What’s the difference between just imagining that it’s you thundering out of the cross-country start box at the Rolex Kentucky CCI****—and one day finding yourself actually walking the course as a competitor?

The stories of three first-time finishers we got to know at the 2014 Rolex Kentucky Three-Day Event suggest that it’s a matter of the right horse, a reliable support network, careful planning and persistence. In this issue, they’ll share details of how they planned and prepared for their attempts at one of the world’s most challenging equestrian competitions. Next month, they’ll give you firsthand accounts of how things unfolded once they and their horses were at the Kentucky Horse Park in Lexington last April and they were living that long-held dream.

Our “Rolex rookies” could scarcely have come at their goals from more varied starting points. Here’s a quick cameo of each:

Rachel Jurgens owns the Pony Espresso drive-through coffee shop in Southern Pines, North Carolina, a business she opened a few years after relocating east from her long-time home in Oregon. Ziggy, her 18-year-old Thoroughbred, was one of the oldest horses running at Rolex this year but finished cross-country with less than three time faults and plenty of gas in the tank. Their completion this year was especially satisfying after an attempt in 2013 ended with elimination.

Kevin Keane is a leading sporthorse veterinarian whose practice, Sports Medicine Associates of Chester County, is based in Cochranville, Pennsylvania. His clients include Olympic gold medalist Phillip Dutton, who encouraged him to try eventing with an off-the-track Thoroughbred. He rode in his first Novice event at age 38 and was “bitten by the bug” when he completed his first Prelim less than a year later. At almost 60, Kevin was among the most senior competitors at Rolex 2104.

Jennifer McFall, whose family operates Dragonfire Farm in Wilton, California, spent most of the first two decades of her equestrian career breeding, selling and competing Morgan show horses. Eventing, which she discovered through Pony Club as a Junior, was just a hobby until High Times (Billy) entered her life as an untested 5-year-old. “I said, ‘I can tell he’s the one,’” she recalls.

Rachel Jurgens: “Ziggy Keeps Taking Me Places!”

Although Rachel Jurgens and Ziggy did not complete their first attempt at Rolex in 2013, Rachel valued the experience and learned how the event ran for a competitor.

About 15 years ago I was running a boarding business at my horse farm in Oregon and riding dressage. I loved it, but there was something missing. Then I went to Kentucky in 2000 and saw Rolex. I thought, “That’s what I want to do!”

At the time I had Ignition, a little mare I’d bred who was a great jumper. Eventing trainers were thin on the ground in the Northwest and the best way to work with top people like Jim Wofford or John Williams was to bring them out for clinics. I was going Training Level with Ignition and had hopes we could move up to a CCI* when Jim Wofford suggested during one of his clinics that the best way for me to do that would be to come east with my mare. So I made all the arrangements to spend three months with Ignition in Middleburg, Virginia.

Literally the day after we arrived from our trans-continental haul, Ignition broke her coffin bone. Jim suggested I make the most of my stay by galloping horses at the nearby Middleburg Training Center, and before long Michele Trufant, the trainer I was galloping for, loaned me a failed point-to-point horse she had for sale. “Take him and go work with Jimmy,” she said.

That was Ziggy. He was terribly hot and not at all easy, but however crazy he was acting—spinning sideways—when he saw the jump, he jumped it brilliantly. I worked with him and when it was time to head home, Jim said, “You need to take this horse with you.” Michelle loaned him to me on the assumption that I would either sell him back home or fall in love with him and buy him. We all know how that turned out.

Working mostly on my own back west, I really didn’t know what I was doing. I was just running and jumping. Ziggy and I did a couple of Prelims and at some point I realized he could be a really neat horse if I got good help with him. I knew it was a long shot that I’d get to Rolex, but I wanted to. I started thinking, I need to go east if I’m going to do this for real. That’s what I mean by how Ziggy takes me places! I already knew Middleburg, and also knew it was out of my budget, so I came back east and looked at other eventing-friendly areas: Ocala, Aiken and Southern Pines. I fell in love with Southern Pines, where the Carolina Horse Park was just getting started. John Williams already lived there, so I knew I would have someone good to work with.

It took about a year to get everything lined up: I put the farm on the market and sold a couple of horses. My then-husband sold his ad agency, and we moved across the country. I left family—my parents and my brother—behind in the northwest but they’ve always been a great support. They say I should do what I really want, and they mean it.

Ziggy and Ignition did their first one-star together in the east and things were going according to plan until Ignition injured herself again as we were preparing for our first two-star. I continued campaigning Ziggy, who seemed to thrive in his new environment. He became a real cross-country machine: He makes time really easily but doesn’t pull. I never need to kick, and I don’t have to set up in front of jumps. I tell people that everyone should ride him once at the gallop, just to see what it’s like.

Meanwhile, the rest of life did not stand still. My husband and I divorced about eight years ago and I needed a way to generate the income that would enable me to continue doing horses. Southern Pines didn’t have a drive-through coffee shop and I personally love being able to pick up my morning coffee without leaving my car, so I found a great location and opened Pony Espresso. It’s a neat little business. I don’t have a lot of overhead. There are no tables and we don’t serve food. Integrating the demands of my business and my horses entails a lot of early mornings, but I’ve found that being there from the start of the day until 9 or 10 a.m. works better than trying to do my horses first and then go in for the afternoon. I’m lucky to have a great staff who can run it for a week if I need to be away, as I did for Rolex.

Ziggy moved up to Advanced three years ago at age 15, the same year that I turned 40, and suddenly my Rolex dream was closer. I started riding in local clinics with Florida dressage trainer John Zopatti whenever I could, but much of our training program was pretty informal. I do everything myself, including grooming, at all competitions but three-day events, when I allow myself the luxury of bringing John Williams’ wife, Ellen, to groom for me. In a way I think my tight budget has helped Ziggy stay in the game as long as he has. I can’t compete a lot. I don’t ship to events far away. He lives outside 24/7, and I try to let him just be a horse as much as I can. We don’t jump much, which I think is good for him, and I’m a dedicated hacker. I don’t even have a ring! We do all our flatwork on the sand and dirt roads or in big fields.

I know some people thought I wasn’t ready when I decided to enter Rolex in 2013. Maybe they were right because our cross-country round ended when Ziggy hung a leg at Fence 7 and I tipped off into the water. But I was glad I had gone because until that experience, I had no idea how the event ran for a competitor. I think the first try was important to knock the cobwebs out of my brain: I was so wrapped up in what people were going to think, making sure my parents, who came from Oregon, got tickets and parking passes—it’s overwhelming. The course scared me to death when I walked it. I just couldn’t believe horses jumped those jumps. I probably came out of the start box feeling a little like that, too—hopeful but not confident.

This year I went with the focus of simply taking care of Ziggy and myself, and it made such a difference. I really believed in him and I wasn’t nervous. I had seen horses do it, and I knew it was all do-able.

Kevin Keane: “I Work, and I Have My Horse”

Veterinarian Kevin Keane purchased Fernhill Flutter (Butterfly) after realizing he had a real desire to ride at a higher level.

I already knew how to ride when I became Phillip Dutton’s vet more than 20 years ago, but I’d never had any quality instruction. I knew a lot of eventers and loved the sport, but I didn’t think I’d have time in my busy schedule to event myself. Phillip and I became good friends soon after he and his horses arrived in Pennsylvania, and he was the one who convinced me that it would be possible for me to compete. He explained that many eventing competitions held all three phases in one day. “You could probably take just one day, go to an event and be back.”

I had an ex-racehorse given to me by Hall of Fame trainer Jonathan Sheppard, also my client. I had trained him a bit on my own and Phillip said, “Your horse can do this sport!” So I started working with Phillip and did my first Novice event just as I turned 38. After three Novice starts I did one Training competition, then went Prelim. That same spring, maybe nine months after I started riding with Philip, I did a one-star at what was then the Essex Three-Day Event.

At Essex (which was in the old Classic format) I rode Valley Girl, a Thoroughbred mare—also doing her first one-star—loaned to me by a friend who couldn’t ride the horse herself. I was intimidated to be competing in the same division with Bruce Davidson and other big-name riders, and I’d never done a steeplechase before. But when we left the start box and I felt the thrill of galloping those fences, I was bitten by the bug. Valley Girl and I not only completed our first one-star, we finished fifth.

There followed a couple of decades in which I enjoyed acquiring horses at the track and training them to event before they went on to another home. There were even periods in which professional commitments kept me from eventing at all. Then about three years ago I felt a real desire to ride at a higher level. Finally I told Phillip, “I would love to ride around Rolex one time in my life.” I didn’t have a horse at the time and thought I might go to Ireland or England and find a good young prospect. Phillip’s response: “Hey, given your age, you better get one that already knows how to jump.”

I found Fernhill Flutter (Butterfly) through Carol Gee, a former member of the Irish Event Team and a friend who had owned him as a 4- and 5-year-old, when he did the Young Horse classes in Dublin. He was brave and already knew how to jump.

We started out at Training, where we were both comfortable, and went through a methodical training and building process with Phillip. He is my coach for all three phases, and we’ve had other trainers come in now and then to help—for instance, hunter/jumper trainer Rodney Bross has worked with us in show jumping on technique for riding lines. A couple of years ago in Florida, Katie Monahan Prudent and Henri, her husband, gave me a lot of help. I’ve also benefitted from clinics with George Morris and Joe Fargis. I am fortunate!

With Phillip’s constant encouragement, we moved up to Intermediate in 2010 and progressed to Advanced in 2011, coming third in 2012 at Fair Hill and Bromont. I’m often asked how, as I’ve campaigned at more demanding levels, I’ve fit the necessary conditioning and training into my already full schedule as a veterinarian. It’s simple. I do two things, really: I work, and I have my horse. These are my priorities. I schedule the hour and 30 minutes a day that I need for my horse as a vet call. So let’s say I have two lameness exams, maybe a standing surgery and then a set of radiographs on a horse. I might follow that by going to Phillip’s barn to hop on Butterfly. If for some reason I get called away, I’ll return later in the day or the evening. If I have to do a gallop, I might be at the barn very early. Phillip and his staff are enormously helpful. If I’m in a hurry to leave after working my horse they’ll take him, give him a quick bath, blanket him and put him away. I return in the evening to give him a rubdown, wrap him and so on.

By 2014, with Rolex definitely on the horizon, I also made an extra effort to get in shape. I’ve always kept myself reasonably trim, but I decided to try to whittle off about 20 pounds. Distributed over my 6-foot-1½ height, it’s not that much difference—and it was not hard to do it by eating more fruit and less Häagen Daz, (and giving up beer).

Then it was late April, and I was headed for the Kentucky Horse Park—but with a difference. After working there as a vet for 20 years, I would be on the grounds for the first time as a competitor.

Jennifer McFall: “This One’s A Keeper”

Jennifer McFall and her supportive husband Earl prepare Billy for the 2013 Jersey Fresh jog.

I grew up on a Morgan Horse breeding farm, Dragonfire, the business that my husband, Earl, and I run now. Started by my mother, Cheron Laboissonniere, the farm has always focused on sporthorses with the idea that the horses we breed are both athletic and beautiful enough to compete in any discipline. This formula has been very successful. Over the years, I’ve been in the fortunate position of promoting and showing these horses to many World titles.

Earl made his equestrian start at a young age as well, spending his time in Pony Club and eventing on Thoroughbreds. In 1998 we began dating and he became a working member of Dragonfire.

Though Earl and I focused primarily on our Morgans, we continued to event on a small scale. Our policy has always been to sell any horse on our farm, as this is the general practice in the Morgan world and I was accustomed to it. And because we were young trainers starting out, it was a necessary, albeit sometimes heartbreaking, reality. But when I got Billy in 2009, I told Earl, “This is the one I am NEVER selling!” An American Holsteiner, Billy, also known as High Times, was my dream horse.

After purchasing Billy, I entered our first Novice event at Woodside Horse Park in Menlo Park, California, about a month later. I cross-country schooled him at a small local facility beforehand and felt confident in my entry.

Woodside has been called the “Novice Olympics” on several occasions and had two half coffins on its cross-country course at that time. The place where I’d schooled Billy had no ditches, and he nearly landed me in the first half coffin with his adamant refusal to cross the ditch. This was to be the pattern for our first Novice season: I spent most of it being first after dressage, then finishing miserably down in the placings after a refusal at the ditch on course.

We worked our way up to the Intermediate level over a couple of years, but continued to have a ditch issue. Although we could see Billy’s obvious talent, Earl and I were worried that this quirk would keep him from the upper levels of the sport. So Earl built a Novice-sized ditch for me on our property, and I jumped Billy over it daily, even if I was in my dressage tack. I filled it with any thing I could think of—poles, flower pots, tarps, even trash—to get him over his ditch phobia. The refusals at ditch-related obstacles ended eventually, but I still ride them with special attention on course.

My coach is Canadian Olympic eventer Hawley Bennett of Temecula, California, a nine-hour drive from Dragonfire. Although we don’t see each other often, she is a force, giving positive energy and strict coaching to her students. She is the one who has made me feel that I had the ability to reach higher. I also take clinics with Buck Davidson whenever possible. Buck is Hawley’s coach, and he has imparted his rigorous and constructive style to her.

Thanks to their guidance and encouragement, my goal of riding at the four-star level seemed within reach, aside from the nagging feeling that you never have enough money to pursue something so monumental when you have a family to consider. It’s a feeling that, just maybe, a goal like that is better left to younger, less practical-minded people. Luckily for me, Earl and my entire family have been fully supportive of the idea and have not made me feel the least bit selfish about concentrating our resources towards Billy and Rolex.

We started our 2014 competitive season by going Intermediate at Galway Downs in February, which is a customary season-starter for all of the upper-level horses on the West Coast. Our first Advanced of the year was a one-day competition at Twin Rivers, and then I moved down to Temecula with Billy and my Preliminary horse, Tim, to train more intensively with Hawley. During my time there, I had a clinic with Buck and ran an Advanced with Billy at Copper Meadows. Finally, we competed at the Galway Downs CIC***. A critical part of my training while down south was to chase Hawley’s spitfire of a Thoroughbred, Gin N Juice, up their long and grueling fitness hill. ‘Ginny’ gave Billy an eye-opening education on how to run at the four-star level. My final preparation before flying Billy to Rolex was an Advanced Combined Test at Twin Rivers.

And then it was time for Rolex.

This article originally appeared in the August 2014 issue of Practical Horseman.