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The principal-turned-trainer found her stride on the platform by harnessing what she learned in the classroom and on the basketball court.

By Michelle Konstantinovsky
April 02, 2021
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Jess Sims had a surreal experience last November. The Peloton instructor was walking her dog Sienna Grace, a four-year-old pit mix she rescued in 2017, and was hit with a sudden wave of anxiety. Caught up in her feelings around the distance she felt from friends and family thanks to the coronavirus pandemic, her camera-ready smile was nowhere to be found as eight months of collective isolation swept over her.

But as she walked through a local NYC park near two friends exercising together, she noticed something that instantly snapped her out of it.

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Credit: Courtesy of Sara Haile

"People are always working out at that park, but I saw they were looking at something," she tells me during a Zoom call while Sienna Grace and newly adopted pit mix, Shiloh, hang out in the background. "I took my headphones out and heard my voice!" As she would later chronicle on Instagram, Sims unexpectedly caught two Peloton devotees taking one of her on-demand strength workouts on the app. It was totally bizarre and absolutely perfect, she says. "I just had this beautiful moment where I'm like, 'I'm not alone. They're not alone.' And especially during the pandemic where folks are feeling exponentially more alone, Peloton is literally uniting us."

Sims is right: Pre-pandemic, in August 2019, Peloton reported 1.4 million active members. Today, the brand has accrued more than three times that with a total of 4.4 million members and counting. (See: These Celebrities Love Peloton Just As Much As You)

As everyone struggled to find a sense of normalcy in a year defined by the abnormal, many have found solace in Peloton — and not just in its endless library of live and on-demand workouts, but its community. Since joining the team in 2018, Sims has emerged as one of the brand's breakout stars, leading running, boot camp, strength, and cardio classes. In turn, she's gained a massive following and even inspired fan subgroups (some of which, including the #CurseOutCrew, are made up of members who love to hate to love her intense sweat sessions). These member-created subgroups use tags to connect with like-minded users and create communities based on individual interests, goals, instructor obsessions, or class preferences. You'll often find these niche communities taking classes together and bonding on and off the Peloton app and across social media.

But, perhaps what makes Sims' such a force within the Peloton family is the fact that she didn't get her start as a fitness influencer or celebrity trainer — instead, the lifelong athlete landed where she is today after a series of planned pivots, unexpected turns, and perfectly fated timing.

As a Massachusetts native raised just outside of Boston, Sims was drawn to athletics early. "I played every sport," she says. "I did ballet, tap, and jazz, figure skating, tennis, softball, and then got super serious about soccer, basketball, and lacrosse." After serving as a three-sport captain her senior year of high school, Sims attended Trinity College in Hartford, Connecticut where she spent three years as captain of the basketball team while double-majoring in psychology and Hispanic studies. It was during this time when she stumbled upon a literal sign pointing her toward her future.

"I'll never forget, I was in the bathroom at the gym, and I saw this flyer that said 'Teach for America,'" she explains. "I Googled it, and I'm like, 'Yup, I'm doing that.'" Sims scored a highly coveted spot in the competitive program and moved to Houston, Texas where she worked in an elementary school while earning a master's degree in education with a focus on teacher leadership. Soon after, she was recruited to be a kindergarten teacher at a new school in Harlem, NY, and later held an operations manager role within the same K-12 network of schools.

But when an opportunity to become an assistant principal in Lynn, Massachusetts surfaced, Sims says she saw it as a chance to come full-circle — it was her father's hometown; the place she was born. It was also where Sims, whose father is Black and mother is Italian, says she encountered racial diversity for the first time outside of the adjacent and predominantly white town where she grew up. "It's where I had my first Black, Hispanic, and Latin friends, who were also my teammates," she says. "We were the same age, same everything, but had drastically different educational experiences and drastically different opportunities afforded to us" despite being in neighboring towns.

Sims took the job, and for a while, felt secure in her career choice. Still, she says she felt as if something was missing. "I was like, 'Okay, everything is beautiful, I'm saving money, I have this work-life balance, but I'm still unhappy,'" she explains of her internal dialogue at the time. "That's when I started to get back into fitness and health and wellness in a different way." While she'd maintained an exercise regimen in the years since ending her collegiate basketball career, she craved the camaraderie and consistency of group workouts. Her boyfriend at the time worked in fitness and pushed her toward a career pivot. At first, she told herself that with a master's under her belt, it was too late to change her career — that she was meant to be a teacher. "Then I had this epiphany where I realized, I could still be a teacher — just in a different setting," she says.

So, Sims moved back to NYC, and six months later jumped into fitness full-time as a HIIT and boxing instructor at various boutique studios. All was well, when, a year later, she got the call that would change everything. She was being invited to audition for a coaching role at Peloton.

"[Peloton instructor] Rebecca Kennedy used to take my boxing classes, and one day she asked me to grab coffee to talk about future opportunities," says Sims. At the time, she says Kennedy spoke about her coming on as a team member for the launch of Peloton's new treadmill. "I was blown away by the idea, but I didn't feel ready — I wasn't [personally] working out regularly yet because I was so focused on my clients," says Sims. "I was only in fitness for a year at that point and felt I had more to learn at my current studios. Plus, I didn't feel comfortable running on camera yet!"

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Ultimately, Sims says she politely declined the audition opportunity that day but had no idea that another chance would eventually come her way. A year later, she ran into a former fitness studio colleague Olivia Amato, who was now working as a Peloton instructor herself. "She was like, 'Girl! You need to come to Peloton,'" explains Sims. "So, I did some reflecting and realized I was ready for it. I reached back out to Rebecca and told her that the timing was much better now. We met up for another coffee, I auditioned, and the rest is history!"

The move was big on many levels, but in particular, it propelled her evolution in one unexpected and personal way. "When I came to Peloton, I was the first woman of color on the tread[mill] team, so I was nervous," she says. Shortly after joining the crew, though, Sims and fellow Peloton instructor Tunde Oyeneyin had the chance to meet members of the Peloton fan subgroup #BlackGirlMagic, who came to New York for in-person studio classes. Together they joined more than 80 women at a restaurant in Harlem.

"I will never forget that night as long as I live," says Sims. "We gave a little speech, and I said that I didn't know how I was going to be received because as a biracial woman, I fit in everywhere, but I also fit in nowhere. That's my perception, of course, but it's also my truth. The group interrupted me, saying, 'you belong here. You are enough exactly how you are right here. We love you. We accept you. We are so grateful that your representation is on Peloton, and let's get to work.' That was such a huge experience for me," she says of the pivotal moment.

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Sims says being a part of the Peloton community has influenced the ongoing formation of her racial identity in numerous ways. "I'm still going through coming into my Blackness because I'm constantly evolving, and I'm okay with that," she says. "With George Floyd and everything that happened last year, I didn't know what I wanted to say or what I wanted my message to be. I wanted it to be authentic." Sims says she ultimately decided to welcome her community of followers into her discomfort via an Instagram video, sharing her experiences with a Black father who's also a police officer. She also told those tuning in "I didn't meet my racist grandfather until I was a junior in high school." "So many members, whether they are biracial themselves or have biracial children, said thank you," she recalls of the feedback she received.

With her now larger-than-life platform, Sims says she also pays special attention to how she speaks about body image and strength — specifically to her female fans. "I don't like [to say] 'strong not skinny' because if you're naturally skinny, you're naturally skinny — skinny is beautiful, thicker is beautiful, whatever you are is beautiful," she says. "Own it and take up space. I want women especially to remember to be strong and not try to hide."

While Peloton has propelled Sims' growth personally and professionally, she's still a teacher at heart. In addition to her "glazed donut" warm-ups (aka her coined phrase for the dewy pre-workout sweat) and her challenging, muscle-shaking programs, Sims leads Peloton's Fit Family classes, some of which are geared toward kids as young as five. There you can see Sims' classroom persona really come to life, calling on kids and participating grown-ups to jump around, learn the names of different muscles, maybe make some animal sounds, and just grow to love movement. "Adults are just taller kids — we have short attention spans, we like to have fun, we like to move around, we like good music," she says. "So whenever someone asks, 'do you miss teaching?' I say no because I'm still teaching and using the same techniques."

No matter what you're coming to one of Sims' workouts for, no matter what goal you want to accomplish, she'll help you get there and have fun doing it. Her jam-packed classes almost always include EMOMs, AMRAPs, listening games (likely another token from her classroom or team sports days), expertly curated playlists (that somehow echo exactly how you feel at the time), and a refreshing perspective on exercise. "One mantra I live by is 'you don't have to, you get to,'" she says. "That comes from college basketball, and it's transcended fitness."

The phrase has also inspired yet another Sims-obsessed Peloton member subgroup (the #YouGetToCrew), who have motivated the instructor to keep showing up for the community, even on her hardest days. "Peloton is my adult team," says Sims. "I'm not always motivated to work out, I'm not always super happy and peppy. I get irritable and annoyed and my life is not perfect. I don't say that to say, 'oh poor me,' but to say it's part of who I am, and I'm proud of it, and I'm a human being just like anyone else. When I go on the Peloton app and high-five someone and get that high-five back, it's contagious. That kind of thing pushes me through."

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