Reed Kessler’s Journey of Growth, Ambition and Philanthropy
From Olympic show jumper to national security professional, Reed Kessler’s journey has been defined by ambition, resilience, and a commitment to making a difference. On February 7, Reed returned to Belle Herbe Farm, where her JustWorld story began, to share how philanthropy shaped her perspective—and ultimately, her career path. Photo by Mike Souza/So Chill Media.
Within the walls of Belle Herbe Farm, headquarters for JustWorld International in Wellington, Florida, Reed Kessler’s evolution has unfolded in distinct chapters.
First, she was the curious 13-year-old introduced to JustWorld by a peer. Then, she became a dedicated Ambassador, spending 15 years giving back and exploring the nuances of privilege, responsibility, and service. And by 18, she made history as the youngest show jumper to compete in the Olympic Games.
On February 7, Reed returned to Belle Herbe after earning a master’s degree from Columbia University and embarking on a career in national security. She’s currently Associate Director of Policy at The Ronald Reagan Presidential Foundation & Institute in Washington, D.C.
During a moderated discussion, Reed offered her first interview since stepping away from equestrian sport in 2018. She reflected on the shift that led to her departure and how JustWorld provided the foundation for her career pivot from elite athlete to national security professional.
A Foundation in Philanthropy
More than a decade before Reed made Olympic history, her passion for horses converged with philanthropy at JustWorld International.
“A lot of Ambassadors—what we have in common is the community,” Reed said. “I became interested in JustWorld and eventually became an Ambassador because of Natalie Johnson, who I rode with at Heritage Farm. She spoke so highly of the program, and as soon as I got to learn a little more about it, I wanted to join myself. I think that’s what’s so unique about the Ambassador program—it sells itself. Once you meet people, see the work they’re doing, and realize how they manage to do that alongside a really demanding riding career, people naturally want to join and be part of it.”
During her 15 years as a JustWorld Ambassador, Reed Kessler visited JustWorld projects like the People’s Improvement Organization in Cambodia and Asociación Compartir in Honduras, strengthening her dedication to philanthropy and global impact.
Reed traveled to Asociación Compartir, JustWorld’s partner project in Honduras, deepening her connection to JustWorld and reinforcing her commitment to philanthropy.
“A lot of us who do horse sport live a pretty privileged life,” Reed said. “That was probably the first time that I saw real poverty, and that was a really impactful moment being there with Natalie and seeing the different projects like the mobile library and school.”
The Education on Wheels mobile library at Asociación Compartir brings books, cultural programs, clean water, and nutritious snacks to children in remote regions of Honduras where economic and geographic challenges make school attendance difficult. Deeply moved by its impact, Reed supported the initiative for years, donating her prize money from show jumping.
“My riding career became something that wasn’t only just about myself and winning, but it also became something that I could do good through,” Reed said. “Those project visits, especially to Honduras and then much later to Cambodia, were really impactful moments in my life.”
Beyond the opportunity to give back, being a JustWorld Ambassador—and the exposure to different cultures—broadened Reed’s horizons.
“It’s no secret that show jumping is a sport with a lot of money in it,” Reed said. “It’s a privilege to wake up every day, ride horses, compete, and travel the world. It’s easy to get caught in a cycle—at my peak, I was competing 48 weeks a year and always on the road. You start to live in a little bit of a bubble that isn’t reality. It was very meaningful, and I’m grateful that, at a young age, I got to go to the projects and have my horizons broadened a little bit.
“By having events [at Belle Herbe Farm] and being tied to the projects, it helped me keep perspective,” Reed added. “Even though I spent all my life in the sport and in this environment, I knew what was outside. I knew what real life was. I think that makes you more grateful for what you have. It makes you more determined that, in the time that you aren’t [at the shows], you want to do something more impactful. It ultimately shaped the person I would become and the change I would make in my career. I’m not sure I would’ve been able to do that if I hadn’t had years of access to JustWorld to play with that idea in my mind.”
A Shift in Perspective
Reed Kessler and Cylana, the exceptional mare who carried her to the 2012 London Olympic Games. Photo by Erin Gilmore Photography.
On July 14, 2018, just five days after her 24th birthday, Reed competed in her final FEI competition. While her decision to leave jumping came as a shock to many, for Reed, it felt almost inevitable.
That February, after the Longines Masters of Hong Kong, Reed stopped in Phnom Penh, Cambodia, to visit the People’s Improvement Organization (PIO), one of JustWorld’s four global projects, alongside initiatives in Guatemala, Honduras, and the United States.
“I’m very drawn to the project in Cambodia because of where I was in my life at that time,” Reed said. “I was approaching the end of my athletic career, and while I’m very grateful for the things I got to do when I rode, I was deeply unhappy at the end of my riding career. It was no longer fulfilling to me. I wasn’t intellectually curious, and I just wasn’t happy.”
Seeing the extent of PIO’s impact—providing education and opportunity to over 1,000 students daily and an alternative for many students who would otherwise scavenge at the municipal garbage dump to help support their families—the moment became a turning point for Reed.
“I just remember going to see the school—[it was] about 900 children just on the edge of the garbage dump—and being really blown away by how happy and grateful the students were to be there, as well as the teachers,” Reed said. “[I really had] to take a hard look at myself [and realize] that I wasn’t happy in my own life—that I wanted to do something more impactful.
“I was so grateful that, throughout my years of riding,” Reed added, “JustWorld allowed me to toy with that idea and be intellectually curious.”
The Courage to Be Imperfect
As a former JustWorld Ambassador, Reed Kessler left a lasting impression on the students at the People’s Improvement Organization in Cambodia.
The drive, ambition, and competitive nature that propelled Reed to the Olympics didn’t fade when she left the sport—it simply shifted direction. Over the next five years, she pursued a dual-degree program at Columbia University in New York City, earning a Bachelor of Arts in Human Rights & Middle Eastern Studies in 2022 and a Master of International Affairs in International Security Policy, Conflict Resolution, and Russia & Post-Soviet States Studies in May 2023.
“Something people ask me a lot [is], ‘How could you step away from that and end up doing something else? Don’t you miss it?’” Reed said. “Sometimes I miss the horses, but you’d be surprised how directly applicable that skill set is—setting goals, working toward something, pushing yourself, and getting out of your comfort zone. It’s something you can find in other places as well, whether in foreign policy or even just as an undergraduate. I went to Columbia, and I was so hungry to do well in school—treating it almost like it was a sport.”
For Reed, transitioning into academia was a liberating experience—one where she could fail, learn, and grow. In the classroom, there were no world rankings, no podium finishes, and no expectations—only the freedom to explore new ideas, challenge herself intellectually, and redefine her identity beyond the weight of past achievements.
“It was hugely liberating to go back and start a fresh page,” Reed said. “Nobody’s watching. I can try new things, be good at them, be bad at them. It was such a blessing to have so much success in the sport at a really young age, but at the same time, I was 18 years old, in my early 20s. That is naturally a very difficult time in a young person’s life as they find themselves, and doing that in a very public setting can be unpleasant at times. It was almost like being a late bloomer—that even though I was 24 at that point, I got to have that moment that I carved out at Columbia.”
In September 2023, with a graduate degree and experience from internships at the United Nations and the U.S. State Department, Reed landed the position of Associate Director of Policy at The Ronald Reagan Presidential Foundation and Institute in Washington, D.C.
“I would say no two weeks or days are ever the same,” Reed said. “We do a lot of work based in convening, so we put on the biggest defense conference in the U.S., The Reagan National Defense Forum, which just happened in December. It’s a pretty cool place to work because you’re constantly pulling together the greatest minds across the national security and foreign policy space to work on difficult problems across the political spectrum.”
Life Experience
After the moderated discussion, Reed Kessler sat with attendees to continue the conversation. Photo by Mike Souza/So Chill Media.
In a Virginia pasture, far from the fast pace of Washington, D.C., Reed’s Olympic partner, Cylana, enjoys her retirement alongside Reed’s former competition horses. The 23-year-old Belgian Warmblood represents a defining chapter of Reed’s journey—the rise to Olympic success, the difficult choices of her professional riding career, and the lessons that shaped her path forward.
“Life is very short, and riding is a huge gift, and you should do that if you wake up and it genuinely excites you—intellectually, emotionally, and what have you,” Reed said. “But wherever you are in your career, if you reach a point where you really don’t feel happy and fulfilled—it doesn’t matter if that’s at 18, 25, 35, 50, or 70. At any time, you can change your life, try something new, and branch out, and I think that’s really cool.”
As the evening wound down, the conversation opened to the audience. Some had spent years in the sport before stepping away to pursue new paths, while others were navigating career shifts, looking for insight and direction. Reed left the audience with one final reflection—a piece of advice she would’ve given to her younger self.
“I think to live a little bit more the way I do now, which is to be less glued to what the result is going to be,” Reed said. “I don’t mean to sound hippy-dippy, but I really try to live my life like, ‘Life is an experience. Who knows how long I will be in this moment, in this job, in this relationship?’ I will show up every day, build a life that makes me happy, try to learn, work hard, be a good person, and show up for my friends and all of that. But if I fail and had a bad week at work, I showed up, I did my best, and that’s what it is. To love and lose and be like, ‘That wasn’t supposed to last forever. That was beautiful while it lasted.’”
