My kindergartener has dreams of playing hockey.

Oscar is five. Hockey is big in Prince Edward Island: recent statistics suggest 14% of kids here play organized league hockey, as opposed to 9% nationally. So once a week, in preparation for living his dream, we cart him off to CanSkate lessons, suit him up in snowpants and a helmet, lace his skates, and set him loose on the ice.

Sure, we tried teaching him to skate on our own. The year he turned two, we bought bobskates – the little double-bladed ones – and a tiny helmet. We have video of him standing in the middle of the ice, holding my hands, chirping with laughter. Then promptly plonking firmly down on his diaper.

The next two winters? More or less a repeat. He’s a kid for whom new physical skills don’t always come easy. He has to work hard just to coordinate himself. When really engaged in something, he frequently forgets whole zones of his body: he is a danger to neglected coffee cups everywhere. Smash. Oops.

I sympathize: I remain the same, to this very day. On the other hand, his father skates like he was born on a hockey team. But alas, sometimes the apple falls from the less optimal tree.

Still, he wants to play hockey, this kid. So off we went to skating lessons.

The CanSkate classes have been good for Oscar. When he started back in October, he could barely walk on his skates. This month, he actually graduated from the beginner to the intermediate group. He came home that night with a badge and shining eyes.

This past week, though, I brought him to his first intermediate class. The beginners had been mostly four and five, like him. The intermediate group? Gargantuan children of seven, most of them. Lined up next to them, he looked distinctly out of place, smaller than he’s seemed in years.

And when the group began to skate, the gap only grew. The teachers led the group around a small circuit of pylons, and the kids followed, gliding and working on their backwards skating. Oscar hasn’t really mastered gliding yet. Within forty seconds, some of the bigger kids had lapped him.

But he was game. He didn’t stop, or disengage, even as the class wore on and it became clear he was by far the slowest in the group.

He just kept skating.

He worked away diligently at the circuit, trying to learn to turn his body backwards. When he fell, he picked himself and dusted himself off, and started again. He wobbled and struggled, and once one of the bigger kids nearly took him out as he flew by. Oscar just kept skating.

I sat in the stands, watching, biting my lip. It’s hard to see your kid fail to keep up. Our culture doesn’t leave much room for it, anymore: we leap in, we mitigate, we try to make sure no feelings of inadequacy are ever fostered.

But Oscar, left to himself, didn’t seem to feel inadequate. He just felt like learning to skate. As I watched, I found myself swelling with pride. Of all the kids speeding around on that ice, he was the one having to work for every step, every last-second-save of his balance. But he wasn’t daunted.

Just keep skating, I found myself chanting under my breath.

He eventually mastered a tuck, and he got up some speed just in time for a spectacular crash. He laughed. I nearly clapped. And then my head cocked, and I looked at him and thought, I want to be like you, kiddo.

I turned forty last week.

I also started two new professional gigs this month, on top of my full-time student status. The learning curves in my life are high, right now. And that’s hard for me, sometimes. It’s easy to notice the people younger than I who’ve already gotten where I want to go. I notice when I’m being lapped by people who started at whatever endeavour after me, but are still racing ahead, making it look easy.

I’m a perfectionist by nature. Most of my life, if I suspected I was the last in my group? At ANYthing? I didn’t do that thing anymore. Enough came easily that I focused where I excelled.

But at some point in life, that’s not enough. At some point, doing what comes easy loses its entertainment value. At some point, if you’re lucky, you start realizing you have something more to gain than lose.

There’s something freeing about forty.

And something wise about five, apparently.

I have things I want to learn, and the learning will take some humility, and some doggedness, and some willingness to put myself out there and probably fail, in public, a few times. I will blush. I will feel exposed, likely, and silly. And I will be tempted to stop.

I need to take a page from Oscar. I need to just keep skating.

I’ll try. I’ll keep at it. And hopefully I’ll occasionally stop and remember to play triceratops with my skates now and then, just to make sure it’s all still fun.

Are you finding yourself more free to learn and grow, as you get older? How have the kids in your life surprised you with their wisdom?