I quit my desk job and opened a Pilates studio in Corktown

As a professional ballet dancer, Jennifer Winter began practising Pilates to help offset the rigours of dance. After retiring from the profession in 2016, she got a job working in admin at Soulpepper Theatre Company. But Winter was miserable sitting at a desk all day, so during the pandemic she quit and opened the doors to her Corktown Pilates studio, Have a Nice Day Pilates, in August of 2021. Here’s how it came about.

—As told to Andrea Yu

“I grew up in North York, and as a kid I’d always put on performances in our home. When I was six, my parents enrolled me in ballet class. Dancing felt like a fairy tale to me–it was whimsical and magical. It was a way for me to escape and be in my own little world.

“At 16, I was accepted into a prestigious summer program at the Juilliard School in New York City. We were dancing four to six hours a day, five days a week. The stress and physical demands on the body were extreme. As part of our curriculum, we took a Pilates class once or twice a week. I fell in love immediately. Pilates is all about tender, low-impact, high-rep exercises that allow you to focus on your body. It was the perfect complement to the rigours of ballet.

“Back in North York after the summer, I was accepted into the dance program at the Cardinal Carter Academy for the Arts. I was used to being one of the only Black ballet dancers around—I just tried to get on with it, but I was constantly reminded that I was different and felt like I was continuously apologizing for just being me.

“After graduating high school in 2006, I packed my bags and moved to New York City to pursue my dream of becoming a professional dancer. I was accepted into the Ailey School’s three-year dance certificate program. The Ailey School is one of the biggest and most renowned ballet and contemporary dance schools in America. It was founded in 1969 by Alvin Ailey, a Black man, at a time when Black dancers weren’t allowed in traditional ballet and contemporary dance spaces. It was inspiring and overwhelming to study at an inclusive school and spend time with so many wonderful diverse movers and human beings from all over the world.

“I continued to practise Pilates while I was at the Ailey School and earned numerous teaching certifications with the intent of teaching classes on the side for a little bit of extra cash. But school was so busy that I didn’t have enough hours in the day. After I graduated from the Ailey School, I had short stints at dance companies in New York, Vancouver and Montreal. Then I moved to the U.K. in 2011, where I landed my big break—a role as a full-time lead dancer in a production of Carmen at the Salzburg Opera House. During the run of each season, we were based in Austria, and I would travel back to London in between seasons.

“It was thrilling to dance for such huge audiences. All of my hard work was paying off—and I was living my dream. Over the course of a year, I performed regularly with the Salzburg Opera. Then my contract was over. I auditioned for roles in London and looked for work in Toronto too, but the opportunities were slim. It was a constant hustle, going back and forth to auditions. I was mentally and physically exhausted. I met my partner, Joel, in London in 2012. He’s from Stockholm, and we decided to move to Sweden the following year. I realized that ballet wasn’t feeding me enough anymore. I was putting so much into this craft and getting almost zero return emotionally, financially and physically. So after we moved, I hung up my pointe shoes for good.

“I still needed to pay rent and eat. So I started teaching my own Pilates and barre classes. At first, I would rent space in art galleries, studios and bars; then after a year, I was hired by a hotel to teach classes five times a week. It felt very natural. I loved the idea of creating and holding space for humans to explore their bodies; it came very naturally to me. I had been going to Pilates and boutique fitness studios all my life, and I was always aware of the lack of diversity, especially in the people who owned the establishments. I thought about how great it would be to open up a Pilates studio of my own. I started looking at spaces in Stockholm, but it just wasn’t in the stars yet, so I put the idea on the backburner.

“In 2018, Joel and I decided to move to Toronto. I had been away from home for over a decade. I was missing my family and had a very strong magnetic pull to move back. I found some work teaching Pilates to private clients, and I also picked up odd jobs, like working the front-of-house at a juice bar. By 2019, I found a full-time job working in admin for the Soulpepper Theatre Company. I needed stable and reliable work but it just wasn’t for me. I was sitting at a desk all day, and as someone who is a natural mover, I found it very limiting. I was pretty miserable. And it got worse over the pandemic once I became stuck at home.

Finding my everyday rhythm was tricky during the pandemic. At home, work and rest were bleeding into one another and I found it difficult to switch off for the day. I was struggling to find the motivation to work. My mental health got knocked with the constant onslaught of doomsday news. It was heavy on my nervous system, and I had to be mindful of how much news I was digesting a day. But movement was my jet fuel—even if I got in 10 minutes a day, it made all the difference. By August of 2020, I couldn’t work there anymore. I knew that there was something bigger and better out there for me, that would challenge me in a much bigger way. So I quit my job at Soulpepper and focused on opening my own Pilates studio.

“The timing couldn’t have been worse. Who opens a Pilates studio during a pandemic? But the fear of not doing it was starting to take over my life. It was something I had fantasized about for so long. It was now or never. I had made so many mood boards and spreadsheets over the years, so I had a plan from the start. My vision was to create a space where folks could hang their nine-to-five at the door and turn inwards. A lot of studios and gyms go overboard with sensory stimulation. There’s a lot of imagery and chaos. I wanted to create a space that was raw, minimal and allowed space for folks to unload their day.

“A few days after I quit my job at Soulpepper, My neighbour Matt mentioned that there was an available unit two doors down from his bar on King Street East. I went to see the space with my partner and a realtor a few days later. It was an almost 700-square-foot unit over two floors in an old Victorian row house that used to be an art gallery. It was extremely charming and I instantly saw the vision for what my Pilates studio could be.

“I signed a lease in September. I needed to renovate the space, so I took out a $10,000 loan from Futurpreneur Canada, an organization that provides financing to young entrepreneurs. I also had some support from family and friends, who helped me install new flooring, paint and renovate the downstairs space. Meanwhile, I was still trying to come up with a name for the studio. One day, I was leaving a store in the neighbourhood and the salesperson said, ‘Have a nice day.’ It was a lightbulb moment. I loved the feeling it gave me.

“I planned to open in January of 2021. But by then, lockdown measures were still in place. So I facilitated classes online instead. I branded Have A Nice Day Pilates as a virtual offering. I started a website and an Instagram account to get the word out. We began with 10 classes a week. I streamed from my studio and people watched via Zoom. My first class had 17 people, and everything that could go wrong did. My Internet was shaky. The alarm went off in the studio. But the people who attended were curious and intrigued. I could sense their excitement. The classes were relaxing—they are more about liberating the body and less about gruelling punishment. People were like, ‘Oh, I can feel good after I do Pilates? Awesome. Sign me up for more.’

“Momentum built from there. Our numbers were pretty good over the next few months. I had dreamed for so long about a studio like this—an inclusive, Black-owned space, and it was important to me to hire folks of colour and people who have been marginalized. In Pilates, we’ve been programmed to think that it’s for one type of body or age group. And it truly isn’t. I brought on additional teachers—who streamed their classes from their homes—and we added online classes like breathwork, HIIT and even vogueing. I wasn’t even close to breaking even, but I still felt optimistic because the demand was building. In March, I started doing classes for corporations. That helped to keep the business afloat.

“By July of 2021, the government announced that fitness spaces could open with limited capacity. Two weeks later, I had my first in-person class, and it was pretty emotional. After eight months of being virtual, my vision was finally becoming real. I had four people in my first IRL class, and afterwards I was exhausted but so incredibly happy. It felt like a release, and I knew it was only the beginning.

“Since opening, we’ve had about six people per class and we’ve been consistently sold out and waitlisted since we opened. The studio is specialized for smaller group classes, and I believe that’s what folks are looking for—something a bit more conversational and intimate with the instructor. That’s made it difficult to turn a profit, but now that capacity limits were just lifted, I’ll be able to have ten students per class which gets me back to my original business model and will allow me to meet my intended targets. We’re running five classes a week in-studio and five classes online. Classes cost $25 each in person and we run as pay what you can for online classes. The demand is huge, and that’s reaffirming.

“I have plans to expand the business from here. I’ll be bringing on a few new teachers by the end of the year so that we can add more classes to meet the demand. I want to offer a more varied schedule of movement classes, workshops and events. It’s about creating a safe spot for folks to come to and move and reflect and pause. Our advertising has just been through Instagram and word-of-mouth. I’ve gotten great feedback so far. People say they’ve always been afraid to do Pilates, but it was one of the best experiences ever because they were so in tune with their bodies and their breath.

“Growing up in the city, I would never have dreamed that there could be a space like this—a Black woman–owned studio on King Street. That is pretty powerful. This is the first Black-owned Pilates space in the city. I never intended to be the first of anything—I just wanted to open up a neighbourhood Pilates studio—so I’m really proud of how far I’ve come. And yet I shouldn’t have been the first. There should be a lot more Black-owned studios all over the city. If this is a step in that direction, then that’s all the success I need.”