Trekking Life’s Pedway

The other day, while working in Downtown Chicago, I found myself in desperate need of movement after spending all morning glued to my computer screen playing email Tetris with my inbox. In search of both a stretch and a snack, I decided to take the Chicago Pedway from my office east of Michigan Avenue into the heart of the Loop. For those unfamiliar, the Pedway is a maze of corridors where you can travel blocks without ever stepping outside—an absolute gift on a frigid day.

It's oddly reassuring to retrace steps through a familiar labyrinth of hallways. As I walked, I wondered how many times I had followed the same path through these corridors—commuting to and from the Red Line, stopping by the Hyatt’s underground concourse to pick up a print job at the now-closed Hotel Copy Service, or grabbing lunch with a friend at the long-gone Marshall Field’s cafeteria. The stairs are worn, the floors polished smooth by years of foot traffic, yet other walkers rarely seem to notice.

"The Official Route"

When I work from home, I’ve found after lunch walks have become my local personal pedway. The first time I walked my chosen route to Merrimac Park, I unintentionally declared it "The Official Route™." Any deviation now feels like a betrayal of an unspoken agreement. It’s not about exercise or even the scenery—it’s about commitment. This is the path, and changing it would feel like admitting defeat.

I love the unexpected moments of human connection during these strolls. We’re all wandering through life with our own internal GPS (some more calibrated than others), and when our paths cross—whether in a deserted concourse or the middle of a park—I like to acknowledge our shared existence with a smile, or at least a mutual look of “What are we doing out here?” (more on this in John’s recent blog). Over the years, I’ve come to know a number of security guards, letter carriers, dog walkers, and maintenance workers, their familiar faces becoming part of my daily routine. The only ones I struggle with? Those oblivious walkers glued to their phones, completely unaware they’re about to collide with reality.

There’s something poetic about how men take the same routes every day—walking the same sidewalks, climbing the same stairs, turning the same corners—while the world around us constantly shifts. Buildings that once seemed permanent disappear overnight, replaced by sleek glass towers or, just as often, an empty lot waiting to become something. Saplings grow into tall trees and are cut down to make way for the next development. Recently, the café where I grabbed coffee for years suddenly closed, its windows covered in brown kraft paper as if the past itself has been packed away.

We stick to the same routes—not just out of habit, but because they give us a sense of continuity. Greenland Sharks have been swimming familiar waters for centuries, and honestly, I like knowing I share that kind of commitment. Our journeys, while diverse and filled with unique encounters, often take us in different directions, influenced by the ever-changing tides of life. Yet no matter how far we wander, we always seem to end up at the same familiar destination—a place that feels like home, rich in memories and a sense of belonging.