I recently sat down for a podcast with my good friend, Derek. With 23 years of continuous travel under his belt, he’s seen it all. Looking at his journey always give me strength, as I see so many people drift away from this life over time. Talking to someone who has not only endured but thrived offers a unique perspective on what it truly takes to sustain this path.

We delved into the big questions: How does one last this long? How has the lifestyle itself changed? And what does the future hold? The insights I took away were both surprising and profoundly clarifying.

The Myth of Invincibility and the Reality of Luck

One of the first things we discussed was longevity. I’ve been on the road for 15 years, and I’m starting to believe it’s something in my DNA that keeps me going. Derek offered a more humble and, I think, more accurate perspective: a great deal of it comes down to luck.

He explained that for him to continue, a million tiny combinations of things had to fall into place perfectly. His work had to succeed, he needed the energy to explore, he had to build a global community of friends, and he had to be able to see his family regularly. If you remove even one of those factors, he admitted, the entire lifestyle would likely become unsustainable.

I loved the analogy we landed on. We imagined ourselves as protagonists in an action movie, constantly dodging bullets. The “bullets” are all the things that pull people back to a conventional life: the desire for routine, the need for a stable community, relationship challenges, or career burnout. Most people get “hit” by one of these bullets early on. The few of us who are still standing after decades aren’t necessarily better or stronger; we’ve just been incredibly fortunate to evade them. It’s a fragile setup, and the awareness of that fragility is what keeps the gratitude alive.

The Four Phases of a Nomad’s Life

When I asked Derek to look back and break down his 23 years, he identified distinct phases that I believe many long-term travelers can relate to.

1. The Exploration Phase: This was the beginning—pure fascination and adventure. The plan was simple: have fun until the money runs out. There were zero answers about career or long-term sustainability.
2. The Survival Phase: Reality set in. The lifestyle isn’t free, so the focus shifted to finding ways to make money on the road, like teaching English or working on ships, just to keep the journey going.
3. The Make-it-or-Break-it Phase: This was the chaotic, five-year chunk of trying to turn experiences into a real, sustainable business. It was a period defined by jumping on every perceived opportunity, trying to find a path that would allow him to continue on his own terms.
4. The Foundation Phase: This is the current period. With a solid business established, travel is no longer the sole objective; it is simply the backdrop to life. The focus is now on building something meaningful while living a lifestyle he loves.

Shorter Stays, Deeper Purpose

One of the most counterintuitive realizations we shared was how our travel styles have evolved. We both used to be advocates for “slow travel”—the idea of spending months in one place to truly soak it in. Ironically, we’re now moving faster than ever, but with a key difference: every trip has a purpose.

Instead of aimless wandering, each destination is now tied to a specific goal, whether it’s work, a project, or visiting friends. My stays have become shorter, but they feel more meaningful and grounded. Derek feels the same, noting that even a three-day stop in his anchor city of Lisbon can be enough to reconnect with friends, enjoy his favorite spots, and recharge before the next journey. This taught me that the quality of our time in a place isn’t determined by its length, but by the intention we bring to it.

The Future: Principles Over Passion

His principles for building his business are refreshingly straightforward and have nothing to do with chasing trends. First, listen to what people actually want, not what you think they want. Second, offer something incredible by focusing on the small details that create a real connection. Finally, be patient and let word-of-mouth do the work. A staggering 70% of his customers are repeats, which speaks for itself.

Perhaps his most potent piece of advice was to let go of the obsession with “passion.” He argued that waiting for a project you’re passionate about can lead to waiting forever. Instead, find work that is good enough, that you enjoy, and that gives you the lifestyle you desire. The satisfaction of building something that other people are passionate about can be just as fulfilling.

Our conversation served as a reminder that a nomadic life isn’t a static achievement but a constantly evolving practice of adaptation, luck, and purpose. The landscape is always changing, but the core principles of building a sustainable and meaningful life on the road remain timeless.

Listen to the full episode here: Spotify | Apple Podcast