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.

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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.

Why I’m Riding the Tour Divide Before I Turn 50… and What It Has to Do With Redesigning a Life

I’ve been thinking a lot about thresholds lately. Some thresholds you choose; some choose you. A year ago, I was limping through airports with a cane, navigating chronic pain from a pair of malformed ankles and a surgical fusion that seemed to have traded one problem for another. Walking hurt. Standing hurt. Most days, just being upright hurt.

Cycling—the sport that once shaped whole chapters of my life—was something I watched other people do.

And then something shifted. Not in a Hollywood moment of inspiration, but slowly, like a tide turning. I realized that if I wanted the next decade of my life to belong to me, I had to design it. Not dream about it. Not intellectualize it. Design it. With constraints, with embodied reality, with the physics of the world and the mechanics of my own body fully acknowledged.

So I decided to train for the Tour Divide: 2,745 miles from Banff, AB to Antelope Wells, NM on the Mexican border. Mountains. Weather. Bears. Isolation. A race so brutally indifferent it never cares who you were before you started.

It’s an unreasonable decision. That’s the point.

Rebuilding a Body, Rebuilding a Self

I’m doing this at 49, after gaining over 100 pounds, after years of chronic pain, after losing the athletic identity I once took for granted. I’m not supposed to be doing this. My ankles aren’t supposed to tolerate it. My schedule doesn’t allow for it. My life is full: family, work, teaching, writing, building companies.

But here’s the deeper truth: I need a project that demands everything from me—physically, mentally, emotionally—because those projects reforge identity. They give you the chance to become someone you haven’t met yet.

Training for this race has already forced me to rethink capability. Systems. Constraints. Time. Energy. Pain. Failure. Motivation. The physical becomes philosophical very quickly when your body becomes your primary design material.

The Tour de Ken Is Not Really About Cycling

This blog, Tour de Ken, isn’t a cycling diary. If it were, I’d have no interest in writing it and you’d have no interest in reading it. This isn’t an homage to gear ratios or wattage.

This is a chronicle of long-arc design, of what happens when you choose a target far enough away that you must become a different person in order to reach it.

The Tour Divide is the spine of the story, but the story is about:

• Self-authorship after a period of loss and limitation

• How systems thinking looks when applied to a body in motion rather than an organization on paper

• Identity reconstruction

• Endurance as a philosophy

• What it means to pursue something wildly hard, purely because you want to see who you become on the way

Why Start Writing Now?

Because journeys only feel linear in retrospect.

Right now I’m in the middle of the messy part: losing weight, rebuilding fitness, learning how to manage pain, rediscovering discipline, figuring out how to train with a full life.

I want to document the reality—the wins, the setbacks, the theories, the data, the discipline, the doubt—not because I have answers, but because I’m committed to the process.

This blog will cover:

• Training updates, honest ones

• Reflections on identity and embodied design

• Lessons in systems thinking from the saddle

• How I’m re-architecting my life to make room for this

• And the intersections with my other major project right now: writing a book about the failures of design thinking and what a more situated, rigorous practice looks like

The Journey Ahead

In 2027—the summer before I turn 50—I plan to stand at the trailhead in Banff, look south, and start pedaling. My goal is simple: to finish. To hug my family and my four dogs at the end. To prove to myself that I can redesign a life from first principles, starting from a place that once felt nearly impossible.

If you want to follow along, subscribe. Or don’t… I’m doing this either way. But if you’re here, I’m glad. I hope something in this project sparks something in your own.

Because the truth is, every one of us is riding some version of our own Divide.

And this one is mine.

—Ken

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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.