Why Small Choices Are Doing the Heavy Lifting Now
Big transformations rarely begin with dramatic decisions. They start with small, unglamorous choices that quietly reshape systems over time. This is a reflection on rebuilding capacity through constraint, attention, and design in the real world.
It’s tempting to believe that change happens at moments of declaration. The big decision. The public commitment. The dramatic pivot.
But that is not how systems actually change.
They change through small, repeated choices that reshape what is possible over time.
Cleaning an office.
Choosing pedals.
Showing up for another ride when motivation is low.
Writing even when clarity hasn’t fully arrived.
None of these things transform a life on their own. Together, they alter the system you’re living inside.
This is something I’ve learned repeatedly as an operator, and I’m relearning it now in my body. Systems respond less to intention than to structure. If you want different outcomes, you need different constraints, defaults, and feedback loops.
Right now, my life is full of small, almost boring decisions that point in the same direction. They are not heroic. They are not optimized. They are simply aligned.
Alignment is underrated.
When your environment, your tools, your routines, and your goals begin reinforcing one another, progress becomes quieter but more durable. You stop relying on motivation and start relying on design.
That’s what this phase of Tour de Ken is really about.
Not proving anything.
Not reclaiming an identity through nostalgia.
But constructing a system that makes becoming possible again.
The big milestones will come later. For now, the work lives here, in the details most people overlook.
And that’s exactly where real change likes to hide.
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 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.