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Nearly four years ago, 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 flat was going up. I realised 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. Since then I haven’t stayed in one place for more than 6 weeks, travelling between Africa, Europe, Asia and the US, running my businesses from my laptop.
I had become a ‘Digital Nomad’.
But I soon realised there were a lot of fallacies and half-truths about the lifestyle I had been sold before I embarked on the journey.
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.”
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 on your laptop.
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. Without either of those two things the adventure would have been a lot shorter.
The truth is, I actually work far harder since becoming location independent than I did before. Admittedly, my schedule does offer more flexibility and I can choose to work or take a break when I want. But strangely that usually means choosing to work more and taking fewer breaks. Because at the end of the day, the weight falls on my own shoulders for how I’m going to make the way.
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 you’re probably, to a large extent, addicted to those things.
But the strangest thing is that they don’t necessarily 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 flavoured water.
So, here’s the bad news: those things you’re addicted to? You won’t realise how much some of them mean to you or to the lifestyle you’re used to until you don’t have them anymore. You may miss some things you didn’t even realise you were taking for granted – like a good pillow or hot shower.
But 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.
This 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 becoming 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 dread most is: “So where do you live?”
Most people just cannot process the fact that I don’t rent / own an apartment or house and that I’m not sure where I’ll be in a couple of months. I see it in their eyes when I tell them. I can literally watch the information short-circuit the autopilot social processes their brains were engaged in.
And it won’t just be those you meet who don’t get it. Many of those closest to you will struggle to accept the way your now living. One of my best friends calls me ‘Teflon-Man’ because it is his perception that my lifestyle means ‘nothing sticks to you’. Or rather, that I don’t “stick with” anything.
You’ll find that some of people might even resent you. This is because they only see the facebook pictures of you doing cool things. They don’t see you sleeping in awkward positions in airports or 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 job or pay-check or what it’s like to almost always feel like a stranger.
More good news though – within the “Digital Nomad” community (which I despise as it seems more and more cliche to say) people don’t ask you anymore “what do you do?” or “where do you live?” It’s like the cultural programming drops away finally so that you’re no longer bombarded with meaningless surface-level questions like that. Or maybe it’s just that Digital Nomads have their own “cultural” program….
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 know when I settle down again that it’s going to take a while to re-integrate. I’ve been ‘institutionalised’. Or perhaps ‘de-institutionalised’.
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 even be some who look at you with fear or resentment. You can live somewhere for a few weeks or months but you’ll never truly be 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.
This is a community of seekers – not satisfied with the life that their parents, teachers or priests sold them, but instead constantly searching for the next zenith.
Over the last four years I’ve had countless 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.
Each of these was itself an incredible experience but the true magic came for the connections they created and in the sharing of the moment. Perhaps the greatest gift this journey has bestowed is the connections I’ve made with like-minded, brave individuals.
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. This lifestyle attracts those who have experiences and stories that will shatter your preconceived notions about how the world works and what’s possible in the human experience.
Most of the people I’ve met during this experience are motivated self-starters – you have to be when you’re the captain of your own ship. Being around them has not only given me countless new business ideas and strategies, but also kept me focused on being more creative and improving my products and services.
Another great hallmark of this community is the members’ willingness to help each other. I’ve been 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
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. Now, my first criteria for evaluating any object that I’m considering acquiring is not ‘How much does it cost?’ but instead ‘How much does it weigh and how much space will it take up in my bag?’
With the exception of a few indispensable items, most of the stuff we own is just clutter anyway.
When I’m about to leave each a location I purge or give away anything I haven’t used at least once during my stay. It’s a ‘mini-spring cleaning’ of my life. This continual process of whittling away the inessential has become one of my most enjoyed rituals. Each time I do it I feel more lucid and unencumbered.
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 of which – a discipline that perhaps I sorely lack. But my freedom is sacred to me. And at this point, the life of the digital nomad offers me the greatest access to it.
I don’t know where I’ll be next month. Or the month after that. And that kinda scares me. I also don’t know how much money I’ll make because there’s no guaranteed salary coming my way.
But knowing that the decisions of where I’ll go, how long I’ll stay and what I’ll do when I get there are up to me is priceless. It makes every gruelling 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
I can feel that I’m close to burning out.
The adventure of the road isn’t quite as appealing as it used to be and lately the idea of my own closet seems like a light at the end of the tunnel.
So why do I keep doing it?
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 staying connected to their tribe 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 do it. Because I can.
There’s a saying that comes to mind often: ‘Wherever you go, there you are.’
Looking back, I can 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 go, life always finds a way of making me face the things it wants me to face. And that’s the biggest truth that I’ve discovered on this path: There is only one thing I can’t run away from.