150 Trivia Rides: A Milestone Worth Celebrating

Tomorrow, something extraordinary happens: The 150th OWL.BiKe Grey Zone Trivia Ride takes place!

That number sounds celebratory — and it is — but the real story isn’t the number. The real story is what it took to get here: 150 Saturdays of showing up. 150 weeks of sitting down on a Thursday night — sometimes tired, sometimes uninspired, sometimes wondering if anyone will even notice — and coming up with questions worth asking.

That’s roughly 3,000 trivia questions over the years. Three thousand. I want to say that number out loud because it still surprises me a bit.

Curiosity as a Practice

I am, as you probably know by now, insatiably curious.

The Grey Zone ride has become my weekly playground for that curiosity. One week it’s a lighthearted exploration of the top songs from the 70s — just for the joy of it, just for the memory of what made us move. The next week, something deeper. Resilience. Purpose. How we age, how we train, how we sleep, how we fuel our bodies in a way that actually makes sense for women in their 50s, 60s, and beyond.

I’ve leaned into topics like Atomic Habits — asking you to think about the small systems that shape who you become. I’ve explored the science of what your body does after 50 and why the rules change. I’ve pulled from nutrition, physiology, cycling dynamics, philosophy, pop culture, and life itself. Not because any of it has to fit a theme — but because curiosity doesn’t stay in its lane. And neither do I.

The variety isn’t accidental. It’s an acknowledgment that a group of women who show up every single week deserve more than one flavor. Some weeks you’re here for the nostalgia. Some weeks you’re here for the empowerment. And some weeks you just need a ride that asks you to think about something entirely different — and that’s okay too.

I Don’t Get Paid for This

I write every single question by hand (well, by keyboard). I spend time researching, shaping, and rewriting the inspirations so they land somewhere real. I do this before my weekend, while the house is still quiet, before anything else can compete for my attention. And I do it for free.

Not because it doesn’t cost me anything — it does. It costs time, energy, attention. It costs time that could be spent otherwise.

But here’s what I’ve learned: the women who show up every Saturday are my payment. Not in currency. In presence. In the fact that they chose this ride — out of everything Zwift (and life) offers on a weekend — and they came back. Again. And again. And again. For 150 weeks.

That is not nothing. That is everything.

Our Extraordinary Little Community

There is a small, fierce, wonderful group of women who have made this ride their own. You’ve turned a concept I dreamed up into something that actually means something. You’ve thrown out guesses and laughed at the wrong answers. You’ve messaged me to say a topic made you pause, think, and sometimes make real, healthy changes in your life. You cheer on women when they get the answer right. You celebrate them when they move up to Podium Level.

That’s the part I never expected.

Turns out I was building something far more valuable — a small, extraordinary community where women show up for each other, week after week

I thought I was creating a trivia ride. Turns out I was building something far more valuable — a small, extraordinary community where women show up for each other, week after week. One that grows a little wider with every milestone, and a little deeper with every Saturday.

Our Happy Ride

Becky and I call this Saturday ride our “happy ride.”

Not because it’s easy — though it is, in the best sense of the word. Not because the questions are always simple — though some of them are. But because it brings us joy. Genuine, pedal-turning, week-anchoring joy.

Saturday is our favorite ride of the week. Not because of the watts, not because of the distance, not because of any metric you’d find on a dashboard. Because every week, we get to ride alongside women who remind us why showing up for each other is the whole point.

150 weeks of that. 150 weeks of joy.

Here’s to 150 — And Whatever Comes Next

I don’t know what question #151 will be yet. I don’t know what topics are waiting around the corner of my curiosity, or what inspiration will find its way into an answer I haven’t written yet.

But I know this: I’ll be there on Saturday. Clip-in ready. Questions in hand. Ready to ride with you.

Because at the end of every Grey Zone ride — the 150th or the 1,500th — it’s never really been about the trivia.

It’s about the women who show up.

And every single week — you do. ❤️

Here’s to the next 150. Hoot! Hoot!

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