"I wanted to do something more with my life," he said. "There was a deep unhappiness. I wasn't excited every day, doing what I love, living a life filled with passion."
He hasn't stopped traveling since. Seven years later, at 32, Leonard makes a living through his travel blog, Tourist2Townie. He not only created the job of his dreams; he's making more money now than he was as a marketing director.
When he first moved to Argentina, Leonard took a job as a bartender to make some cash. The plan was to stay there a year, learn Spanish and share stories with family back home through his website.
After 12 months abroad, Leonard had hoped to find his next business idea. Little did he know he had already started building one.
Source: Gareth Leonard
His plans shifted as he booked his next destination, Colombia, where the possibility of turning travel into a full-time job became more of a reality.
"Once I got my writing and traffic, I started getting offers from advertisers and brands," Leonard said. The companies were looking for social media mentions, sponsored posts and product reviews.
Today, he works with brands like SoBe, Fruit of the Loom and Marriott, as well as tourism boards in places like Australia and Brazil. For written posts and banner advertisements, he's made anywhere from $100 to $400. Videos have a greater payoff, he said, delivering anywhere from $1,000 to $20,000 per project.
Source: Gareth Leonard
Leonard's goal for his website is to show his audience what it's like to become a "townie," whether it's living in a new community for six months or a year. That's why he spends enough time at every destination to experience what it's like to live as a local there.
He said he wants to stop and get to know the streets, the food and the people "in a local and substantial way that isn't forced."
He's blogged from Bolivia, Brazil, Australia and Thailand, and said one of the best ways to get to know a community is to find roommates who are already living in the area. Craigslist, Airbnb and Couchsurfing have become his go-to websites to search for housing in a new location.
While developing relationships with locals is one of the best parts of the job, Leonard said it can also be one of the hardest, especially when it's time to move on to the next destination.
"I have met so many incredible people along this journey, but when you're moving around all the time, there is always a need to say goodbye," he said. "That's tough when you develop these amazing and authentic relationships."
As he reveals in one of his blog posts, he didn't become a millionaire by 30 as he had planned when he was a sophomore in college. But he is still chasing his dreams, and loving every minute of it. He doesn't plan on switching back to a 9-to-5 job anytime soon.
Making income from his passion is "the most exciting thing in the world," he told CNBC.
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