I was watching my daughter in the horse show, on the far side of the fairground, when I got the text from my son.

“I won,” he wrote.

He attached a photo of himself holding an ostentatious first-place ribbon.

This was a bit shocking. It was our fourth year doing the county fair—an exhilarating, exhausting several-day event that both of my kids normally looked forward to for months. But one thing was different this year: My son was 15. He’d been slouching around the fairground in aviator sunglasses, scowling and sighing, and was even sent out of one competition to change out of flip-flops into proper footwear. And now he’d won an entire division. Specifically, the Pack Goat division—whereby he had to lead his pet goat over bridges, through tunnels and puddles, and around tubs of foliage.

His follow-up text was even more shocking.

“Now I have to do Master Showman.”

Even in the best of his adolescent years, when he still loved the fair, competing in Master Showman—in which the winners from each division compete in a final ultimate event—would have been unnerving. And for me, a transplant from the city still barely managing to navigate the entirely foreign culture of the county fair, the thought of my son competing in this ultimate showdown was overwhelming.

Even in our small, sleepy county in the upper Hudson Valley, for many kids, winning Master Showman was the ultimate goal. It was the holy grail they worked toward for years. It was not uncommon to see teenagers in tears after the show, in their last year of competing, and not having finally won.

A county fair was not a natural fit for my creative, artsy, formerly urban family. I come from a process-oriented, gentle-parenting background. It’s how I was raised and how I mostly raised my kids. Effort is what counts, not winning trophies. Creativity and individuality were my primary concerns with my kids, not standing in line with military precision, following rules, dressing alike, and submitting to authority. But the fair had been putting all my parenting instincts through the wringer ever since we’d started participating in it four years ago.

And now my son was going to be thrown in with the top lions...