When I was fourteen in my first rehab in Minnesota with nothing other than a piece of paper and my imagination, I began dreaming of freedom. By the time I reached my second rehab in Louisiana when I was fifteen, I had immaculate plans to run away and be liberated once and for all. By the time I was sixteen in a behavioural modification center, or rather, a “therapeutic boarding school” as it was once called in Georgia, I had sketches of VW buses all over my sketch pad and a collection of books by Jack Kerouac. I was determined to travel like he had, and to live a life full of adventure like the ones he wrote about in his stories. By the time I ended up in my last institution in Utah, a wilderness program meant to prepare me for survival in the woods, nature became a huge inspiration and metaphor of harmonious living for me. It was time to escape. Right before I turned seventeen, I ran away from it all and traveled for the next fifteen years. I learned many travel hacks, from how to find places to sleep, road trip hacks, how to meet new people, travel packing hacks, how to eat like a king with no money, how to earn money from nothing, and all sorts of travel tips and tricks I’m about to share with you. Consider this travel hacking 101 for the wandering soul. I’ll start with how I navigated my way through South America with no money, agenda, or clue of what to do…

Traveling is a Real Job

I had just broken the Guinness World Record for longest road trip and was determined to maintain the spotlight and continue my trek as a professional traveler. It’s all I ever wanted: to be known for travel. And you may wonder what a professional traveler means. Well, to me it means making money off my travels and doing it as an occupation. 

I interviewed Emilio Scotto once on my podcast (which no longer exists). Emilio is the greatest traveler of our time. He’s an Argentinian traveler that traveled over a half million miles on his motorcycle from 1985 to 1995. He rode his bike through every country except five (which remains a secret as to which countries he never made it to), and told me in the interview:

[to paraphrase in his accent] “People always told me ‘traveler’ wasn’t a real occupation. I asked why? In school all we do is study travelers and explorers. How it can’t be a real job?”

The man was right. As long as I could make a living traveling, I was a professional traveler, and you can be too. Here’s how I did it…

Travel Writing Paid for Most of My Expenses

The biggest of all travel hacks is how to make money on the road, and the way I did it was writing about my adventures and reporting my journeys to the world. But I always made sure there was a market for the story before I left. In fact, I would rarely even leave for a trip before I had pre-sold at least one article about the non-existent adventure to come. So, after I fucked this chick from Montevideo in the bathroom of a hostel in Madrid, Spain and temporarily fell in love with her, I was determined to find some kind of article idea that would pay for my trip to South America. I pitched an article idea about circumnavigating the continent and got it picked up in the press. I then had leverage. Travel + Leisure was writing about me, Time Magazine was writing about me, and so I was ready to pitch and sell my first article. That’s how my arrival in Uruguay came about. 

The key to traveling with little in your savings account (never zero; a little is required) is to make money before you even leave.

That’s a big thing people are always fucking up. They write the article first and then try to sell it, but contrary to belief, the money is best made before you even leave. You sell the idea for the article first, and then you write it, and then you plan the trip. After all, you don’t want to plan a trip to Kenya for a month if you have no way to pay for it. Some people capitalize on social media but I won’t be talking about that since I find social media one of the worst things to ever happen to humanity. For that reason I never made it a part of my strategy. I always depended on my ability to place magazine articles. 

So what I would do is I would send out an article pitch to hundreds of magazine editors with ideas for articles that I believed would make an interesting read. Like the time I had sex behind the dumpster of a diner in the middle of the desert in Arizona and discovered all the many secretive hideouts to fuck while on a long-term road trip. I submitted that article to ELLE. Or I’d pitch a story about how to negotiate with tour guides in Peru or meet love interests in hostels. I sold those stories to Bravo and Playboy. I wouldn’t stop until someone wrote me back and said:

I like this.

Then I would negotiate a fee…

Then, and only then, would I book my flight. That’s how I traveled and made money along the way while simultaneously building my career as a travel writer. I should say that if you want to make a lot of money, or even more money than just enough, this plan isn’t for you. But if you want to travel for free and have enough money to get to your next destination, travel writing makes a ton of sense. 

There are far more lucrative travel trades to do on the road, like client-based businesses that you can do from your laptop. I did public relations for many years and digital marketing towards the latter years of my life as a wanderer. Here are all the travel trades I’ve used to fund my life on the road…

  • Travel Writing (this is the most fun but the least money)
  • Being a Publicist (best trade since you only need one client that pays a lot… this pays more than digital marketing and is easier to manage)
  • Digital Marketing (this gets a bit too complicated sometimes to coordinate from random hostel living areas)
  • Social Media Management (this job just sucks. I hate and I’m not good at it, but I’ve done it for some months at a time so I could travel)

Don’t Plan Too Much; Take the Leap

One of the biggest mistakes people make is planning too much. Plan too much and you’ll never take the leap, and taking the leap is truly the only necessary ingredient to traveling. If you never leave, you won’t see the world. If you’re trying to earn money as a travel writer and you pitch an idea to editors and someone says yes, it’s now your job to buy the flight immediately. That’s one of the most important travel hacks of all: buy the fucking ticket. If you look for cheap flights here and there and then look for cheaper flights elsewhere, you’ll never leave. You’ll soon exhaust your search ability and say to yourself:

I’ll come back to this tomorrow. 

Only problem is, you won’t. You won’t come back to it tomorrow. You’ll build stories in your head that’ll convince you why maybe it’s not such a great idea to head to Santiago next month. So the real trick of it is to not think about anything for too long. Just book the flight and the rest will fall into place.

Don’t Look for Cheap Flights

It’s a waste of time. The amount of money you will save from one of those travel sites that preaches cheap flight travel hacks is such bullshit. You’ll waste endless hours to save $60. Is missing out on a potentially life-altering adventure worth $60? Fuck no it isn’t. Anything that gets in the way of you taking out your wallet and purchasing that flight should be avoided at all costs.

Don’t Book Round Trip Tickets

Never book round trip flights. The whole point of an adventure is to allow yourself to end up in random places with odd people, and if you’ve got an agenda to fly out from Sao Paulo next week on Thursday, you won’t be able to take off with the Argentinian cowboy you met last night at a salsa club in Buenos Aires. The best way to not book a round trip flight and still get across the border is to buy a one-way ticket and then a refundable bus ticket or a refundable one-way flight out of the country that you can get refunded as soon as you get past customs. The reason for this is many countries require you to show them proof of exit (they want to make sure you don’t plan on living there). So, just buy a one-way ticket, and another one-way ticket (make sure it’s refundable) and then refund it when you land. Now you can go wherever the hell you want and whenever you get bored or scared or sad, just hop in a cab and go to the nearest airport.

Meeting People While Traveling

It’s all about positioning. You’ll want to position yourself correctly. It doesn’t matter how old you are, you want to be at a hostel. A hostel is a place where other travelers go to meet other travelers. That’s you, right? So that’s where you want to be. Meeting people becomes very difficult if you’re cooped up in a hotel room where nobody needs anything from you. But when you’re surrounded with explorers, you’re bound to meet tons of people and probably get laid at some point. And getting laid while traveling is very important. You want those fuck memories littered throughout the world. But anyway, back to my point about meeting people, if you’re a resource for someone else to have a better time than you’ll be called upon.

Like the time this Belgian chick hit me up and asked me if I wanted to go paragliding in Medellin. I never woulda gone without her, but with her I was a team. I could do more with her than I ever could on my own. Not only that, but we had to hitchhike through Pablo Escobar terrority (what used to be Escobar territory) on our way back and going through the slums in Medellin with someone who knows how to navigate through the war zone (what used to be a war zone) is an incredible experience that you can’t watch in a movie.

Travel Packing Hacks

As far as packing, I can assure you one thing: you won’t use more than one sweatshirt, one pair of sweatpants, and you’ll be in your flip flops for a majority of your time traveling. So if you want one of the best travel packing hacks I can think of, or travel hacks in general, it’s minimalism. Take only one of everything, and if you find yourself needing more, buy it on the road.

When you’re packing your backpack, you want to be able to get to your toiletries first, so they go in last. You want everything organized, so buy those packing cubes. You throw your pants in one cube, your tee shirts in another, your long-sleeve shirts in another, and your socks and underwear in another. That’s it.

Oh and make sure you have a microfiber towel, a bandana (for dust and covering your nose and mouth on bus rides), some duct tape (for fixing just about anything), ear plugs (screaming babies), and non-expensive everything else. Don’t ever have the best of anything when you’re traveling. Be very mindful your bag will be thrown under buses all the time, so if you have anything valuable, you’ll want a second backpack for those.

Ever see travelers carrying one backpack on their back and another on their chest? That’s why. You throw the big sack under the bus and take the little one on board with you.

Embrace Your Nerves and Take Risks

If you’re feeling nervous, that’s good. Don’t shy away when you feel uncomfortable. If you’re not sure whether or not that girl from Lima wants to have breakfast with you, if you don’t ask, you won’t know. And when you’re traveling, you have better odds than you ever had at home. So when you’re on the road, take risks like no other time of your life. Everybody on the road is looking for help. Everyone wants to meet people. Everybody needs a tale to take back home. Travel flings are in the air, and international friendships will keep you educated for years down the road, so just don’t shy away from anything. You hear me? Nothing. Do it all. 

The best thing that can possibly happen to you is you get rejected and are able to carry on to the next adventure without feeling shitty for more than a few hours. A few hours is fine, but just cause that dude said he’d visit you in LA when he was done parading around Ecuador doesn’t mean it’ll actually happen, no matter how sincere the promise was at the time. It just won’t. Any “real love” you find on the road will dissipate. It doesn’t exist. Travel flings are disguised as romance so it’s likely you’ll think you’re going to have to move to another continent, but it all fades away. And there’s nothing wrong with that. Just enjoy it while it’s there and eventually, and I promise you this, you’ll be happy it happened even if it was an emotional roller coaster that left you crying one Saturday afternoon.

After all, it’s quite easy to be in love when you’re in a magical place without any of the real challenges you generally face at home. When you see people at their best (and you are always at your best on the road), everyone seems amazing. But wait till you move in with each other and have to decide who’s going grocery shopping… So don’t do it.

If you’re feeling like maybe this type of adventure isn’t the adventure for you, that maybe there’s another way to travel… You’re wrong. This is the skeletal structure of all great adventures: high emotions and lots of memories. 

The moral of the story is, there’re many travel hacks that people will preach, but there’s only two travel hacks that truly matter: the desire to do it and the ability to impulsively buy a one-way flight to Vietnam. So don’t think about anything, just place yourself in a bizarre situation and everything will work out. Whether it’s a terrible experience or a wonderful experience, you’ll come back a new person.

Now here’s a story about the time I broke the Guinness world record for longest road trip.

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