Gate Checked

There’s a moment, typically the night before a trip, when I glance at everything spread out before me and think… this used to be so simple.

I used to catch the 5:30 Delta Shuttle to Boston and arrive at the old Marine Terminal at LaGuardia with minutes to spare. My rule was that if I didn’t miss an occasional flight, I was spending too much time at the airport. Think of OJ back when he was still a Hertz spokesman. Not the guy he became.

Now it’s a process.

Travel, for me, starts well before I leave the house. It’s the extra gear, backup supplies, and the mental checklist: Did I pack what I need, and what I might need if something goes sideways?

Because things do go sideways.

Getting through the airport isn’t just about time anymore. TSA isn’t a line I walk through; it’s a stop. A process. They check every inch of me, then the chair. Swab, scan, questions. Everyone’s doing their job, and I respect that. But it takes time, especially when they have to pull someone off break to handle it.

The airlines prefer I board first, before the crowd fills in. There’s a choreography to it: transferring into the aisle chair, watching mine disappear down the jet bridge, trusting it will be there when I land. And when we land, I wait.

Everyone else is up, grabbing bags, and moving on with their day. I stay put until the aisle clears, until my chair comes back up, until my chair is brought back up. First on. Last off.

Then it continues. The car needs to be large enough for the chair, which sometimes means waiting. The hotel has to work, though “accessible” can mean many different things depending on who’s defining it. Thick carpeting that looks great in the lobby feels like quicksand. Long hallways. The accessible room is rarely near the elevator. The beds aren’t lower. The doors are heavier than they need to be. It all adds up.

Dinner the night before speaking with long-time but definitely not old friends

All of that was on my mind earlier this week as I prepared to head to Atlanta, where I had been invited to speak at the National Association of Benefit and Insurance Professionals Forum Day. They asked me to share my story and what I’ve learned about risk, disruption, and what happens when the standards we rely on fall apart. It’s a message I want to share, even if it takes more from me than it used to.

While packing the night before, I overlooked how simple it once felt.

Still, I’m glad I made the effort.

Because amid all that friction, planning, waiting, and extra effort, there’s still that sense of movement, of going somewhere, of not being stuck.

I felt it moving through the Atlanta airport, even at my pace. Not exactly the same feeling I used to have, but still living it. A reminder that life isn’t limited to one place.

There’s more to consider, but the main idea stays the same. Showing up in new places. Reconnecting with old friends. Engaging with people and ideas outside your daily routine. It takes more effort on my part to make it happen.

Maybe that’s the tradeoff: less convenience, more awareness; less ease, more appreciation.

Thank you, Don Schamay, for making it all happen

I no longer take travel for granted like I used to, when it was just part of the routine: flights, meetings, hotels, repeat. Now, every trip demands something from me, but it also gives something back.

A reminder that even when the path becomes more complicated, it doesn’t have to get smaller. That movement and showing up still matter. And that freedom, however it looks and how much effort it takes, is still worth the trip.