If you have ever stood at the edge of a party, a neighborhood, a new city, or even a new gym class, and felt like the outsider who doesn’t quite know how to break in, this episode is going to hit you somewhere specific.
Because here’s the thing about that feeling: we tend to treat it like a flaw. Like proof that we’re bad at this. Like everyone else got the handbook on how to walk into a room and just… belong. And we didn’t.
Tom Karrel spent five years in Uganda, including time living in a 350-person rural village called Kasambika, and what he found there didn’t just change how he thinks about community. It changed how he thinks about what we’re all doing wrong when we try to build it. Tom is the author of The Lost Art of Random Conversations (LARC), and with over 10,000 hours of group facilitation across 45 countries, he has spent his career studying what actually makes people feel connected and what quietly gets in the way.
This conversation is one of those that stays with you for a few days. The kind where you’re loading the dishwasher two nights later and something Tom said just surfaces again. So let’s get into it.
The Village That Changed Everything
Tom grew up in Westport, Connecticut, a wealthy town where, by most measures, he had everything. Loving family, solid upbringing, all the resources. And yet, he says, he never felt comfortable just showing up uninvited at a neighbor’s house. Nobody welcomed him with a chair and a cup of tea. Nobody’s kid climbed a tree to grab him a mango.
He didn’t have language for what was missing until he landed in Kasambika.
He was there as a public health student, doing door-to-door interviews, running health education presentations. And within the first 24 hours, he was sitting with the local mayor. By day five, he was at a Ugandan wedding. The community didn’t wait to see if he’d earn his place. They brought him in.
But here’s the part that stayed with me: it wasn’t effortless. Tom was fumbling. He was learning words in Lusoga, the local language, getting laughed at, getting hugged, trying again. He was visibly an outsider, and everyone knew it. And the thing that cracked open belonging for him was choosing to go first anyway.
He has a line in his book: if I want something, I have to go first. Not as a performance. Not as a networking strategy. As a practice. As the actual work.
If you want to hear Tom walk through what those first days in Kasambika felt like, including the wedding that became his threshold moment, listen to the full episode because the details are the whole story.
Why Going First Feels Harder Here
Here’s the thing I kept sitting with during this conversation. Everything Tom described doing in Uganda, trying the language, looking a little silly, following the urge to connect, we already know we need to do that. We say it to ourselves. We read it in books. And then we join a new gym or move to a new neighborhood or try to make a friend as an adult, and we feel like the outsider, and suddenly one awkward attempt feels like proof that we’re bad at this.
Tom is halfway across the world, pooping in a hole and learning a language from scratch, and it’s obvious he’s going to look silly. It’s obvious he has to try. But in our everyday lives, somehow we hold ourselves to a different standard. The awkwardness feels like a character flaw instead of just… the process.
Tom talked about this through the lens of certainty. We have built lives so optimized for certainty, Ring doorbells and Google searches before we even pull into the parking lot, that we’ve removed most of the in-between moments where connection actually lives. The stranger at the door. The person at the coffee shop. The neighbor we haven’t met because we already know what the Ring camera shows.
He put it plainly: certainty is a core human need. We need enough of it to feel safe. But clinging to it at all costs is a recipe for the exact loneliness we’re trying to fix. Because love and connection, the things we actually want, require us to risk some of that certainty. To go first. To not know what’s on the other side.
The Seattle Freeze, the Ring Doorbell, and What We’re Actually Choosing
I live in Seattle, which is known for the Seattle Freeze. If you know, you know. People pass each other on sidewalks looking down, no eye contact, no acknowledgment. And one of my favorite experiments is to walk through a new neighborhood and just smile at people.
Some ignore me. Some look bewildered. But the ones who light up, who stop, who say something about the weather? Almost always elderly people. People who may not have had another real interaction that day.
Tom’s concern, and I think it’s a fair one, is that the Seattle Freeze is becoming the baseline for a lot more places. Not because people are choosing to be cold, but because the technology and the architecture of modern life are quietly eroding the inclination to reach out. DoorDash instead of the corner restaurant. Airbnb instead of knowing your neighbors. Google before asking the person next to you.
None of those things are evil. But if we don’t notice what they’re slowly removing, we end up with less social trust, less practice, and a growing sense that going first is somehow strange or risky.
The good news, and Tom is clear on this: you can choose otherwise. It can be as simple as putting your phone down and looking up. He has a challenge in his book: do it three times a day. Notice what’s around you. That’s where the stuff worth talking about actually lives.
Can We Actually Build a Sense of Belonging Here?
I asked Tom the question I’d been holding the whole conversation: after five years in Uganda, after experiencing belonging at that level, does he think it’s actually possible to build something like that here?
He said yes. And I believe him, but I wanted to understand why.
His answer wasn’t a commune or a tiny house village, though he admits he went down that rabbit hole. His answer was simpler and harder at the same time. Belonging, at its core, is a sustained feeling of being wanted or needed by the people around you, consistently. It’s knowing you play a role. It’s being reaffirmed by what people say and do, day after day.
And that can happen here. It just requires more intentional effort because our buildings, our behaviors, our workplaces, our whole infrastructure is not designed to face each other. It’s designed to face inward, to be self-sufficient, to outsource what used to require community.
So we have to build it on purpose. Which means going first. Which means not waiting until the conditions are perfect. Which means smiling at the person on the sidewalk even in Seattle.
Tom ended with a challenge that I think is worth sitting with. Close your eyes and think about someone in your life you’d love to get a random call from. Someone who, if their name showed up on your screen for no reason at all, would make your day. Now think about the fact that you might be that person for someone else. And then call them.
If you want to hear Tom’s full answer on why belonging is possible here, and the story he told about a man in a medical mask at a Chipotle that I promise you won’t forget, listen to the full episode at friendshipirl.com/episode197.
The Story That Opened the Book
Tom’s book, The Lost Art of Random Conversations, opens with a story from 2019. He’s flying back from Uganda, lands in New York, and goes with his dad to Chipotle. Standing outside is an older man in a medical mask and latex gloves, which in 2019, before COVID, was a genuinely strange sight.
Tom wasn’t on his phone. He noticed. He felt a pull. And instead of looking away, he walked over and asked how the man’s day was going.
The man paused, took off his mask, and said: “I think this is the best day of my life.” He had just become a grandfather for the first time.
That’s the whole argument in one story. We never know what someone is carrying or celebrating or desperately hoping someone will ask about. And most of the time, we’ll never find out because we don’t look up.
For the complete conversation about what it actually takes to build a sense of belonging in a world designed to keep us apart, listen to the full episode at friendshipirl.com/episode197.
