The Moment I Realized Shallow Understanding Runs Deep
Most lessons don’t announce themselves. They slip in quietly, disguised as something forgettable—a stray comment, a half-formed idea, a meeting you almost slept through.
This one arrived on a gray Monday morning, months before I ever imagined riding the Tour Divide or rebuilding myself mile by mile. Back then, I was holding the pieces of my life together the best I could. My body hurt constantly. My mind was stretched thin. I was working hard but not always wisely, and I had only the faintest hint of the language needed for the deeper shift that was coming.
Then came the Culture Pass.
It surfaced during a senior leadership meeting—one of those mornings when the screen glows brighter than you feel, the dogs bark at absolutely nothing, and you sip lukewarm tea because somehow you’re already behind.
Darin, our CEO—sharp, caring, intellectually earnest—came in energized. He’d been thinking all weekend, and you could feel it. He described the idea: give our members access to museums, concerts, cultural events. Something enriching. Uplifting. Affirming. A gesture of dignity. A marker of care.
And it made sense. A handful of members had said they wanted more activities and outings. Not many. Not loudly. But enough that you could build a story around it if you wanted to.
Maybe that was the problem: the story came too easily.
I remember the little choreography of alignment that happens instinctively on Zoom: people leaning in, nodding, smiling in that way that signals “I’m with you” even when they’re still trying to understand where “with you” is.
It would have been easy to nod too.
Move fast. Turn a suggestion into a narrative. Turn a narrative into a strategy.
But something felt off. Not dramatically. Just...off, like a single string out of tune in an otherwise stable chord.
I sat with it.
Then I said, “I think we should slow down. I’m not sure the logic holds across the populations we serve.”
The room paused. Not a heavy pause—just a subtle shift in momentum, the kind that reveals speed is not the same thing as progress.
The idea didn’t die. It simply exhaled. It went from “this is obviously the right thing” to “wait…what are we actually seeing?”
And that was enough.
I didn’t know it then, but that morning would become one of the small turning points I carried with me into later seasons of my life. A moment that taught me something I would need months later, when I decided to ride the Tour Divide and rebuild myself from the ground up:
Shallow understanding is the easiest kind to trust, and the most dangerous kind to follow.
Nothing in that meeting was malicious. No one was careless. Everyone was acting in good faith. And still, the idea drifted away from reality faster than anyone noticed.
Why?
Because momentum is seductive. Alignment feels moral. A good narrative can outrun the truth by miles.
And because it’s easier to believe we see clearly than to admit we might be wrong.
In the months that followed, I kept returning to that morning—not because the Culture Pass was a bad idea, but because it revealed something truer:
We were responding to the surface of what we heard, not the depth of what our members lived.
They didn’t need concerts. They needed something harder to name. Something structural. Something deeper.
I hadn’t yet fully formed the language for this then—not the systems, incentives, and constraints that shape behavior in the real world. I hadn’t begun rebuilding my life or my body. I hadn’t started training again. I hadn’t dreamed of mountain passes or long gravel miles or the version of myself I’m trying to become now.
But that morning planted the seed.
A lesson I wouldn’t fully understand until much later:
The difference between shallow and deep understanding isn’t intellectual. It’s moral. It’s about attention. It’s about the discipline of seeing the world as it is, not as we wish it to be.
Tour de Ken, in many ways, is my attempt to live by that discipline. To train in it. To build a life around it.
Not just on the bike, but everywhere—at work, in my relationships, and in the quiet parts of my mind where the real conversations happen.
The Culture Pass wasn’t a failure. It was a mirror.
It showed me how easy it is to reach for the quick explanation, the comforting clarity, the tidy narrative. And how quietly, almost imperceptibly, we drift off course when we do.
I didn’t know it then, but I know it now:
The shallows aren’t safe. They just feel that way.
Ken Wake is a designer-philosopher, entrepreneur, EIR and Professor at Georgetown University, and founder of Watershed LLC. He is training for the 2,745-mile Tour Divide before he turns 50.
