When I was younger I picked travel destinations without too much thought. I went to Italy to ski because I heard the Alps were great for skiing, and besides Italy seemed cool for everything else. Venice was Venice – it seemed like a place people should go. I went to Cambridge because a friend lived there, and then to Amsterdam because, well… it’s medicinal. Then Paris, then Barcelona, then a more nakedly Spanish party town, Alicante, all because they seemed like cool places.
God knows how I arrived at these decisions. In College, the “Grand Tour” I took with my sister seemed to pluck big, well-known cities off the map of Western Europe because the aggregate of everything we’d absorbed in that time (before the Internet made minute research into every detail of a place the norm) it seemed like the right move. We were College kids, and we didn’t know any better. After College, my horizons expanded somewhat, but I still picked places in “bucket list” fashion: a place I should go because I just felt like I should go.
By then I had learned something about my personal travel tastes. Primarily, I liked to eat the local food and drink the local booze, and do no more than one, maybe two tourist things a day. Sleep in, wake up, get coffee and breakfast, see a sight, walk around the city a bit, have an early afternoon drink, then back to the hostel or wherever I was staying, and prepare for a night out.
I graduated College with a history degree, and so I added some consideration for a place’s past into the mix. That’s how Istanbul got on my list. Add that city’s food, drink, and nightlife to the centuries of history layered upon history and I would put it against any city in the world. Of course, the Hagia Sofia remains the most stunningly gorgeous building I have ever set foot in. Later in life, I would excitedly sign up for a flight to the Czech Republic that included a 24-hour overnight layover in Istanbul because, if nothing else, I wanted to step foot in that glorious building once more.
Thinking back on my travel choices at the time, I was also seeking wilderness. For years I was guided by a passage from Willi Unsoeld I’d encountered while on a course with the National Outdoor Leadership School:
And so what is the final test of the efficacy of this wilderness experience we’ve just been through together? Because having been there, in the mountains, alone, in the midst of solitude, and this feeling, this mystical feeling if you will, of the ultimacy of joy and whatever there is. The question is, “Why not stay out there in the wilderness the rest of your days and just live in the lap of Satori or whatever you want to call it?” And the answer, my answer to that is, “Because that’s not where people are.” And the final test for me of the legitimacy of the experience is, “How well does your experience of the sacred in nature enable you to cope more effectively with the problems of mankind when you come back to the city?”
I loved being in the mountains and being disconnected from everything, enveloped by nature, and walking along a forest trail. Motivated by this love and guided by Unsoeld’s exhortation to use such sacred experiences to enable me to better be “where people are,” I sought out travel as renewal experience. And so, in addition to the cities of Western Europe, I found myself backpacking through New Zealand, hiking solo through Denali National Park in Alaska, gazing upon the Himalayas from Pokhara, Nepal, and pining after Patagonia, a place I have yet to make it.
Then, two things happened: I had my son, and I discovered kitesurfing. For most, having kids means an end to adventures of the sort they seek out in youth. But in my case, becoming a father was followed not too long afterward by becoming a single father, with custody split so that at times I was more or less bound to my home outside Washington DC, or at least travel acceptable to a toddler, and at other times still available to roam.
It was during an early period of roaming that I took myself to the Dominican Republic. This was the first trip I took not because of the destination’s history, or food, or nightlife, or the wilderness it offered. No, this trip was about recovery. Following the separation from my son’s mom I sought somewhere I could be alone, anonymous, and yet among people, while trying my hand at kiting the surf, for which the north coast beach town of Cabarete was fast-becoming known. By the end of my two weeks there, I had a new reason to travel: for the wind.
After that, kitesurfing threatened to overwhelm all the other reasons to travel. History, food, nightlife, atmosphere – all were subsumed by my overwhelming desire for a cheap beach with steady wind. Besides, I was getting older, I thought to myself, and didn’t it make sense to stop gallivanting all over the globe and instead focus on a leisure activity? But kiting was more than leisure, it was a glorious obsession. It produced that ephemeral quality of flow in which time falls away, my brain could be emptied of the problems of ordinary life, and for a few hours at least I could be at peace flying the kite through the wind, surfing across the ocean and the waves.
The map of the globe was no longer a list of world-historic cities and wilderness areas; it was a list of wind-strewn sand and surf. Meanwhile, work and kids narrowed the scope of my search to places closer to home and cheaper to reach. Thankfully there was a kid-friendly, world-class kitesurfing destination practically in my back yard. In seven hours, I could drive from my home in Maryland south to the Outer Banks, North Carolina. I’ve made four separate trips there in the past five years, two back to the Dominican Republic, and one each to Jamaica and Belize, all to kitesurf.
Then, I underwent another evolution. It was prompted by some combination of the money that came from moving up in my career, and the freedom of place that came from transitioning that career to majority remote work. When the evolution occurred precisely is difficult to say, but what was clear was that I didn’t know anyone else exactly in my position. Some people had time, but no freedom; others freedom but no time. There were people on the Internet of course, the travel bloggers who quit everything to go travel the world and write about it, and then there were the lifestyle bloggers, who made money supposedly by telling other people how to quit their day job and make money. Neither of these applied to me. I was not interested in quitting everything and traveling indefinitely, nor was I in need of a side hustle, the purpose of which would be to fund travel.
What I became interested in, is what my life would like if I merely switched cities. But not just any city: an international city. What would it be like, I thought, to truly live somewhere else, outside the U.S.? I’m not gonna say the election of Donald Trump had nothing to do with this; it certainly did. There are many wonderful things about America, but the election only reinforced my as a citizen of humanity first, and an American somewhere around fourth or fifth. I’d never truly lived outside the U.S. What, I wondered, would that look like?
I began looking at the map of the world very differently, but the new view raised other questions, deep life questions. What sort of place would I be if I could be any place? What was important to me? I knew that a beach with wind nearby was important, but what else? The new questions were a culmination of sorts, a bringing together of all previous desires. I wanted amazing food, cheap living, a particular atmosphere, culturally interesting but not over the top bustle. I began casting about for options, and thus I visited Lisbon, worked remotely in Prague, and made a point to see my sister in London more often.
Then came Unsettled. In April, 2017, the NY Times ran a story about the young company, The Digital Nomad Life: Combining Work and Travel. Within a day of publishing, two separate family members had emailed it to me, knowing how closely I would identify. Unsettled certainly knows its audience, and its right there in the name. It is for those who are unsatisfied with whatever kind of status quo life they may be leading. They are unsatisfied by a 9-to-5, unsatisfied bowing to whatever residual cultural expectations might prevent one from moving, from shaking up their life and work, from traveling while working, or seeing a new way of being, or simply living the kind of life they really wanted. I thought, these are the people I want to be around. They won’t have answers, but at least they’ll be thinking about the same questions.
With my son away for the month of August with his mom, I booked the city that Unsettled had available at that time: Medellín, Colombia. Had I had my choice of timing, this is not where I would have gone (yes, Buenos Aires!), but still, I’d heard that Medellín was a fascinating city, now among the safest in South America despite its troubled history, and increasingly populated with international businesses and expats. I’d heard that Medellín was also an innovative urban project, recovering as it was from decades of violence, and apparently having transformed itself into one of the most dynamic urban success stories on the continent.
In fact, I am writing now from a co-work space in Medellín’s Poblado neighborhood. After a little more than a week here, I am still adjusting to what a different kind of travel experience this is. I’m not here to be a tourist, though tourist things I will do. But those are reserved mainly for weekends. In the mean time, I have more or less ported over my schedule from home to my time here. I wake up, I make myself some coffee and breakfast, or I walk to a nearby cafe for a latte and a croissant. I go to the co-work space (shout out Global Express), and I do my job as usual, taking conference calls, sending emails, and writing, writing, writing. The restaurants in Poblado are cheap, varied, and generally fantastic, so my lunches are spent sampling from the more than 100 that are all within a 10-minute walk. In the evenings I spend time with the rest of the group from Unsettled, more than two dozen fellow travelers from around the world. I dance salsa, I eat the local food, I drink the local booze, and I try to connect with the place, its people, and those others who have come here for the same reasons I have.
It’s certainly an evolution from what I’ve done before, packing in the sights daily, moving fast, switching cities, playing tourist. And so: what do I think? Ask me when it’s over. Certainly, there will be more writing to come.