One month ago, I flew 30 hours, 13,464 kilometres and 12 time zones across the world on a one-way ticket.
It felt like a huge and terrifying move at the time. The result of spending the first quarter-century of your adult life following the beaten path is that deviations start to look much more intimidating than they actually are. In retrospect though, it was actually pretty easy. If you’re considering making a similar move, this post is your handy guide to escaping the swamps of corporate America:
1) Picking A Destination
If you’re making a first attempt at indefinite, long-term travel, the safest place to start is on the bunny slopes of the vagabonding scene: Western Europe and Southeast Asia. The latter in particular is a giant playground for European and American tourists, reveling in the last remaining years of their civilization’s wealth and good fortune. You will experience many of the shocks and hard landings that await any novice traveler, without ever actually being in any sort of danger. You will also be constantly surrounded by outgoing vagabonds and vacationers, eager for whatever sort of single-serving friendship you can offer them.
Western Europe is similar, but at about 3-5x the cost. It is safe, it is familiar, and there is a lot to see and do. If you’ll be living off savings though, it will probably be stressful to watch your bank balance decay as fast as it will.
2) Quitting Your Job
You will be tempted to make grandiose gestures that will clearly delineate your future life as a vagabonding explorer from your present cubicle-dwelling persona. You will want to shit on the conference room table, kick your boss in the junk, and blow up your condo full of IKEA knick knacks. Everywhere you go, people will ask you – do you know Tyler Durden?
You will be tempted to burn bridges. I was too. But you should resist that temptation.
One reason for this is practical. Yes, I am 99.9% sure that I am going to live out my dream of becoming a famous, wealthy and world-changing-ly influential writer. But in the event that the unthinkable happens – say, I lose both index fingers, the only ones I use to type despite a decade of primary school home row instruction, in a tragic luge accident – it’s good to have a fallback. More options are always better than fewer.
It’s also psychologically important to have an attractive alternative to the vagabond life. Otherwise, like a weak man in a relationship with a good woman, your mind will be unable to determine if your appreciation of life on the road is genuine, or merely the subconscious realization of a lack of better options. I know that I have a happy, comfortable life waiting for me back in North America, and that I will only continue to travel for as long as the latter appeals to me more than the former. Having the ability to jump right back into my old career makes me honest about my decision not to do so.
3) Making A Plan
I’m sure many great trips have been had by travelers with nothing but a one-way ticket and a desire to see where the wind takes them, but I don’t recommend it.
If you’re traveling long-term, you will eventually want to settle into city for a while, and build a mini-life and social circle. In my case, I did this right off the bat – I flew directly to Chiang Mai and rented an apartment for a month. Others will want to hop around with a backpack for a while, before settling in, which is actually a better idea in most cases, since you might as well get a taste of a few cities before committing yourself to putting down roots in one.
When you decide to cool your heels for a bit, you’ll quickly find that there are a lot of hours in a day, especially now that your workday no longer exists. You need to figure out how you’re going to spend those hours.
In my case, I’m training Muay Thai 3-6 hours a day, orchestrating a book launch, drafting a new book, building a website, and devouring books.
Your plan doesn’t have to be the same as mine, or even similar. If you want to go out until 5am every night and sleep until noon, that’s awesome. You’ll still need something to do from noon to 11pm. So what is it you want to do? Start a business? Write a book? Learn a language? Try a new sport? Whatever it is, the greatest gift of life on the road is that you unleash a vast reservoir of free time. Rather than think of it as a burden (my least favourite idiom:, ever “Killing” Time), use it to pursue whatever you want, with a gusto that you’ve never felt pushing papers for someone else’s bottom line.
4) Meeting People
I’ve made a lot of very short-term friends over the past month. On planes, in restaurants, food courts, on the street. You meet people, you share a conversation, and then it’s gone. I enjoy these encounters, but they aren’t a replacement for real friendships.
Single-serving friends are easy to find. Just introduce yourself to people, and find others with similar immediate goals. Looking for food? Going to the bar to meet girls? Cool, let’s go! Done.
If you want deeper friendships though, you need to find a scene. You need to see the same people, repeatedly. You need to share experiences. you need to find people who are similar to you in a fundamental way – rather than just in superficial details, i.e. where you’re from, where you’re traveling to next. You need to have something to offer them, and they need to have something to offer you.
This goes back to point #3. If you have a mission, it will naturally choose your scene for you. If you just want to party, you’ll meet guys with the same mindset. I’m here to train, write and work, and I’ve found a few cool groups of people who are doing the same thing. Not only is it fun and useful to be surrounded by people taking on the same challenges you are, it’s also a strong motivator. When the people you spend your days with are all doing incredible things, you start to see the ‘incredible’ as normal.
5) Fixing What’s Broken
You wouldn’t want to run away from your life if there wasn’t something wrong with it.
Some will say that any man who wants to do what I did – i.e., leave indefinitely, rather than just for a vacation of predetermined length – must have some sort of personal problem that they need to address. I disagree. Something’s broken alright, but that doesn’t mean it’s you.
Maybe you’re sick of a consumerist culture of status symbols and junk. Maybe you’re frustrated with a comatose economy, and the bureaucratic pointlessness of most ‘good’ jobs. Maybe you’re turned off by the shallow and impersonal American dating scene, vapid and immoral political contests, and governments that squelch innovation while propping up the lazy, unproductive and criminal classes.
I think there’s more wrong with someone who doesn’t at least consider escaping all of that, than someone who does.
It’s not our choice to live in the world that we do, though. From my perspective, the society I was raised in is broken. From that society’s perspective, I am the broken one. I am the square peg in the round hole. If you’re reading this blog, you probably are too. At some point, you will either have to make your peace with the West as it is – or leave it for good.