“You can do it! You’re almost at the top!” I screamed as I huffed and puffed my way up a huge hill, following my five-year-old on his bike. A cookie stand with fresh-baked treats awaited us at the top. But first we had to get there.

We were on the sixth mile of a 12-mile bike ride, by far the longest my son had ever ridden. It was one route on a local charity ride where the rest stops give away cookies to riders. As slow as we were pedaling, he wasn’t going to walk. He had done this hill before and for goodness sake, he was going to do it again.

As he pulled over the last square of pavement, I yelled, “You did it! You did it!” His face lit up, smile wide, eyes peeking out of his mop of bangs. After chowing down on the requisite cookie – white chocolate with lavender – he did a celebratory dance, a combination of the Mario Party “Yeah!” high-five and the Running Man.

While pride swelled in my heart at the end of the ride, that climb up the hill was the highlight. It was the culmination of so much hard work.

Although I’ve been participating in this ride for years, it was the first time he had done it under his own power. I first rode it when I was pregnant with him, back in 2013. Then two years later, I rode it while pulling him along in a bike trailer. 

Since he’s been riding a two-wheel bike, he’s wanted to participate. He loves tooling around the park on his bike, but because I’m also watching his brother, I can’t ride with him. Getting ready and riding together would be our special thing. The promise of being able to eat seven giant cookies in a single day was a major motivator as well.

I loved the opportunity to share one of my passions with him and giving him the chance to show off a skill he’s really proud of. I just finished reading Raising Resilient Children and they recommend encouraging and supporting kids’ “islands of competence,” areas that the child takes pride in. Perfect.

So I promised him that this year was the year. We trained for distance, going as far as we could on a local trail before dinnertime. He climbed giant hills, pumping up and flying down the other side with me yelling “Use your brakes!”

As my heart felt like it was about to beat out of my chest, I taught him how to ride on the road. He learned how far you should stay from parked cars, how soon you need to start breaking for stop signs, and that under no circumstances should you stop unexpectedly in the middle of the damn street! (Except not in those words.) Even on our quiet neighborhood streets, I had to do a lot of deep breathing to stay calm enough to instruct him. Thankfully, everyone we passed was patient and understanding.

On the day of the ride itself, my biggest concern was that my husband would get the kids to the start line on time. (I had to be there early as a volunteer.) My son is a night owl and getting up early was going to be rough. Once I saw them walking across the parking lot towards me, I knew it was going to be all right.

We started out strong, then started lagging at mile four. Thankfully, he mysteriously gained strength when we ran into one of his kindergarten classmates at a cookie stop. We rode the rest of the ride with her, her sister, and their dad, all of the kids offering each other the motivation to beat the others. Not having to be the sole source of encouragement was a relief!

While the physical accomplishment was impressive, I was most proud of my son’s mental and emotional strength. Riding in a group of people is hard. You have to be aware of not only yourself but everyone around you. Despite my voice almost going hoarse from yelling “Stay on the right!” he did everything he was supposed to. He rode in a straight line, didn’t randomly stop, and stayed focused. He did collide with his classmate when they kept trying to pass each other, but it was totally fine. It was so powerful to see him show such maturity and the training to pay off.

At the finish line, my mom asked my son if he was going to do it again. He immediately said, “Yes!” She didn’t ask me, but I’d say the exact same thing.

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