Going the distance

From the Ironman World Championship to the Ultra-Trail du Mont Blanc, Heather Jackson '02 on winning, losing and growing as a professional athlete
Heather Jackson ’02 has a system for packing, honed after years of globetrotting. One bag contains wetsuits and goggles. Another holds bicycle shorts, sunglasses and anti-chafe tape. Her running shoes go into a third bag. She also brings a pillow, to ensure a proper night’s sleep. That was an especially important piece of luggage as she prepared to fly across the Pacific Ocean to Hawaii with a uniquely grueling intention.
When the sun rose over Hualālai on October 6, 2022, Jackson and 49 other female professional racers would begin the Ironman World Championship triathlon. The race started with a 2.4-mile swim across Kailua Bay, followed by a 112-mile bike ride through the lava fields along the coastline on the Queen Ka’ahumanu Highway. The final challenge — a 26.2-mile run to Kona — led to a finish line flanked by tropical flowers and roaring spectators.
Race day in 2022 — the first year the World Championship was split into separate men’s and women’s races — was Jackson’s sixth time on the course. But this time, Kona was sweltering, with only a faint breeze. As Jackson huffed past Pahoehoe Beach, the halfway point on the running course, she braced herself for an agonizing three-mile stretch known as the Energy Lab where racers are exposed to some of the strongest, skin-crisping sun rays anywhere in the United States.
Sweat flying, lungs burning from a recent case of COVID-19, Jackson knew she would finish. She had placed among the top five women four times at Kona. But this time, something was different. Jackson was tired, and not just tired in the expected ways. “There was a sense of bittersweetness,” she says. “I was glad to be there, but I knew that this was the last one.”
This Ironman was the closing chapter of Jackson’s triathlon career. At the age of 38, she had “retired” from the regimented training that occupied her waking hours. But she was approaching a far more intimidating juncture: what comes after being a champion.

“The training is all consuming,” says Heather Jackson ’02, pictured here on a ride in the Oregon woods.
Part I: A triathlete is born
When Jackson recalls her childhood, many memories are rooted in the woods, fields and streets of Exeter: being outdoors, moving around and loving it. “I was one of four kids, and growing up, we’d get out of school and then we would pretty much be outside playing street hockey or playing tag until dinner,” Jackson says. “I remember our mom saying, ‘Be home before the streetlights come on.’ That was the rule.”
Jackson’s family lived one mile from the Academy campus, where she enrolled as a day student in 1998 and honed her ice hockey skills. “When I thought about what kind of career I wanted, I assumed I would end up coaching at a school,” Jackson says. “There weren’t a lot of options after college if you were a woman playing ice hockey. The thought of actually becoming a professional athlete had never crossed my mind as something that was possible.”
After graduating from Princeton in 2006 with a dual degree in political science and East Asian studies, Jackson contemplated her next moves back in Exeter. She had been captain of Princeton’s women’s ice hockey team and had played with the U.S. national team, but did not make the 2006 Olympic team roster. One summer day, her parents — both outdoor adventurers — offered a brief escape from the uncertainty — an escape that required another kind of athleticism.
“They were heading up to the White Mountains to enter this sprint triathlon called Race to the Face,” Jackson says. The race at Cannon Mountain — where New Hampshire’s Old Man of the Mountain used to loom over Interstate 93 — involved a half-mile swim across Echo Lake, a 12.4-mile bike ride through Franconia Notch and a glute-busting 3.1-mile run up the steep, exposed skiing slopes. “It sounded cool and like a lot of fun, so I just went with them,” Jackson says. “I entered the race with my parents and tried it.”
Swimming in the lake, gasping with each vertical foot of climbing Cannon Mountain, Jackson was walloped yet hooked. “I went home and immediately dove into learning about how triathlons worked, and where the biggest races in the world took place,” she says.
This surge of curiosity is integral for those who pursue the sport. “You have to go for a long run, bike ride or swim before you reach the point where it really gets hard, and that’s the point the curiosity starts,” says ultra marathoner and author Doug Mayer ’83, speaking from Chamonix, France, where he manages his own ultra-running tour company Run The Alps. “The runner Courtney DeWalter describes this as going into her ‘pain cave’ and what we’re trying to do is make the cave bigger. For many of us, racing is all about what happens at that moment and how we cope with it.”
First, Jackson tried her luck at a triathlon in the Lakes Region of New Hampshire. Then, while teaching English in Chiang Mai, Thailand, she completed the Laguna Phuket Triathlon, one of the oldest and most storied triathlons in Asia. She returned to the U.S. and placed second in her age group in her first long-distance triathlon, the 2007 Ironman Lake Placid in New York.
Soon after, Jackson moved to California to teach world history at The Harker School in San Jose. But just a few weeks after arriving, another door opened, unexpectedly. With her impressive finish in Lake Placid, she earned an invitation to compete in the Ironman World Championship in Hawaii.
The thrill of being there, under the broiling sun, shoulder to shoulder with the top triathletes in the world, was electric. Jackson persevered and won her 18-24 age group. It was the adventure of a lifetime. But until then, triathlons had been only adventures. When Jackson returned to San Jose, the idea of racing professionally started percolating on a long bike ride with a local triathlon training group.
“On that ride, I met the person who would become my husband,” she says. Sean “Wattie” Watkins, a professional cyclist, was struck by Jackson’s strength on the roads. When the conversation turned to triathlons, she recalls, “He was the one who said to me, ‘You should really give this a try.’ He saw something.”
Part II: The routine
The road from weekend warrior to professional triathlete runs through a series of finish lines and podiums — where stars are born, and sponsorship deals are earned. But every racer needs a routine to hone mind and body for maximum competitive output. Jackson rebuilt her life. She left her teaching job and established a foundation of daily, meticulously scheduled triathlon training and conditioning.
“My long game goal was always competing in Kona,” Jackson says. “And I worked backward from there, when thinking about my training.” Her rise-and-grind rituals, which carried her through 15 years of competing in triathlons, often began before dawn. “Almost every day, I would be at the pool from around 6 a.m. to 9 a.m.,” Jackson says. “Then I’d come back home, eat breakfast, and from there, I’d either get on the bike or start running; either of which could last anywhere from two hours to six hours.”
Whichever activity Jackson left for the final hours of daylight served as her “recovery” activity, after wolfing down a restorative late lunch. “There really aren’t off days,” she says. “There are lighter activity days, when I had a little more time to get back to sponsor emails or to run errands. But the training is all-consuming.”
Her tough regimen paid off in sponsorships as Jackson reached milestones like setting a speed record at the 2011 Wildflower Triathlon in California and winning the 2013 Escape from Alcatraz Triathlon — famous for its ice-cold swim across the San Francisco Bay. Her early deals came in the form of free gear: a race bike or a pair of running shoes. When she started to earn money, the checks were relatively modest and usually contingent on her performances.
“I would place fifth and receive a check for $1,500, and that would still feel like winning a million,” Jackson says of being paid to do something she loves. “During that time, Sean and I would drive all over the country for different races. We would be staying in friends’ houses or sleeping in our car. And it was so fun.”

Training for Heather Jackson ’02 includes hiking, swimming, biking and running. “there really aren’t off days,” she says.
Mayer describes going from one-off checks or free gear to sponsorship as a series of concentric circles. “You begin from a place of having fun,” Mayer says, “but you’re winning regularly enough to come on to the radar of a few sponsors and then, both parties — the racer and the sponsor — start to think, ‘What if…?’”
By the time Jackson had earned more lucrative deals with sponsors like Herbalife, which makes nutritional products, and Shimano, a Japanese cycling parts manufacturer, the job had expanded too. “When a sponsor is paying you $10,000 a year, plus bonuses for placing in races, you’re doing a lot more than just racing,” Jackson says. “You’re also doing photo shoots, going on podcasts, attending meet-and-greets, making appearances at 10K runs, and when you work with multiple sponsors, you’re flying all over the map for these things. It involves a ton of time management.”
But even as her global footprint expanded, the mountains of Kona loomed highest. The island kept calling. Having gotten a taste of reaching the podium at the Ironman World Championship, Jackson continued to pursue the grand prize. She made it through the punishing course five times and won the bronze medal in 2016. To augment the Ironman training, Jackson and Watkins split their time between the Cascades Range trails of Bend, Oregon (now their primary home), and the desert outside of Tucson, where the triple-digit temperatures mimicked the conditions of the infamous Energy Lab segment of Kona’s Ironman course.
The more time Jackson spent cycling and running in Arizona, the more the high-heat training offered something beyond strength and stamina- building. “The elevation down there is around 5,000 feet above sea level — you’re higher than you think you are,” Jackson says. “You look to the horizon and you can barely see anyone out there. It’s just you and the landscape.”
Part III: Redefining “Winning”
One of the tensions of being an athlete is the unanswered question, How long can I keep doing this? “What tends to happen is that their victories and their sponsorships are this series of cascading events until they hit a plateau in their mid-to-late 30s,” Mayer says. “And then they have to find something else to do.”
After finishing fifth among the female pros in the 2019 Ironman World Championship, Jackson decided that the 2020 edition of the race would be her final shot. “I had been trying to win this race for 10 years,” Jackson says. She had mostly avoided overuse injuries, but a stress fracture that sidelined her for eight weeks in 2015 was a glimpse of what she would probably face down the road.
Then the COVID-19 pandemic forced race organizers to cancel the 2020 Kona Ironman, and Jackson’s “retirement” was postponed indefinitely. She and Watkins started spending more time in the mountains and the desert, enjoying the quiet, immersive beauty of the outdoors.
“There was absolutely no racing,” Jackson says. “We were primarily living in our camper van, and I was riding my gravel bike a ton; running around on long trails through the woods and the desert with no one in sight.”
The solitude of Jackson’s new adventures awakened her desire to go further, higher and deeper. Even something as thrilling as the Ironman World Championship can become routine. As her life started to return to normal after a brutal year of social distancing, Jackson felt that something had shifted. “I was adjusting to these two new sports, trail running and gravel biking, and I was having so much fun doing it,” she says. “I had fallen in love again.”



By the time the Ironman World Championship race was rescheduled for October 2022, she had found a new path that felt like a natural segue from 15 years of professional triathlon racing. But how would it feel to learn the grueling mechanics of less familiar gravel biking and trail races that were hundreds of miles long? How would it feel to make this leap while approaching 40? And would Jackson’s sponsors follow her?
“When you’re in your 30s, you often get the sense that life is changing,” Jackson says. “I had no idea what I would ultimately be stepping into, if I walked away from what was familiar, but I also wanted to try new things while I still could. I was still fit and healthy. And life isn’t infinite.”
Jackson needed a new mountain to scale — a gateway like Cannon Mountain, where she learned to love the triathlon. And just a few weeks after wrapping up her last Ironman on Kona, she entered an ultramarathon in the parched mountains of Arizona’s Sonoran Desert. At 100 miles, with almost 8,000 feet of elevation gain, the Javelina Jundred would test Jackson like nothing before.
“I had never run anything longer than a regular marathon,” Jackson says. She led for the first 26 miles and kept up her strong pace, doubling the distance and leading the runners at Mile 52. “And then, around Mile 80, I just imploded,” Jackson says.
But falling behind the other front-runners felt more like being awestruck. “I had just gone for it,” Jackson says. “The word ringing in my ears was, ‘Whoa.’ Being out there, trying this and diving in … that felt like a victory, even though I obviously didn’t win the race.”

By vaulting into the unknown, she had a taste of what was still possible. “I had been thinking about this for such a long time,” Jackson says, “and coming out of the Javelina Jundred unscathed, I wondered, What was I waiting for?”
It’s a question many of us might ask ourselves when thinking about the curiosities that call out to us; the shots not taken. What are we waiting for?
Two years after Kona, mountain trails and gravel bike courses have become Jackson’s training grounds. Still a sponsored athlete, and still an adventurer, she has run and pedaled her way back onto podiums, through the hills of Sonoma County in California and historic stagecoach routes in the desert outside of Phoenix.
In August, she plans to head to Chamonix, France, for the 106-mile Ultra-Trail du Mont-Blanc (UTMB) race, where runners set off at 6 p.m., chugging into the darkness with only their headlamps (and a lot of extra batteries). It’s a race that Mayer once considered “crazy” and completely out of his wheelhouse, before running it for the first time in 2017. “As you get older and more experienced, you start casting about for new ways to grow,” Doug says. “It’s a progression of many small steps.”
For Jackson, who’s now doing most of her running practice at night, the UTMB is uncharted territory — literally running into the dark, which she describes as “a scary challenge.” And yet, it’s hardly her first leap into the great wide unknown.
“I know that there will be a time when I can’t compete at the highest level as a professional athlete,” Jackson says. “But, I’m not sure if there’s ever really a good time to say, ‘I’m done.’ Because you need to believe there’s more in there. And out there.”
Miles Howard is a writer and author based in Boston. His work has appeared in The Boston Globe, The Washington Post and National Geographic.
This article was first published in the winter 2025 edition of The Exeter Bulletin.