Ron Silver, the owner of the Bubby’s restaurants in Manhattan, was fighting with his business partner. His marriage was collapsing. So he decided to disappear.
He told people he was going to California, to visit his uncles. But on the morning of his departure, he decided on Mexico. In the cab he had a new idea: Havana.
In Cuba, he began to feel like himself again. He spent time with what he described as the internal posse he carries around in his head — Robert Frost, Plato, T. S. Eliot, Shakespeare — and he fell in with people who had nothing to do with his life back in New York.
“You’re like a stranger in the world at that point,” said Mr. Silver, who made his sudden trip to Cuba in 1996, when he was 34. “Nobody has any expectations. Nobody knows your history. Nobody knows what they want you to do.”
The theme of self-transformation through travel has been a staple of literature since before Homer. You can find it in Mark Twain’s “Roughing It,” Jack Kerouac’s “On the Road,” John Steinbeck’s “Travels With Charley” and on and on, all the way up through Cheryl Strayed’s “Wild.” For those who depart from the hard-worn path for points unknown, such a journey can be more than just a vacation.
“On the second day I was there,” Mr. Silver said, “I was outside of central Havana, sitting at this makeshift cafe sitting with eight or nine other kids, and we were all drinking beer, and there was live music playing, and the sun was out, and it was hot. That was a moment of, ‘All right, everything is just chilled out.’”
Mr. Silver, 53, hadn’t contacted anyone he knew for roughly three weeks when he called his wife to say he would be home soon. (They ended up divorced.)
Although Mr. Silver came to see that Havana was not the answer to his troubles, he believed he had gone through a genuine change during his time away. A confidence he had lost somewhere along the way returned to him in force.
“I was able to take a moment and say, ‘I’m being too affected by other people’s weaknesses,’” he said. “Going to Havana helped me to rethink and get clear about what kind of man I am and to come out swinging, hit it, when I came back home.
“When you’re in a day-to-day situation and dealing with people’s problems, it’s like having a bunch of rocks in your shoe. Whereas, if you’re on your own, you can take out the rocks. Or you don’t have to wear shoes at all.”
Sartori in Des Moines
After feeling isolated in Los Angeles, Ross Langley found himself building a treehouse just outside Des Moines.
“This was the happiest I’d been since I was a kid,” Mr. Langley said. “I would sit in Des Moines at night, looking over cornfields, sipping whiskey and listening to sounds I’d never heard before — like deer, which make very unpleasant sounds, but mostly loons in the lake. You’d hear these loons at night and you’re watching fireflies dance in the air, and you realize how unhappy life has been.”
Mr. Langley was born and raised in Sydney, Australia. Having trained as a classical actor, he went to Los Angeles with big ideas, only to discover he was unprepared for a life of near-constant auditions, few callbacks and superficial social interactions.
In May 2014, an old friend called him with the idea of a road trip. Mr. Langley was hesitant. He worried that if he were to leave, if only for a day, he might miss out on something big.
To support himself, he was working in construction. One lunch break, he told a co-worker about what he was going through, and the man said, “Is that how you’re going to live your life?”
That was that. Mr. Langley joined his friend for a two-week trip through the American West. Upon his return, he received a call from a woman who asked him if he would be her date at a wedding in St. Louis. He said yes, using the new trip as a springboard for another journey.
He stayed away from Los Angeles for close to two months, during which he built the treehouse, on property that belongs to his wedding date’s father (she accompanied him for part of the trip). He also drove through the Badlands and the Black Hills, through Native American reservations and to Yellowstone and Glacier National Parks. He spent time on an island off the coast of Washington that had once been a kind of family homestead, where he saw his grandparents’ initials carved into a sea wall.
He had dinner at campsites and morning coffee looking out onto lakes with people he had just met. No one cared about what roles he had gone out for.
“I think the whole experience, for me, was just about knowing who I was,” said Mr. Langley, 26, who now works as a web designer in New York. “There’s this feeling of being in a place like Glacier National Park and being dwarfed by nature that’s equally terrifying and freeing. I realized the experience I was having in Los Angeles, even in an ideal world where I was successful as an actor, would never truly satisfy me.”
Going It Alone
After college, Jonathan Kesselman returned to his hometown, Los Angeles, in 1999 with the notion that he would work for a while before attending the graduate film program at the University of Southern California.
But he proved good enough at his job, working with medical databases, to earn six figures. When he was rejected by U.S.C., he felt the golden handcuffs tightening.
He bought a one-way ticket to Australia. For three months, he traveled extensively with no clear idea when he might return. He drank, smoked marijuana, took Ecstasy. He danced on tables. He sky-dived. He slept around.
“I’ll tell you what I discovered when you travel alone,” said Mr. Kesselman, now 41. “You’re only alone when you want to be alone. You make friends so easily, and when you get tired of people, you hop on a train for somewhere else.”
After his return, he was accepted by the U.S.C. program and went on to direct a cult comedy, “The Hebrew Hammer,” and more recently, “Jimmy Vestvood: Amerikan Hero.”
“The person I was when I was in the states was not the person I was when I traveled abroad,” Mr. Kesselman said. “I had all the baggage from my formative years. I was tightly wound and intense. I loved traveling by myself because it made me feel like a man. I thought if I could do that, I could do anything in the world.”
Jeff Wardell, 51, spent nearly two decades as a financial adviser. By 2008, he was working at Lehman Brothers, managing the fortunes of well-heeled clients.
Two days after the firm filed for bankruptcy protection, he left for another investment bank. There, he did his best to rescue people’s assets from the financial crash. Some days he felt he might have a heart attack.
He stayed in the business just long enough to tie up the loose ends. He had to get away from San Francisco, away from America, away from the news. And he had to be on a motorcycle.
He found one, a BMW R1150GS, in Milan. He had no set path, just a return date three months from the day he started. Some days he would ride 50 miles. Others, 300. He gunned his way north, to Scandinavia.
“My day was non-tech-driven,” Mr. Wardell said. “My concern was, ‘Is the motorcycle running correctly?’ You don’t want to be in the middle of nowhere and have something go wrong. You’re whittling around these corners, and that’s where the attention and focus is. You can’t concentrate on anything else, because you’re trying to stay alive.”
He made a point of visiting repurposed buildings, like old grain mills and factories, that had found new lives. He had been interested in design his entire life, and had even considered architecture school at one point. By the trip’s end, he knew a life in finance was not for him.
Mr. Wardell now runs an art consultancy and design firm with his girlfriend, Claudia Sagan. One of his projects is the search for what he describes as an “adaptive reuse structure,” in Portland, Ore., inside of which he can carve out a hotel. Mr. Wardell hopes the business will be ready to open in 2018.
Aside from helping him to realize that he was on the wrong career path, the three-month trip did something else for Mr. Wardell. It “reaffirmed my belief in the human spirit,” he said.
“I bought this massive chain lock with an alarm, thinking, ‘I’m going to have to use this or my bike is going to disappear.’ Then I started heading into these towns and putting this lock on, and people were just laughing at me, asking: ‘Why are you doing that? Your bike is not going to get stolen here.’”