why I’m choosing to live Unsettled a second time

I wrote the following reflection in early April following a month with Unsettled in Medellín, Colombia. I never published it on my blog nor have I shared it with anyone, until now. I’ve been sitting on this post as I wanted to get it “right.” I wanted to capture exactly what my month with Unsettled meant to and for me.

In hindsight, I realize I’ll likely never get it “right” in that way. A month with Unsettled is something that needs to be experienced to be understood.

That said, rather than keep the reflection that follows to myself, I thought I’d share it here — on the eve of embarking on my second Unsettled experience in Cape Town, South Africa. I think it captures a large part of my motivation for living Unsettled a second time. So cheers to this next adventure, my expanding Unsettled family and many more moments spent embracing the unknown.


On my final Wednesday evening in Medellín, I stood among a group of people who’d grown from strangers to friends to family in only a month’s time. The heavy storms of the afternoon had passed, leaving behind a calm, quiet evening. From the second-floor patio of the restaurant, which can best be described as an Anthropologie store within a greenhouse, we could see across Medellín’s valley to the western Andes. Thousands of lights scattered the space between.

We had the patio, and more or less the restaurant, to ourselves. Candlelit tables were pushed to the edges of the deck.

As Jonathan, one of Unsettled’s co-founders, asked us to stand in a circle, conversations faded to whispers and then nothing at all. I looked around the circle at 15 familiar faces, at people I’d grown to know and love well in only four weeks. The moment was still, silent and warm. Memories of a rich month hung in the air. So did thoughts of impending goodbyes. It was a moment of deep love and gratitude.

For me, there were thoughts of how quickly a month can go by. How complete strangers can become friends within hours and then family within a month.

It was a bittersweet moment. There was a heaviness in the air at the thought of goodbyes to come. The thought of moving on. Separately. Individually. This group will always exist, but this was perhaps the last time we’d all be gathered in one place together — and at this point, we were already down by six. Then again, who knows. Maybe we’ll surprise ourselves with a group reunion down the road.

This moment was a celebration of life. It was a celebration of the lives we’d lived throughout the past month. It was a celebration of the ways in which we’d inspired, encouraged and empowered one another. It was a celebration of the ways in which our lives would never be the same. It was a celebration of the ways in which we’d breathed life into our lives.

As we stood in a circle, Jonathan asked us to close our eyes and then led our group in a reflection, one that extended well beyond our month in Medellín.

“Who were you, where were you when you first discovered Unsettled?”

I flashed back to my first week in Buenos Aires in early November. I was a different person then. I was fresh off the plane, thrown into a completely new city in a completely new country. I didn’t know anyone. I didn’t speak Spanish. I saw myself in the tiny kitchen in the Airbnb I’d rented the first week I was there. I’d received an email from my aunt. She’d written a brief message and shared a CNN article titled “Why adults are embracing communal living.”

My aunt had mentioned other companies, similar to Unsettled, in her email; the article did as well. I don’t recall looking those other companies up. I only remember looking into Unsettled. The name and the experience spoke to me. This was something I wanted to be part of. This was a community I wanted to be part of.

Jonathan asked a second question. “Where were you when you first felt a pull to this experience, when you signed up to spend a month in Medellín?”

I emailed Jonathan and Michael, Unsettled’s other co-founder, the same week my aunt sent me the article. Jonathan responded and invited me to an Unsettled event in Buenos Aires. (Unsettled was leading a retreat there at the time.) My second Tuesday in Buenos Aires, I met a warm, welcoming group of people from all around the world, Unsettled Buenos Aires participants, and knew I wanted to be part of a future Unsettled experience.

I think I signed up for Unsettled Medellín in December, just before the holidays. I’ll be honest: I had no clue what I was doing. I didn’t know if I’d want to spend a month away from Buenos Aires. I didn’t know if doing so was a good idea. I didn’t know if I could afford a month with Unsettled financially. I didn’t know if I could afford the plane ticket to get to and from Medellín. I didn’t know if I’d click with the group. There were a lot of unknowns, but something about a month in Medellín with Unsettled felt right. The timing felt right, too, as I knew I’d be without a home in Buenos Aires in March. So it felt like a natural break, a good time to leave the city for a month, reset and try something new.

I didn’t know what I was doing, but I felt as though I owed this month, this experience, to myself. Even with all these unknowns, committing to a month in Medellín with Unsettled felt right. It felt like the right move for me. I’d read about Unsettled, met Jonathan and the group in Buenos Aires and wanted to see what the experience was like for myself.

Jonathan spoke again. “How did you feel when you got on the plane to Medellín and then landed in Medellín?”

I flashed back to the evening before I left Buenos Aires. Sitting on my bed with Ida, my roommate, talking about how much I didn’t want to leave Buenos Aires, how bittersweet it was to be leaving that apartment and the city because I’d felt as though I’d really started building a community for myself there. I was excited to go to Medellín and knew I’d chosen this month with Unsettled for a reason, but there were so many reasons to stay in Buenos Aires as well.

I recall my 4:40 a.m. flight out of AEP on a Friday. Traveling from Buenos Aires to Mendoza to Lima to Bogota to Medellín. Arriving after dark in Medellín. My luggage hadn’t made it. In fact, it was still in Buenos Aires. I remember finding the driver who’d take me down to Medellín, to the hotel I was sharing with another Unsettled participant, Diana, that night.

I remember driving out of the airport and down the mountainside into Medellín. Since it was night, I couldn’t see much, but I so clearly remember feeling relieved. Feeling relieved at the cracked windows and the fresh mountain air. The cool night air. Hearing the crickets and the sounds of nature outside as we drove down the quiet road into Medellín. I remember talking with the driver in Spanish the whole way down. I remember feeling proud that I’d spoken in Spanish with the agent at the airport about my lost luggage and that I was speaking in Spanish with the driver, too. A feeling of accomplishment, as I couldn’t say the same of my arrival in Buenos Aires four months prior.

I remember when the driver pulled over at a stripmall for a bathroom break. I remember him leaving the driver’s door ajar and me not being able to lock the car. I remember thinking, “Sh*t. It’s my first night in Colombia, and all my family’s fears [about me being here] are going to come true.”

I then remember laughing a little at myself, and my silly worst-case scenario thoughts, when the driver returned to the car a few minutes later.

I remember not knowing anything about Medellín or understanding the layout of the city when I arrived that Friday night. There’s something about arriving in a new place after dark and not knowing how it really looks until you wake up the next morning. With Medellín, that first morning, it was love at first sight.

“Who was the first person you met here? What was that moment like?”

I remember Diana, a fellow Unsettled participant from Mexico, arriving in Medellín after midnight that Friday and walking through the door of our hotel room with her luggage. We’d both arrived a day before Unsettled officially started, had connected through Facebook ahead of time and agreed to share a hotel room.

I remember I was waiting up, reading in bed, in the same clothes I’d worn all day on my flights. (Due to my bag not making the trip, I had nothing to change into.) I remember Diana and I talked for a little while that night and then went to bed.

I remember waking up the next morning and looking out the window and seeing Medellín and the beautiful, vibrant, green mountains for the first time. Both Diana and I were in love with this stunning city already. I remember we went up to the roof of the hotel for breakfast, where we continued to talk and take in the views. I remember meeting a guy from Detroit at breakfast. Small world.

I remember showering and getting ready in the hotel room; putting on the same old clothes from the day before; and then — just as Diana and I were about to walk out the door for lunch with some other early Unsettled arrivals — finding out that my bag had arrived at the hotel. Sweet freedom. It felt good to put on clean clothes, especially when going to meet new people for the first time.

“Do you remember that first morning at Urbania Cafe? Telling someone your favorite color’s favorite color or the last time you peed your pants?”

With every prompt, memories, scenarios and emotions flooded my mind. Jonathan continued on. He spoke to everything we’d done in one month together.

One. Month. Together. How had it gone by so quickly?

We’d traveled to Guatapé and Jardín. On various trips, we’d also covered Salento, Bogota, Cartagena and Guachalito.

We’d ridden on top of jeeps through the Colombian countryside; gone paintballing at Pablo Escobar’s mansion; ridden boats through a reservoir; tasted coffee in Guatapé; and climbed to the top of El Peñón de Guatapé together.

We’d gone paragliding above Medellín; competed in a local pub trivia night; and gone on a story-filled graffiti tour in Comuna 13.

We’d visited a coffee finca outside Jardín and had an amazing lunch there — one of the best I’ve had in a long time. We’d gone horseback riding, one of the wildest horseback rides, through the Colombian Andes at sunset. We’d spent the night in cabañas overlooking Jardín; I’d slept in a hammock outside and woken up the next morning to the sun illuminating the mountains surrounding the pueblo. We’d ridden up and down the hillside there in mototaxis and also a garden shed of sorts.

We’d watched futbol matches among the locals; ridden through the mountains surrounding Medellín in a chiva; studied Spanish; hosted workshops; discussed our progress during Wednesday “Lunch & Learns”; shared countless meals together; the list goes on.

After recapping the month, Jonathan asked a second series of questions. “Who are you now? What has this month meant to you? What has this experience and this community meant to you? How are you feeling? In this moment? At the end of this month?”

Some had decided to stay in Medellín. Some had decided they weren’t going “home”; they were going to embrace the digital nomad lifestyle. Some were quitting their jobs.

The outcome of the month was different for everyone, but for all of us, something had shifted.

Jonathan paused.

The thoughts and visions running through my mind seemed to settle. The personal montage I’d been watching hung in the air. I surrendered myself to the moment, surrendered myself to the feeling of not only this moment but this month as a whole.

Throughout the reflection, a feeling of warmth had grown within me. I was smiling. Even though no one could see me, I was smiling. Not a toothy smile, more of a grin. I was smiling on the outside; I was smiling on the inside. I was standing tall, confident. For the first time in a while, I was rooted in who I was — who I know I am — again. It felt indescribably good.

My heart and my being felt full. Full of love, support, inspiration and encouragement. Full of all the good things.

The way I’d lived my life in March was good and fitting and right for me for all the right reasons. It was a reminder of how I want to live my life and the type of community I want to have in my life, the kind of people I want to surround myself with.

The way I’d lived my life in March was unique, but it also wasn’t a one-time thing. It doesn’t have to be a one-time thing. It is not easy, but it is something to strive for every day.

I’d reflected on our month together as it was unfolding, but on this final Wednesday evening, as I was literally surrounded by people I’d come to love dearly, the glow of a month lived well was fully there. Burning within me.

“Okay,” Jonathan said. “Now open your eyes.”

I blinked and looked around at the people I loved, the individuals who in a month’s time had grown from complete strangers to family.

“Now I want us to go around one-by-one and share what we’re thinking and feeling,” he said.

Unable to keep what I was feeling to myself, I raised my hand. Not usually the first to speak up in group situations, I was the first to do so that evening.

“I feel as though the world is at my fingertips,” I said. “I feel as though my life is at my fingertips. This experience, being in community with all of you, has made me realize that it is possible to live this way, to live as a digital nomad, to live a bit unconventionally and adventurously. I feel as though the world and my life are mine for the taking, and it’s thanks to this experience and all of you. So thank you for being here, for showing up, for being part of this experience and for being part of my life.”


As I was leaving Medellín a few days later, I wrote the following:

I do not have all the words at the moment, but I know this much: I am glad I chose Unsettled.

I am glad that, even with my hesitancies, I chose to get on a plane way too early in the morning on Friday, March 3 — and then three more planes after that — and fly to Medellín. I am glad I chose to hear out my family’s concerns about Colombia, acknowledge them and continue on with my journey. I am glad to consciously be making my own decisions. I am glad I chose to embark on my first Unsettled experience in Medellín. In Colombia.

And because I made these decisions and chose to show up, be present and be in community with 21 strangers who quickly became family, I feel so incredibly blessed.

I feel blessed to have spent a month in an amazing city in an amazing country. I feel blessed to know Colombia and to have seen various sides of her beauty. I feel blessed to have pursued a life of adventure — so many adventures — this month.

And more than anything, I feel so, so blessed to know — to really know and have connected deeply with — 21 people from around the world. 21 people with diverse backgrounds, experiences, stories, skills, hobbies and lives. I feel blessed to be in community with them, to have shared myself with them, to have shared moments and stories with them. To have jumped in with them in vulnerable ways far quicker than I have with any group of people before. I feel blessed to know them and for them to know me.

I cannot put into words what Unsettled means to me, what this experience and these people mean to me. I just know that this has been one heck of a ride and that I am so grateful to be living this life, to be living a life that embraces experiences like this one — and because of that to be meeting people who feel and live the same.

My Unsettled Medellín family at a coffee finca in Jardín, Colombia. Photo: Jonathan Kalan

September 28, 2017

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