Tom Karrel grew up in Westport, and is a 2012 graduate of Staples High School. His new book, “The Lost Art of Random Conversations,” has just been published. Tom writes:
“If we want things to stay as they are, things will have to change.” — Giuseppe Tomasi di Lampedusa
The other day, my partner Taylor and I stopped by the Organic Market. After a month full of eating all the sugar and bread we could find, we decided it was time to reset with a juice cleanse.
Tom Karrel
While waiting, a woman overheard us chatting and introduced herself. Within minutes, we discovered she is living in my hometown of Westport, but had grown up in the same neighborhood in Santa Barbara, California, where Taylor and I are moving this fall.
What started as a spontaneous moment turned into a genuinely meaningful conversation. We skipped the standard “What do you do?” scripts, and talked instead about how each of us has learned (or struggled) to make friends in new places.
We talked too about what makes a community feel welcoming enough to lower your guard, offer a compliment, or check in on a deeper level with a stranger.
Returning to Westport this summer, I’ve spent time driving around the Staples campus to see what looks different and what has stayed exactly the same. I’ve taken slow drives through the neighborhoods of old friends, grabbed a greasy sandwich at Fortuna’s and a toasted bagel at Village Bagels, and walked the familiar shores of Compo, Burying Hill and Sherwood Island.
While marveling at everything that looks fancy and new in town, what stands out most are those childhood memory spots that have not aged at all, in the absolute best way.
However, alongside that beautiful nostalgia is a louder realization: We’re all glued to our phones. Walking along the Saugatuck River, sitting on the wall at Compo or waiting for a table near the Black Duck or Kawa Ni, I notice heads constantly tilted down toward glowing rectangles.
We live in one of the most beautiful, idyllic towns in America. Yet so often we stare at our phone screens instead of actually looking up, or stopping to take in all the beauty and diverse people around us.
Sitting on the Compo Beach cannons — with cell phones. (Photo/Fred Cantor)
We all know it. But if nothing changes, nothing changes.
Whenever I come back to town, I get caught in this too. So this time, I’ve made a point to reach out to fellow Staples grads now spread across the globe.
As we catch up on where life has taken us, the conversation inevitably drifts toward the same realization: No matter how impressive our careers or titles may look on paper, everyone is hungry for a genuine sense of community and belonging, wherever they are.
Few have truly found it — myself included.
At Staples we were taught to strive, lead, and make our mark on the world. Westport excels at raising high achievers. But in a world where artificial intelligence automates routine tasks and screens consume our attention, shouldn’t our definition of success evolve?
Are we teaching our young people to be leaders who know how to build real human connection, or are we just training them to chase status and wealth?
True leadership is not just about financial success; it’s about having the courage and capacity to bring people together, lower social barriers, and make the places we live feel like tight-knit communities again.
In my new book, “The Lost Art of Random Conversations,” I advocate for LARC: the daily practice of starting spontaneous, face-to-face interactions in an increasingly lonely, anxious and phone-addicted world.
“Random” doesn’t mean aimless, though. It means being open to unscripted moments of human connection with anyone, from complete strangers to neighbors, colleagues, and our closest friends and family.
Prolonged loneliness carries health risks comparable to smoking 15 cigarettes a day. One in 4 adults worldwide report feeling profoundly isolated. We are the most digitally connected generation in history, yet statistically we feel the most alone.
The true measure of a strong community isn’t found in real estate values or pristine beach passes. It comes down to one question: If you disappeared for a month, how many people in town would notice?
Maintaining Westport’s strong, welcoming community doesn’t require a complex Town Hall initiative or new non-profit. It starts with simple micro-choices made by each of us individual Westporters every day. For example:
Unplug in local lines. Put your phone in your pocket while waiting at Gold’s, CVS or the Farmers’ Market. Look up, make eye contact, and ask about something interesting you notice about the place and the person behind the counter.
The other, while printing labels at the UPS Store opposite Fresh Market, Tom Karrel (right) and Taylor had a great conversation with 2014 Staples grad Gene Tsai.
Go beyond the usual script. The next time you’re chatting with a shop owner or parent at a baseball game, ask one question beyond “How’s your week going?” Try: “What’s been a standout part of your summer so far?” Genuinely listen to what they say. Follow up, and show you’re actually curious to hear more.
Acknowledge familiar strangers. If you pass the same person walking their dog along the road every morning, smile and say hello. Say the thing you’re both thinking: “Hey, we walk by each other all the time but I’ve never said hello. I’m [your name]!”
Westport’s community sustains and grows when we decide to look up, take a breath, and risk having an honest, spontaneous conversation with the person standing right in front of us. Making one another feel truly welcome and at home in this place, rather than just another busy adult running around from place to place.
The next time you feel a small nudge to reach out to someone in town, go for it. You never know when a simple conversation might remind both of you what it really means to belong to this beautiful place.
(For more information about Tom Karrel’s new book, “The Lost Art of Random Conversations,” click here.)
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