Last year for my 40th birthday, my husband, Andrew (who is a saint), bought me riding lessons. But not just any riding lessons. Dressage lessons with Hilda Gurney.

Among many other accomplishments, Hilda won a bronze medal at the 1976 Summer Olympics aboard Keen, an off-the-track thoroughbred she trained herself. Oh, and by the way, she was a school teacher before becoming a household name in dressage. Did I mention that she didn’t always have access to a dressage arena when she was training for the Olympics? So, she practiced on the trail. On. The. Trail.

That last bit gives me the shivers. It’s proof positive that you can achieve greatness without all the fancy (in this case, a perfect arena and horse) and a healthy dose of determination and grit. In contrast, I’ve spent a lot of time riding on the trail daydreaming about being great at dressage, but have yet to make it past training level.

When the day of my first lesson arrived, I was so nervous I almost wasn’t hungry. However, I fought through that and proceeded to have a delicious birthday lunch at The Old Place, where, surrounded by the heady aroma of a wood-burning grill and between gulps of tea and truly memorable steak fries, I fretted that:

Occasionally, a fantasy in which I got on and rode like Charlotte Dujardin crept in. This I chalked up to my chicken sandwich and the smoke. Meanwhile, my non-horsey husband tried to convince me that all would be well. I did not believe him.


The drive to Keenridge, Hilda’s ranch (barn? I still don’t know what people call stables out here in California), settled me somewhat. Our route from Malibu to Moorpark took us through rolling hills filled with produce trees lined up like soldiers, roads lined with massive eucalyptus trees, and past sweet horse farms tucked away behind shrubbery.

When I spotted the sign for Keenridge, my mouth went dry. Through our open windows, I could hear someone giving instruction to a rider practicing a half-pass. No one else was around, so, with some trepidation, Andrew and I followed the sound to a dressage arena surrounded by bougainvillea and capped by a large white pavilion. Ensconced there in a white lawn chair sat Hilda, still dressed for a show she’d been in earlier. She apologized to us that she was running late and invited us to sit and watch the lesson taking place.


  • I would forget how to ride.
  • Hilda would be horrified at my terrible dressage riding.
  • Everyone at Hilda’s would roll their eyes at my terrible dressage riding.
  • I would begin giggling and not stop.
  • I wasn’t anywhere near a good enough rider to have a lesson with Hilda.

Pre-lesson things you should know about riding with Hilda so that you don’t giggle uncontrollably or make inane, vaguely embarrassing small talk:

  • When you call to make a lesson appointment, Hilda sometimes answers.
  • When you tack up one of her horses, she may help you or even do it herself.
  • It does not matter if you have never ridden with spurs or a double bridle, she will make you ride with both anyway.

Before my lesson, Hilda asked her assistant, Elizabeth, to school Willa, the horse I would be riding. Watching them, I was simultaneously awed and mortified. Poor Willa was in for a shock. Here is what it looks like when you forget to breathe and want to exit stage right:

Elizabeth was very nice to me and told me what not to do when asking Willa to canter or she’d think I was asking for a tempi change. I did what she told me not to do anyway, because I forgot her advice the minute Willa and I passed through the hedge opening and into the arena.

Miscuing Willa happened a lot that first ride. Everything I did seemed to make her do something dressage-y such as passage or perform some sort of lateral movement. By the end, I’d quieted down enough to ride less like a disaster. I even got to change leads on purpose.

If you think I am exaggerating about my bad riding, know that during my second lesson Hilda commented several times about how much I’d improved. I did not want to disappoint her by telling her that I’d been so wound up the first time around I’d forgotten how to steer.

That day, I may have proved myself unequal to riding an FEI unicorn like Willa, but I glimpsed what was possible if I kept trying. I had always told myself that I had no business taking lessons on an experienced horse with a celebrated instructor. At least, not until I became a better dressage rider. The potential for embarrassment was off the charts, and I didn’t see how anything I could learn would translate to riding normal horses.

The experience changed my mind. In the span of 40 minutes, I learned:

I had three more lessons after the first, and each one was an education. Not just in riding, but about how a fear of failure can hold you back. Overcoming that fear isn’t easy, but knowing it’s there, lurking toad-ugly and waiting to foil my plans, better prepares me to boot it out of the way.