A little while back, I shared a flight home with members of my Charlotte based team. As we regrouped in the terminal at Charlotte Douglas Airport, I mentioned a fascinating conversation I’d had with the gentleman sitting beside me.
One of my teammates looked at me and laughed.
“Wait ... you talk to people on a plane?”
My longtime business partner and cofounder, Kirk, couldn’t resist the opportunity to land a subtle jab.
“Are you kidding me? You should hear the random conversations this guy finds himself in.”
This specific team was, and still is, a lovable group of shit talkers, so the friendly chirping was both expected and welcomed. I smiled.
“Absolutely. There are always unique inflight opportunities.”
Many years ago, my father gave me a piece of advice that has stuck with me ever since. If I remember correctly, I believe it originally came from my grandfather.
“Always dress sharp on an airplane.”
Naturally, young and naive, I asked why.
“Because you never know who you may share a row with.”
For whatever reason, that simple advice never left me.
Spend enough time in airports and on airplanes, and you begin to notice things you never used to. One of those things is that people dress like slop-tarts.
Borrowing from my grandfather’s advice, I still ask the mirror a few questions before leaving for the airport.
What does today’s inflight attire say about me? What do I need it to say? Is it professional enough if I happen to get bumped to first class?
For what it’s worth, I refuse to pay for first class. That said, I often find myself sitting there thanks to airline status earned from years of travel.
And somewhere along the way, I’ve realized “dress sharp” doesn’t necessarily mean dress formal. Sometimes it’s fitted jeans, a clean black T-shirt, and my timeless checkerboard Vans. Other times it’s trousers, a wool sweater, and boots.
The common thread is intention.
Ironically, I’ve also noticed the casual version can create more curiosity in first class, while the more polished version can do the same in the main cabin.
What’s the 45-year-old guy doing in checkerboard Vans?
Why the hell is this guy dressed so proper?
Different questions. Same curiosity. And both often lead to the same outcome: conversation.
I never lead the dance. But I’m happy to engage.
Here’s how I see it.
For a few hours at 35,000 feet, social barriers get strangely rearranged.
You’re sitting beside a complete stranger. They know nothing about you, your line of work, or your story. They didn’t click on your website. They weren’t referred by a trusted friend. And they aren’t whoring themselves out to your inbox because of some clever AI algorithm.
They simply happened to book Seat 4F, and you happened to get upgraded to 4D.
Every flight presents a puzzle, and I love these rare opportunities.
People often assume it’s about selling.
It’s not.
These aren’t sales calls. But they are live reps.
I’ve found that even the smallest amount of trust starts with curiosity. That usually begins with a simple icebreaker, followed by thoughtful questions and genuine interest. You listen more than you speak. You learn about their story, their perspective, and their interests.
Only then do I feel like I’ve earned the right to share a little of my own.
And even then ...
There’s a very good chance they aren’t buying. That’s perfectly fine.
The point was never the sale.
The point was the puzzle.
These random conversations have led to unprompted dinner reservations, concert tickets, introductions to interesting people and places, and even opportunities for businesses I’ve been involved with.
But that’s probably the least interesting part.
They’ve also exposed me to perspectives I wouldn’t otherwise hear and stories completely different from my own. And somewhere along the way, all those live reps have made me increasingly comfortable talking to just about anyone.
Somewhere around 35,000 feet, everyone becomes briefly accessible.
Every flight is a room you’ll never be invited into again.
You never know who you’ll share an armrest with.
Or what you’ll learn from them.
Brandon Cullen
In search of life’s [im]perfect soundtrack ...