Maybe We Should Talk to Strangers
· Connection
When you talk to strangers, the world suddenly feels a lot more human and a lot smaller. Sometimes the person sitting right next to you has a story that might change the way you see the world.
To some of you that may sound like terrible advice or your introvert self was like..um, hard pass. And of course most of us grew up hearing, "Don't talk to strangers."
Somewhere along the way, though, that rule didn't just stick with kids. It became the unspoken rule for adults too. Headphones in. Phone out. Eyes down. You get on the plane. You get in the Uber. You stand in line for coffee. You step into the elevator. Everyone quietly pretends the other humans around them don't exist.
Have you ever noticed how strange that is?
Two hundred people sitting at the same airport gate… and no one talking. Someone six inches from you on a plane for three hours… and somehow we all silently agree not to acknowledge each other. It almost feels like the social contract of modern life is simple: stay in your lane, don't make it awkward, don't talk to strangers.
But lately I've been traveling a lot. And I've been breaking that rule. Not in some big dramatic way. I've just been smiling and saying hello. And what I'm rediscovering is that when you talk to strangers, the world suddenly feels a lot more human and a lot smaller.
A few mornings ago I was sitting at breakfast with Sarah at a hotel when I struck up a conversation with a man named Orlando. It started the way most travel conversations do. Simple questions. Where are you from? What brings you here?
Then Orlando began telling me his story. He came to the United States from Cuba in 1991. Not on a plane. Not through a visa process. He paddled here in a small boat across the ocean.
For 10 days.
He and eight other people were in a small boat trying to make it across the water to the United States. Ten days in the open ocean, chasing the hope of a different life. A better life. At one point I asked him something that seemed obvious. "Were you scared?" He paused for a second and smiled. "No," he said. "I was a fisherman. Being on the water didn't scare me." What motivated him, he told me, was the hope of a new life.
Hope was stronger than fear.
Eventually they made it to Key West, Florida. But the story didn't suddenly become easy. When Orlando arrived, he was immediately picked up and taken to Guantanamo Bay. He stayed there for three years. Three years waiting. Eventually he was released to Miami, where he started the long immigration process. Today he's an American citizen, and you could see the pride on his face when he said it.
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As he talked, I kept thinking about what must have been happening in his life that made that journey make sense. Ten days on the ocean. Eight people in a small boat. The hope of something better strong enough to outweigh the risk.
Now listen, I believe systems matter. I believe immigration should have a process. But hearing Orlando's story reminded me that life is rarely, if ever, black and white. Sometimes people aren't just chasing opportunity. Sometimes they're escaping something far worse than we can imagine and unless we stop long enough to listen, we'll never understand that.
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A few weeks before meeting Orlando, I had another one of those moments. I hopped into an Uber and started chatting with the driver like I often do. Just normal small talk. Where are you from? How long have you been driving? Then he casually says something that makes me pause.
He had just gotten off Shark Tank. No joke.
So suddenly what I thought would be a quiet ride across town turned into a conversation about pitching a business in front of Mark Cuban and the rest of the Sharks. Right there in the front seat of an Uber was someone chasing a huge dream.
More to come on that story.
Then there was the guy sitting next to me on a plane. Within a few minutes I realized this conversation was going to be… different. He started telling me about aliens. About how we have to be careful what we say out loud because everyone is listening. You know those moments where you quietly remind yourself, Okay Justin… just stay present here.
So I mostly listened. And then out of nowhere he leaned over, kissed me on the forehead, and said: "It's good to see a fellow alien."
I'll be honest. That was a first, and if I am honest, I'm hoping it will be my last.
But that moment reminded me of something important too. Not everyone we meet is in the same place in life. Some people are chasing dreams. Some people are rebuilding their lives. Some people might be struggling with mental health in ways we can't fully understand.
Sometimes people just need someone to treat them like a human being for a few minutes.
Other times I've talked with someone who was clearly having a rough day. You can feel it in the way they sit, the way they answer a question, the quiet sigh between sentences. But if you stay present long enough, the conversation sometimes opens up. They talk about their kids. Their work. Something they're carrying. And sometimes the most powerful thing you can do is simply listen. And sometimes I say hello… and nothing happens.
Silence.
Two people sitting next to each other on a plane. And that's okay too. Because you never really know what someone needs in that moment. Maybe they need a conversation. Maybe they need encouragement. Maybe they just need quiet.
What's fascinating is that science actually backs this up. Researchers studying commuter behavior found that when people talked with strangers on trains and buses, they reported higher levels of happiness and connection than those who stayed silent.
Most people predicted the conversations would feel awkward. But the opposite happened. Even small interactions made people feel more connected to the world around them. Humans are wired for connection. Sometimes it just takes a simple hello to remind us of that.
Leadership and Curiosity
From a leadership perspective, I think there's something powerful here too. Great leaders are curious about people. They don't just look at titles or roles. They ask questions. They listen. They stay open to stories that challenge their assumptions.
Leadership isn't just about strategy. It's about understanding people.
And understanding people begins with curiosity. Listening to Orlando gave me perspective on immigration. Listening to someone share a difficult day reminds me that everyone is carrying something. Even the guy who called me a fellow alien reminded me that kindness doesn't require understanding.
It simply requires humanity.
The truth is, there are entire lives unfolding all around us. Dreams. Struggles. Fear. Hope. Joy. And most of the time we walk right past it all with our heads down.
I know I do.
But every once in a while, if you slow down enough to notice the people around you, you're reminded of something simple. The world isn't just happening to you. It's happening to everyone around you too.
And sometimes the person sitting right next to you has a story that might change the way you see the world. You just have to be willing to say hello. Maybe we've been wrong all along.
Maybe the world needs a little more talking to strangers.
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