In July of 2019, I stepped onto an airplane at JFK with a one-way ticket to Colombia. I’d just exited my lease, left my decade-long career and ended my engagement to my fiance. I opened a Medium account and started writing.

With the color of hindsight, it’s difficult to recall exactly what I was expecting. I know I had visions of beautiful sites and beaches. I know I envisioned slinking into cafes and meeting locals and all those hazy fantasies one pictures when they think about travel. But, deep in my bones, I knew I wasn’t quite going on vacation.

Not long before I left, I read Tip of the Iceberg by Mark Adams. In it, he describes a belief held by the adventurer John Muir. Muir believed there’s a key difference between a vacation and an expedition. A vacation is a journey to get away from something. An expedition is a journey to find something.

There was a reason I decided to leave, of course. I felt heavier than I ever had. I felt slower than I ever had. I heard the whispering creep of age, I tracked the glow on the horizon of the dawn of the years in which I really should know what I’m doing. And, somehow, I had less of an idea what I was doing than I had on each day of each year of the prior eight.

I don’t exactly think my experience was unique - I think something happens for people in their late twenties. They feel the desperation to find their thing. When they find it, they’re locked. When they don’t, they panic. Trouble was, I thought I had found my thing. And, all at once, I realized I hadn’t.

I was weighted with the baggage of regret.

In my soul, I desperately wanted my trip to be an expedition. But, ultimately, those first few months really were a vacation. I was running. No question.

But then something happened. I realized I wasn’t falling in love with beautiful beaches and mountain vistas. Those were lovely, of course. But what I really came to appreciate were people. Humans. Folks of all varieties - from all sorts of places around the world - showing up as their authentic selves and genuinely craving insight. These people were themselves. And they were curious. And I loved that. They weren’t pretending their baggage didn’t exist. They were claiming it. They were naming it. And as they did, their baggage shed, their weight lifted, and they found their full footing once more.

About two months into my trip, I’d posted maybe a half-dozen entries on Medium. As a throw-away line in an impromptu check-in, my brother made a comment that took me months to process. He said, “Honestly man, I think starting to talk genuinely is almost as big a revolution for you as getting on the airplane.” In other words, the authenticity is bigger than the trip.

At the time, I didn’t think much of it. I let it fall away.

A few months later, I realized how right he was. It was the ownership of baggage - of human flaws and mistakes and regrets - that was changing who I was. It was storytelling. It was communicating honestly about the human condition that I was falling in love with.

Folks love beaches and mountains, obviously. Folks love following Instafamous twenty-somethings who post pictures on the beaches of Bali or Thailand or Brazil. Why, exactly, do we follow these people? Why are we drawn in?

I really don’t think it’s because the sunsets are pretty. I mean, that’s there, of course. But it’s deeper than that. The pictures represent a mentality - a way of being. They represent freedom from the chains of one’s own mind. They represent kinetic energy over stagnation. They represent progress and learning.

So I decided that I’m all done with the representation. I don’t think the world needs more travel-envy.

Stuck in quarantine, far from the pristine beaches of Cartagena and the mountains of Peru and the salt flats of Chile, I started writing. I wrote about the little moments. The weight I felt in the airport. The terrifying, world-changing near death experiences. The most awkward misunderstandings with complete strangers. And, really, I wrote about the feeling of claiming the baggage. And a few months later, I said hell with this, let's make it better. And I started recording.

So we’re here.

Let me be clear: this is about as direct about my intention as I’ll ever be. Baggage Claim is a podcast of travel stories no one tells. They are stories, first and last. They’re not religious experiences. They’re not self-help. They are tales of an imperfect man making imperfect decisions and deciding, eventually, to fall in love with the nature of his own imperfection. Because that’s what makes him human.

The first three episodes of Baggage Claim will drop on Tuesday, and there will be a new episode every Tuesday for twenty-eight Tuesdays. The trailer is available here on your streaming platform of choice. And you can text CONNECT to (332) 877-9540 (or click here) for weekly show alerts.

See you out there.

Will Conway


Former political software guy. Now a traveler and adventurer, which isn't a job, and host of the @heybaggageclaim podcast, which really isn't either. Travel stories no one tells.