Flying Lessons on Connection

I’ve always loved to fly. Not in the “I want to be a pilot” way, but in the “get me to the airport, let me people-watch, and let’s GO somewhere” way. There’s something exhilarating about waking up in one city and having dinner in another—like magic, but with seatbelts and tiny bags of (gluten free) pretzels.

My love affair with flying started in 7th grade. Back then, air travel felt like something reserved for the rich and famous or serious-looking business executives in power suits. So, naturally, I treated my first flight like a red-carpet event. I bought a pink suitcase and a matching outfit (because coordination is key when you’re entering high society at 12). When I stepped onto the plane, I was hit with the intoxicating scent of brewing coffee and the sight of flight attendants who looked like they had just walked out of a fashion magazine—perfect hair, bright lipstick, and an air of effortless sophistication. And the endless supply of free soda pop! Clearly, I had made it.

Fast forward to my son Jackson, who must have inherited my fascination with flying. From the moment he could talk, he was obsessed with airplanes. We fueled that obsession with model planes, books, and weekend trips to Hobby Lobby for yet another jet. At the age of three, he would camp out with his face pressed to the airport windows, confidently naming every airline as if he were an air traffic controller in training. "Southwest. American. Delta. Jet Blue." He dressed as a pilot for Halloween one year—and, he wore that costume past the point of embarrassment - for him and me!?

I think one of my favorite memories is the time he told a Delta captain, “I’m going to be a pilot for Halloween!” to which the captain replied, “So am I!” That moment—pure connection. A shared love of flight, a brief exchange between a wide-eyed little boy and a seasoned pilot, but an interaction that meant the world to him (and to me). Many pilots noticed his enthusiasm and invited him to sit in the cockpit before takeoff, his tiny hands touching the controls, his eyes lighting up like Christmas morning.

Airports, for me, have always been places of connection. Sure, some people see them as chaotic hubs of stress and overpriced food, but I see them as places where human stories intersect. Every gate holds a different story: a long-awaited reunion, a business venture, exciting new relationships waiting to begin. As I walk through the airport, I love to imagine where people are going and what awaits them on the other side.

As an executive leader, flying became a regular part of my corporate life. It was a way of life and in the beginning it was how my team and built connections. All of us traveling from different parts of the country to be together in solidarity. Swapping war stories of travel and grateful to be in person - eyeball to eyeball - heart to heart.

When I started my serious travel adventures, my brother gave me two critical pieces of advice when I started traveling for work: "Never get mad at flight delays" and "Never make plans with loved ones on the night you're supposed to arrive home." (Wise words that have saved me many times. - shout out Michael Henneberry - you are a sage.) Despite the countless number of flights I have under my belt (and the points to prove it), I've never lost my excitement for being in the air. Because for me, it was never just about the destination—it was about movement, progress, and the potential of who I might meet along the way.

In my coaching and leadership work, I talk a lot about energy and connection. The truth is, as humans, we crave connection. We are wired for it. Planes, quite literally, bring us together. They shrink the miles between loved ones, open doors to new opportunities, and remind us that we are never as far apart as we think. My son’s close bond with my mom—who lives in another state—is possible because of flight. The moments we get to spend together are worth every delay, every layover, and every turbulence-filled adventure. So as I head off to yet another destination I am excited by the new people I will meet and the new friends I will have when it is over.?

So yes, I love to fly. Not just for the thrill of takeoff or the view from 30,000 feet, but because flying is, at its core, about what truly matters: connection.