Jenn Sheffield is not your average beauty pageant contestant. Then again, there’s very little about Jenn that fits into “average.” When we met, she was days away from preparing for the Mrs. Canada Pageant 2025, set to take place this July in Montreal Quebec. It’s not her first time stepping onto a stage beneath bright lights—Jenn has competed in pageants across the country: Miss Cape Breton, Miss Nova Scotia, Mrs. British Columbia, and Mrs. Canada Globe, to name a few. “I’ve either been a semi-finalist or finalist in quite a few,” she says with a grin. “It’s something I’ve always loved doing. It gives me a platform.”
But Jenn’s platform isn’t just about the crown. Born in Florence, Cape Breton, Jenn grew up the oldest of three daughters in a racially mixed family. Her mother—an indomitable force—was the first Black woman in their town. “She was a trailblazer,” Jenn says. “I experienced racism firsthand. But she carried herself with strength, and I learned to do the same.”
Today, she’s noticing how her hometown is changing. “There are more people of colour now in Cape Breton. Last time I visited, it was heartening to see that diversity growing.”
Education took Jenn to Dalhousie University, where she earned a Bachelor of Science in Psychology. That led to work in occupational therapy, focusing on end-of-life dementia care. “Everything I did was about helping people cope with their final moments,” she explains. “It was meaningful, but it took a toll.” After a break working in a general hospital, she returned to dementia care—drawn to her passion for working with seniors—but ultimately had to step away. “It was just too emotionally heavy.”
That’s when she leaned into another lifelong passion: yoga. Jenn had practiced yoga for years but never envisioned herself teaching. “At the time, I weighed around 400 pounds,” she says. “I didn’t think I looked like a yoga instructor.” But she got certified, started teaching—and found her way back to herself. “Yoga probably saved my life. Through movement, I lost about 100 pounds naturally. But more importantly, I found confidence.”
That transformation unlocked something in her. She began running, dancing again, and teaching adult dance classes. Then, in a move that surprised even her, Jenn took up trapeze. “I started teaching trapeze dance and performing as a trapeze artist,” she says, smiling. “I’ve danced in Indonesia, across the U.S., and throughout Canada, leading workshops and shows.”
But like for so many performers, COVID brought that world to a halt. Jenn pivoted once again—first to Canada Post, then to long-haul truck driving across the U.S. “I loved it,” she says. “There’s something freeing about the open road. But as a woman driving alone, there were safety concerns.” Eventually, she made another shift—this time to the skies as a flight attendant for Porter Airlines.
Throughout all of it, Jenn felt the quiet scrutiny of societal expectations. “I was still a plus-sized person, living confidently, loving life,” she says. “But I knew I didn’t fit the industry’s idea of what I should look like. Still, I was proud of the work I did.”
Eventually, Jenn made the personal decision to undergo gastric bypass surgery. “I weighed 265 pounds the day of the surgery. Today, I’m 140,” she says. But her story isn’t about weight loss—it’s about reclaiming agency. “It was about doing what felt right for me.”
Now newly settled in Sarnia with her husband Robin, Jenn is focused on the future—both her own and that of the next generation. She’s currently working with the Canadian Coast Guard and training to become a Marine Communications & Traffic Services Officer. And through her pageant platform, she’s pushing for something close to her heart: better career education for young people.
“I want to go into schools and talk to junior high and high school students,” she says. “We need to stop pushing this idea that university is the only path. I want to be the first speaker who tells them: college is valid. Trades are valid. No post-secondary is valid, too. What matters is finding what fits you.” She uses the Coast Guard as an example. “You can go to Coast Guard college for four years and get paid. Most people don’t even know that. But they should.”
She dreams of a speaker series—real people from real careers talking to students, either in person or via Zoom. “We’ve got the technology,” she says. “Why aren’t we using it to open kids’ eyes to what’s possible?”
Jenn’s story is one of relentless reinvention—from end-of-life care to yoga studios, trapeze stages to truck stops, airplane aisles to Sarnia’s shores. She’s lived many lives already, each one shaped by resilience, self-discovery, and a refusal to be boxed in. “I didn’t fit the mold,” she says. “So I made my own.”
"Humans of Sarnia" founder Art Connolly is a man fuelled by curiosity and a passion for connecting with people in Sarnia. Inspired by the renowned “Humans of New York” series, with a camera in hand, he captures the very essence of the individuals he encounters, preserving their stories through his lens. Follow his series on Instagram and Facebook.