Writing on living a deliberate life, focused on building businesses rather than cabins by ponds. Content about strategy, life, and philosophy all building to being more deliberate and living a more amazing life.

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Once, I traveled to discover new worlds. Now I travel to remember where I left my curiosity.

We arrived a couple of days ago in the land of beaches, Ronaldo, and bacalhau.

There was a time when an intercontinental trip like this — to a country with a new language and culture — felt thrilling, even dangerous. It wasn’t a step outside my comfort zone; it was a fall off the comfort zone cliff, with nothing to hang on to, and I’d land a different person.

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The thrill is mostly gone now, but not the opportunity for change. I’ve learned it isn’t the travel that matters — it’s how we approach it. And therein lies the opportunity.

When I arrived in Mexico City alone at eighteen, an ignorant, monolingual white kid from Sacramento who’d never been to the gritty core of any city, let alone one in a developing country, I was terrified.

I worried that around every corner there’d be somebody waiting to rip me off.

Of course, all things become familiar. Mexico City is now a place I visit for nights out and tacos. I now know there are people waiting to rip me off, but they’re in New York, too, so there’s nothing special about that. These days, I sometimes wonder why I wasn’t ripped off more on that first trip. I still remember the face of a taxi driver when I tipped him three cents, thinking it was three dollars, and I wonder why he didn’t just take the rest.

I was a fool. Mexicans must be saints.

The truth is that most people aren’t out to get you. But when you don’t know what you’re doing, every step requires thought and planning. Ordering food takes practice. Nothing is automatic. Assumptions crumble. The day-to-day becomes an adventure — slightly dangerous, fully alive.

And it can change you.

If you let it.

I’ve learned there are two types of travelers: Disney travelers and open travelers.

Disney travelers expect everything to meet their expectations. They see the world as a kind of Disneyland — a place to visit and photograph but never truly touch. They don’t want a challenge; they want comfort. They collect pictures and selfies and return home exactly the same.

Open travelers absorb. We let the experiences change us. We expose ourselves — our Selves — to the unfamiliar and come back different than when we left. Every trip, every encounter, opens a new possibility.

I’m no longer the monolingual kid from Sacramento afraid of Mexico City. Well, I’m still white, that’s not going to change, but my identity is much more expansive.

I see people I’ve known my entire life stuck in the same patterns they were in thirty years ago, approaching the world with fear: fear of change, fear of the other, fear that their identity or values might be challenged. But growth, and I think true happiness, is in the challenge.

My mental poster child for the Disney traveler is an American who studied abroad with me in Madrid in 2002. When a class discussion turned toward Islam and America’s cultural warfare in the wake of 9/11, the class dared to suggest that Muslims were mostly decent people. He was incensed. He left the room, complained to the school, all because his identity felt threatened.

I don’t know what happened to him afterward, but I imagine him walking through life like a live wire with crumbling insulation - always sensitive to that next slight.

Since that first trip to Mexico, I’ve traveled a lot. I don’t honestly know how much; I stopped counting intercontinental flights after the first few dozen. I’ve lived in seven countries, learned languages, become a diamond sorter, negotiated with dictators, and once even ritually slaughtered a goat.

Most of the adventure is gone.

It doesn’t feel dangerous anymore.

So why bother?

Perspective.

I once read a criticism of Thoreau that Walden Pond wasn’t far from civilization, he wasn’t really living on the edge. But that was never the point. He wasn’t seeking danger; he was seeking perspective. He broke his routine to see differently, to give his mind space to wander.

For the last few months, my rhythm has been to wake up, make coffee, read, go to the home office, plug in, work, eat dinner, watch something on Netflix, and go to sleep. Each day feels the same, and that sameness begins to define the extent of my life.

My mind starts to believe that’s all there is — that what I see every day is the world itself. My assumptions calcify. My identity contracts. It becomes easy to believe that my experience is reality, that what’s familiar must also be right.

It would be easy to become someone who can’t stand to be challenged.

But you can’t reinvent without challenge, without, well, reinventing.

So, travel is, in a way, my Walden Pond: not dangerous, but it’ll challenge you if you let it.

It makes me think that it isn’t the travel at all that matters. It’s openness.

You can travel and get nothing from it. So maybe we can gain perspective right where we are. Whether you venture across continents or just down the street, the true opportunity lies in letting go of our fragile identities and absorbing.

Of course, it only changes you if you let it.

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