Who Tells Your Story?

Chicago doesn’t let you stay on the surface for long.

We set out that morning with a question that sounded simple at first: what makes something last? In small groups, we embarked across the city, from Millennium Park, across the river, and toward Navy Pier, looking for something monumental, something ephemeral, power in a public space, and even absence. But the goal wasn’t really to find these things. It was to understand why they existed, who they were for, and what they meant.

The decades-old architecture stood out immediately, not just for its beauty, but for the intention behind it. At the same time, we kept noticing what was quieter. The stories and people that weren’t as visibly represented.

As Claire Aicken of the San Diego County Department of Agriculture, Weights and Measures put it: “Exploring Chicago challenged us to move past the visible and engage with the underlying aspects of the community. It made me realize that as leaders, our choices today can have ripple effects that persist long after the choices we make.”

Chicago feels layered. Things aren’t built once, they’re rebuilt, reinterpreted, and carried forward, while other things quietly fade away.

Sitting Still Long Enough to See Something

The afternoon slowed us down in the best possible way.

Inside the Art Institute of Chicago, the assignment was simple: choose one piece, sit with it, and notice what it made you feel before reading anything about it. It sounds easy, but it isn’t. We’re so used to moving quickly that sitting still long enough to really see something feels unfamiliar. What stood out was how often our interpretations didn’t match what the artist intended, but that gap didn’t diminish the experience. If anything, it made it more honest.

One piece that sparked real conversation was a collection of hieroglyphics from an ancient Egyptian village called the “Place of Truth” – a community of artists who lived and worked specifically to build and decorate royal tombs. Even thousands of years ago, systems existed to support people whose skills were considered worth sustaining. What we choose to value, and who we invest in, has always shaped what endures.

As Josh Enos of Carriere Farms reflected: “Whether it was Van Gogh, Lichtenstein, or something completely unfamiliar, everyone found something that felt personal and moving.”

What lingered wasn’t just the art itself, but the realization that everything in that building exists because someone decided it was worth preserving. Which naturally leads to a harder question: what didn’t make it there? Whose voice was never given the chance to last?

Leadership as a Creative Act

That question carried straight into the evening, when we had the unique opportunity to experience Hamilton. After a day spent thinking about permanence and absence, it landed differently than it might have otherwise. The story held the tension we’d been sitting with all day: who tells the story, and who gets left out?

One moment seemed to settle over the whole group, a character asking, simply, “Do they know how hard it is to lead?” It didn’t feel rhetorical. It felt like a weight everyone in the room recognized.

Natalie Collins of the California Association of Winegrape Growers put it into words: “It made me think about what it would have looked like if more voices were included when our country was being built, and what that means for the systems we’re part of today.”

Leadership, we realized, is a creative act. The choices we make, the people we bring along, the voices we elevate, all of it becomes part of a story that will eventually be told without us in the room. Things don’t last by accident. They last because someone built them with intention and believed they were worth carrying forward.

And at some point, whether we’re ready for it or not, we won’t be the ones telling that story anymore.

What we’re really building isn’t just systems or outcomes, it’s legacy. It raises a question that’s hard to ignore: when we’re gone, who will tell our story, and what will they say? Will they see something that included others, created opportunity, and reflected intention? Or something that left voices out and faded without meaning?

So the question we left Chicago holding wasn’t just what makes something last? It was this: what are we creating right now, and what will it say when it does?

With gratitude,

Claire, Natalie, Josh, and Class 55