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I’m Trotting Along the Backside of My Riding Career—And Grateful for Every Lap

©Jess Windhurst Photography

There’s a downed branch in the back field. It’s just a little thing. 

You could barely call it a log, really, but it serves our purpose. After weekly lessons, my fellow-40-something friend and I walk our horses along the path to the back field to cool out. Then, we test our mettle.  

As an ‘older’ adult-amateur rider, you don’t get these kinds of opportunities very often.

Even if you’re not really the timid, perch-and-pose early-Millennial/Gen X rider most of us are assumed to be. The point is, with your junior years far behind you, nobody’s lining up to give you extra horses to lesson on or hack. 

You’ll fall off, they assume. You’ll pull a hammie. You have small children at home. Don’t you know you have small children at home?

Maybe it’s all in my head, but that’s how it feels trotting along the backside of my riding career.

Riding is one of the rare sports where years and experience are often considered an asset. So much so that the average age of our three, competing, 2024 Olympic silver medal-winning riders was 46. Two out of three of them are nearly a decade older than I am now. 

But that’s the five-star level, and this is the unsupervised back field. I’m no longer the hotshot who gallops head-long at a spooky fences like they do at the Royal Ascot: The devil-be-damned, and take off spots, too!

I know what it feels like to “yard-sale” into the last big oxer in the schooling ring, hitting the dirt, hard, minutes before I was supposed to head into the ring for my trip. I’ve been bucked into the arena kickboards by a cold-backed mare who didn’t appreciate my inconsiderate leg, or my crop on takeoff. (She was right, I was wrong. I haven’t repeated that mistake.) 

And I know how it feels to fail to make a decision at a jump and leave long, off three legs, to nothing. That rare but potentially disastrous place that makes even the weather-beaten, pack-a-day pro leaning against the rail sit up and take notice.

“That’s the one that will get you,” they’ll say, taking a deep drag while gesticulating the danger with a wave of their cigarette, the butt perched equally precariously between life, death, and two fingers. “That jump gets a ‘D’ for dangerous.”

I think about these tenuous moments of my past as I canter down to the fallen log. And then, I don’t.

Forty years has taught me not to dwell on falls that were or might have been. Which isn’t, of course, to say I’m not your archetypical, spastic working-mom in normal life.

Regularly, at 2 a.m., my heart rate quickens like a fox in the hunt field, the sweat beading on my forehead, at the mere thought of an email I failed to write that day; the “essential” chicken stock I somehow forget in spite of my $240 grocery bill. 

Aside for a paltry sleep score, though, giving into your anxiety on your dark and indifferent Sleep Number is a lot different than giving into it on the back of your horse.

Many moons ago, when I was first learning to do the jumpers on a gelding I’d (for better and worse) mostly trained myself, I let my apprehensions get the better of me. Even then, proverbially brave and stupid, I didn’t know how to separate my body’s emotional reactions from my young horse’s needs. 

The pressure I put on myself to succeed became pressure I inadvertently put on his mouth. My very real fears of disappointing or embarrassing my trainer traveled down my rigid spine, through my saddle, and into my horse’s back and subconscious. Add to that a couple of inexperienced refusals on his part, and suddenly, every course was an opportunity to freeze up, lock up, and prepare for the worst.

Needless to say, the only thing this particular stratagem prepares you for on young horses is the worst. And a swift trip to the out-gate (you’ll be the one walking). 

I did eventually get to the bottom of the issue with that horse. But it wasn’t until years later and the chance to ride a very educated, 22-year-old ex-equitation champion, that I was properly schooled. That horse would also stop if you froze up, locked up, and prepared for the worst. But when you rode correctly, he echoed in kind. 

By necessity, and a few false starts, the two years on I spent on his back taught me to ride to a jump, in my current trainer’s words, “Like I wanted to get to the other side of it.”  

Self-assurance, finesse. Some junior riders are lucky enough to develop these skills early on. But I wasn’t one of them. Any rodeo clown can flap and kick to the base, and for sure, there is sometimes a need for that in our sport. But it took me decades to start to ride the way most horses need to be ridden on most days; with full conviction while doing far less.

It’s about learning to be Josh Allen: The kind of quiet, confident, and dependable teammate a 1,200-pound prey animal actually wants calling plays in the huddle.

Today, the bright fall sun is surprisingly warm and high in the sky, glinting off the orange leaves and refracting across the top of the log. A few strides out, I see my distance and I wait. I don’t change my course or my body position when I feel my horse’s head raise up, just slightly.

I know he’s studying it; the strange, foreign object in the middle of the vast field, the dappling of light across the ground. Studying and stopping are not the same thing, but most riders don’t start out knowing that. It’s a luxury you learn over years, with an extended opportunity to ride a brave, trust-worthy horse.

For me, now, that’s a sensitive bay gelding I wouldn’t have been “good” enough to ride in my 20s, or even my early 30s. It’s only now, a half-lifetime of lessons in my rearview—and in my back pocket when I need them—that I can not only appreciate the horse I have, I can be the kind of rider he needs me to be. 

I might not have the physical strength to stick a spin or ride through a crow hop like I used to. I might not have the courage I did at 18. But as my horse obediently lifts off from the clover-covered hill, on a crisply beautiful autumn day, all I’m thinking about is how it feels to soar. 

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