leon with yellow car
Credit: Courtesy of Leon Logothetis

After watching “The Motorcycle Diaries,” a romanticized tale of Che Guevara’s travels across South America and the kindness he encounters along the way, London-based broker Leon Logothetis decided to quit his job and travel the world.

“I realized, wow, there’s another way to live and that I didn’t have to sit behind a desk to follow someone else’s dream,” Logothetis told Travel + Leisure. “That was a tipping point for me, because I remember walking into work every day and spending 16 hours a day at work and thinking, ‘Why am I doing this to myself?'”

“On the outside, I had everything you could want, but on the inside, I had nothing,” he said.

He decided to challenged himself to travel across the United States on just $5 a day, leaving the rest to the kindness of strangers. That meant relying on people he'd met along the way to help him with everything from food to accommodations.

Since then, he's traveled to more than 90 countries and now works as a television host and author documenting his adventures. He has continued to receive gestures of kindness regardless of where he lands, from a woman in Vietnam who treated him to a noodle dinner to a rickshaw driver in Delhi who opened up his home as a place to sleep.

leon playing cricket
Credit: Courtesy of Leon Logothetis

While quitting your job to travel isn't easy, Logothetis has come to learn certain lessons that made it both easier and more enjoyable.

The first? Don't let moments of struggle keep you from pursuing your dream.

Logothetis realized this when he found himself back in the corporate world after his expedition across the U.S. due to a need for financial stability.

“Be gentle with yourself; many of us feel that vulnerability is a weakness, but it’s not…I was pushed through pain to quit my job in the first place, but when I realized I wasn’t making what I needed financially, I went back to what I was doing and I was unhappy,” he said.

leon with kids
Credit: Courtesy of Leon Logothetis

“There was this sense of misperceived stability in the corporate world, but I think life is a rollercoaster and it's not just an upwards angle towards success, so you’ve got to take a risk,” he added.

While Logothetis didn't work during his travels, he recommends sites like and taskrabbit, since you only need a computer and internet connection to make some money during your trips.

Other options include Roadie, which pays road trippers to transport items in their trunk, or WWOOF, where you can volunteer to work on organic farms around the world in exchange for free stays.

He also found other people can be interested in your travels too, if you know how to frame them, which can lead to a career of its own.

leon on motorbike
Credit: Courtesy of Leon Logothetis

“You need to create a story around your travels, and through creating a story, you’re then able to start a blog or a video diary to catch attention,” he said.

He did just this with his book and television series, "Amazing Adventures of a Nobody," which documents his trip around America, and with his recent Netflix series, "The Kindness Diaries," which follows his travels around the world on a yellow motorbike called Kindness One.

Logothetis found that the stories showcased in these works revolved around two themes: the desire to break free from an ordinary life and a search for kindness in the world.

However, trying to navigate through the U.S. and Europe on just $5 a day and traveling through some 20 countries on a yellow motorbike while relying on strangers is no easy feat, which is why Logothetis knew he had to start with familiar territory.

“Sometimes you have to start small…take a leap of faith, but take a calculated leap of faith when starting because you don’t want to overwhelm yourself and not follow through with what you’re doing,” he said.

For exploring, he recommends Sidexix for finding prime local spots. The app creates walking paths based on highly rated places from local bloggers.

Logothetis says locations in Southeast Asia, like Cambodia, Thailand, Laos, and Vietnam, are great options for budget travelers, who can travel cheaply by bus and sleep in youth hostels for as little as $1 to $3 a night.

leon bike
Credit: Courtesy of Leon Logothetis

Once you feel more comfortable on your journey, Logothetis says remote destinations can be incredibly rewarding.

"The kindness and connection to people is so beautiful, and that doesn't necessarily happen in larger cities," he said, recalling a visit to Halapur, a small village in India where hundreds of locals greeted him.

Finally, he has found that traveling can change you for the better.

“All the things that we think are virtues get tested when you travel…you learn things like patience and they become part of who you are,” he said. “Travel is the greatest teacher because you’ll be put into situations you wouldn’t on a daily basis.”