It's Your Whole World: Heather Jackson's Serial-Minded Pursuits

by Chris Bagg, reprinted courtesy of ENVE Composites 

Heather Jackson, the many-times Ironman and Ironman 70.3 champion, once ducked two flight attendants to run down a closed jetway, like the pre-teen protagonist of Love, Actually in order to deliver a pair of borrowed running shoes. It was early in her relationship with now-husband, Sean “Wattie” Watkins, and the two had discovered their flight reservation, booked with Watkins’ mother’s frequent flier miles, came with strings attached: a dress code. Jackson wore sandals, and learned that, in order to board the plane, she would have to put on closed-toe shoes. At first indignant, then practical, Jackson asked around the departure area, eventually securing a pair of sensible tennis shoes, size nine. Unfortunately, the two were on standby, and learned minutes before the door closed that they wouldn’t be flying that particular plane. “I had to return those shoes,” Jackson said, “but they wouldn’t let me down the jetway.” Ignoring their requests, the former Division I hockey player and Olympic hopeful dodged through the gate and down the ramp, tossing the shoes almost through the closing doors onto the plane. Jackson, unbelievably, wasn’t arrested. “I suddenly wasn’t sure who my girlfriend was,” Watkins recalls. “Whatever,” Jackson says. “I had to return those shoes.”

Jackson went to Princeton University, the wildly prestigious Ivy League institution in New Jersey from which she graduated in 2006, but she doesn’t remember much of it. “People always say ‘You went to Princeton? That’s so impressive,’ but I really only went there to play hockey.” Pre-season began in the fall, as soon as the students returned to the New Jersey campus, with the team captains leading practices until October (Jackson captained the team twice: in her junior and senior years). Their coaches joined them in mid-October, and the season ran until March “or April if we made the NCAA tournament.” School wrapped up a month or two later, and then Jackson removed to Lake Placid for the summer, but not for any endurance or summertime pursuits—the Olympic training center was her home for the next few months as she trained to try and make the national team. Come August she would return to campus and start the entire cycle over again. “I almost didn’t graduate,” she remembers. “My senior year we made it to the Frozen Four (ed. note—NCAA hockey’s version of March Madness’ Final Four), so that season ended in April. My senior thesis was due about two weeks later and I hadn’t started it.” Jackson wrote the thesis in ten days (“It was terrible,” she summarized), turned it in, and then waited to see if Princeton would allow her to graduate. “I got a C+ and a B-, which averaged out to a B-,” she says. “I graduated on time.”

She grew up in Exeter, New Hampshire, alongside three siblings: an older half-brother and a younger sister and brother each. She remembers “playing all day long—that’s where I first encountered sports. I don’t remember my first organized sports teams, but the four of us and the other kids in the neighborhood played all the time.” Both of Jackson’s parents worked full-time jobs, her father Chris as a New Hampshire State Trooper (he pronounces it “Troopah”) and her mother Diane as a P.E. teacher. “We didn’t have much, so our parents just sent us outside to play and compete. Somewhere in there I resolved to be as good as the boys at the sports we played.” Jackson’s family reflects a New England pattern: families stay close, with many generations living in the same town. “My grandfather came home from World War II and helped build most of the structures in town,” she says. “Then my parents grew up here and worked here, too—I got my work ethic from them and my grandparents. My grandpa basically worked up until the day he died.” When she talks about her grandfather, whom she called Daida, Jackson gets quiet for a few minutes and lets me ramble through a few more questions. He died last year, during the pandemic, and Jackson couldn’t travel to be with him in his final days. Like his granddaughter, Jackson’s accounts of Daida sound eerily familiar: a small-framed package of energy that rarely stopped moving or working. 

As she graduated from elementary to middle school, Jackson moved from the neighborhood to the sports field, playing soccer and hockey, discovering that she would need to prove herself to coach after coach, the way she’d had to with the boys in her play group. Teams went either direction, the coaches either holding Jackson out of the game because she was a girl, or accepting who she was and letting on-field performance dictate playing time. “One coach, Coach Almond, didn’t treat me differently because I was a girl. He just told me to hold my own out there, and I think he was the first to instill that,” Jackson remembers. “If one of the boys checked me or hit me hard, he’d ask ‘And did you return the favor?’ It literally did not matter that I was a girl. Another coach, though, resented her place on the team (at the time, there weren’t girls’ hockey teams for her to play on). “I was a better player than his son, and he hated that, I think,” Jackson says, relaying one universal unfairness of childhood athletics. “He would put me on a lower line than his son, and I just played as hard as I could, so our line would come away with a goal and he wouldn’t be able to ignore me.” More than two decades later, those qualities persist in Jackson’s endurance racing and training: she’s trained so hard she’s driving herself into hyperventilation, or vomiting at the end of mile repeats. Once, when this author still trained at a fairly high level, I listened to Jackson desperately gasp her way to the top of Mt. Lemmon, hanging onto the wheels of several professional male triathletes—today her times up the iconic climb are faster than almost all of the boys. At the time, I thought it wasn’t out of the realm of possibility that she might actually die rather than get dropped.

By high school, Jackson had played her way onto several elite teams for soccer and hockey, and also into a spot at Phillips Exeter Academy, another wildly prestigious academic institution. Jackson attended Exeter as a day student, however, instead of as a boarding student, occupying a role she had cultivated in a lifetime of playing on boys’ teams: the outsider. Day students at elite New England boarding schools face all of the usual challenges of adolescence, with an additional dollop of having to prove oneself to the (usually) more privileged boarders from elsewhere. Day students typically aren’t full pay at these institutions, which shades them lightly but unmistakably in their peers’ eyes. Jackson responded as she had her whole life up to that point: as if Exeter were a field upon which to prove she belonged. The strategy worked, with Jackson ending up at Princeton after being recruited to several top schools for both hockey and soccer. “I still remember high school more clearly than Princeton, though,” she says. “High school was smaller, and sports (although they were important) weren’t my whole world. My teachers were also my coaches, so I’d have them in class and then at practice from 1 to 3pm. Then we’d usually go back to class until six. It was this whole shaping of a person. You had a choice there, I think: you could either grow as a person or just cruise along in class and do the minimum. If you chose the first option, your teachers saw that and kept challenging you. So it was hard, but it was also an incredibly rich time for me. Being fourteen is already hard, but our teachers cared about us, and that made it incredibly important to me.”

Eventually Jackson took up teaching herself, after the senior year that saw her cut from the National Team, the Frozen Four appearance, and an 80-page thesis in ten days. After learning she would graduate from Princeton, Jackson was accepted to one of the university’s programs teaching English in Thailand. “That whole period was such a whirlwind,” she recalls. “I hadn’t really processed getting cut from the National Team, because I had my senior year of hockey to focus on. The games were in Torino, in February, and our season ran for two more months. Then the thesis, then graduation, then Thailand.” As many of us do, Jackson looks back on that period with the National Team with some poignance. “I wasn’t going through the motions,” she says, “But I also didn’t leave every single stone unturned, the way I do now when I prepare for Kona. I went to practice, did my work, and then when I was cut it was just, like, ‘Okay.’” I think I was doing what many 18, 19, 20 year-olds do, when you think there will always be another chance at something. But at some point that year I realized I wasn’t going to the Olympics, and I think the whirlwind of my senior year helped, since I couldn’t focus on that devastation. Then I was in Thailand and that was that.”

Subvert the Dominant Paradigm, Yo

Jackson taught English for a year in Thailand, came home in the spring of 2007 and, as many former high-level collegiate athletes in their early twenties do, wondered what was next. She applied for a teaching job in California, got it, and completed her first Ironman in a familiar place: Lake Placid. She qualified for Kona on her first try, drove across the country with her younger sister Becca (who goes by “Biffster,” when Jackson addresses her, and sounds more like a twin than a younger sibling), and started teaching high school in San Jose, after negotiating a few days off around the second weekend in October. “I brought a camera with me on that first Kona,” she recalls gleefully. “One of those early digital flat silver cameras—I stopped in Hawi and took a bunch of pictures. “I loved those early races,” she remembers. “I always felt like it was just a chance to go out and race and to be competitive.” One August evening after her first year of teaching, she met a charismatic bike racer named Sean Watkins on a group ride in San Jose. As many local weekly rides do, this one built into a race simulation, and Jackson and Watkins found themselves working together to close a gap to the front group of the ride. The two bumped into each other again at Kona that fall (Jackson had requalified for her second Kona), and Oceanside 70.3 in the spring of 2009 before deciding that they were actually dating at the legendary Wildflower Triathlon. Watkins convinced her that she could always return to teaching, so when she got back home from Wildflower Jackson let her principal know she wouldn’t be back in the fall. Still not sure whether cycling or triathlon held her future, Jackson moved in with Watkins in Los Angeles, trained at the velodrome for the pursuit and the omnium, raced the local criterium series, and hired her first triathlon coach. London 2012 beckoned, with a possible place on the track cycling squad, but triathlon eventually won out when Jackson nabbed a spot on the 2010 TREK/K-Swiss Elite Team, one of the early triathlon super teams. She joined Chris Lieto, Joe Gambles, Julie Dibens, and several other elite athletes, all of whom dominated podia around the sport that year and beyond. Jackson immediately made headlines, taking 5th place in the 70.3 World Championships that year, only three seasons removed from her first triathlon. Triathlon took notice of the small, powerful former hockey player from New Hampshire, and maybe not just for her results; the sport, over a decade ago, hadn’t evolved much from its staid, traditional look: you might describe the TREK kits as classy, but you could also describe them as boring. Jackson inked her first tattoo that year, remembering her grandmother, and the sport’s eyebrows arched, not necessarily in judgment, but perhaps in wary interest. Tattoos still lingered at the edges of what was (and mostly, still is) a conservative sport. When the couple tried to purchase their first house together, in Bend, Oregon, banks seemed reluctant to give them a loan. “My income appeared in big lumps,” Jackson recalls. “We wore flat brim hats and had tattoos. Eventually we figured out that the bankers thought we were drug dealers.” LAVA Magazine decided to take that dissonance head on, putting the young pro on their cover in 2012, tattoos front and center (by that point she had two more), announcing Jackson “coming up on your left.” When Jackson and Watkins got married in 2015, she wore black while he wore white. They were married by the late, great Sean English, wearing a Pope costume (mitre included). Whether she invited different athletes into the sport, or simply gave those athletes permission to step forward, Jackson changed something about triathlon and its participants. Watkins and Jackson had already formed their eponymous brand Wattie Ink. in 2009, inviting triathletes to join a team with them, but Jackson’s burgeoning success, the LAVA cover, and the sport’s hunger for a new look all elevated her to household status (at least within the confines of multisport homes). Interest in the Wattie Ink. Elite Team surged, with Jackson and Watkins sifting thousands of applicants each fall to this strange new model for a brand: a group of athletes united by a shared interest, all with the robust support of committed sponsors, under a few committed and charismatic leaders. These days teams such as the Elite Team are commonplace, but in the early 2010s they still drew bemused curiosity from other athletes. Soon Jackson and Watkins stood at the head of a die hard community of triathletes, all proudly sporting the gothic “W” the couple chose for their logo (they didn’t have to look far for the inspiration—it is literally tattooed onto Watkins’ chest). By that year she stood on the podium at 70.3 World Championships, cementing her reputation as the middle-distance American triathlete of her generation. A star, as the cliché goes, had been born.

Norming, Transforming

Another cliché, this one from the business world, states that organizations move through three states as they develop: storming, or taking over/moving into a new sector; norming, where the company assimilates the new sector into their organization and business model; and transforming, where the now-assimilated part of the company turns into something totally new. From 2013 until the beginning of the COVID-19 pandemic, in early 2020, Jackson moved into the norming phase of her career: she continued landing on world championship podia, rising as high as 2nd place at the 70.3 distance in 2014, while also graduating to the Ironman distance and Kona, where she quickly rattled off several top-five positions (Jackson has been 5th twice, 4th, and 3rd in Hawaii). The company that she and Watkins founded, Wattie Ink., changed from a brand and community without a product to an in-the-flesh triathlon and cycling apparel company based in Vista, California, founded on the principle that high-quality gear can still be manufactured in the United States. The venture grew into a $6-million-a-year business. Two more teams—the Hit Squad and the Gravel Collective Project—joined The Elite Team, bringing the number of athletes directly connected with Jackson to almost a thousand. Other top professionals joined the brand, and soon what had been an edgy newcomer joined triathlon’s mainstream. Jackson changed coaches twice, moving from Cliff English to fellow professional Joe Gambles and then finally to Ryan Bolton, with whom she works today. At some point, she looked around and realized the sport made up the scaffolding of her life. “I’m in this weird midlife crisis: ‘this has been my life for twelve years,’” she says. “I’m not done, but I wonder what’s next. It’s been my whole career since giving up teaching, but it feels like it was a minute—it went so fast.”

The pandemic, as it has done with many companies, organizations, families, and individuals over the past twelve months, gave Jackson a chance to reflect on her rapid dozen years in the sport, think about what remained in triathlon, and what would come next. As all norming periods do, this one ended when Jackson and Watkins, as the rest of us did, retreated to their homes for hibernation or metamorphosis. In April of 2020 Jackson and Watkins took their small Honda Element and several bikes and headed for the Arizona desert, to camp outside of a town called Patagonia and to ride bikes all day long, taking social distancing to a new level. “I think one of the things I’ll take out of the pandemic is that there are so many different ways to prepare for triathlon. I tried for so long to do it just one way: swimming, cycling on the road, and running, but riding our gravel bikes has changed that. Wattie and I and friends like Ben Hoffman or Sam Long or Paula Findlay and Eric Lagerstrom strung together huge rides: the backside of Mt. Lemmon, or 240 miles from Tucson to Nogales and back. The pandemic also made me realize just how much I still want to put in a top performance at Kona. There are times when I hate the sport, when I’m tired of it, and sometimes the dominoes start to fall—I stop enjoying the racing, then the training, and then I just want to be done, but this past year has made me just want to get back to where I started, when the race was really just a race, and I didn’t think about all of these other things: ‘whose feet should I follow in the swim, what are my watts, am I running too fast?’” Jackson, long a wrestler with pre-race anxiety, has started trying to leave those questions behind as she approaches her races. “You can second-guess yourself all the way until the start,” she cautions. “Now I try to leave all of that behind a few days before the race, so I can just race. That’s one of the reasons why I’ve loved gravel this past year—it reminds me of growing up in New Hampshire with my brothers and sisters and neighbors, and playing in the street or the yard. There was only the goal to get to the end quicker than the others around me, and these days that’s when I have my best races.”

At this point in her career, there isn’t much left for Jackson to accomplish, except for the goal that many professionals chase but only a few can claim: a world championship. On the 70.3 side, Jackson has been 5th, 4th, 3rd, and 2nd. In Kona, she’s placed 5th (twice), 4th, and 3rd. When I asked her how she felt about that pattern, she told me “Those races are some of my best career results: the accomplishments of which I am most proud. I performed at the biggest races of each season and showed up when it counted. They are bittersweet memories, too, because the 70.3 championship results were when I was still relatively new in the sport: 2010 through 2013. I had only been racing a few years. Same with Kona. When I was 5th in 2015 or 3rd in 2016—I was new to the Big Island. I didn’t have any expectations, and I got to race the way I race best: just going out there, no science, no analysis, and just racing fucking hard. Once I had some results at that level, the mindset shifted: analysis, tactics, trying to swim with this athlete or ride with this other athlete, that kind of thing. That analysis is good—it means that you deserve to be at that level—but I never did that in the early years of 70.3 Worlds, or Kona, and there was something freeing to it. These days I’m trying to get back to that mindset.”

Jackson’s racing hasn’t been the only realignment during the pandemic. In early 2021 she and Watkins parted ways with the apparel company they founded, the one that still bears Watkins’ name: Wattie Ink. The couple attempted to purchase their shares back from their partners, but ultimately were unsuccessful, and as Jackson toed the start line of her first Ironman of the year, in Tulsa, she did so wearing a kit fashioned by one of her original apparel sponsors, Zoot Sports. The community they’d founded (the Elite Team, Hit Squad, Gravel Collective Project, and The Unbreakables) alternated between poised restraint and ardent outrage about the split (primarily directed at the couples’ former partners), but the general message was one of unwavering support for Watkins and Jackson. The teams, it seems, collectively have the couple’s backs, a remarkable display in what is, at its essence, a sport for individuals.

When I reached Jackson for this call, she was recovering from Florida 70.3, a “Kona-like” barrage of heat and humidity in The Sunshine State. Jackson finished third, improving upon her 4th place at Galveston 70.3 the week before. Racing was back. Ironman Tulsa was exactly one month away. A family of Javelinas had wandered through the wash behind Jackson and Watkins’ home in Tucson, where she trains through the winter, and she’d published a picture of them to her social media feeds. The couple planned to race Tulsa, return to Tucson, and then drive their camper van back through the Western states to Oregon, where Jackson would map out the rest of her season before Kona. Unbound Gravel, a race Jackson has flirted with for several years, was still a possibility, but Coeur d’Alene, the site of her Ironman first win, had reappeared on the ever-evolving post-COVID Ironman schedule. Kona (and the races that lead to it) still dominate Jackson’s imagination and aspirations. “Last summer I read Relentless by Tim Grover, right at the end of August or the beginning of September—when normally I’d be in final preparation for Kona. I’d done some things like some huge multi-day gravel rides, and I ran almost 400 miles in August, mostly to see what that was like, and I read that book right when I was starting to feel ‘OK, I’m over this—I’m ready for things to get back to the way they were.’ It’s about the mindset of giving something everything you’ve got, day after day. And that’s how I want to prepare for Kona—leaving nothing undone until it’s race day, and then I just get to go out and do what I’ve always loved: racing.” I asked her what else had been on her bookshelf over the past year, and she told me she’d had three types of books in rotation: “Something like Relentless, you know, sports and sportswriting, then some kind of nonfiction, and then a trashy beach read.”

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