Pro Travelers Share Life Lessons from the Road

“In the end, I had to shut out the noise and make my own decisions.”

Illlustration by Chandler O'Leary

Famed travel writer Pico Iyer once said, “We travel, initially, to lose ourselves; and we travel, next, to find ourselves.” No matter who you are or where you go, travel is likely to change you. (Whether that change is permanent or something that wears off can be a subject of debate.) But for those who make seeing the world a major priority, rather than an occasional escape, getting some new perspective becomes a matter of course.


GOOD asked four seasoned wanderers to share their most memorable travel moments—the ones that truly transformed them. Read below find out what they’ve learned while trekking through Central American jungles or on rainy Italian nights, from amusing mishaps that revealed previously untapped strengths to unbelievably dramatic events that actually did change everything.

Aleah Taboclaon, Blogger, The Solitary Wanderer

Lesson 1: Strangers really can be kind.

Aleah Taboclaon in Bolivia. Photo courtesy of Taboclaon.

From the age of three, Aleah was used to life on the road. She bussed around the Philippines with her mother, who traveled to various cities for work. By 11, she was traveling alone several times a year, making 12-hour bus trips to and from her residential high school. While studying in Manila as a teenager, she found herself locked out of her friend’s apartment, where she was staying until her dormitory re-opened for the new semester. Looking back, the seemingly minor crisis made a huge impression.

“I couldn’t get in. I was 15, didn’t have money, didn’t know anyone else in Manila, and it was an hour before New Year’s Day. I couldn’t call my parents as cell phones didn’t exist at that time. The cab driver was just driving out of the apartment complex when he noticed me. He asked me what was wrong and when I told him, he told me to go back to the cab. He drove me (for free) to a small hotel, paid for my stay there, and told the receptionist to keep an eye on me as I was by myself. Before he left, he also gave me some food and a bottle of water, and told me not to go out from midnight onwards.

[quote position="full" is_quote="true"]That act of kindness really stayed with me and strengthened my faith in humanity.[/quote]

“I sat alone in my small room munching on the biscuits to celebrate New Year’s Day, looking out the window at the noisy revelry outside. Instead of being lonely and miserable, all I could feel then was gratitude for the unnamed cab driver who went out of his way to help a young girl lost in the city. That act of kindness really stayed with me and strengthened my faith in humanity.”

Will Hatton, Blogger, The Broke Backpacker

Lesson 2: Leaps of faith aren’t optional.

Will Hatton on the road. Photo courtesy of Hatton.

Will is an adventurous traveler who is currently several months into a two-year trip from the United Kingdom to Papua New Guinea, and was last spotted hitchhiking through Iran. Growing up, Will’s childhood dream was to join the Marines; he officially enlisted when he turned 19. He wanted to squeeze in one last adventure and set off for a 10-week backpacking trip in Central America. While trekking across the jungle, his life took an unexpected turn.

“Three days in, I got terribly sick. Infection raced up my leg and into my blood, sending me mad with pain and hallucinations as I struggled through the jungle. Finally, after an intense day of wandering along waterlogged paths, I found a ranger station. One very bumpy evacuation later, I arrived in intensive care. The first doctor to see me told me that they would probably need to amputate my leg. Fear consumed me. My travel plans, my adventure, possibly even my ability to walk—all were about to be taken away from me.

[quote position="full" is_quote="true"]Determined to not be beaten by this series of events, I gave myself a metaphorical and literal slap across the face.[/quote]

“Two weeks later I was back in the U.K., on crutches and slowly recovering. My leg had not been amputated, but it was permanently damaged and my dream of joining the Marines was now impossible. I was crushed. Unsure of what to do and unhappy with my available options, I [was] determined to make a change, to not be beaten by this series of events. I gave myself a metaphorical and literal slap across the face and got a [crappy] job. I worked 60-hour weeks unloading lorries (trucks) until I scraped together $5,000 and bought a one-way flight to India. I started a new adventure, and I have been traveling ever since.

“Before I booked that one-way ticket, before I took a leap of faith, I was incredibly lost. I was unsure who I was or what I wanted to do. On the road, everything was different. I found new purpose and new passions.”

Chandler O’ Leary, Illustrator, Drawn the Road Again

Lesson 3: Be in the moment. No, really.

A self-portrait of Chandler O'Leary.

Chandler grew up in a military family in the U.S. and moved to a new home every few years. She inherited her father’s love of maps and road trips, and when she grew up to be an artist, she combined the two. Chandler is able to intimately study the land and cityscapes she encounters and to commit them to memory in her sketchbooks through the slow, patient act of drawing. However, she can sometimes be overwhelmed by her powerful urge to record what she sees.

“I spent a day and night in Verona and fell in love with the city. I remember the weather being awful, and trying to paint with watercolors in the pouring rain. I was determined to see and draw everything that day, but Verona is a big place, and no matter how efficient one is, drawing is a slow medium. I remember staying up all night, darting through the streets after dark, and trying to sketch and paint by the light of street lamps.

[quote position="full" is_quote="true"]Now I try to be in the moment, and treat every visit to a new place as the first of many to come.[/quote]

“At around 3 a.m. I finally stopped trying to draw; I found a pay phone and called a friend back in the States. I sort of lost it over the phone; I was so upset that I would lose this race with time and fatigue, and I didn't know when I'd ever get back to Verona again. My friend talked me down and reminded me that I'd seen so much already, and that just making an effort to get what I saw down on paper was a good antidote against taking my experiences for granted.

“I still have this phobia of missing out on things, this need to make the most of my time wherever I am, because I know that I may never get the chance to return. But I also have gotten better about just being in the moment, and treating every visit to a new place as just the first of many to come.”

Chris Guillebeau, Author, The Art of Non-Conformity and Born For This

Lesson 4: Ignore what you ‘should’ do.

Chris Guillebeau in Sydney, Australia. Photo courtesy of Guillebeau.

From his childhood years in the Philippines to volunteering for a medical charity in West Africa, Chris is a life-long travel junkie. He took it to an extreme when he resolved to visit every country in the world, a feat that he achieved by his 35th birthday. His experiences helped him develop his philosophy of non-conformity, based on questioning conventional wisdom and thinking for yourself. Now, through his books and talks, he helps others do the same. But first he had to learn to live his own life the way he wanted to, rather than how he thought he ‘should.’

“For the first few years of ‘going everywhere,’ I traveled with a camera and dutifully tried to capture good shots. Every traveler needs a camera, right? But I was a pretty bad photographer, and what’s more, I didn’t enjoy taking pictures, besides capturing quick snaps on my phone. Writing was my medium.

[quote position="full" is_quote="true"]In the end, I had to shut out the noise and make my own decisions.[/quote]

“I noticed in my early days of being a travel blogger that lots of people had opinions about how I was pursuing [my] quest. Some said I was ‘doing it wrong’ or that I had to meet various requirements to somehow justify the whole project. In the end I had to shut out the noise, make my own decisions, and learn to travel the way I wanted to. The lesson isn’t ‘Leave your camera behind,’ because obviously many people love photography and are very skilled at it, unlike me. The lesson is—figure out how you like to travel, and then do more of that.”

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