The End of a 40+ Country Journey of Long-Term Travel

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For four years, I traveled the world freely.

If I got bored, I jumped on a plane. I never read the news, looked at the weather forecast, or checked for visa requirements. I just went.

Except for political instability in Nicaragua, this strategy took me to 40 countries without any real problems.

I funded this journey with a six-figure, fully remote job. After growing up in Orlando with a mom who made $14,000 a year, my life seemed like paradise:

Freedom. Income. Adventure.

In my first 18 months, I grew tremendously. I learned about myself, the world, and the people I met. This period of work and travel shaped my thinking in enduring ways.

But as much as I enjoyed my life, I felt guilty. I often asked:

Why do I deserve this?

I never felt deserving. As hard as I had worked to live a good life, I felt lucky. In many ways, I was. To ease my guilt, I started helping other people. Losing myself to the service of others felt good. My life had meaning again.

Still, I felt dissatisfied.

As enjoyable as it is to live an untethered life of work and travel, it has disadvantages in the long-run.

It’s transient.

You meet amazing people. You have incredible experiences. But people move on to the next place – and so do you. The longer you do this dance, the more you wonder if all the people and memories are as meaningful as they once seemed.

It’s ungrounding.

Life blends together when you sleep in 50+ beds a year. You don’t have much to grasp onto. That’s fine when life is good. But when you lose a parent or have a tough breakup, it’s tough.

It’s numbing.

In the beginning, the new experiences, people, and sensations stimulate your mind. The first year is amazing.

But then travel fatigue sets in. Like a drug addict, you acclimate to the stimulation. The MDMA doesn’t hit as hard. So you need more.

Only exceedingly beautiful or exotic places get you going. You find yourself in wonderful cities feeling exhausted and disinterested.

Over time, every new country seems like something you’ve seen before. So does every person.

If you travel for long enough, your freedom-filled life starts to feel hollow and meaningless.

Tired of feeling exhausted and groundless, I knew that I needed to settle down. I didn’t know where. I had friends in New York and San Francisco, but I didn’t want to live in either city.

Thankfully, I stumbled upon a sleepy town in Southern California. With the good surf, nice weather, and friendly people, it checked enough boxes for me. Above all else, it felt like home.

It took a lot of courage to settle down. As dumb as it sounds, laying roots is scary once you get used to a nomadic life.

Giving up freedom is like giving up coffee. You could do it, but you don’t want to.

One big concern I had: owning stuff.

Living out of a backpack for years taught me that you need very few possessions to be happy and productive. Living with less put my soul at ease. I didn’t want to lose this feeling. I feared getting trapped in the honey pot of materialism.

So I committed to continuing a life of minimalism. I wouldn’t live out of a backpack, but I also wouldn’t buy things I didn’t need.

But there was a bigger problem: I tied my identity and ego to being nomadic.

As a nomad, it felt good to describe my sexy, travel-filled life to friends and strangers. As wanderlust filled their souls, I felt a small hit of dopamine about the life I had built.

Being a long-term traveler made it easy to be interesting. I had endless stories of exotic places and adventures. In a world where it’s hard to stand out, it felt good to be interesting.

I had the life of many people’s dreams.

Who would I be if I lived in California all year?

Just another California bro who enjoyed sunshine, healthy food, and surfing? That’s not sexy. It’s average. I didn’t want to feel average.

But I also wanted to feel grounded and energized again. Laying roots would help me get there.

Instead of adapting to new cities, I could focus on creative endeavors. Instead of meeting new people, I could deepen relationships with friends. Instead of visiting new cafes, I could go to the same coffee shop every morning.

To get there, I had to accept the tradeoffs.

Less freedom. Owning more stuff. Being less interesting.

I’m two months into laying roots.

I bought a car, signed a one year lease, and moved in with my girlfriend. To me, it’s a big deal. To many people, it’s life.

So far, it feels right. I’m on a path to focusing on the meaningful parts of life.

I’m not chasing novelty – I’m chasing depth.

Depth in my career and creativity. Depth in my giving back. Depth in my relationships. Depth in my experience of one city.

When I’m on my deathbed, that depth is what will matter.

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