Plans Rarely Go As Imagined: What a 17-Hour Travel Day Reminded Me About Leadership

It's 5:00 AM. I'm standing in the Ithaca airport with my kids, sleepy eyes, boarding passes in hand, and ready for the first leg of a three-flight journey to Montana. I had a plan. I'd built in buffer time. I knew our gates, our layovers, our seats. And then the text came: the middle leg of our trip, the second of three flights, was cancelled. The text came as we were boarding our first flight, so we didn't have much time to process or think through our options.

That was the first domino of the day. It would not be the last.

The Plan Meets Reality

The gate agent's advice was a bit unsettling: get on the first flight anyway, fly to DC, and sort out the rest once we landed (because, they noted, it would be easier to rebook from a major hub than from Ithaca). They also assured me they would try to work out an alternative for us while we were in the air. So we boarded a flight not knowing what we'd learn when we landed, trusting that motion was better than staying stuck.

We landed in DC to find we'd been rebooked onto a flight leaving five hours later, with no seat assignments, and instructions to check with the gate agent to get our boarding passes. However, with 5 hours to spare, there was no gate agent for our flight, and none of the other gate agents were able to help us. So we sat at the gate and waited. And waited. When the gate agent finally showed up, she was overwhelmed, and said she was not to help yet. "I'll call your name when I'm ready for you," she said. So we waited more.

But then boarding began and she hadn't called my name and we didn't have boarding passes. I went back up to check. And that's when I learned the real situation. After waiting 5 hours at the gate, I learned we weren't actually confirmed on this flight. It was overbooked. She said "I don't know why they put you on this flight". She told us we had to keep waiting and she would “try to work something out”. I saw her offering other passengers alternative flights, but didn’t see anyone bite. We waited until everyone was boarded, until the last calls were made. And somehow, at the final moment, we made it on. We were the first people at the gate that day and the last people to board.

Our new flight landed in Chicago, with a connection to Whitefish, MT that was tight but doable. And then the jet bridge broke. We sat on the plane, doors closed, unable to deplane, watching our connection window shrink by the minute. When we finally got off, we ran, from terminal to terminal, to make our third flight. And just barely, we made it to the gate…only to then sit on the tarmac for another hour waiting for takeoff clearance. Eventually, we did get up in to the air.

Despite all that stress and uncertainty, we made it to our final destination, the same day as planned, only four hours later than expected. We were exhausted from 17 hours of travel and all the ups and downs of the adventure. But my kids and I were together, in the beautiful state of Montana, and most importantly, we were safe.

What This Has to Do With Leadership

I didn't set out that morning thinking about leadership. I was thinking about gate numbers and snacks and plane activities for my kids. But somewhere along the way, it hit me: this is exactly what leadership feels like on the hard days.

As leaders, we plan. We need to plan. We build a vision, develop timelines, budgets, contingencies. Planning isn't the opposite of adaptability; it's the foundation that makes adaptability possible. Leaders aren’t supposed to just skillfully improvise their way through chaos with no structure at all; and at the same time, the plan is not the full picture. The plan is a hypothesis about the future, and the future rarely cooperates exactly as expected.

What separates leaders who navigate disruption well from those who get swallowed by it isn't just the quality of their original plan. It's what happens in their body and mind the moment the plan breaks. It is their capacity to navigate uncertainty with a regulated nervous system so they can adapt and keep their team focused.

Your Nervous System Is a Real Leadership Tool

Every one of those moments in the airport — the cancellation, the uncertain boarding, the overbooked flight, the broken jet bridge, the sprint, the tarmac delay — was an invitation to spike into fight-or-flight (pun intended!). And each time, I noticed the pull: the tightening chest, the sensation of something bubbling inside me, the urge to raise my voice at a gate agent who delivered the bad news but didn't cause the problem, or the temptation to catastrophize in front of my kids about whether we'd get there at all.

Leadership in uncertainty isn't about eliminating that activation. It's about noticing it, naming it, and having enough somatic awareness to come back into your body before you react. Viktor Frankl reminds us that "Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom." And so I reminded myself to lean into that space. I took a few slow breaths at that gate. I counted in my head, to ensure my breath out was longer than my breath in. I felt my feet on the floor while I waited. I imagined being connected to the earth. I reminded myself that my kids and I were safe. I named out loud to my kids, "Yes, this is frustrating, and we're going to find a way through it," not because I was certain of the outcome, but because I needed to regulate myself in order to help them regulate too.

That's a big piece of the real work. Not eliminating uncertainty. You can't. Not having a backup plan for every possible failure point. You can't do that either, no matter how experienced you are. The work involves building the internal capacity to stay clear and calm enough, amid setbacks and unknowns, to make the next good decision. And then the one after that.

By the time I took the above photo on Main Street in Bozeman, the travel ordeal was already behind me. No longer important, the memory had faded, replaced by the simple pleasure of an old yellow truck rumbling past brick storefronts on a sunny afternoon. We were just here now, enjoying Montana.

Leading From the Runway, Not the Itinerary

Here's what I keep coming back to: my kids won't remember the original flight itinerary. They may remember that we ran through an airport together and made the flight. But they will definitely remember our time in Montana. I hope they will also remember that when things fell apart, I didn't fall apart with them. That's not because I'm unshakeable, I'm certainly not. It's because I've spent time building the somatic awareness and reflective practices that help me find my footing when the ground moves.

That's what I want for the leaders I work with, too. Not leaders who never get thrown a canceled trip, broken jet bridge or an overbooked flight, because every leader will. But leaders who've done the internal work to meet disruption with a regulated nervous system, clear presence, and the humility to adapt the plan in real time while staying grounded in their values and remaining connected to their team.

So here's my invitation to you: think back to your own broken jet bridge, the partnership that stalled, the funding that fell through, the restructuring that was imposed upon you, the plan that fell apart in front of your team. What did your body do in that moment? Did you notice the space Frankl describes, or did you move straight from stimulus to reaction?

You don't have to figure this out alone, and you don't have to wait for the next crisis to start building the capacity to meet it well. If this story stirred something in you, I'd love to hear about your own version of it, and I'd love to talk about what it might look like to help you build somatic practices into your leadership practice. Reach out, and let's have that conversation.

Learn more about my services here: https://www.healplaylead.com/work-with-me.