Designing in the Dark

"Designing in the dark is not a metaphor. It’s what we do every time we set out with only partial knowledge, hoping the road we’ve planned will carry us through."

We Regret Nothing

"I’ll be working through a headwind or climbing a hill, lost in the blur of greens, browns, and greys: trees, ditches, shoulders. It all blends into one long smear of effort. Then I remember to look."

Why Difference Still Matters

"We can be close. But closeness isn’t the same as sameness. Friendship lasts longer when we remember that. Because you can be friends with someone and still insist they respect your difference."

The Routine is Fine

"If you’re not rising at 4:45 a.m. to deadlift your feelings and journal about your five-year plan to out-alpha your shadow self, are you even growing?"

Ride Your Own Ride and Other Lies

“The truth is, no one rides their own ride. Not all the way through.”

Nassagaweya, and Other Minor Calamities

"Randonneuring has this odd way of asking everything from you, and then, almost sheepishly, giving something back. Not a prize. Not a medal. Just a vague but persistent sense that you’re a little more human than you were yesterday. A little more tired. A little more grateful."

How the MS Ride Became My Ride

“I can’t ride their ride. But I can show up. And ride alongside them for a while.”

Some Truths Take a Moment to Land

"The best crews I worked with didn’t pass the problem up the chain. They gathered around it. They asked questions. They took responsibility, not to cover themselves, but to complete the work."

A Siege in Huron County

"People asked how I could possibly ride that much distance in a week. The answer is: I don’t. No one does. You ride one pedal stroke at a time."

We Could Have Seen It Coming

"The techniques have names. Prompt injection. Jailbreaking. Bias manipulation. Sponge-style denial of service. They work because most security tools don’t know what to look for. They weren’t designed to watch an AI model work."