When I was kid in elementary school, I used to draw horses. And trust me—I was not a gifted artist. But on the inside of every notebook, on the margins of math tests and the errant post-it note; horses were popping up everywhere. They weren’t the horses I knew, but the horses I hoped to know.

I was a scrappy short-stirrup rider who refused to count strides and had never been to a jumper show, but I would draw my fantasy grand prix horses, soaring over wide square oxers.

What I didn’t draw was horses stopping, bucking me off on the back side, or me making that “Jesus take the wheel!” face when the distance just fails to appear. We all start with this hearts and butterflies interpretation of riding. And while the hearts and butterflies moments do exist, there are many more bruised egos and broken body parts along the way.

I’ve written about mental baggage getting in the way of good riding before but I realize more and more just how much of mental game this riding business is. I’ve had a great spring, and riding good horses had a lot to do with it. But a huge component was riding a better mental game than I ever had before.

Niles the wonder horse (aka “Nine Links”) went from the race track to the 1.15-meter 5-Year-Old Young Jumper classes in less than 18 months. I set out with this goal in mind last fall when Niles started to show us that he was an exceptional jumper, but I never expected to actually realize it. Usually, when they’re that nice, they sell quickly. Maybe it was Niles’s cribbing and small stature (he’s a mighty 15.3 hands) that kept the buyers at bay for these last few months or maybe it was just dumb luck. Either way, I shoved my mental baggage aside, jumped bigger fences and put in more clear rounds than I ever have before.

Of course, this kind of success doesn’t go unnoticed. And that is the point of the exercise after all. So when Niles sold during Upperville, which was supposed to be his biggest show yet, I wasn’t sure whether to celebrate or drown my sorrows with an expensive bottle of champagne.

I could not have picked a more perfect person to buy him. His new owner is a lovely rider, loves Thoroughbreds and trains with the absolute best in the business. Niles will spend his winters in Wellington getting a tan while we all freeze up north; he’ll never want for anything. Not a bad landing for a little brown horse who showed up looking like a fuzzy, ewe-necked wheelbarrow a year and half ago.

Yes, of course I am sad to no longer be riding him. Of course I will miss his tiny pony head (no joke, my cob bridles were big on him) and his giant bat ears. But what I’m left with most of all is a deep appreciation for what that horse gave me as a rider. He gave me my confidence back.

A few horses I’ve known have made it clear in my mind that I’ve chosen the right path in life. He’s one of them. And it’s hard to let those ones go, but that’s part of the gig. And honestly, he’ll be happier for it. It’s too much weight for one horse to shoulder all my aspirations.

When I think back to those penciled horses leaping over the open water in wide-ruled composition notebooks, I realize that not only was I drawing Niles, but all the horses who would help me along the way. 

Chronicle blogger and hunter/jumper trainer Paige Cade works at Tebogo Sport Horses, a facility in Delaplane, Va., devoted to the re-training and sales of off-the-track Thoroughbreds.