olsens bonita springs horse dressage in the pavillion
Photography by Tina Sargeant

The Bonita Springs Rider Taking on Elite Dressage—Her Way

With her mom as coach and rescue horses as teammates, 21-year-old Jenaya Olsen is rewriting the playbook for elite equestrian sport.

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By dawn on any given day, Jenaya Olsen is already moving—heading to the stalls to feed, walk and groom one of the 1,000-pound equine dance partners she’s been training with for months. As the sun rises, she braids the horse’s mane and begins her mental run-through. “I have my two hours of me-time with my horse, and no one can talk to me,” she says. “It’s two hours of me sitting with my horse, visualizing the test and preparing.”

From the spectator stands, dressage presents an illusion of effortless grace—a rider seemingly motionless atop a floating horse, directing a sequence of choreographed movements (called ‘tests’) with invisible cues. But behind the stillness is staggering athleticism. Often called ‘ballet on horseback,’ the discipline requires gymnast-level body awareness and core strength, and the mental focus of a chessmaster. Every stride, half-pass and pirouette reverberates through the rider’s body, absorbed and adjusted through the legs, core and lower back. Thighs engage like a vise, calves apply calibrated pressure and seat bones shift by millimeters—all while the hands stay feather-light on the reins and the face betrays no strain. The pair moves in perfect harmony. 

Meanwhile, the rider balances on an approximately 1,200-pound, thinking, moving partner. “It’s not like track or football, where the track is not going to change,” Jenaya says. “With horses, you rely on them for 80% of what you’re doing.” Riders must memorize and execute complex routines while constantly reading and responding to their horse’s energy, timing and mood. Judges assess the horse’s suppleness, obedience and athleticism, but the rider’s isometric strength and balance are the invisible engine behind the performance. “You need to be physically and mentally fit to deal with the pressure, the politics, the pure money that goes into the sport—it’s a lot,” she says. 

The 21-year-old, who dabbled in track and cross country in high school, trains accordingly, working with her mom and coach, Nicole. The two stretch daily and hit Burn Boot Camp five to six days a week for strength and cardio conditioning, augmenting Jenaya’s nearly 25 hours per week in the saddle and Nicole’s equal time teaching. The high-intensity interval training (HIIT) classes at Burn weave balance and power, building the stamina and core strength needed to take on equestrian sports. Their diet focuses on organic, whole foods sourced mostly from local farmers markets. The regimen is designed to prevent injury and help Jenaya stay competition-ready across a seven-month season (and two summer championships).

Jenaya, who grew up around her mother’s horses, has been training for this since childhood. Nicole had been riding since she was 7. Despite Nicole gifting her show ponies and encouraging her to ride since she was a tot in Switzerland, Jenaya showed little interest until they relocated in 2011 to Southwest Florida, where Nicole vacationed as a child. Here, a fateful introduction to a Hanoverian named Welcome changed her mind. When Nicole asked her 9-year-old daughter to visit the newly imported mare during quarantine, Jenaya reluctantly agreed. “The moment I touched her face, it was over,” she says. Welcome became her muse, and soon, Jenaya began competing. By 13, she had earned her USDF Gold Medal, a distinction many dressage riders pursue for decades. Over nearly a decade, they competed, trained and amassed top wins together—before Welcome’s passing earlier this year.

As Jenaya’s talents developed, so did the family’s ambitions. After a 30-year competitive career and more than 50 blue ribbons, Nicole stepped back from showing in 2017 to coach her daughter and focus on training horses. That same year, they opened Olsen Dressage at Magic Dream Farm, their Bonita Springs facility where they breed, sell, train and board horses. They also provide affordable opportunities for local youth to engage in the sport. “Our working students get free lessons every day, and they get to ride our horses,” Jenaya says.

The Olsens stand apart from elite dressage’s typical model, where success often hinges on imported horses valued in the millions and entourages of groomers and trainers. Instead, the duo muck their own competition stalls; ride and train their horses themselves; and rely on a few trusted farm staffers, along with current working student Lily Pegeus, to help with chores around their farm. The women save millions by investing in overlooked and rescued horses that have survived injuries or abuse. They also breed foals, cultivating champions through years of dedicated training. “I’m competing against girls that have $200,000, $2 million horses, and I’m on my little $10,000 horse,” Jenaya says. The thought crosses her mind often: I’ll never win anyway, so why am I doing it? But instead of giving in to the doubt, she keeps showing up—and winning. 

During the November-to-May dressage season, Jenaya competes almost every weekend. It’s a constant mental and physical battle to stay in the game. On competition days, she spends time near the arena, visualizing the tests ahead of her, down to the smallest half-halts and corners, where she may need to ask for more from her horse. She watches videos of past tests to analyze for pitfalls and victories. With the right headspace and support from Nicole, Jenaya has seen great success. Though she trained and worked in Wellington and Germany as a teenager, she eventually recognized that her mother was her ideal coach. Today, Nicole guides her development, and they work with Wellington trainer Lehua Custer—all aligned in a hands-on, horse-centered approach.  

For the Olsens, the health and fitness of the horse is as critical as the rider’s well-being. They prioritize open pasture time, provide science-backed feed and ensure each horse receives individualized, ethical training. In an industry long criticized for pushing horses too young, too fast, the Olsens take their time, never rushing horses to be show-ready or relying on harsh training shortcuts. Jenaya credits her success to strong bonds with her horses, which she earns by employing gentle, humane training methods with minimal spurs and whips. Jenaya, who dreams of joining the U.S. Olympic team, embodies the ethos. “I’d rather let everyone around me down than let my horse down,” she asserts. “If I’m on my way to the Olympics with my horse and he doesn’t feel 100% fit, sorry, we’re not going.”