Cyndi Jackson, 44, is a Grand Prix rider and trainer based in Glendale, Arizona. She most recently earned the open Intermediaire II and open Prix St. Georges championships at the Great American Insurance Group/USDF Region 5 Dressage Championships (New Mexico). She’s also an avid long-distance runner and is running a 100-mile trail race Saturday, Oct. 29.

I’ve always kept kind of a crazy schedule. In high school, I worked the graveyard shift as a waitress at Denny’s to support the horse who started my dressage career, a Tennessee Walker-Quarter Horse mare named Maxine. My first Grand Prix horse had anhidrosis, so I’d routinely get up in the middle of the night to ride him at the coolest part of the day, then catch a few hours of sleep before starting my own workday.

These days, the crazy hours are so I can go running. I’m training for a 100-mile race called the Javelina Jundred. (Javelinas look like wild boars and roam the Arizona desert in little herds. The “j” is silent, so it’s pronounced like “havelina,” and the organizers of this race are really committed to the silent-j thing.) Daytime high temperatures in Phoenix are still in the 80s and even 90s well into October, so that means lots of early morning alarms so I can in get my own miles before I start riding and teaching.

Running is something I picked up just a couple of years ago, when I was going through a really stressful time during the winter of 2017-2018. It was sort of my version of a midlife crisis. I went for a run one day to blow off some steam, just running for as long as I could, and then walking, and then running some more. Then eventually I could run for 30 minutes at a time, which was pretty amazing.

I did four or five half-marathons and then did my first full marathon in February 2019. I actually qualified for the Boston Marathon and was planning to go, but that was supposed to be in April 2020, and of course it was canceled because of covid. All the other races were canceled too, so I starting to run on the trails. And the trails caught me; they just got my soul.

When I first started running, I was so stressed out with so many different areas in my life, between motherhood and work and everything else. It was the one place I could go where I wasn’t a wife, I wasn’t a mother, I wasn’t a horse trainer, I wasn’t a business owner, I wasn’t a daughter. I was just just me, unapologetically me, just out there, doing something for me. My whole life revolved around trying to give to others, so it’s like my one selfish thing I do for me. I have kind of a demented sort of self-care… going out and running until my feet feel like they want to fall off my legs!

2:30 a.m. Wake up, feed the dogs (Riley, a rescued Lab mix; Oakley, a full-sized Australian shepherd; and Bailey, a mini Aussie) and pack lunches for me and my son, Ronin, who is 9. My husband, P.J., is out of town on a three-day business trip, so everything is on me today!

My husband P.J. isn’t here today for me to take his picture, so here’s a recent family photo. Photos Courtesy of Cyndi Jackson

3 a.m. Make breakfast, which I’ll eat in the car on the way to the trailhead.

3:15 a.m. Leave for my parents’ house with a still-sleeping Ronin in the car. I carry him in the house and leave him sleeping on the couch, then head out to the trailhead.

3:55 a.m. Throw on my pack (which contains water, electrolytes, and snacks, as well as emergency supplies like Band-Aids, Neosporin and of course tweezers for any unfortunate interactions with a cactus) and hit the trail. It’s currently 76 degrees, and I’m doing 8 miles today with a couple of friends. The fact that I had people meeting me at 3:55 in the morning to go for a run is pretty special. That’s my social life, from 4 in the morning until like 5:30. Normal people go get drinks after work with their friends; I go run with my friends before work starts.

A quick 8 miles with my girls before heading off to the barn! I often get some great sunrise photos out on the trail, but we were done before the sun came up today.

5:20 a.m. Finished with my run, now I head off to work.

5:45 a.m. Arrive at my barn, Bar A Ranch, a gorgeous 20-acre dressage facility in Scottsdale, Arizona, with a covered arena (an absolute must in Arizona) and access to trails. (My business, To The Max Dressage, shares the facility with Missy Gilliland Dressage. I love working alongside Missy!) I drag my horse’s supplement baggies into the barn and restock, and do a quick wardrobe change.

It’s still dark when I arrive at the barn before 6 a.m.

I have 12 horses in my program at this location, plus my mom’s horse, who lives at her place. They range from 3-year-olds to FEI-level, and I usually have 10 or 11 of them on any given day, either for a ride or a lesson.

A freshly groomed arena awaits me when I start on my first horse.

6 a.m. I’m on my first horse at 6 sharp. Florisson (“Jack”) is my sponsored horse, owned by Ann Damiano. He is my superstar and is just coming back from a joint injection that got infected earlier this year; we definitely thought we were going to lose him a few times. Then while he was laid up, I had a fall and broke my arm and some ribs and tore my rotator cuff. He is going really well, and I’m super excited to have both of us back in good health again.

Florisson (“Jack”) is my superstar!

One of the horses I’m working with today is Fanfare, a 3-year-old Oldenburg by Fidertanz that I bought as a weanling from Hidden Springs Ranch in California. Kristina Vahe, who is Missy’s assistant trainer, started him for me. I co-own him with Allen Kalchik, one of my clients (who also owns Ehrengold, the horse I rode in the I-2 at Regionals).

Fanfare, my 3-year-old, being ridden by Kristina Vahe, who started him for me.

Allen went in on this horse with me three years ago because he really wanted to help me get my own personal nice horse. He’d seen some nice horses come and go out of my program, and saw a little bit of heartache each time a good one left that I was hoping to spend some time with. So he and his husband, James Cramer, decided that they would like to invest in a baby horse with me.

I also have a quick interruption to meet with the vet to recheck a horse that’s set to go back into work after a lay-up.

9:35 a.m. I take a break to switch horses in their turnouts. My groom (Michelle Ross, who is amazing) hurt her knee, so she tries not to do a lot of walking! So I’ll take a 10-minute break and swap horses out of my four turnouts and then go back to work. We don’t have grass pastures, but our horses get some time out in paddocks every day to stretch their legs, roll and act like horses.

Leading Jack out to his turnout. Notice all the cacti in the background… it looks a little bit different here in Arizona!

12:15 p.m. I have to stop in the middle of a ride on a 3-year-old to FaceTime with Ronin about his schoolwork. 

12:30 p.m. I finish up my last ride and help bring horses in from turn-out.

1 p.m. I leave the barn for the day and head to my parents’ house to pick up Ronin.

1:30 p.m. Arrive at my parents’ and have a quick chat with my vet, who’s there floating teeth and doing vaccinations. (Normally I would also be riding and/or teaching here, but the horses have the day off because of the vet visit.) We briefly discuss a melanoma on one of my retirees, and he tells me that my own personal FEI horse is the worst horse he’s ever done dental work on! 

I’m very involved in all of my son’s education, but the one thing that I don’t do is manage his riding—he rides with Grandma. He has a 10-hand Shetland pony named Midnight, who is owned by our good friend Amy Jackson; she has been generously sharing Midnight with us for the past few years. Ronin trots a tiny bit, and then he mostly gallops around the arena, then he washes his pony and puts him away. (He does longe the pony first, but it’s mostly the pony free-longing around the round pen and Ronin just trying not to hit himself with the whip.)

My son, Ronin, on his 10-hand Shetland pony, Midnight, with my mom Kay Lorenzen in the background on her horse.

1:45 p.m. Back at home. I do a little school work with the kiddo. Like everybody else, we were doing school remotely in 2020, and in 2021 we had the option to continue doing school online, which we decided to stick with. There were no vaccines yet, and with my parents being older, I didn’t want to put them at risk. Even when Ronin was going to in-person school, I would drop him off at my parents’ house in the morning, and they would take him to school, because I would have to go to work too early. And my husband is in construction, so he starts early too.  

So we did online school for that whole next year, and while it had improved from the crash course they had to put together at the start of COVID, I still didn’t love it—it was too much screen time. So we decided to buy a curriculum and start homeschooling. He does worksheets in the morning, and then in the afternoons we’ll do actual lessons and work through things. Our actual sit-down-together schoolwork is probably an average of a couple hours a day, six days a week. My husband helps with a lot of schoolwork on the weekends and his days off.

If Ronin comes to work with me, which he does a few days a week, we go over what his schoolwork is going to be the night before, and then he does his schoolwork in the clubhouse at the barn. Once he’s done, he can go hang out with my groom, he can help with the horses, or he can have some screen time until I get done with my work day.

Ronin takes care of his schoolwork.

2:40 p.m. We leave for Ronin’s music lesson. He has a riddle book, so I spend the entire drive answering riddles.

3 p.m. Ronin’s music lesson starts, and I’m now going to do my second run of the day to get 5 more miles in. 

My second run of the day, when it was 90 degrees.

4 p.m. Music lesson is over, and Ronin and I head back home. There are more riddles. 

4:25 p.m. Arrive back at home, feed the dogs, and finally—after running 13 miles and riding a bunch of horses—I get to shower.

4:45 p.m. Start making dinner. Our whole family is vegan. I fold laundry and have the kiddo read some of his school book to me while dinner is on the stove.

5:30 p.m. Eat dinner and start to fade away…

6 p.m. I get everything ready for the next day—Ronin’s clothes, my clothes, lunches made and in the fridge. And then everybody is in bed by 6:30 p.m.