The Friends Who Aren’t My Type
I’ve had a handful of conversations this week about the kind of people I like to surround myself with, and they’ve all pointed toward a pattern I didn’t expect.
For years I assumed I gravitated toward men who were like me. This week I realized the opposite is true — and it’s infinitely more powerful. Sure, my closest friends and I share some common interests. But my best friends are different from me in almost every way that matters, and somehow that’s exactly why it works.
Sean
I’ve known Sean for 25 years. We’re nothing alike, physically or in personality. I’m the taller, outgoing one; Sean is quieter. He’s a badass engineer, the handy type who’s renovated his entire house from the studs up. I couldn’t change the oil on my 4Runner without a YouTube tutorial open on my phone.
We had lunch this week and got to talking about our friendship. I asked him if we’d ever had a real disagreement in 25 years. Not once. I think I know why: we’re not competing for the same ground.
Todd
Today I recorded a podcast episode with my friend Todd (more on that soon). Todd’s from Rochester, New York. I’m a Southerner — he called me a redneck today, which, is fair. Like Sean, we share a few interests, but beyond that we’re built differently. Todd is a whip-smart sales guru, second only to my older brother in my mind, and he’s willing to take risks at a level I’ve never matched.
Imagine having to shut down a business because your partner stole from you — and responding by throwing caution to the wind and chasing the next passion anyway. That’s Todd. He told me today those risks keep him up at night. But he also has complete faith he’ll figure it out, because that’s what he’s done his entire life. I wouldn’t bet against the guy.
If you’d asked me years ago, I wouldn’t have called either Sean or Todd “my type of guy.” Even with what we had in common, they didn’t initially feel like the men who’d end up as my closest friends. But it works. And I think I finally understand why.
Stephen
My other closest friend is Stephen, who I met at work when he became my boss. He was a great one. Years later, I became his boss, and working together turned into a real friendship. Stephen is easily in my top three friendships — a brother, the same way Sean is.
Stephen is Scottish by descent. He loves soccer, BBC shows, and travel above almost everything else. None of that is me. And I adore that guy anyway. The hard part is he lives across the country in San Diego, so we don’t get much time together — this past September was the first time we’d been in the same room in years, and those three or four days were glorious. They reminded me why Stephen is worth investing in for the rest of my life. He once backed me up when I was about to get in a fight — I didn’t even ask. He just lined up behind me, knowing things were about to come to blows.
Why it works
Sean, Todd, and Stephen all feel different from how I see myself. And yet they’re my closest friends in the world. Here’s what I think is actually going on:
It’s precisely because they aren’t like me that the friendships work. With almost every other guy I’ve tried to be close with, competitiveness eventually creeps in. My best friend from high school spent years essentially trying to become me — same car, same taste in women, the whole thing. On nearly every front except maybe sprint speed, where he had me beat, he couldn’t compete and I think that is what drove a wedge between us.
Sean, Todd, and Stephen don’t compete with me, and I don’t compete with them. On plenty of fronts, we simply can’t — my strengths are their weaknesses, and vice versa. We’re not fighting to be the best at the same thing. We’re bringing different things to the table.
It’s easy, in life and in business, to fall into the pattern of surrounding yourself with people just like you. It feels familiar, comfortable, safe. But it’s a trap — because people who mirror you can’t help you grow.
Sean, Todd, and Stephen were never “my type of guy.” Turns out they’re exactly the type I need — whether they’re down the road, out in Greeneville, or all the way in San Diego.
So here's the question worth sitting with: look at your closest friends. Are they there because they're comfortable, or because they make you better? If every one of them could be your reflection, you might not have a friend group — you might have an echo chamber.


