Posted: 7/26/16 | July 26th, 2016
Today marks exactly ten years I’ve been on the road. On July 26, 2006, I said goodbye to my dad, got in my car, and started my year-long journey around the world by first taking a road trip across the United States before heading to Europe.
Eighteen months later (six months later than planned), I finally came home.
Back home and broke, I got a temp job filling in for someone on maternity leave. There, sitting down in the office, I knew office and corporate life was not for me.
My soul burned to be back on the road.
Travel was not done with me yet.
There was no going back.
So I did what anyone with no money or responsibility would do: I booked a flight and made plans to go away again.
Coming home felt stale to me. I yearned for the excitement of the road. That summer, I traveled to Europe, went back to Thailand where I taught English, and started putting time and effort into this website.
Now a decade has gone by.
The last ten years have been a long, winding road filled with one happy accident after another: from the people I met who got me excited about traveling, to the Thai classes I took that led to living in Bangkok, to the cubicle that got me to start this website, to becoming a travel writer.
It has been one exciting and unplanned adventure.
But ten years is a long time and, in the last year, I’ve begun to (finally) wind down my nomadic ways. After many false starts, I planted roots in Austin. I no longer plan multi-month trips on the road and I’m now focusing on the next chapter of my life: part-time traveler, hostel owner, cook, reader, and early riser (but still international man of mystery).
As one chapter comes to a close and another opens, I want to share my favorite stories from the last ten years on the road:
1. Making Friends on a Road Trip
At the start of my first trip, I was very much a quiet introvert. I didn’t know how to meet people, and I spent a lot of time driving around the country and sightseeing by myself. Traveling wasn’t the social amazingness I thought it would be. I was mostly alone and often bored.
That is, until I entered a hostel in Tucson.
There I met a Brit (also named Matt) in my dorm. We realized we were both going to the Grand Canyon, and so we ended up hiking it together.
Back at the hostel, we picked up another Brit named Jonathan, meet some cool people on trip to Sedona, and, in a hostel outside Albuquerque, an Austrian named Vera. Together we drove through New Mexico and Colorado before splitting up in Boulder.
I remember that road trip with great fondness — singing ’90s pop songs, sharing each other’s music collections, the night out where we convinced some college students I was Australian, the giant meals we cooked, and the explorations we had together.
It was this experience that finally helped me become comfortable saying hello to strangers and making friends.
2. Living on Ko Lipe
The month I spent living on the Thai island of Ko Lipe in 2006 is, out of all my travel memories, my favorite. If there’s a heaven for each of us, mine would look like Ko Lipe.
While it’s a big tourist destination now, back then it was a sleepy little place with one nice resort, a few bungalows, and limited electricity. Though you could see the island was going to be the next Phi Phi (one massively overdeveloped place), in that moment, it was still paradise.
I went there to meet a friend. On the boat ride over, I bonded with Pat (an older Irish guy) and Paul and Jane (a British couple). I somehow managed to lose my flip-flops even before we got to the island and decided to go barefoot during my stay. “It will only be a couple of days,” I said.
Those couple of days turned into a month.
Pat, Paul, Jane, my friend Olivia, and I met a few other people who never seemed to leave the island too, and we formed a tight-knit group. During the day, we would lounge on the beach, play backgammon, snorkel, or head to one of the other islands in the national park.
At night, we would dine on cheap seafood, drink beer, and make up beach games until the lights went out. We spent Christmas together, gave each other gifts, and bonded with the locals, who invited us into their homes and sparked my interest in learning the Thai language.
But, when my visa finally expired and I had to run to Malaysia to get a new one, I had to say goodbye. It was bittersweet, but all good things come to an end sometime. (I did end up running into all of them around Thailand in the months thereafter.)
This experience has remained with me forever and taught me that the best things on the road happen when you least expect them.
3. The Shit Story
While in Barcelona in 2013, I stayed in a hostel where a very drunk roommate decided to take a shit in our dorm room, and in the process of cleaning it up, locked himself out. When I woke up to let him in, I realized what happened (thanks to the shit on my hand), freaked out, yelled, and washed my hands like I’ve never washed them before.
Out of thousands of nights in a hostel, this was the grossest thing that has ever happened to me.
Afterward, I vowed to only stay in dorm rooms if I absolutely had no choice — and definitely not in a hostel with a reputation for partying.
4. Living in Amsterdam
In 2006, I visited Amsterdam for the first time. I ended up staying close to three months while playing poker (fun fact: I funded some of my original trip with poker winnings). During my stay, I met some wonderful, hospitable people, but none stick out like Greg.
Greg and I always seemed to be at the casino at the same time, and he kept inviting me to join him for private poker games he ran. When you have a lot of someone else’s money in front of you, you tend to have a suspicious eye when they invite you out later.
But the more I learned about him and how people talked to him, the more I realized he was just a good guy and that this was his way of welcoming me to town. Eventually I said yes, and his social group became my social group while I was there. We would eat, drink, and play poker.
They taught me Dutch, introduced me to Dutch food, and showed me the sights of Amsterdam.
Sadly, Greg was killed in a robbery a few months after I left Amsterdam, but my experiences with him taught me to be more open and welcoming of strangers and that people aren’t always ill-intentioned.
5. La Tomatina
Back in 2010, I went to La Tomatina (a tomato food-fight festival) in Spain.
Entering my hostel dorm, I met two Aussies, two Americans, and a guy from Malaysia. We were going to be my roommates for the next week, as the hostel required everyone to stay four nights during the festival.
In that time, we six just hit it off. All of us quickly bonded and spent the next week having the time of our lives, pelting tomatoes at each other, drinking sangria, nursing hangovers with gelato, and being led around by Quincy, our Malay friend with impeccable Spanish.
Deciding the fun shouldn’t end, we kept traveling together to Barcelona.
There, I remember one girl joining our crew and mentioning how it was so weird that such a geographically diverse group was so close. “How did you all meet each other?” “We just met last week!” we replied. “Really? I thought you guys had known each other for years!”
In the years since, though we don’t see each other often due to the geographic distance between us, we’ve stayed connected. When we do visit each other, it’s like we’re back in Spain and no time has passed at all.
When you click with people, you click with people. No matter where I go, I carry that time with me.
6. Learning to Scuba Dive in Fiji
On a whim, I decided to fly to Fiji while I was in New Zealand.
There, my friend pressured me into scuba diving. “You’ve always wanted to do it. It’s cheap to learn here. Stop being a wimp!”
He was right.
I had no excuse, so I signed up for a certification class. However, I was nervous. “What if I drown? Can you really breathe underwater?” During my first dive, I was hitting that oxygen tank like a stoner hits a bong! I went through the tank in under 30 minutes, when it should normally have lasted close to an hour.
And — though my dive partner kicked my regulator out of my mouth and I almost drowned — learning to scuba dive was one of the greatest experiences of my life. Seeing the ocean from below the surface was earth-shattering. I had never been surrounded by so much natural beauty and diversity. It was definitely one of those “wow!” moments in life.
After that experience, I decided I should be a little bit more adventurous. It’s led me to try rollercoasters more (I hate heights), helicopter rides (seriously, I hate heights), and canyon swings (fuck heights); attempt more adventure sports; and get outdoors more (nature is too wonderful not to).
(P.S. – Watch me scream like a baby in this video on my canyon swing.)
7. Safari in Africa
In 2012, I went on a safari through southern Africa, visiting South Africa, Namibia, Botswana, and Zambia. I slept under the stars, saw the Milky Way in such detail I thought the sky had been photoshopped, and spied elephants, lions, and countless other animals I had only dreamed of before then. Africa was raw and unbridled, and it rekindled a love of nature that I hadn’t felt in a long time.
Like scuba diving, it was just one of those “wow!” moments, when you realize how wonderful life and nature are. Being in Africa was an incredible adventure, and its beauty and the hospitality of its people have stuck with me ever since.
8. Living in Bangkok
In 2007, I moved to Bangkok for a month to learn Thai. I spent most of the first few weeks in my room, alone and playing Warcraft. I was staying in an area where more locals lived, as I wanted to get out of the touristy, backpacker area, but I also felt very disconnected from the city.
However, I had just decided to extend my travels and go to Europe the next year, so, low on funds, I needed more money! I decided to find a job, as I had heard teaching English paid a lot money. At the same time, a friend found out I was staying longer and introduced me to one of his friends in Bangkok, who introduced me to more friends.
Suddenly, I found myself living in an apartment with a circle of friends, and having a girlfriend and a life. It wasn’t easy at first, but the longer I stayed, the more I got out of the house and the more of a resident of Bangkok I became.
It was this experience that taught me I could make it anywhere — that I was a capable, independent person who could start a life from scratch.
Because if I could start a life in a place like Bangkok, I could start a life anywhere.
9. Finding Family in Ios
In 2009, I flew from Asia to Greece to meet a friend and explore the Greek islands. Upon landing in Ios, we found we had arrived too early in the tourist season and that the island was empty. There were only backpackers looking for work at the bars and restaurants. We got to know a small group of them quite well, and when my friend moved on, I decided to stay. I couldn’t leave my new family just yet.
Our days were spent on the beach, we hosted BBQs for dinner, and our nights were a blur. As my newfound family found jobs at the bars on the island, I wrote and blogged. It was so much fun that when I found out most were returning to Ios the following year, I did too.
Ios, to me, is that wild, carefree summer where you feel the world is your oyster and nothing can stop you and your friends from conquering it.
Though the years have passed, I still stay in touch with many of the people I met in 2009, running into them in NYC, Australia, Hong Kong, Scotland, and various other parts of the world.
This year’s trip to Patagonia was one of the defining moments in my travels because it taught me that I am not Superman and can’t juggle it all.
After trying to find a balance between work and travel, I finally cracked. I could not manage both well at once and started to get bad anxiety. It changed how I travel: no longer do I travel and work. If I try to do both at once, one will always suffer.
So now, if I’m in a new place, I’m in the new place! The computer is away. I’m there to explore, not work.
It was a hard lesson to learn, and it will be interesting to see how it plays out over longer trips, but with my eye twitch gone and the panic attacks subsiding, I’m in a much better place.
I’ve created more memories than I can remember in the last ten years. I often find myself remembering something that has found its way back from the dark recesses of my mind and saying, “Oh yeah, that did happen. Damn. How did I forget something like that?”
It often feels like my mind is running out of room.
I count myself lucky to have been able to experience all I have in the last ten years. Not everyone gets a chance to travel, especially for as long as I have. I’m often amazed at the trajectory my life has taken by simply saying “I quit” one day.
Was it always fated to be this way? Did the universe conspire to make this happen?
Or was it simply chance that brought me to where I am? Was this in me the whole time, and I just had to realize my potential?
As the poem goes, “two roads diverged in the woods” — and the one I took did make all the difference.
I don’t know what that other road was like and, frankly, I don’t care. I never wonder about it. I never think “what if?” The road I’m on is not one straight path upward but it’s a better road than I could ever imagine.
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
- SafetyWing (best for everyone)
- Insure My Trip (for those 70 and over)
- Medjet (for additional evacuation coverage)
Want to travel for free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodation. They are what keep me traveling so much for so little. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.
Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.