September 8, 2026 Jamie Michelson

The Mystery of the Single Shoe

I was running on the trail last weekend when I came upon a single shoe sitting in the dirt. Did someone literally get knocked out of their sneakers? The rest of my run was consumed by the mystery.

Was Barry Sanders running here recently? (For the football fans.) Was Joe Jackson stopping by? (For the baseball historians.) Was Florence Welch here? (For the music buffs.) Or was it Cinderella, in a hurry to make her midnight curfew? (I suspect that last one might yield a cease-and-desist from Disney.)

A single shoe—whether on a trail or on the shoulder of the highway—is jarring precisely because we expect two. Our brains just won’t let it go.

As business leaders, we live with one-shoe moments all the time. The prospect who ghosts us. The budget that gets halved. The meeting that ends without a next step.

The mystery isn’t why the shoe is there; it’s why we’re so quick to keep running past it.

So here’s the choice: stop and look for the missing half—or double-knot what you have and make sure nothing else comes loose.

P.S. Regular readers will notice this is the companion piece to my musings on sock heights and the economy. Consider this the missing half of the pair.