Talking To Strangers

The day of your next flight, I want you to observe the apps you spend the most time on. iMessage, X, Instagram - whatever that looks like for you.

But what if you just… didn’t?

What if you didn’t have those dopamine boosters and were instead forced to make conversation with the people around you.

Most of the really interesting people I meet are because of intros - either someone in my network surfaces one of these high velocity individuals to me or vice versa. But just because the distribution of individuals in my network are irregularly distributed with a strong bias towards tech, engineering, venture capital/ private equity and a few other relatively tight niches. Now, this is a good paradigm - I’m in a (tight) circle of people but what if I want to optimize for meeting new people.

I’m writing this on a four and a half hour flight to LAX from YYZ. While I’d usually use my time at the airport to hammer out emails, write a blog or do one of the numerous things on my never ending task list - I made a conscious effort to strike up a conversation.

In the 4 hour period I was at the airport, I met -

  • An actor/ writer who’d contributed something to the tune of 200 productions
  • A VP of sales for a company selling shock suspensions (most notably for race car teams)
  • An investment banking associate on his 47th flight of 2024
  • An performance marketing engineer attending a concert for an indie rock band which played live once every decade

The people I met were not highly curated. They were random individuals I just stumbled into.

These conversations were an incredibly refreshing change from the conversations I’m used to having and the thrill of getting into a conversation without knowing anything about their person.

My Uber driver from the airport graduated Summa Cum Laude from UCLA and scored a 175 in the LSATs but gave up the dream of law school because of the cost to attend even with an 80% scholarship to USC and started a long distance trucking company and drove Ubers in the off season.

Do I ever think I’ll bump into this Uber driver again? That’s statistically incredibly unlikely. But if asked if I’d rather spend that 30 min ride working on emails or listening to a podcast, I’d prefer that conversation hands down any day of the week.

If forced to introspect, I can accredit quite a few friendships in my lifetime to me saying hi to random people in random places - I met some of my best friends at gyms asking for a spot, coffee shops asking if they recommend I buy a specific piece of tech or once even starting a very heated conversation with them after accidentally bumping into them and striking up a conversation about an economic philosophy book they were reading. Now I can’t imagine my life without any of them.

So the next time you’re at an airport, a coffee shop, a hotel, a restaurant, a bar - compliment someone’s backpack, ask them about the book their reading, a podcast they’re listening to or just complain about Air Canada delaying your flight by almost 3 hours. You’ll surprise who you’ll meet.