In a moment that encapsulated the divisive times, I overheard a young boy, no older than eight, turn to another and declare, “You’re not welcome in my home.” The reason? A simple, stark question: “Trump or Clinton?” The answer, “Clinton,” was enough to draw a line in the sand. They moved on, continuing their childish debates, and likely, remained friends despite their differing views. It was a stark reminder that sometimes, actions speak louder than words, and sometimes, they don’t speak at all.
This encounter made me reflect on those who are all talk, or paralyzed by fear, or perhaps a blend of both. I strive to be different. I aim to listen, to generate ideas, and to cultivate gratitude. Listening is the gateway to learning, and learning allows for the heartfelt expression of “thank you.” It also brings to mind the countless individuals who proclaimed dramatic departures if a certain political outcome materialized. But how many truly acted?
There’s a compelling reason to consider a significant change, a reason articulated by Bobby Casey, a man who didn’t just talk about change—he embodied it.
Unpacking the High Cost of the American Dream with Bobby Casey
“[Living] in the U.S. is insanely expensive, Americans just don’t understand,” Bobby Casey asserted during a podcast interview. These words weren’t just rhetoric; they were the catalyst for his life transformation. In 2009, in the wake of the market crash, Bobby divested himself of all possessions and embarked on a journey outside the confines of his home country. Today, he operates globally, guiding others toward a life less tethered to traditional norms, a life “off the grid.” I was driven to understand his motivations and the mechanics of his drastic yet liberating move.
“Can You Fly Bobby?” I wondered, thinking about the courage and audacity it must take to leave everything behind.
“I hated my customers,” he confessed, cutting to the core of his discontent. “I hated my employees, I hated my job, I hated my business.” This wasn’t a tale of mere dissatisfaction; it was a narrative of profound unhappiness prompting radical change.
My questions mounted: “What made you believe you could liquidate your life and traverse the globe indefinitely?” “Weren’t you terrified of financial instability?”
“I just knew I’d work it out,” he responded with unwavering confidence. “I’d make some money.” This leap of faith is daunting for many. Uncertainty can be crippling when the unknown threatens to overwhelm our sense of security. Yet, for Bobby, the motivation was paramount.
“My happiness and my quality of life is much more important than cashing out on a business,” he declared, prioritizing well-being over conventional success metrics. “I didn’t care. I wanted to be happy again.”
This pursuit of happiness led to a complete shedding of his former life. He gave away his collection of 27 motorcycles and purchased two one-way tickets to Prague—one for himself and one for his nine-year-old son. “We’d never been there,” he mentioned, embracing the spontaneity of his new path. The rest of his family joined them weeks later, expanding their adventure to a family affair.
“What about friends? And school?” I probed, considering the practicalities of uprooting a family.
“My daughter, she’s 20, she’s a rapper in London. She did two years of virtual school. And she can make friends anywhere. It’s her personality type.” His other two children integrated into local schools, demonstrating adaptability in the face of change.
My curiosity was insatiable. “How did you gain such confidence? What kind of freelance work sustained you? How did you manage financially?” Bobby patiently detailed the financial strategies that made his lifestyle viable, unveiling the economic advantages of international living.
“I did the math on this,” he explained, revealing a startling figure. “You won’t believe this, but I pay $42 a year for a 10,000 euro deductible plan.” This minimal annual cost for comprehensive health coverage was just the tip of the iceberg. “Anything after 10,000 euros, he’s covered. I could get airlifted to John Hopkins if I wanted and that would be covered.”
Furthermore, he highlighted a significant financial perk for Americans abroad: “You can make about $150,000, tax-free, as an American living abroad.” Bobby elaborated on the podcast, illustrating the tangible benefits. Earning $100,000 gross in the U.S. might net you less than $60,000 after taxes. However, earning the same $60,000 abroad could be tax-free (for those qualifying for the Foreign Earned Income Exclusion), supplemented by a housing allowance, and coupled with incredibly affordable healthcare. Suddenly, financial constraints seemed to dissolve.
This revelation evoked a sense of melancholy. The practicality and appeal of Bobby’s lifestyle were undeniable, yet the inertia of established life felt heavy. It’s a common human trait to resist radical change, even when presented with compelling alternatives. Rationality often takes a backseat to comfort and familiarity.
Each of Bobby’s insights sparked a cascade of new questions. Initially, his approach seemed elusive, almost unattainable. But then, he shared his fundamental principle, a simple yet profound secret that illuminated his entire journey.
Bobby and his son found themselves in Estonia, having left Prague and purchased a house without a concrete plan. Chance intervened when someone overheard them speaking English. “You’re American?” A conversation ensued, leading to a serendipitous connection. “What are you planning to do for your kids for school?” Bobby admitted his uncertainty. The local resident responded, “I have a son who’s your son’s age. We found a really good school up the hill. There’s a meeting tonight for foreigners who want to enroll their kids.”
This was Bobby’s secret revealed…
“I figure it out as I go.”
This simple philosophy, “figure it out as I go,” encapsulates the essence of Bobby Casey’s transformative journey. It’s not about having all the answers upfront, but about trusting in your ability to adapt, learn, and navigate the unknown. It’s about taking the leap and learning to fly, just like Bobby did.
