When Taylor Diepold was the captain of her high school swim team while growing up in the Hudson Valley area, she was hard to beat. She was also, more often than not, living in fear — fear of failing to meet expectations, of not achieving or appearing to achieve success. Any enjoyment that came from being the star of the team, winning races, or setting records was often accompanied by the pressure and weight of those expectations, and over time, it sucked the joy out of the sport she loved.
A story arc that is familiar for many elite athletes followed — Diepold, who suffered from childhood depression, fell into substance abuse and dealt with eating disorders in her late teens and for most of her 20s. But over time, she learned an important lesson about fear.
“When I was in my 20s, I was ruled by fear of failure and what other people thought of me, and anything I did was just to overcome fear,” she said. “Now, it’s the other side of that yin and yang; you need fear, but you can also turn your back on it.”
That’s exactly what Diepold did on August 27, when she completed a roughly 7-mile-long swim around North Haven, starting at Long Beach in Sag Harbor, on the south-facing side and the narrowest part of North Haven, starting off in Sag Harbor Cove and making her way toward the bridge. Less than four hours later, she finished the swim in Noyac Bay, on the north side of Long Beach. She is believed to be the first ever woman to accomplish the swim around North Haven. Accompanied by two friends, Evelyn O’Doherty and Nehal Hakim, who kept on eye on her while following on standup paddleboards, Diepold finished the open water swim in just 3.5 hours.
The 29-year-old — who splits her time between Shelter Island, Aspen, Colorado, and southern California — works as a movement specialist, offering mindful fitness instruction, breathwork and massage therapy to individuals and small groups, based on her own personal experiences and after earning a degree in physiology. She says she became motivated to teach the kind of mindful movement and meditation she shares through her business after experiencing first hand how it helped her overcome substance issues and change her mindset as it relates to success and failure. The idea to swim around North Haven came about organically, a function of spending time outdoors either working with clients and swimming on her own at Long Beach.
“I believed I could do it, and took the time to plan it,” she said. “And I did it because I trusted myself that I could do it and also let go of the fear of not being able to do it. Just by starting the swim, I accepted any risk and was OK if I didn’t finish, which made it even more likely I would finish, because it took the pressure away.”
Of course, Diepold still put intentional planning into the challenge, which meant monitoring the tides, particularly in the area around the South Ferry, and building in short breaks to hydrate and refuel her body. She set a tentative goal to finish in 3.5 hours, knowing she was capable of swimming between 18 and 36 minutes per mile, depending on the water conditions. She was originally planning on completing the swim on August 22, but then Hurricane Henri rolled into town, which caused her to reschedule. Setting aside enough time to complete the swim and take the necessary rest required ahead of time while still honoring her work commitments proved to be the biggest challenge, Diepold said, casually adding that shortly after completing the grueling swim she gave two massages and also taught yoga to a few clients.
While the swim was certainly challenging and physically demanding, Diepold says she also thought of it as a meditation, adding that she rediscovered the joy in the sport she’s always loved when she eliminated the winning and losing from the equation and found the value in simply moving her body through the water without a finite end goal.
“Swimming has always been an outlet for me, because it’s a place where you can feel weightless,” she said. “The weight is literally taken off your shoulders.”
The right mindset was only part of the recipe for success that day. Diepold’s raw talent as a swimmer and her impressive physical conditioning were just as important as her attitude. She certainly impressed O’Doherty, who met Diepold just a few months before the swim, after a mutual friend, chiropractor Glen Goodman, introduced them, saying simply “you should be friends,” aware of their mutual love of the water and how much they had in common.
O’Doherty said she immediately said yes when Diepold asked her to accompany her on the swim, and O’Doherty recruited another experienced SUP boarder, Nehal Hakim, to join her and support Diepold.
“She was so efficient in how she put it all together,” O’Doherty said. “She’s incredible. Her swim stroke is perfection; there’s not a drop of water or ounce of energy wasted. Her physicality is impressive, to say the least, and so was her focus and her overall game, from nutrition to preparation and training. She’s really inspirational.”
O’Doherty said she was also impressed by the fact that Diepold wasn’t asking for monetary donations, but instead made a much simpler request of anyone she spoke to about the swim — asking people to donate a “moment of stillness” for every mile she swam.
Diepold said she made that simple request based on her background studying the benefits of breathwork and meditation, saying studies have shown it can greatly increase focus and vigilance.
“Instead of asking for money, I wanted people to think about their choices and their own well-being,” she said. “That’s what makes us all better, when everyone tries to better themselves.”
Unlike what she experienced during her years as a standout high school and collegiate swimmer, there was no medal handed to Diepold after she finished the swim, no tangible award or victory, no official record broken — although to her knowledge she is the only woman to ever complete a swim around North Haven. There was no huge crowd cheering her on either, although she did have not only the support of O’Doherty and Hakim, but the unwavering support of her boyfriend, Sag Harbor resident Daniel Schlaegel, grandmother, longtime Shelter Island resident Jane Babinski, and mother, Jill Diepold, who popped up during different parts of the swim and cheered from the beach, with cowbells. Diepold’s reward for finishing was more interior.
“My biggest takeaway was learning the language of my body, and realizing that my body is going to support me as best it can in anything I want to do,” she said. “And to constantly check in with my body and say, ‘Are you still OK?’ It was a feeling of, I can do this, my body is going to support me.”