Growing Confidence — One Turn of the Pedals at a Time

The other day on my walk, I saw a little girl in our neighborhood take off down the sidewalk—helmet slightly askew, streamers flying from her handlebars, and the biggest look of concentration on her face. A parent jogged behind her, just in case. I smiled, remembering that moment with my own kids. Later that evening, what are the chances that I saw a post about National Bike Month? No joke!

This moment watching this little girl learn to ride her bike stuck with me though—not just because it was sweet, but because it felt like the perfect metaphor for this season.

May is full of transitions. Students are wrapping up the school year, graduating, summer camps will be starting, and then in the fall, kids are moving on to new schools, starting boarding school, or heading off to college. These changes can feel a lot like those early rides—unsteady, exciting, and occasionally full of wobbles.

Learning—whether on a bike or in life—is messy. Progress isn’t always linear. And as much as we want to protect our kids from falling, it’s often through skinned knees and shaky starts that real growth happens.

I think of a favorite client who started at a new boarding school last fall—one that stretched her socially and academically in ways she hadn’t anticipated, not to mention living far away from home. The first few months were tough—full disclosure here. There were moments of doubt, homesickness, and calls wondering if she and her parents made the wrong choice. But little by little, she found her footing—she joined the soccer team, connected with a teacher, and made such a nice group of friends. Fast forward to this spring as I just met with her by Zoom to check in…. she wasn’t just adjusting—she is flourishing!

Her story reminds me of a Churchill quote: “Success is not final, failure is not fatal: it is the courage to continue that counts.”

As a parent, I’ve had to learn when to step back. And as an educational consultant, I get to run alongside students and families in these pivotal moments—steadying the bike, adjusting the course, and then cheering them on with joy as they realize: I’m doing it!

Here’s to scraped knees, brave transitions, and the ride ahead.