Going Pro

If I could have afforded to stay at Jimmy’s and be a working student forever, I would have. Like a vast majority of equestrian professionals, I earned my new designation through necessity. I needed money.


I started freelancing as I was transitioning out of Jimmy’s trying to make ends meet. As a budding professional, I galloped flat horses at the Middleburg Training Track starting at 5:30 a.m. I would gallop six or seven (or eight) before heading back to Jimmy’s to muck 8 stalls and ride two horses there. I would then head to a neighboring farm to ride several more. When I was finished, squeezing in as many horses as I could before dusk, I would head back to Jimmy’s to do lates.

The first year I was a professional, I had my taxes done by a local accountant. Imagine my surprise to find out I owed $750 in taxes. How could that possibly be when every penny I made I put back into my business?  It seems like a small amount now, but honestly, I didn’t have it then. It was hard to wrap my head around how I could be broke all of the time, working my ass off, and still owe even a dollar of taxes when my bank account said zero…

Welcome to adulthood.


I galloped flat horses as part of my freelancing effort. Everyone should gallop race horses at some point in their career. It made me a much better rider and gave me a lot of useful skills that I took back to my event horses.

The first race horse they put me on needed long spurs and a whip. I only ran across this twice in my career—a race horse that didn’t want to go. I thought they all wanted to go forward, but I can attest to the fact there are some who don’t want to whatsoever. I learned quickly to put my stirrups down for that two-year old. It’s a lot harder to motivate a lazy youngster with short stirrups! It didn’t take long to figure out a goer is a lot more fun, and easy, to ride than a pokey one.

As a junior jockey, I rode all yearlings and two-year olds while the seasoned riders rode the horses with more experience. Those horses were all bigger and stronger and knew the drill. Once I hopped off a two-year old colt, who was a pleasure to gallop, and was taking my tack to the next one while the groom took my horse out of the barn to wash off. I hadn’t even gotten to my next horse’s stall before I heard screaming and a lot of commotion. People started running and barking orders. The colt I had just galloped had stood up at the groom and boxed. He caught the top of her forehead with the toe grip on the bottom of his shoe and peeled her skin like a banana. Blood poured down her face. It all happened so fast, and it was such a close call (she could have been dead instead). It knocked the wind out of me thinking about it. It also made me very vigilant in the barn as a result. It was a valuable lesson at someone else’s expense.

It is when you least expect it something bad usually happens, and more times than not, it happens on the ground and not from the back of a horse.

I also learned, galloping race horses, to say “no.” I realized that the only person that was going to look out for me was me. Not that anyone was trying to intentionally put me in harm’s way, but I realized I needed to advocate for myself and that my well-being and safety was up to my own agency.

One day the trainer asked me to pull in a big, stroppy colt from the paddock. He was a stunning specimen of an athlete, but his testosterone was brimming over the sides. I went to snag him and he stood up and towered over me at the gate. Any time I went to clip the chain on him, he was all teeth and legs boxing the air. After three failed attempts, I went in and asked the head groom to help me. Lalu was about my height, but he was built like a miniature sumo wrestler. He got the chain on the colt, and it looked like he was walking a 1200-pound flying kite with sharp edges all the way back to the barn. It was hard to admit my shortcomings, or to curb my enthusiasm and try to do everything, but admitting my limits was one of the first signs of maturity in my riding.

If you’re ego is behind the wheel driving, someone is bound to get hurt. Most likely it will be you and the horse in your care. 

Every now and then, we’d get a really tough one in that didn’t want to play ball. At all. When these horses showed up, the trainer called in a certain freelance jockey to help show the begrudging fledgling the way it was going to be. That’s all this jockey did was ride the tough ones for the many trainers at the track. When I saw him out there, I gave him a wide berth, because I knew something was going to go down at some point and I didn’t want to get stuck in the crossfire. This guy was in his early forties when I met him, and again, he was about my height, and all muscle without an ounce of fat on him.

This guy was tough.

One day I was on the far side of the track finishing up when he galloped past me, and kept on going past the on-ramp. He was flying. That old saying, “all elbows and assholes,” yep, that was him. He was working hard to teach this horse how to gallop. I watched him with interest because this. guy. was. good.

His horse was flying down the long side when I saw the horse put it in reverse. It was incredible to watch. How can a horse be galloping, and taking you, one second and be wheeling the other direction the next? If I didn’t see it with my own eyes, I wouldn’t have believed it was possible. The horse turned so fast that he almost fell over. What was so amazing was the jockey never moved. He was in the middle of it the entire time, and not only that, he never strayed from the mission. There was no moment of just hanging on and surviving so he could then get back on task. Nope. He was on that horse’s case all the way through the issue, and had him turned around and galloping a good clip before you knew it.

To this day, it is one of the most expert pieces of riding I have ever witnessed.

I don’t know what he charged, or what people paid him, but I can tell you it wasn’t enough. He could ride the worst of the worst by whatever means. He could finesse them or be strong and tough with them, and even more importantly, he knew what part of that equation was needed when. One of the highlights of my time at the track was breezing with this jockey. It was my first time breezing a horse and he coached me through it. He wanted me close to his horse so, in his words, we could “clank irons.” Breezing is an unbelievable feeling.

Breezing with another rider, clanking irons, is a world-class experience and one I will always remember.

All of that galloping made me very fit. Early on, I got dumped twice in one day, for a total of three times that week, because the muscle fatigue induced by galloping caught up to me. I bought a lot of beer for the barn that week. (That was the rule). I got through that and got fitter, but the downside was it was also hard on my body. It takes a lot out of you when you are riding so many other horses as well, all day long. It doesn’t give you a chance to recover physically.  I had to pick what was more important because I was riding so many, so I decided to seek out more sport horses to ride.They also paid a lot more which was another incentive.

The Big Operation

Like I said, in the afternoons after mucking and riding at Jimmy’s, I went to another farm to ride as many as they would give me to ride. It was a really big operation with no less than 50 horses on the property at one time. When the mares foaled out, the numbers went up drastically from there. Besides all of the breeding they did, they flipped a lot of thoroughbreds off of the track as sport horse prospects, they imported some sport horses, and they also did a lot of pinhooking. In short, they always had a lot to ride and it was always very interesting.

If you are lucky enough to ride a lot of horses, the funnest part is the sheer variety. I loved riding all the different types, sizes, breeds, personalities and levels of education (or more accurately, levels of non-education). It was brilliant. At this farm, I had one of my best experiences riding as well as one of my worst.

The best experience was taking the pony stallion hunting with Piedmont. The pony was having an issue with stopping at home, but it boiled down to him not trusting his current jockey. I could see, when the pony did jump, that he could really jump. That was actually part of the problem (for his current jockey). Bragging what a great pony he was, I told the manager of the farm he was a hell of a jumper, good enough that I wouldn’t think twice about hunting him with Piedmont. At that time, Piedmont had a reputation for being the toughest, gnarliest hunt in our area.

Well she decided I should put my money where my mouth was.

I started riding the pony around the farm and started jumping small stuff until it gradually got bigger. I went down to a three-foot coop and the pony started to lose a little heart. He tried to stop at the bottom of it and I cracked him hard with my stick. It was good timing. The pony jumped from almost a standstill and didn’t get his teeth pulled out of his head in the process. It was a defining moment in our partnership. In that instant, trust was built, and neither of us ever looked back. To this day, he is the best horse (except he was a pony!) that I have ever hunted. He jumped everything that anyone else jumped that day. Ripping across the field on a good run, we came upon a pretty good-sized groundhog hole. Before I could react, the pony tied his little Superman cape tighter around his neck, and adjusted his feet accordingly, jumping across the top of it safely and carrying on with the pack.

Literally. Worth. His. Weight. In. Gold. 

Best. Pony. Ever. He was absolutely brilliant to hunt!

The worst experience I had there was riding a three-year old warmblood stallion. It was a super hot summer day, and we were hacking around the farm. Because it was so hot, I decided I would wear my ball cap instead of my helmet. He was young, but he was incredibly well-behaved. (This right here is an example of the rationalizing that all horse people do). We were going under a tree when a branch lifted my cap off of my head. As soon as it happened, I reached back to grab it. I didn’t catch it. The cap landed on his behind, spooking him. He bucked, putting me up in the branches, and then took off. The branches very unceremoniously pulled me off backwards and I landed under the tree on my hip. That one really hurt. When I stood up, I had bleeding scratch marks across my face and I couldn’t put any weight on my left leg. He had only gone a few strides before he stopped to eat grass. I grabbed his reins, but I was a long way from the barn. I parked him next to an embankment and hopped up on him pushing off on one leg. Adrenaline is an amazing drug… It was a stupid way to fracture my hip. I was cursing myself for my cavalier decision.

Good judgment comes from experience, which comes from poor judgment.”—Robert Byrne

Canadian Cocktail

I started my new business away from Jimmy’s at a small four-stall barn on a private farm, mostly because the owners invited me to come. They also did a lot of different things with their horses and had a beautiful farm with great turn-out and vast amounts of ride out. It seemed like a good fit, and like most things, it started out that way. They offered me a full-time job working for them, but my gut said “no.” I politely declined. Things went south after that pretty quickly. I don’t think the owner was used to hearing “no” and I think he was offended. Soon after, he walked the one horse I had living in the main barn over to my small barn and handed him to me. He was carrying the horse’s buckets with him, and said, “Sorry, I don’t have a stall for him anymore.”

I knew the gig was up. It was time to get out of Dodge, quick.

I moved the horses to a new farm with a twelve-stall barn. The horse the previous landowner had kicked out of his barn was one of my first horses in “training.” He actually came to be rehabbed from an old injury.

He also happened to be a Grand Prix show jumper.

But I didn’t know that fact about him until much later. His name was Canadian Cocktail, or CC for short. He was a quirky chestnut thoroughbred gelding, with a dishy little Arab face and big, round doe eyes. CC was quite the character. Despite his big soft eyes, he had a history of going after people in his past. I was mindful of this, but didn’t have any problems with him. He was incredibly smart and classy, but he was also scrappy. That was the part that made him great, but it was also the part you had took out for. Honestly, his vast education and experience aside, he was exactly the type I loved to ride.

It wasn’t until much later, when CC was well on his way to recovery, that I asked the owner about a game plan for him. I had started jumping him and wondered what was next. The owner stated her wish to sell him. She was an older woman and was “getting out of the business.” That’s when I found out he had actually done a few Grand Prixes. She priced him at $100,000. I almost dropped the phone when she said it. I had no idea the scruffy little redhead with the big brown eyes was such a super star.

I started jumping him bigger. 

I took CC to Culpeper and jumped around the 1.20m classes, by far the biggest course of jumps I had ever tackled. CC was beautiful to jump. God had blessed him with fabulous balance and a fabulous canter. Not only that, he had a beautiful, pristine mouth. I could see a distance on him a mile away because his canter was so good. He felt like a cotton ball taking off and landing, but with huge power over the jump.

I remember landing off an oxer and looking over my left shoulder in preparation for the turn, but I must have stepped into my left stirrup because he turned so sharply, I became the unlucky recipient of centrifugal force. I didn’t fall off, but I wobbled in the tack trying to find the middle of him again before the next line.

It was very clear he knew way more than I did. He was the professor of our relationship and I was the student. He was incredibly generous and he gave me the education of a lifetime. He taught me how a proper, well ridden course should feel. He also taught me one of the most valuable lessons you can learn when riding—Less is more. I just had to stay in the middle of him, stay out of his way, and let him do his job.

CC was what I called “a real operator.”

He was an absolute dream to ride.

CC competing in a Mini Prix before he became injured. He had the most beautiful face and expression. Photo credit: Reflections of Killington (1997)


My second horse in training was Noah. He was a 15.2 hand, little, short-coupled thoroughbred with a wall eye. Noah wasn’t 100-percent sound when he showed up and I called the owner often, concerned about his well-being. Lucky for Noah, his owner was one of the best horsewomen I have ever met (even if I didn’t know that at the time). She always said the same thing, “Keep riding him.”

So I did.

Noah didn’t really have much of a trot on a good day, but that’s where the lameness showed up. He’d be fine, and then suddenly, he wasn’t fine, and there were moments when he would hop behind. When that happened, I would walk him for a bit and then try again. It was on and off like this for a while, but the owner said, “Just keep doing what you’re doing.”

So I did.

Instead of walking when his trot went “wonky,” I started cantering him for a few strides. That seemed to help him, too. This is how we fitted him up. He eventually worked out of it completely and came sound. His issue was up high, in his hips, or his stifles (or both). His owner spent a lot of money on chiropractic and acupuncture for the horse which also helped him a great deal.

Noah was also an incredible asset to my education.

He taught me it is sometimes it is better to keep going, and do a little when things aren’t right, instead of stopping altogether. 

I loved riding him. (Remember? Variety is the spice of life, especially when riding horses!). When he really got going well, we started jumping him. Lo and behold, that little pocket rocket could really jump. Not only that, he had a heart of gold. He would try all day long. Noah eventually went on to compete at the novice level before he returned to his owner and went on to have a prolific career as a whipper-in’s hunt horse.



Next time: More amazing horses and more lessons as a “neophytic professional”…


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