Frequent Flyer Feelings

“Catch flights, not feelings,” as they say. It’s a saying that I embodied for much of my 20s. For better or for worse, the last decade was a mix of freedom and fleeing. Looking back at my peak travel years, I was constantly in motion (literally, 20+ countries in a year at times), chasing cheap flights and open itineraries like it was a game. And I had a serious advantage: my cousin’s Delta Companion Pass, which let me fly (standby) almost anywhere for next to nothing.

That Companion Pass unlocked so many new experiences for me, but it also came with its own kind of chaos. 

The first time I flew standby, I didn’t even make it onto my flight to London. Instead, my cousin and I pivoted last-minute to a city I’d never heard of (Shout out, Düsseldorf! Fun fact: that was also my first time ever flying first class.) Needless to say, what was supposed to be a straightforward trip to London turned into a whirlwind adventure across Germany, Belgium, and the Netherlands. We missed trains, rerouted on the fly, and made decisions with no more planning than what felt right in the moment. It was messy and unpredictable, but it was also the kind of trip that got me out of my comfort zone and made me feel like anything was possible. 

The chaos in those early years didn't always come from last-minute flight changes either. Back in 2017, I took my first-ever solo trip to Japan. I successfully got on my standby flight there (no first class this time 🙁), but once I landed, I was on my own in a way I hadn't fully anticipated. I didn't speak the language, and I didn’t realize international data plans or eSIMs were an option, so I was navigating the city on spotty WiFi, physical maps, and a lot of hoping for the best. Every day brought a new challenge: figuring out train systems, getting lost more than I'd like to admit, learning to double-check the details (like the time I showed up to the wrong airport). And yet, those mistakes became part of the experience. They forced me to slow down, to problem-solve, and to trust myself in unfamiliar places.

Looking back, that Companion Pass was the impetus for what would become my reputation as the "always traveling" friend. One year, it took me to Rome, where I rang in the New Year over a three-course meal as fireworks displayed above the Coliseum. Another time, it pushed me to my limits, climbing some of the steepest peaks in Patagonia (see my blog: Mountains Beyond Mountains…Literally). There were bucket list moments too, like when my cousin and I made our way to Morocco and slept in the Sahara Desert. And it even showed up for milestones, flying me back to London for my college graduation trip.

It opened my world in ways I couldn’t have imagined. Flying standby felt like the perfect metaphor for how I moved through my twenties: always ready to go, but never entirely sure where I’d land.

What I didn’t realize at the time was how easily that mindset seeped into the rest of my life. A cheap flight makes spontaneity addictive. And when you spend your twenties optimizing for departures, you get very comfortable with movement, and a little less practiced at staying.

Now in my early 30s, that rhythm has started to change. Not all at once, but gradually. The trips didn’t stop. I still travel often. But somewhere along the way, the reasons began to shift. The excitement of going somewhere new is still there, but it’s no longer the only thing pulling me onto a plane.

Instead of chasing new destinations, I find myself booking the same flights, again and again, to visit the same people. New York, DC, Denver, and Bethany Beach, Delaware are all on permanent rotation now. 

Bethany Beach is the place I think about most in between visits. Not because anything happens there, but because nothing has to. It's where my core friend group goes to do nothing, on purpose. Eleanor always curates the menu, and the kitchen becomes a lab of sorts (we've tested more new recipes there than I can count). Someone finds a show to binge for the weekend. We invent reasons to be together beyond just being together: a cake swap where everyone bakes for someone else, a Bob Ross paint-and-sip afternoon, a full tea party for a Bridgerton binge. Nothing about that weekend requires a boarding pass to somewhere new. It requires showing up, again, at the same house with the same people.

It's the same instinct that shows up in how I move through a place, too. Instead of squeezing as much as possible into a few days, I leave room for slower moments: lingering conversations, familiar spots, long walks through neighborhoods I've already explored. Back during COVID-19, I lived in Adams Morgan, DC with my friend Lauren. Our condo was right by Rock Creek Park, and I made a habit of exploring a new path through the neighborhood every day (forever an explorer, even when we couldn't go anywhere). I loved that condo, and I loved that neighborhood. It was the perfect blend of walkability, nature, and historic charm. And the best part was that it was close to all of my friends, so we could plan last-minute hangouts, order takeout, and watch trashy reality TV together. No planning required, just proximity. Now, whenever I'm in DC, I still walk those same blocks. I'm not looking for anything new. I'm just retracing my steps, reminiscing all the memories I made there.

If someone asked me to describe my travel identity now, I'd say I've traded distance for depth. Less about how far I can go, and more about who (or what) is waiting for me when I get there. I still love the hum of an airport, the quiet anonymity of a long flight, watching cities shrink beneath the clouds. But these days I'm less interested in where a cheap flight might take me and more interested in where I want to invest my time.

"Catch flights, not feelings" was a fitting motto for a decade built around motion. But lately, I've started to suspect the two were never meant to be mutually exclusive. The best trips aren't the ones that take you the farthest, but the ones that bring you closer to what matters.