The Airport Bar and the 18-Year Gap

Original article created for Substack on 3/07/2026

What Going Home Teaches You About Leadership

By the time you read this, I’m in Poland.

I’m somewhere between a family dinner table and an emotional time machine, sitting with people I haven’t seen in 18 years, watching faces I knew as a child now etched with life, laughing at stories I’d half-forgotten, eating food that somehow still tastes exactly like I remembered.

But let me start at the airport. I always seem to start at the airport.

 A few months ago, I posted something on LinkedIn from an airport bar as I was heading to Chicago. Pre-flight drink in hand, heading to see old friends, I wrote about how airports give me this feeling I can’t quite shake: anticipation, possibility, movement. About how every person around you is in transition, heading somewhere new, leaving something behind. And how that mirrors almost exactly what happens inside organizations during mergers, acquisitions, and major change.

The post resonated. A lot.

But here’s what I didn’t fully say then, and what I understand better now, sitting in a completely different kind of airport, on a completely different kind of journey:

There is a version of transition that isn’t about going somewhere new. It’s about going back.

And going back, it turns out, might be the most clarifying thing a leader can do.

What 18 Years of Distance Does

I’ve been building Anthilles Consulting , working with executives navigating transformation, helping organizations bridge the gap between bold vision and human reality on the ground. I spend a lot of time thinking forward. Anticipating what’s next. Helping clients move.

So this trip wasn’t just personal. It was a kind of confrontation with my own origin story.

When you go years without seeing certain people, your memories quietly calcify into a version of them that feels permanent. The aunt who seemed impossibly old when you were a kid. The cousin who was five and still somehow running circles around everyone. The house that felt enormous. The neighborhood that seemed like the whole world.

You keep that snapshot in amber and build your identity partly on top of it, without ever checking whether it still matches.

And then you show up. And someone who was a child is now a fully formed adult with their own children. And the aunt is still there, smaller maybe, but with the same laugh. And the house is fine, but you realize the enormity was never about square footage.

The world didn’t freeze. You were just far away. 

Why Leaders Stop Going Back

Here’s what I’ve noticed in the executives I work with: somewhere between the climb and the arrival, many of them stop looking behind them.

And I don’t mean this in a sentimental “remember your roots” way, I mean it practically.

The higher you rise in an organization, the more you optimize for the next thing. The next quarter. The next acquisition. The next phase. There is enormous pressure on leaders to maintain forward momentum, to project confidence, to not look like you’re dwelling.

But there’s an enormous cost to never returning to the baseline.

When was the last time you went back to your frontline not to inspect, but to genuinely remember? When was the last time you sat with someone three levels below you and tried to feel what the organization felt like from their vantage point? When did you last revisit why you got into your industry in the first place not in a speech, but in the quiet of your own honest reflection?

The executives who navigate transformation best, and I mean the ones who actually land their organizations in a better place than where they started, are almost always the ones who can hold both. Forward vision and backward clarity. Where we’re going and where we came from.

 
The Airport Is Not the Destination

I love airports. I’ve come to love them the way I love in-between moments, conversations that happen on long drives, confessions that come out during layovers, realizations that arrive when you’re too tired to filter them.

There is something about being suspended between places that creates an unusual kind of honesty.

In transformation work, I call this the transition gap, the space between when an organization announces a change and when that change is actually lived by the people inside it. Most leaders rush through this gap. They want to close it fast, get to the other side, declare success.

But the transition gap is where the real work happens. It’s where people decide whether they trust you. It’s where culture either holds or fractures. It’s where the distance between what leadership said and what people actually experienced becomes visible.

You can’t shortcut it. You can only be present in it.

Reconnecting with family I haven’t seen in 18 years, there’s a transition gap here too. Eighteen years of unexperienced shared life. Eighteen years of change on both sides of the gap. The only way across isn’t a plan. It’s presence. It’s showing up and being willing to meet people where they actually are, not where your frozen memory placed them.

That’s leadership too.

 
What Going Home Teaches You That Going Somewhere New Cannot

New destinations are exhilarating. New markets, new roles, new strategic directions, there is real value in the energy of the unfamiliar.

But returning somewhere teaches you something different. It teaches you what has genuinely changed versus what you only believed had changed. It shows you which values survived the distance and which ones you quietly abandoned for convenience. It lets you measure yourself not against an imagined future self, but against who you actually were.

That kind of feedback is hard to get anywhere else.

At Anthilles, a lot of what I do is help leadership teams see their organizations with fresh eyes, the kind of eyes that neither idealize nor dismiss, but just see clearly. It turns out that clarity is a skill. And one of the best ways to practice it is to return somewhere you thought you already knew.

The organization you’ve led for seven years. The client relationship you’ve managed for a decade. The team you promoted through three cycles. When did you last really look?

 
The Drink at the Bar, Revisited

Back in December, sitting at that Chicago airport bar, I wrote about how frontline employees are all sitting in their own version of the airport wondering: Where am I going? What happens to my career? Will I matter there?

I still believe that. I still think the most underrated skill in organizational leadership is the ability to translate vision into personal relevance for every person who has to carry it out.

But I’d add something now:

The best leaders I know don’t just know where they’re taking their people. They know where they came from. They remember what it felt like before they had the answers when they were the one sitting in the departure lounge, uncertain.

That memory isn’t weakness. It’s the compass that keeps you honest about what transformation actually costs the people inside it. And it’s the thing that makes you, in the end, not just a strategist, but someone worth following.

 
I’ll be back home soon.

Filled up with pierogi and old stories and the particular exhaustion that comes from feeling something you didn’t know you’d been missing.

And I’ll sit back down at my desk, back to the work of helping executives build organizations that move forward, carrying all of it with me.

The airports. The return. The 18 years in between.

Because it turns out the best preparation for helping others navigate transition isn’t always knowing the destination.

Sometimes it’s being willing to make the trip home.