‘It’s supposed to be fun, guys!’ Except, fun can seem frivolous.

Fun can seem like a distraction from the hard ‘work’ that we’re taught will make us better. Fun seems like a useless 5 mph zone on an expressway to your goals of riding at 1.20m, or getting to the 2* level, or nailing that flying change. 

It seems like horse sports draw in the ambitious, type-A types like flies to honey. Probably because those are the kids who seem coachable in the traditional way that kids are taught to ride in the U.S.; lots of structure, lots of reps, and often a pretty ‘buttoned up’ environment.

So when I find a rider who breaks that mold—who is successful and playful, fun-focused, and lighthearted—I get excited. 

Skylar Wireman has been called ‘the future of show jumping’, is mentored by Olympic gold medalist Peter Wylde, and is now riding consistently on teams and putting on a big show in the 5* classes. At just 20 years old, though, she hasn’t let any of that pressure kill her simple joy of riding and loving the horses.

This episode is proudly sponsored by Connaway and Associates Equine Insurance Services. Listen in around 24 minutes for Laura’s discussion on age restrictions on insurance policies in horses and how they may be changing. 

She’s my latest guest on the Horse Person podcast and I think listeners will be pretty shocked to hear how she takes her show horses camping, riding in the ocean, and how she makes time to play gymkhana-type games like Sit a Buck (the best!) on horseback.

Even Wireman’s course walk strategy is intentionally low-stress; many riders I’ve interviewed have a “protocol” for walking their courses—they do ‘X’ the first time they walk, ‘Y’ the second time, every time. For Skylar, since she’s grooming and braiding and hauling all of her own horses, she has to remain flexible and hope she even has time to get it all done. 

Skylar’s story will also feel like a beacon of hope to riders who don’t come from a fabulously wealthy background. Much of her competitive success has been on borrowed horses, catch rides, or homebred horses that she’s developed herself with the help of her mom, Shayne. Skylar and I explore the other ways, besides money, that she’s been supported in this overwhelmingly expensive sport. Her ‘wealth’ is in her village, she explains. 

This episode also supported by We Ride Together—because every athlete deserves to train and grow in a safe and healthy environment. 

Skylar and her mom, Shayne, still do all of the work themselves: the braiding, the hauling, the riding, dragging the ring, managing the lesson program at their home farm of Chestnut Hills in Bonsall, California. Together they’ve created a do-it-yourself operation that champions resilience and resourcefulness, and Skylar says she prefers it that way.

“I think even if we could afford [to do it another way], I’d still want to do it myself,” the 20-year-old says. Despite her rapid rise in the sport, Wireman remains grounded, focused on building a career that emphasizes both excellence and joy.

Whether you’re an amateur rider, a parent of a young equestrian, or someone who loves a great underdog story, this episode offers something special. Skylar Wireman’s journey is a testament to the power of passion, resilience, and joy.

Tune in to hear her full story, including her strategies for riding borrowed horses, her engineer-like approach to course strategy, and her reflections on making the leap from junior to professional:

Horse Person is a podcast hosted by 4x-award winning podcaster and equestrian media professional, Caroline Culbertson. Hit Subscribe on Apple Podcasts, or Follow on Spotify, to get biweekly episodes downloaded onto your phone before you wake up and drive to the barn.