What Chicago Leaves Behind

Chicago is not a city that lets you leave untouched. It has too much to say, too many layers to press into you before you go. By Thursday morning, after three full days of walking its contradictions, Class 55 gathered one last time to do what the city had been teaching us all week: look carefully, name what we saw, and sit with what it meant.

In six small groups, we presented three photos and three words that captured our experience of the city. Then a full circle, every fellow sharing a leadership insight they were carrying out of Chicago, and how they might lead differently because of something experienced here.

What We Saw

Each group had named their experience differently, but the words kept finding each other. Disparity appeared twice. Resilience and resilient appeared in two more. Words like stratified, layered, enduring, and intentional pointed in the same direction: toward a city that does not resolve its contradictions so much as build on top of them.

Chicago is a city written and rewritten over itself, home first to the Potawatomi, Ojibwe, and Odawa peoples who gathered at the place they called Checagou, then remade by settlers, raised from a swamp, razed by fire, rebuilt in a generation, then layered again with covenants and redlines and expressways that told certain people, in the language of infrastructure, exactly where they stood. If you looked carefully, you could still read it all in the city we walked this week.

Earlier in the week, we had been sent out into the city with a charge: find the monumental, the ephemeral, framed perspective, power in public space, and absence. The photographs our groups brought back told the story of a city in full. Tulips in bloom along Michigan Avenue. A church entrance bearing a sign that all are welcome. Public art splashed across walls and plazas. The skyline seen from the Ferris wheel at Navy Pier, the city spreading in every direction, vast and indifferent and alive.

And some images arrived in the gaps between the grand ones. A place where the city splits into two levels, an upper road in full sunlight, open and clean, and a lower road running beneath in shadow. No sign marks the difference between them. None is needed. The architecture does the work quietly, as it always has. And a photocopied flyer, taped under a bridge: a photograph of a young woman, her name, and two dates, 2002 and 2025. Twenty-three years. Someone had made this by hand and put it somewhere the city would keep moving past.

What emerged across all six presentations was not a single verdict on Chicago but a shared willingness to hold its complexity: to name disparity without despair, and resilience without sentimentality.

Slow Down and See

The day before, at the Art Institute, we had been asked to find a work we were drawn to and observe it for two minutes before reading anything about it. No label, no context. Just looking. Henri Matisse’s Jazz was on exhibit, those vivid cut-paper compositions made at the end of a life marked by illness, loss, and war, shapes so saturated with color they seemed to push back against everything that had tried to diminish him.

Chicago asked us to do this again and again: to slow down, to be present with our own observations before rushing to judgment. To look at a contradiction and sit with what it meant before explaining it. To remain in curiosity and discomfort long enough to feel something before reaching for a conclusion. As we learned earlier in the week, this is the prerequisite for understanding anything durably. Observe before concluding. Diagnosis before prescription.

Turning the Page

By early afternoon, Chicago was behind us.

Captains Jordan Albiani, Omar Gonzalez-Benitez, and Jon Neugebauer moved twenty-four fellows and three faculty through a complex travel day with calm efficiency, which is, of course, its own form of leadership. O’Hare to Reagan National, luggage to Metro, Metro to the Hyatt House in the heart of the nation’s capital. The group was organized, unhurried, and good company.

In the lobby, before dinner and the evening on our own, we gathered briefly. The message was not complicated: our time in Washington will ask something different of us. Lean into the things that make you uncomfortable. We also carry a new quest into this week, a question to sit with as we move through the capital: what has this seminar changed about how you understand leadership?

Chicago showed us systems, how they accumulate, how they stratify, how they persist beneath the surface of things. Washington is where systems get made and contested and remade. For eighteen of us, a familiar skyline. For six, a first impression. For all of us, new territory in the ways that matter most.

What Chicago revealed, and what we carry forward, is that leadership is rarely simple or static. It is dynamic, evolving, and shaped as much by what sits beneath the surface as what is visible in front of us. Proximity matters. The closer we get to people, to place, to lived experience, the more complex our decisions become, and the more necessary it is to resist oversimplifying what are, in truth, deeply layered challenges.

We saw how easy it is to reach for practical solutions to complex problems without fully understanding the systems and histories that produced them. But with the right perspective, and the willingness to sit in that complexity, we can begin to recognize what is actually needed. Leadership, in this way, is not about having immediate answers. It is about cultivating the awareness and engagement required to ask better questions.

That begins with invitation. If we do not actively invite engagement, we risk reinforcing absence, missing voices, missing stories, missing insight. Pride can close us off or open the door; when grounded in humility, it becomes a pathway to deeper connection and shared ownership.

Context matters too: the histories, lineages, and narratives that shape the present. Who tells the stories matters. Whose stories are told matters even more. As communicators and leaders, our role is not simply to build and share content, but to ensure we are not leaving out those who are closest to the work yet furthest from the conversation.

Building community requires intentional outreach, especially toward those not already in the room. There is value we cannot see if we do not create space for it. And often, what we need most will only emerge when we take the time to invite it in.

What We’re Carrying

Chicago did not resolve its contradictions for us. It showed them clearly, in stone and shadow and things left behind, and asked us to sit with them long enough to actually see. We leave having added layers to our own understanding, of this city, of these systems, of ourselves as people who move through places and are changed by them.

Class 55 extends our gratitude to captains Jordan Albiani, Omar Gonzalez-Benitez, and Jon Neugebauer for their steady leadership through a long travel day. Thank you to Dr. Dane White, Judy Sparacino, and Dr. Casey DeAtley for the framework that made five days in Chicago so much more than a visit. We came to understand. We are still working on it.

With gratitude,

Casey Kirchhoff, Kiaran Locy, and Logan Robertson Huecker & Class 55