The Departures Board

Picture this: You are standing in an airport. Not rushing, for once, you have a few minutes before you need to head to your gate. And instead of reaching for your phone, you look up.

There it is. The departures board.

Dozens of destinations, all at once. Cities you have been to. Cities you have always wanted to visit. Cities you have never even thought about. The board flickers and updates, new flights populating, times shifting. And for a moment, the whole world feels possible.

I have done this for decades, whether the actual departures board or watching each gate pass by and looking to see where that plane is headed. Thirty years of travel for work, luxury hotels, industry events, client meetings across the globe, and somewhere along the way, looking at the departures board or gate signs became a ritual. Not a formal one. Just something I do. I look up. I take it all in. I wonder.

Where is everyone going? What pulled them here, to this airport, on this day? What is waiting for them on the other side of that flight?

But lately, I have been standing at that board and asking a different question, not about the other travelers. About myself.

Am I flying toward the destination I actually chose or to a destination someone booked for me a long time ago?

You Have Put the Bricks Down. Now What?

I recently wrote about carrying bricks; about the mental, emotional, and professional weight we haul from one chapter of our lives into the next, and the quiet courage it takes to finally set some of it down.

But here is what comes after.

Once you have put down what you have been carrying, you must figure out where you are actually going. And that— that moment of open possibility, can feel just as disorienting as the weight itself. Because a lighter load doesn’t automatically mean a clear direction.

The departures board has always been, for me, a meditation on that exact feeling. So much possibility. So many directions. And the beautiful, terrifying reality that you have to choose.

Most People Are Not Flying — They Are Just On a Plane

Here is what I have noticed after three decades of watching organizations, leaders, and myself: most people are moving through their lives the way you move through a crowded airport when you are late. Head down. Focused only on the next gate. The next meeting. The next thing on the list. No time to look up at the board.

Someone else, a boss, a family expectation, an old version of themselves, booked the ticket. And they have been on that flight ever since. Not miserable, necessarily. Just…in motion. Moving without quite choosing.

The board doesn’t do that to you. The board just shows you. It doesn’t tell you where you should go. It doesn’t prioritize or judge. It simply presents what is available and waits.

That is an act of radical respect, if you think about it. Here are your options. The choice is yours.

In leadership, we talk a lot about vision and strategy, setting direction for teams and organizations. But we talk far less about the personal equivalent: pausing long enough to look up at your own departures board and asking whether the destination you are headed toward is still the right one.

Not whether it was right when you set out. Whether it is right now.

Choosing — Again, and More Intentionally

When I launched Keep Wondering Why, I made a choice. After thirty years in a family business with memories, relationships and accolades that could last a lifetime, I knew I needed to try something different. I was at a crossroads, and I chose a new destination.

But what I have been sitting with lately is this: launching something new doesn’t mean you have finished choosing. If anything, the early days of something new require more choosing, not less. More intentionality about what you take on and what you don’t. More clarity about the kind of leader, the kind of person you want to be as you build.

I find myself looking at my own departures board more honestly these days. Not just where am I going, but how am I going there? With what values? With what presence? At what pace?

The destination matters. But so does the way you travel.

We Have More Choices Than We Think

This is the thing I keep coming back to while standing at that departures board: there are always more flights than the one you are already booked on.

We live as though our options are fixed, as though the path we are on is the only path available. We inherited a direction, built momentum, and now the idea of looking up at the board and genuinely considering something different feels reckless. Disloyal. Naive.

But that is not what the board shows you. The board shows you that at any given moment, dozens of journeys are departing. Some of them are ones you have never seriously considered. Some are ones you quietly filed away as “someday.” Some are ones you didn’t even know were possible until you looked up.

You don’t have to rebook everything to acknowledge that. Sometimes it is enough to just look. To let yourself see that you have options. That you are not stuck, even when it feels that way.

Curiosity is what makes you lift your eyes in the first place. It is what keeps the departures board from becoming invisible, just another screen in a terminal you move through without seeing.

The Wondering

Think about the destination you are currently headed toward, professionally, personally, or both. Not the one you wish you were heading toward, or the one that sounds right when someone asks. The actual one. The flight you are on right now.

Ask yourself:

• Did I choose this destination, or did I inherit it?
• When did I last look up at the board, really look, to see what else is available?
• Is there a destination I have quietly filed under “someday” that might deserve a closer look?
• And, if I am on the right flight, am I traveling the way I want to? With intention, presence, and the values I actually hold.

Five Minutes at the Board

Find a quiet five minutes — no phone, no notifications. Take out a piece of paper or open a blank document.

In the first column, write honestly, not the aspirational version, but about the actual trajectory of your professional and personal life right now. The habits, the commitments, the defaults. Where does this path lead if you stay on it?

In the second column, write what you would put on the board if you were booking the ticket today, with everything you now know about yourself.

Then sit with the gap between those two columns. You don’t have to fix it right now. You just have to see it.

Seeing it is where every intentional journey begins.

My Intention

I am still a traveler at heart. And I have learned that the most important skill in any journey isn’t packing efficiently or knowing the fastest route through security.

It’s the willingness to look up and see possibility.

To pause in the middle of the movement and ask: Is this still where I am going? Is this still how I want to get there? And if the answer shifts,  be willing to rebook without guilt.

That is what I am practicing these days. Not more speed. Not more optimization. Just looking up more with curiosity, with intention, and with the quiet confidence that the board always has more options than I think.

The wondering continues.

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With curiosity,