In 2004, while soaking up the sun in Ko Samui, Thailand, I made a bold declaration to my friend Scott: "I’m going to quit my job when we get back." He didn’t believe me, but I was serious. I was inspired by the freedom of the travelers I’d met in Chiang Mai, and I wanted to be part of their world, a world without 401(k)s, bosses, or scheduled vacations.
While still in Thailand, I bought a Lonely Planet guide to Southeast Asia, even though I had no concrete plans. But buying that guide made my dream of traveling feel more tangible. It was my commitment to this new path. The guide was like a treasure map, filled with clues on how to navigate this new world. How could I stretch my money for a year? How could I communicate without knowing the language? How could I avoid scams? The answers, I believed, were in that book.
I devoured the guide on my flight back to Boston, planning routes and highlighting destinations. But once I was home, reality hit. I had no idea how to make this dream a reality. There were so many questions: Would I finish my MBA? How much money would I need? Where would I go? How do I get a round-the-world ticket? Are hostels safe?
Back then, in the days before travel blogs and iPhone apps, planning a trip was daunting. Information was scarce and often outdated. But the biggest challenge was telling people about my plans. My parents, naturally worried, tried to talk me out of it. But I was determined.
I remember the conversation with my boss. He was a kind man who had taken me under his wing. I told him about my plans, about how I couldn’t stop thinking about traveling since my trip to Costa Rica, about how I knew I had to travel before starting my career. He was disappointed, even a bit angry. He saw potential in me, saw me as a future executive. But I was firm. I promised to stay until July, finish my MBA, and then leave for my trip.
Quitting my job that day felt like quitting my life. I was walking away from the American Dream: marriage, houses, kids, 401(k)s, the whole package. At 22, I was already working long hours and planning the next 40 years of my life. But a trip to Thailand made me realize that I was unhappy. The corporate grind wasn’t for me.
So, at 25, I hit the road. I thought I’d return to the "real world" after my trip, but I soon realized I could never go back. The day I quit my job, I wasn’t just quitting a job. I was quitting a lifestyle. I was quitting the American Dream. And in doing so, I found my own dream and have never looked back. And who says quitting is for losers?
