Holly Bennett: A Marriage of Triathlon and Writing

There are so many paths presented to us throughout our lives and, as we reflect on our previous years, it can be pretty rewarding to see where we were and where we stand today. Triathlon writer Holly Bennett—newly named as Marketing and Communications Director for Challenge Family Americas—has taken many winding and fascinating roads during her ever-changing and packed-with-adventure life to finally land in the triathlon mecca of Boulder.

She has worked for some of the biggest names in the triathlon industry and has allowed the rest of us to feel connected to triathlon on every level. Whether she’s interviewing Kona’s best or giving us the rundown on the latest races, Bennett’s knowledge and insight on triathlon has kept our reading interests peaked for years and has been an insightful part of our triathlon experience.

Where are you from?

That’s not as straightforward a question as you might think! My father worked in academia where, similar to the military, it’s common to move around quite a bit. I had a very privileged education yet a very nomadic life. I went to 10 different schools before high school!

I was born in Hartford (CT), lived in Bethesda (MD), Tulsa (OK), Dallas (TX), Santa Fe and Taos (NM) and the Boston area before spending the four-year stretch of high school at boarding school (Northfield Mount Hermon School) in western Massachusetts.

When it came time for college, I hightailed it 3,000 miles across the country to Santa Cruz (CA) where I stayed put for a long time. Eventually I took a job in the Bay Area and spent two years outside of Oakland, then moved to the Boulder area in 2010.

What was your “original” plan for a career and where did you go post high school?

Originally–and by that I mean my very first career dreams as a kid–I wanted to simultaneously be a writer, a private investigator and a zoo doctor. I desperately wanted to nurse infant wild cats back to health with baby bottles! At age 11, I was given a behind-the-scenes tour of the San Diego Zoo, which included viewing autopsies on a reindeer and a lemur. I was horrified, thus my baby lion and tiger-rearing dream was dashed.

It was not a direct path, though. Throughout my life I was torn between the influence of my father (an academic) and my mother (an artist). I had talent and interest in both realms, but no real clue how to reconcile those competing elements into something harmonious. For the first time in my life I wasn’t fully engaged in school; I was going through a period of personal and family upheaval; and, well, I was 18. I stayed in college for a year, took a leave of absence and, aside from some coursework, never went back.

Instead, after doing more than my fair share of waitressing and bartending, I found a sales job in the bicycle industry. That job led to another and another and another, all in sales, and ultimately in marketing, and my focus shifted from the bike industry to endurance sports. Along the way I discovered and began racing triathlons, which meant my personal and professional passions were aligned. And with marketing (and subsequently writing) I had finally landed on something that fueled both my intellect and my creativity.

What influenced you to start writing?

I did a huge amount of writing in high school. I loved everything from critical essays to creative writing, and I had the opportunity to take several independent study electives in poetry. I would hang out with my staff mentor in her apartment and drink café au lait from bowl-sized mugs (we thought we were oh-so-European) while she critiqued and encouraged my work. She was definitely my first editor!

One of my English lit teachers asked me to share a personal essay assignment aloud with my class (an “essay” I wrote in poem format on a very personal topic–and, for the record, for which I earned an A++), and it actually made a few of my classmates cry. That experience stuck with me–the power of words to tap into and release raw emotion.

What was your first writing gig and did you know then that you were interested in writing as a career?

Oddly enough, although I was a prolific writer in school, I went on hiatus from it for many years. Then I took a job in advertising sales at Competitor Magazine, and being involved in the publishing world reawakened my desire to write. I had to finagle my way into my first gig, but finally I found an interested editor and wrote a piece for the online edition of our northwest regional magazine.

Slowly and steadily I uncovered more and more opportunities. I wrote a regular blog for Triathlete Magazine’s website, I covered one or two races and did my first ever athlete interviews (with Colorado triathletes Mirinda Carfrae and Andy Potts) and finally I pitched my first print article–a humor column for Triathlete. It was well received, and next thing I knew I was assigned a regular column.

I had no intention of becoming a journalist; my column was simply an ideal creative outlet, and an opportunity to push beyond my comfort zone. Then I left that marketing job for another (which brought me to Colorado), the company was restructured and my role eliminated more or less as soon as I started, and I was left to wonder: What now?

Panic is a great motivator! I begged, pitched and pleaded for every magazine assignment I could find, plus added marketing, public relations and copywriting clients into the mix, and basically created my own career as a freelance journalist and communications specialist.

What were your favorite topics or types of triathlon articles to write?

I always enjoyed writing that humor column–which I did monthly for six years. It was oftentimes self-deprecating humor that I think many readers related to in terms of their own triathlon experience. I’m certainly not shy about sharing my personal foibles, especially if they help others feel more “at home” in the sport.

I also adore travel writing. Exploring other countries and cultures via swimming, cycling and running is a phenomenal experience and something I’ve worked very hard to encourage others to do without fear.

Finally, I find long-form personal profiles to be deeply rewarding as a writer–digging into a person’s life story and what drives them, interviewing the individual, their friends and family, and ultimately honing in on +/- 3,000 choice words that do their story justice.

Is there anything you find particularly challenging in writing about triathlon/triathletes?

Did I mention transcribing those interviews? Definitely the bane of my journalistic existence! I did learn over time to be more concise with my questioning, thus saving myself hours of transcription time. That’s not necessarily a challenge specific to triathlon, but I think that because I knew so many of my interview subjects personally, the conversations tended to flow–which subsequently meant major transcription projects.

What did you learn about the sport/people from writing about the triathlon community over the years?

I always find it interesting that there are so many different approaches that can be equally successful–different training philosophies, race strategies, nutrition plans, must-have gear, mental/emotional tools, you name it. I love learning about the slightly off-the-wall or unconventional methods that people adopt, especially when they work. You’ll find athletes that believe things must be done a certain way; yet what’s true for one person may be completely opposite what is true for another, and I really like that there’s no single correct formula. For example, triathletes always say, “Never try anything new on race day.” But interview Andy Potts and he’ll tell you he tries something new every time he races.

I’ve found that in order to balance life–career, friends, family, and sleep–with this sport, and in order to truly enjoy the process stress-free, you have to be flexible. Triathletes tend to get very hung up on strict adherence to a training plan, yet for the average age group athlete, flexibility and willingness to go against the grain of what they might think is a must is critical.

My own system for race prep follows a fairly simple equation, based on what I can fit into my schedule. It boils down to roughly 90% heart plus 10% training. I’m not winning any world titles, but it works OK for me!

What is your current role at Challenge Family Americas and your main objectives as you begin this new journey?

Early this year I took on a new role as marketing and communications director for Challenge Family Americas. It’s such an exciting opportunity!

I’ve gotten to know the Challenge Family race series and the people behind the scenes at Challenge Family over the past few years, covering and racing several of their events around the world, and I’ve become a huge fan of the brand and everything it stands for.

Now I get to really dig in deep with the team and work to help our events grow and thrive in the Americas region. Challenge Family events are athlete focused first and foremost. They’re about making sure the experience is an unforgettable and positive one for every participant, from the winning pros to the final finishers, as well as the family members and friends on hand to spectate.

We offer relay, aquabike and kids divisions to make sure there’s something for anyone that wants to participate. My main goal is to educate triathletes, triathlon fans and people that are perhaps unfamiliar with the sport as to what the Challenge Family brand is all about.

What makes Challenge Family Americas such a great place to work? 

The people and the vision that drives us all. Everyone involved in the organization is devoted to creating the best possible race experiences–races that are a whole lot of fun and all about the athlete. There’s something very special about working with a team where every person is equally dedicated, positive and eager to tackle the tasks at hand. Plus, we’re all over the world, yet there’s a real “family” bond within Challenge Family.

Are you still keeping your hand in the “writing” cookie jar? If yes, what are you working on?

I do have the opportunity to do a fair amount of writing in my role at Challenge Family Americas, plus I maintain a small portfolio of copywriting, marketing and PR clients. But I’m not currently doing any journalism work or any personal writing projects. That said, I’ve felt a pang here and there to write a few things, so I’m considering starting a blog.

What do you like to do when you are not writing or working?

I do like to swim, bike and run–especially run! I love good food and restaurants, plus experimenting with recipes when I have time. Good red wine is a passion, and the company of good friends coupled with red wine is even better.

Travel will always have a grip on me, especially international travel. When I’m home I’m fairly low-key. I value my down time and savor the moments spent with my boyfriend, my BFFs and my sweet pup, Viggo (aka, the coolest dog in the world).

How many triathlons have you done and which ones were your favorite and why?

I couldn’t possibly count! I think my first triathlon was in 1998. In July I’ll tackle my ninth full distance long course race at Challenge Roth, so I’ve certainly logged a lot of racing miles. Some of my favorite race destinations thus far include Phuket (Thailand), Penticton (Canada), Taiwan, Vietnam, New Zealand, Australia and Costa Rica.

But if I had to pick one favorite among all the races I’ve done, it’s easy: Challenge Roth. There’s nothing quite like the Challenge Roth experience. I’ve been three times–once purely to report on the race, once as part of a relay team and last year to race the entire thing. It was the hardest, slowest full distance event of my entire triathlon career. I was (unknowingly) quite ill with an intestinal parasite, which left me unable to eat, so it was a long and very surreal day.

I took a nap in T2 before finally running the marathon solely fueled by Coke (and lots of it)! Yet I loved every moment of that crazy day. The few minutes climbing up legendary Solar Hill on the bike, with the crowds 10-12 deep and screaming like mad, made my entire 14 hours of suffering worthwhile, as did the crowds on the run. Just thinking about it gives me goose bumps!

What is your favorite part about being a triathlete?

Aside from the fact that the triathlon lifestyle keeps me fairly healthy and fit, I’m fascinated by the mental and emotional side of the sport. I’m an extremely introspective person, and I have learned more about myself–about my resilience and courage–on triathlon racecourses than anywhere else. I love being pushed to my limits and finding my way through the peaks and valleys that are inherent in long distance racing.

What is it about Boulder that has kept you here even though you can work remotely?

It’s hard not to love Boulder–between the natural beauty, the training opportunities, the social atmosphere and the fantastic restaurants that cater to just about every tweaky diet imaginable. I’m a natural born nomad, but with a strong nesting instinct–which makes absolutely no sense, yet is true to the core of me. So who knows where I’ll be a year from now!

What is it about triathlon that keeps you near and involved in the sport both professionally and personally?

My personal and professional lives have been intertwined for so long now, it’s hard to imagine it any other way. Occasionally I’ve thought, what if I worked in marketing in a completely different industry? Because my job–and the roles I’ve held previously in this industry–is certainly demanding, but it is so much fun!