Estimated reading time: 10 minutes

Self-Improvement For Vagabonds

If you haven’t read Vagabond Secret 3: HOW TO MAKE THE MOST OF YOUR TIME WHILE TRAVELING, do that shit now.

It all started one day when I was living in Los Angeles feeling shitty about life and not sure what to do. My career as a writer was beginning to fade in the back of my subconscious horizon. I had lost all my enthusiasm and everything that I was able to get off the ground came tumbling down as fast as it flew up. I had a book halfway done but no platform to promote it on. I was beginning to feel helpless, like all those dreams I had in my early twenties were actually not possible. I was desperate for self-improvement.

Still I found solace knowing any adventure in the world I could muster up in my imagination was achievable. Those moments of realization always jazz me up. So, I made a decision in that one second that completely altered my life and accidentally built my career as a vagabond writer. What is a vagabond writer? Well, a writer that travels; a travel writer. Any full-time vagabond needs a way to cash in on all the travel they do. Whether it be writing, photography, art, or business, it all starts with the question: What expedition can I take that’ll capture the attention of the world and put me on the map? That’s the magical anecdote to make any dramatic shift in your life.

For me, I asked myself on that day in Los Angeles, “what if I took the greatest road trip in the world?” That would be awesome, I responded to myself. What would that look like? What would I have to accomplish to make that a reality? Then started my manic Googling research phase, where I’m so hyped up about an idea that Google could literally bring back any result and my mind wouldn’t have changed. But nonetheless, I searched the Internet for wild road trips and stumbled upon four Indian dudes with the then-held Guinness World Record for Longest Journey by Car in a Single Country. They had done it in 19,000 miles. It was the perfect challenge; I could totally beat them. A raging burst of energy filled me with ideas.

Building Self-Esteem Through Adventure

I clicked the “apply” button on the Guinness World Records website and filled out an application. I was notified that they usually try to respond to everyone within twelve to fifteen weeks. Wait four fucking months to hear back? But I want to leave tomorrow! Well, good news popped up in the form of a bribe… An expedited response was available for a fee of eight-hundred bucks or so (maybe it was a bit less, I can’t remember the exact price). Anyway, if I paid the money, I’d hear back within a few days. Well, that seemed a whole lot better than three or four months, so they got me; I did it. I didn’t even really think twice about it and it’s not like I had millions of dollars in my checking account. I had a nest egg of fifteen grand or so that I’d saved up.

Then came the acceptance email from Guinness. I barely read it. Without thinking, I took a screenshot of the email and posted it on my social media… the crowd went wild. Fuck, now I have to do it, I thought. That’s when I knew I was onto something big, but along with the acceptance email came some more fees. They wanted me to send them a full layout of how I intended to break the record and I couldn’t start until they approved my game plan. The approval process would take another four months… unless—you guessed it—I paid another eight-hundred bucks (or thereabouts) to expedite the response. I pulled out my credit card right away. This was the right move, and I knew that right moves require an investment.

I started drafting my first press release that I was going to send out to all the major media outlets. Everybody will know about this, I thought to myself. I built a website:; it may or may not still exist when you find this book. Some startup media company contacted me about a potential sponsorship, then another company sent me clothes. I got a call from a reality TV show at one point. Meanwhile, I hadn’t even left yet (or gotten the final approval…) and did I mention I hadn’t even brought it up to my then-girlfriend? I just assumed she’d want to come along on a grueling five-month road trip.

Bettering Yourself Through Challenge

Upon approval, Guinness sent me a rulebook full of guidelines that had to be upheld, one of which was that we could not make a round trip, backtrack or leave the country borders. Basically, we would have to zig-zag all over the place to rack up the miles we needed to break the record. I stayed up all night putting together a map of how my then-girlfriend and I would travel the country to get to over 19,000 miles. Some other rules they required were: to keep a video log every day (ten minutes per twenty-four hours) time-stamped with a clock in the background, maintaining a witness logbook of people vouching for our journey, send in photographic evidence of national landmarks, any press clippings that were written about us, and oh—get this…

The hardest bit of evidence was to submit a KML file of our route when we were done. If you don’t know what a KML file is, that’s because nobody does. I asked all over and couldn’t find an answer. I asked Guinness to help me a thousand times and their only response was: everybody else was able to figure it out. I had to Google that shit for months even while I was on the road before I figured out exactly what a KML file was.

After what seemed like a century-uphill battle to find out what the fuck that damn KML file was, from calling truck-driving companies and GPS companies and asking everybody on the customer support team who might know what a KML file was, I eventually cracked the code. Not that you care, but here’s what a KML file is: It’s a file used in Google Earth that records your entire journey from start to finish with all required metrics. The metrics are called “tracks, waypoints, and routes” in the Google Earth world. The file is initially created in your GPS, then opened in GPS software and exported as a GPX file then imported to Google Earth, at which point you can “save as” a KML file. Sound confusing? Yeah… But at the end of the day, it’s pretty fucking cool and now I’m going to tell you how you can use it for your road trips too. As a matter of fact, not just road trips, any bike trip, motorcycle trip, boat journey, skateboarding route, shit—any journey of any kind that you want to record.

If you use a GPS system and download the software that corresponds to whichever GPS you’re using, you can set it up to track your entire journey—from tracking your speed at any given moment on your trip, the altitude you were at, your exact stopping points and what time of day it was and of course: all the precise roads that were taken (even parking lots you pulled into!) All the information will auto-populate onto your GPS and you can then plug it into your computer and open it in your GPS software to import to Google Earth. It’s a bit complicated, but if you ever want to take a wild trip of any kind, be it for self-improvement, bettering yourself by tackling an insane obstacle, or if you’re just bored, and never forget it… Take that GPS data and print your route with dates and times and speeds and frame it for your wall and stare at that shit constantly.

Summary of the immense shit we needed

To sum up the other requirements needed to obtain our record, we also had to keep a mileage log that had to be logged every time we stopped and started the car, including bathroom breaks. Yeah, you need to pee? Write that shit down and make sure you keep track of where you were when you stopped, what time it was, what the odometer read, and what time it was when you got back on the road. No resting for longer than two weeks in any given location, no replacing vehicles, and there can’t be any gaps in your GPS tracking, so we always had to leave from exactly where we stopped.

That’s what we did for 122 days and 36,123 miles. It felt like a full-time job at times and less than a trip, but it was also the greatest investment I’ve ever made. Now I have enough content to make my travel-writing career last a lifetime, even though I don’t contribute to magazines anymore. I simply lost interest. The media world drives me nuts. But that’s all beside the point. The point is: not only did the story go viral but I was asked to contribute articles all over. I wrote about fifty articles throughout the course of two years after that trip for many publications, including Playboy, Elle, USA Today, Bravo, and so on. I was presented with “opportunities” to go on game shows, went on national TV, and was interviewed by journalists all over the world. You know that half-written book I was telling you about at the beginning of this chapter? I finally finished it on the road and made sure to bring it up in every interview I did. That sold some copies, not many, but some.

So that’s how you do it

That’s the type of journey you need to shoot for to build self-esteem: a journey that nobody can ignore. It’ll put you on the map (no pun intended) and give you a reason to be proud as fuck. If you do that, you’ll be able to make travel a full-time job, or a part-time job at the very least (if you want), simply by writing about it. You’ll simultaneously build your professional resume and make your press portfolio strong enough to garner the attention of brands, magazines, and media companies. And it doesn’t have to garner the attention of the entire world, but it’s best if you initially strive for an expedition or adventure of that nature. But before we move on from the Guinness World Record road trip, I have to tell you about the shittiest and most miraculous day of the trip…

Remember I said the photographic evidence was a very important part of the trip since it was required for us to obtain the record? Well, here’s what happened…

We nearly lost it all

One day at Yellowstone National Park, my then-girlfriend dropped our Samsung with all our photos into a boiling and poisonous geyser from twenty feet above ground. We had driven about twenty-thousand miles at that point and all our photos were now at the bottom of a steaming geyser. The trip was going to be disqualified. Talk about an uncomfortable relationship moment… It was the saddest day on Earth, not only because we lost the record, but because I knew it was a mistake that she might regret for the rest of her life, and I could see how incredibly horrible she felt about it. People make mistakes, what are you going to do?

I had one last idea: risk my life. Fuck it, I thought. I ignored all the “DO NOT ENTER! BOILING ACID WATER! VERY DANGEROUS!” or whatever signs they had all over and walked straight into that damn geyser as the crowd awed and grabbed that damn phone and walked out. Luckily, the water wasn’t that hot, and the acid didn’t rot my legs away. To our surprise, the phone STILL WORKED! All our photos were still there! A miracle. Samsung should make a damn commercial out of that day. I will say this: from that day on, I flinched every time my ex touched the phone…



To sum it all up… we got the record and my life has never been the same since. It’s simply the greatest conversation starter in the world. But you don’t need to do what I did. However, you do need to push yourself to the limits. Just ask yourself: What vagabond adventure—if completed—would capture the attention of the entire world? This isn’t an easy process. I made it sound simple telling you this story, but I left out the intense writing exercises I did prior to coming up with that idea. A good way to brainstorm your vagabond adventure is to write down your travel bucket list for five minutes and don’t stop until you start writing down ridiculous shit… that’s when you know you’re about to strike gold: when you start writing travel to every country in five minutes. Don’t think about realism, just write down fantasies then review them to see if any of them actually can get done. Circle the ideas that excite you the most. It’s time to do something big.

The secret to self-improvement is to do the impossible.

Pin It on Pinterest