6 Lessons From 6 Years On The Road.

Singapore, Malaysia, Thailand, Laos, Vietnam, Hong Kong, Jamaica, Mexico, Colombia, Canada, America, Bulgaria, Spain, Portugal. I’m not the person I was when I left home. That much I know.

I’ve found myself lost and lost myself more times than I can count. Home is the only place that feels foreign to me anymore.

I’m coming into my 6th year of extended world travel. 6 years of feeling like a stranger in a strange land. I’ve been on the road, mostly on my own, since I was 21. Have I been traveling to find myself or lose myself? This story is my attempt at making sense of the last 6 years. What I’ve learned, what it’s meant to me, and where I hope the story goes from here.

1. Life is just collecting stories.

I wish I’d learned this lesson sooner. I mean really learned it. I feel lucky that I’ve learned it now, sure, but it’d be so much cooler if I learned it sooner.

Nothing matters besides the story. It’s the only thing anyone cares about; for themselves and from others. People want good stories. Facilitate other people’s acquisition of good stories and you’ll have a surplus of friends, hospitality, influence, and access. Fail to add quality to a story and you’ll be edited out in the first draft.

Master stories and you’ve mastered life.

I have never been as good about writing my stories down as I’d like to be. The phases I’ve gone through where I document more, I’m happier, and life is more interesting. Often it takes writing it down for me to recognize and appreciate just how amazing my life has been and continues to be.

Find your story, tell it.

2. Bring the fucking guidebook.

When I first left the US I was leaving a dark place. A dark place for me I mean, America is awesome. I had been living the typical existential angst fueled binge drinking that appropriate at the time and it was wearing me down.

That first trip for me was pure, unadulterated escape. The sorts of literary inspirations I was drawing from instilled a disdain for the sort of travelers that clutch a Lonely Planet, traveling from one tourist sight to the next. That wasn’t “real travel.” That was my early instruction. Get off the beaten path, go where other people aren’t going, that’s where real travel, the kind my angst must require, would happen.

This was a big mistake.

As a result, I’ve missed out on a lot of experiences I would have otherwise likely enjoyed; simply because I’ve intentionally remained ignorant to them. This was a very stupid, naive, pretentious in a bad way ideal that took me far too long to abandon.

Information is power. Travel guidebooks are filled with useful information, they can bring more color and depth to a trip anywhere. I’ve wasted so much time “learning it on my own” when I could’ve just “read it” and avoided boring time in uninteresting places.

I’m fortunate in that I can more less entertain myself anywhere for any period of time without really getting bored. I’m comfortable being alone with my thoughts. I can sit in Starbucks for 8 hours (and have) with nothing but a cup of coffee and consider it an eventful, productive day.

But I can do just about anything else too and be happy. In the past year I’ve done more doing. I’ve let other people facilitate experiences for me and just gone along for the ride. This has brought me a lot of joy. Other people know things I don’t. Other people are often excited to share what they know with me either for free (friends) or for a modest fee (paid tour guides).

3. It’s the people, not the places.

When I think back on the really amazing, mind blowing, life changing experiences I’ve had while traveling, I think about people. I think about the long dinners rolling into late nights of bull shitting. I think about the close calls and bad ideas we shared. I think about the awkward situations we would later have to explain to an uninvolved third party. I can usually name the places these stories took place at, sure, but it’s always a less important detail in my mind, it’s just the setting. The people make the stories, being alone sucks.

4. Being alone is cool.

Travel affords you a luxury of quiet time. On any given day of my choosing I can sit in near silence from waking until sleep. No one bothers me. No one can access me. It’s liberating.

Most of the work that I do involves some level of thinking. As a solo entrepreneur that’s running an ever growing and changing business, my primary unoutsourceable role is to have the ideas that guide the company. I then have to communicate these ideas. So I do a lot of writing, a lot of talking, a lot of content creation. And when I’m not doing that, I’m thinking.

I’ve had a lot of my most brilliant and impactful ideas on planes and in airports, and in the backseats of Ubers, and at Starbucks. I love the situation of being around people, yet alone. Travel isn’t a necessity to do that, but it sure does provide a lot of spaces that make sense to do it at. So I find myself doing it a lot more when I’m “on the road” versus living somewhere for an extended period of time.

I hated being alone when I first started traveling. I’d get depressed and just stay in my room watching tv on my computer for days on end. I’d become anti-social and just drift through existence. Then after a few times of that, I got better at being alone. Now I’m pretty good at being alone.

5. Comfort is the enemy.

This is just a self awareness thing. No good stories come out of “I was comfortable and then…” No brilliant ideas. Nothing. Comfort is the enemy.

I actually don’t think I’m the first one to have this idea, believe it or not. But here’s my take on it.

Soft beds and comfortable bedding are not the enemy. Hot showers and well chosen hygiene products are not the enemy. Nice clothes and air conditioning are not the enemy. Netflix is not the enemy.

Comfort is the enemy.

Poverty is not a virtue. Living like you’re in poverty is not a virtue. Being in poverty is certainly not a virtue. You don’t need to only eat plain rice and water and wear scratchy burlap clothing. Stoicism is hugely over-rated (this took me too long to learn).

No matter where I am, however familiar or foreign the place may be, I can choose the comfort path or I can choose the path with less comfort.

The comfort path = going to the same few places over and over again because I know it’s good. I know they make the pork right, and I like it. That’s comfortable and it’s human nature to go that path. It takes the slightest bit of discipline and creativity to take a different path.

We’re all slaves to habit, that much we know. So, use consciousness and try to resist. Walk to new places. Eat new things. Schedule activities that force you out of your comfort zone. That’s where the freedom is.

When you’re outside of the familiar, in the unknown, you’re freed from expectation. No one, not even you, could reasonably expect you to know your way around a place you’ve never been. So you’re gifted with the freedom to explore.

6. More freedom, everywhere.

I’ve sometimes felt something like guilt when I assess my life. I’m not really exaggerating when I say that nearly everyone I’ve met in the past 6 years has had less freedom than I do. In some cases there’s a mild difference, they’re career requires physical presence so they have to live/work in one place and only get to travel on vacation. In other cases it’s been quite extreme and that’s jarred me.

Seeing someone in extreme poverty hurts, every time, and while maybe it makes me appreciate what I have more than I otherwise would, and take less for granted; more often it just makes me feel bad/sad.

I’ve cured this internal angst with a pretty simple policy: Look for ways to help other people have more freedom, and then do something about it.

Macro Level: Oppose any ideas that are anti-freedom. Support any ideas that are pro-freedom.

Micro Level: Help people out. Share stories and encouragement. Try to inspire people. Tell people how I did it, show them the way. Intervene in other people’s affairs as much as I consensually can, on behalf of freedom. Give people permission.

I don’t know where I’m off to next. I think I’m going to spend a little bit longer in Bangkok, writing some things down. That’s the end of this post.