1. Dean

Amsterdam, Netherlands — 2005

I met Dean in the basement of the Flying Pig, coming down from my first bad mushroom trip, feeling shaky and misplaced in the world. He was much older than me, and was the first person I’d ever met who had made a life out of traveling. He wasn’t vacationing, or backpacking through Europe, or on a Gap Year. He had no home base.

I trusted him immediately because his unmooring was so much more unstable than I felt — and he had chosen it. He had spent several months in Amsterdam, and was friends with the proprietor of the coffee shop that that year had grown an award-winning bud for the Cannabis Cup. As we smoked, his truths became mine. “It’s possible to live on dreams,” he said. “Don’t ever let anyone tell you otherwise.”

2. Annelise

Madrid, Spain — 2004

Annelise was from Argentina. She had a fiery, curly moptop that perched above a sun-worn face and laugh wrinkles around her clear green eyes. She dressed like she was Ginsberg’s muse. Every night she’d recite her terrible poetry in the hostel kitchen, and one evening, bolstered by wine, I told her I was a poet too. She dragged me out that very night to one of the poshest bars in Chueca, where hip Madrileños sipped expensive cocktails, seated in red velvet banquettes.

It was not an open mic night, but Annelise “knew” the proprietor and convinced him to let us perform. No one present had any reason to listen to an older Argentine croon “Porque, porque porque porque” or a young American slam about frustrations with the Iraq War and President Bush. I felt my cheeks flush hot and was almost crying after finishing, the tittering and cruelty of the posh Madrileños almost too much to bear. Annelise toasted me and told me that I had been “fucking fantastic,” and she meant it. Sometimes it doesn’t matter if the crowd laughs or even if they ignore you completely: Sometimes you just have to do something for the sake of doing it. Once you’ve faced a serious fear, it’s no longer a fear at all.

3. Geoffrey

Goa, India — 2012

It sounds cliché, but one look into Geoffrey’s eyes and anyone could sense he understood things differently than the rest of us. He didn’t have a hint of malice or anger or disappointment in his body — and how could he — tanned and strong and knowledgeable as he was after spending the past decade on the road. He taught me how to fix my dreads, where to find holy babas in Banyan trees, and, most concretely, how to sustain travel without any sort of trust fund or money from home.

Geoffrey didn’t live on dreams. He had more work experience and know-all than almost anyone I’ve ever met, having worked in hotels and cruise ships and farms and seed nurseries around the world. Last I heard he had just headed back to Australia for the millionth time.

4. Trivia

Oregon, USA — 2008

I was a WWOOF volunteer on Trivia’s goat farm in the middle of nowhere, southern Oregon for six weeks. She was admittedly a little wacky (a Scientologist conspiracy theorist who I’m sure was severely disappointed when the world didn’t end with the Mayan calendar), but she had more innate knowledge about how the land works and was more comfortable in her solitude than anyone I’ve ever met.

She never made apologies or excuses for her strangeness, and if you were in her presence, she expected you to believe too. “The thing about being a mystic,” she told me, “is that you remember. If you follow that train, which in mysticism is deep meditation, it takes you all the way back to past lives.”

5. Robbie

Koh Rong, Cambodia — 2014

Sometimes when shit hits the fan, the only thing to do is run.

There’s absolutely no shame in this, despite what pop culture may dictate. Sometimes it takes more strength to leave than it does to stay. Some people go to therapy; others go traveling. Such was the case with Robbie (and, full disclosure, myself on more than one occasion). Robbie had left an impossibly rough situation in his home country and found a new family, a new life, a new purpose on the fabled shores of Koh Rong — an island meant for misfits and miscreants with good hearts. It’s never too late to redefine yourself and start again.

6. Eder

Barcelona, Spain — 2004

Eder was one of those hippies — ubiquitous on Spanish streets—who wore hemp and had tangled dreads and played the djembe on street corners for a living. We sang Bob Marley as we passed cheap boxed-wine in the traditional Spanish botellón style. Once a tiny crowd of like-minded young people gathered, we moved down to the dock, looking out to the fabled lights of Ibiza in the distance, where surely electronic music pumped and swirled and fabulous people danced under neon lights.

We were all grunge and dirt and dreads and drums, though, and Eder laughed as I kept pulling out my journal to jot down random details I wanted to remember: the way the lights looked in the distance, the way the white djembe leather stood out against Eder’s dark hands, the way the soft hash felt as it crumbled between my fingertips.

It was one of the first times in my life I’d taken the time to notice these small, almost imperceptible niceties, and Eder is the reason it’s a habit I’ve kept up. At some point in the evening before I returned to my hostel he grabbed my journal and wrote: Keep making your small discoveries in this world. Nothing is real, but nothing is illusion. Remember your small truths are your beauty.

7. “Open”

Beijing, China — 2006

Open, as he called himself in English, looked like the geeky Asian brother of Harry Potter and moved with the grace of a gangly baby giraffe. He was smarter than even most other computer programmers, and had the gentle demeanor of someone who wants something but was too scared to reach out and grab it — but he wasn’t what you’d call a nerd.

He shattered every expectation you’d have upon meeting him. Spending just a few hours with Open and his group made me feel, for the first time, closer to complete strangers than to my friends back home. After a few days, my feelings were solidified: I had learned how to feel equally content with the ever-changing strangeness of new places and new things as I was with the tried and true experiences of home. Even if you can’t always understand another person’s language, there are underlying things connecting us all that defy conventional communication.

8. Marietta

Quito, Ecuador — 2010

Marietta was one of those women by whom you’re immediately intimidated—too hip, too beautiful, too cool, too calm. I met her at a communal breakfast on the roof of our hostel in Quito.

I had big plans that day to visit the Museo Nacional del Banco Central, which houses one of the most renowned collections of pre-Incan and Incan art in the world. Something about Marietta made me doubt this, and feel an inclination to wander in and out of the city’s hippest markets and bars instead. At the last minute, I decided to stick with my original plan. Much to my surprise, Marietta said she’d like to join. Between oohing and ahhing at the impossibly gold masks and ceremonial trinkets, Marietta stopped to read every placard on the display cases.

It’s never uncool to be smart. You’re never too hip to be a nerd.

9. Denis

Berlin, Germany — 2005

Denis was a transplanted Russian artist who worked in a loft in the Kreuzberg neighborhood of Berlin, the hipster, graffitied, bombed-out-warehouses-turned-nightclubs district. He was the first painter I’d met who made a living doing so. One evening we were out in Neukölln and I was fretting over whether or not to buy the fancy cocktail I really wanted, or to stick with a cheap beer that I didn’t. Denis wasn’t rich. He didn’t have a trust fund, and though he was making it as an artist it’s not like investors or collectors were banging down his studio door.

Regardless, while I sat still debating, Denis excused himself to the bathroom and returned with my coveted, far-too-pricey cocktail. “Don’t forget, my dear,” he told me. “In ten years you won’t remember the money. You’ll remember the experience.”