure would have been a lot shorter.
The truth is, I actually worked far harder since becoming location independent than I did before. Admittedly, my schedule did offer more flexibility and I could choose to work or take a break when I wanted to. But strangely that usually meant choosing to work more and taking fewer breaks.
2. You Will Be Uncomfortable
“There is nothing like staying at home for real comfort.” - Jane Austen
If you’re reading this, it’s more than likely that you are one of the most privileged people on earth. You’ve grown up in a world of comfort, security and luxury beyond your ancestors’ wildest dreams. And at this point you’re most likely addicted to those things.
But as with most addictions, they probably don’t make you happy. Some argue that they actually do the opposite. And yet most of us cling to them. We think we need our TVs and routines and supermarkets with 15 varieties of flavored water.
So, here’s the bad news: those things you’re addicted to? You won’t understand how much some of them mean to you or how habituated you are to your current lifestyle until you don’t have them anymore. You may miss some things you didn’t even realize you were taking for granted - like a good pillow or hot shower.
But here’s the good news: discomfort isn’t always pleasant but it’s often rewarding. Few things will make you feel more alive than stepping off a plane that you were certain was going to crash a few hours earlier. And few things will sharpen your awareness as much as being alone in a foreign, less ‘developed’ country.
The Digital Nomad lifestyle is not for everyone. It’s a juxtaposition of extremes. Some of those extremes will take you further from comfort and security than you’ve ever been. But they will also take you closer to finding out who you truly are.
3. You Will Be Misunderstood
“Conformity is the jailer of freedom and the enemy of growth” - John F. Kennedy
One of the questions I used to dread most was: “So where do you live?”
Most people just could not process the fact that I didn’t rent / own an apartment or house and that I wasn’t sure where I would be in a couple of months. I could see it in their eyes when I told them. I could literally watch the information short-circuit the autopilot social processes their brains were used to initiating.
And it wasn’t just those I met along the way who didn’t get it. Many of those closest to me struggled to accept the way I was living. A friend of mine a the time called me ‘Teflon-Man’ because it was his perception that my lifestyle meant ‘nothing sticks to you’. Or rather, that I didn't “stick with” anything.
You’ll find that some people might even resent you. This is because they only see the facebook pictures of you doing cool things in exotic places. They don’t see you sleeping on the floor in airports or lying awake at 3am in a strange bed suffering from jet-lag. Unless they’ve experienced it themselves, no one can really understand what it’s like not having the security of a pay-check or fixed address and what it’s like to almost always feel like a stranger.
4. You Will Be Alone
“If the path before you is clear, you're probably on someone else's.” - Joseph Campbell
There will be times when you feel rootless and adrift. ‘Home’ will move on without you, and social media will make sure you’re aware of it.
After long enough, you might even lose some ability to relate to those who have chosen more well-trodden paths.
I knew when I settled down again that it was going to take a while to re-integrate. I’d been ‘institutionalized’. Or perhaps ‘de-institutionalized’.
My wife doesn’t know this, but for the first year or so of living ‘back in the system’ I kept a bug-out bag packed and ready for a strategic exit from settled life if it proved too much. Even to this day the allure of the road is always there.
Because the digital nomad community itself is transient, it can be difficult to create relationships with real depth. Often you’ll find yourself in a city filled with people you've met but longing for just one true friend.
And being a foreigner is inherently solitary. No matter how friendly the local populace, you will never truly be accepted. There will those who look at you with resentment or even fear. You can live somewhere for a few weeks or months and even develop routines and a social circle, but knowing that it’s only temporary will mean you’ll never truly feel at home.
5. You Will Connect
“Shared joy is a double joy” - Swedish Proverb
I’ve heard it said that ‘Life is made up of small moments’ - those peak experiences which stand out in our memories.
Digital Nomads are a community of seekers: not satisfied with the life that their parents, teachers or priests sold them, but instead constantly searching for the next adventure, the next high, the next connection.
During my 5 years in the lifestyle I had countless ‘small moments’ and each of them had a common element. Whether I was dancing in the middle of dust storm at Burning Man, drinking Ayahuasca in the jungles of Peru or training jiu jitsu in Japan, there was something that was always there: others.
There were countless wonderful experiences but the true magic came for the connections they created and in the sharing of the moments that sprang from them. Perhaps the greatest gifts the journey bestowed were the connections I made with like-minded individuals becoming part of a tribe of amazing people that are spread across the planet.
6. You Will Evolve
“Liberty, when it begins to take root, is a plant of rapid growth.” - George Washington
The constant juxtaposition of locales and cultures will force you out of stale patterns. (Unless you’re that guy who arrives in a far-flung locale and heads out to find a McDonald’s or Starbucks. Don’t be that guy.)
And being around new people will expand your awareness. The lifestyle attracts those who have experiences and stories that will shatter your preconceived notions about how the world works and what’s possible within the human experience.
Most of the people I met were motivated, courageous self-starters. You kinda have to be that way when you're the captain of your own ship. Being exposed to all of these self-actualized individuals exposed me to countless new business ideas and strategies and also forced me to raise my game and grow in ways I never could have imagined.
Something else that stands out in my memories was the willingness of the nomads to help each other. I was given thousands of dollars worth of free consultations on everything from internet marketing to physiotherapy.
7. You Will Not Need Much
“Sooner or Later, the things you own start to own you.” - Tyler Durden
If set out on this path, you will not need much, and in fact, eventually you will not want much. One of the most valuable things I’ve learned from living this way is the power of less, especially with regard to personal possessions.
When you’re constantly on the road, every ounce you carry is multiplied. Back then, my first criteria for evaluating any object that I considering acquiring was not ‘How much does it cost?’ but instead ‘How much does it weigh and how much space will it take up in my bag?’
I learned that, with the exception of a few indispensable items, most of the stuff we own is just clutter anyway.
When I was about to leave each a location I would do a mini ‘purge' and give away anything I hadn’t used at least once during my stay. It was like a ‘mini-spring cleaning’ of my life. This continual process of whittling away the inessential become one of my most enjoyed rituals and is a habit I carried over into normal life when I returned.
8. You Will Be Free
“No price is too high to pay for the privilege of owning yourself." - Friedrich Nietzsche
The world will tell you that personal freedom is one of the most precious ideals to which to aspire. And then it will do everything it can to constrain you.
I make no judgements on anybody who chooses the stability of a fixed address or a family. It takes much discipline to successfully maintain either - a discipline that perhaps I sorely lacked when I left.
But my freedom is sacred to me. And at that point, the life of the digital nomad offered me the greatest access to it.
Most of the time I didn’t know where I’d be the next month. Or the month after that. And that kinda scared me.
But knowing that the decisions of where I’d go, how long I’d stay and what I would do when I got there were completely up to me was absolutely priceless. It made every grueling flight, every lonely moment and every strange look worth it.
9. You Will Question Yourself
"I think that's the single best piece of advice: constantly think about how you could be doing things better and questioning yourself." - Elon Musk
Around the third year I hit a point where I could feel that I was close to burning out.
The adventure of the road started to lose its appeal and little things I used to take for granted, like having my own closet, started to seem tantalizing. And the even the thought of airports started to make me nauseated.
So why did I keep doing it for another two years?
We are living in an age which presents opportunities beyond anything our ancestors could have imagined. The idea that someone of moderate means could detach themselves from a fixed place of work and travel the world whilst still staying somewhat tethered to their roots would have been unfathomable just a few generations ago.
Just the fact that this option exists means that those who have this opportunity should at least consider it. That’s one of the reasons I did it. Because I could.
There’s a saying that comes to mind often: ‘Wherever you go, there you are.’
Looking back, I could see that when I left my stable life, a part of it was about running away. Running away from the constraints of society. Running away from having to grow up and be an adult. Running away from the complexities and difficulties of deep relationships.
But no matter where I went, life always found a way of making me face the things it wanted me to face. And that’s the biggest truth that I’ve discovered on that path: There is only one thing I can’t run away from.