The Conversations You're Not Having

I walked past a job fair on the University of Toronto campus last week. Banners, folding tables, students in blazers clutching CVs. Companies with clipboards looking for interns.

I didn't stop. But I slowed down.

Because I kept looking at the students who glanced in, did a quick mental audit of their qualifications, and kept walking. Not because the opportunity wasn't for them. Because nobody had told them it was.

A few days earlier my sister and I had been talking about university. About how, when we were students, there were internships and schemes and open doors we simply never heard about. It wasn't that we weren't qualified. We didn't know they existed. And other people, sitting in the same lecture halls, clearly did. They arrived already knowing which companies came recruiting, which programmes to apply to, when the deadlines fell. The information reached them and it never reached us.

I used to call that bad luck. I don't anymore.

A lot of opportunity moves through people, not systems. Job boards are the official record. The real thing tends to travel through conversation. The internship that turns into a job. The project that turns into a company. The introduction that changes what you thought was possible. It moves when someone says "I know someone," or "you should meet," or "have you thought about."

The question is whether you're in those conversations at all.

I've been thinking about how I got into them. It wasn't sudden, and it didn't come naturally. It's a practice I built slowly. Through the years after university. Through a long stretch in a job where I was quietly certain I would be found out. Through a lot of travelling. Somewhere across all of that I started talking to strangers, and kept at it until it stopped being something I had to steel myself for.

There was David, an investor I met at a climbing wall in Nairobi. We got talking between climbs, and I was candid about what I was chasing, even though I couldn't yet name it. He owed me nothing. But over the following weeks he made introduction after introduction, to founders I had no other way of reaching. One stranger on a wall, and a whole city opened up. I've written about where that went in The Stumble.

There was Ashish Sood, who I met over coffee at Sokkool, a co-working space in Bali. We fell into conversation one morning as strangers, and I had no idea he ran a venture fund until we were well past small talk. Then he introduced me to a collective of creators and builders I hadn't known existed. A whole world that had been invisible to me an hour earlier.

And there was Yelena, and her friend Mahmoud, who I met by chance in a shopping mall in Beijing. I don't remember exactly how it started. I think one of them asked about something I was carrying. We ended up talking for an hour.

Three countries. Three completely different rooms. The same small impulse underneath each one, and each one opened a door I didn't know was there.

Most people who hear this assume I find it easy. I don't.

I have a stutter. It's always there somewhere in the background. In the half-second before I speak. In the moment I choose a word because it's easier to say than the one I actually wanted. It makes starting a conversation carry extra weight. Not impossible. Just heavier than it looks from the outside.

What I have instead is curiosity. Real curiosity about people. Where they're from, what they're building, what they think about. And I've found that curiosity, when it's genuine, does most of the work. People can feel the difference between someone who wants to talk to them and someone who wants something from them.

But here's what I've learned from doing this across enough countries and enough rooms. The willingness to start a conversation is not evenly distributed. And it isn't about personality.

It's about permission.

Some people grow up in environments where talking to strangers is just what you do. Where curiosity across social lines is normal, modelled, unremarkable. Where they watch the people around them move through the world as if the room belongs to them.

Others grow up learning the opposite. That deference is appropriate. That unsolicited conversation is an imposition. That the person on the other side of the room, the senior one, the one who seems to already know everyone, is not someone you approach.

Culture shapes this. Class shapes this. Race shapes this. Whether you went to a school that surfaced certain opportunities and not others shapes this. Whether you grew up watching people who looked like you walk into rooms with ease shapes this.

The effect is that some people never try to start the conversation. Not because they can't. Because the idea that they should never occurred to them.

And the cost is invisible, precisely because the conversation that didn't happen leaves no trace.

I'm not going to pretend the fix is simple. "Just talk to people" is the self-help flattening of a structural problem. Access is real. Networks get built early, and often inherited.

But there is something worth saying to the person standing outside the room, capable, unsure whether they're allowed in.

You are. The conversation doesn't have to be perfect. It doesn't need a brilliant opening line. Curiosity is enough. Most people, when someone is genuinely interested in them, will meet you more than halfway. The ones who don't were never going to be worth the weight you'd have given them.

And there's a harder thing to say to the rest of us, the ones already in the room. If you're the person others come to for an introduction, some of this is yours to carry too. The conversation that never happens isn't only theirs to begin. You can be the one who notices someone at the edge and says the name. It usually costs you nothing. Now and then it changes everything for them.

I walked past that job fair and thought about a younger version of myself. Less sure. Less practised. Convinced that confidence was something other people had been handed and I hadn't. I don't know exactly when that changed. It wasn't a single moment. It was slow, and it took years, and a climbing wall in Nairobi, a coffee in Bali, and an hour in a mall in China were only the most recent proof of it.

I also thought about my sister, and the internships neither of us heard about. We weren't unqualified. We just weren't in the conversation.

So start it. Not because it's easy. Because the ones you don't start are the ones that haunt you.