How I learned to ride at age 30 and what it has taught me

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I’m at work early today, taking off my helmet as I lock my bike to a lonely rack on the third sub-floor of my office parking garage. I change out of my kit in the women’s bathroom and rummage through the expert drawer of provisions at my desk to make me look like I drove in by car that day instead. Amidst files and documents, I peruse women’s kit online and daydream about how to spend the little money I have in the bank. Can I squeeze just one more jersey out of last week’s paycheck? I promise I won’t eat out this week. I do the whole routine in reverse on my commute home, except I have the time before darkness to add a few hill intervals. I record my ride with Strava, then Training Peaks to study the data. I quit racing, but it never quits you.

And to think that five years ago, almost to the day, I didn’t know how to even ride a bike.

I was seven years old when I was presented with a pink Huffy, the one with the pink streamers on the handlebars. That bike was a rite of passage, and I waved to my mom at the front door as I took to my quiet street alone. But after several frustrating attempts to ride it, I dragged it back to the porch steps. I didn’t touch it again for weeks. No one asked me about it, or checked in to see if I wanted to try again.

I did well in school and that became a source of self-esteem for me, not the pretty pink bike in the basement. My mom encouraged me intellectually because I was always told the Dolan family was not an athletic family. We never did well at sports, they said. You’re better off studying and going to a good college, they said. At the time, it never occurred to me that their argument had one big hole in it – should you only try at sports if you can win?

Fast forward to the year I turned 30.

Turning 30 is a momentous occasion for many, a time for course corrections and life appraisal. For me, I had quite a lot to face. I was in denial about my post-college weight gain that lasted longer than the years I was in college. I was unhappy at work, losing sight of a career, and utterly sad that I didn’t have that husband and baby I expected by this age.

Give me a fix, I thought, something to take away the raw feeling of failure. I ran to my junk drawer in the kitchen in the apartment (why are they always in the kitchen?) and felt in the far back for that folded up piece of paper with my new year’s resolutions. I set a few of the same ones every year, blinded by the naïve hope that this year I will act like a more ambitious version of me. My eyes scanned down the list: learn to the play the accordion, balance a monthly budget, stop online shopping for 30 days, learn to ride a bike. There, that one! I can accomplish something with two months left in the year!

Bing, bang, boom, I’m registered for a class at REI, and panicking that it will be a class of eight-year-olds, their grossly supportive helicopter parents, and me. The night before class I even dreamt that the kids would point and laugh at me, and I wavered in my commitment to attend. Why would a grown adult choose to put themselves in a position to fall? Outside, on the ground, in front of other people! What did I really think I was going to do after the class – ride a bike?

Siobhan Dolan

But I don’t flake on my commitments, that’s not my thing, so I got in the car the next morning and drove an hour to the class location. When I arrived two guys standing next to a Sprinter van filled with bikes ushered me into the open van door. I took the last seat and looked around at the others. All women!

Over introductions I learned that these eight other women were active, healthy, smart women in their 30s who just happened to never learn to ride a bike. Some, like me, simply weren’t encouraged to learn. For others, it had been culturally frowned upon to use a bicycle as a woman. Yet here we were, ready to challenge the people who held us back and find our own path to empowerment. And we were starting this grand journey in a parking lot.

While obsessing over this class for weeks leading up, I had forgotten that I actually had to ride the bike. One of the instructors scanned me up and down, whizzed through some adjustments of questionable legitimacy and handed me a Novara bike with no pedals.

“Um, isn’t this bike missing something?” I asked.

“Oh, you’re not ready for pedals yet. You need to understand how to ride,” he responded.


“Easy. Circles.”

And circles we did. Nine adult women push pedaling in circles around an empty parking lot, circling the drain of success or failure. One woman exited the circle game, graduating to pedals. Then another and another, until I was the last one still pushing, still circling. I was ready to give up, congratulate the women riding successfully, and admit defeat. I didn’t see the point in continuing if I wasn’t going to get the hang of riding. I’d quietly fall back into my routine of living inside the box and settle for a life unchallenged. Was I going to accept that failure as a sign to discontinue trying like I always do? Isn’t that what brought me to this class in the first place?

I resolved to keep pushing, spinning round and turning my negative thoughts into feelings of flight. I pedaled like a silly fool until I mastered ever longer stretches of balance. I felt the wind lift the hair out of my face and a smile crept wide across my face. I had done it! I was understanding how to feel the bike and soon I, too, graduated to pedals and spun faster in circles with these amazing women. We were now more amazing for tackling this skill, together.

In the five years since that class I have ridden thousands of miles. I hired a coach and raced as a Cat 4 on the road. I even raced a fixed gear bicycle on a velodrome. I have never won a race. I never even came close to winning a race but I have loved every mile of it. I’ve crashed and broken bones and healed again. I’ve been hit by a car. Twice. I never did get any faster, but I’m OK at climbing. I’ve met my partner through riding and hope to one day raise a family that bikes. I’ve changed the entire course of my life with that one decision to learn to ride and I will never regret it. Learning to ride has taught me that you’re never too old to try. The mere act of trying, not winning and not being the best, is how more great things happen in your life. It’s how we can become something better than we were.

Siobhan Dolan is a thirty-something finance worker from Los Angeles who’s behind the popular instagram and website @womenskit.

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