Teshyla Bailey: Founder Of Sis To Sis Toronto On Creating Empowering Community Spaces For Black And Racialized Women

By Nehaa Bimal

From personal development workshops to open discussion and relief sessions, Sis To Sis Toronto is a community organization focused on personal development for young black and racialized women.

Spearheaded by its executive director, Teshyla Bailey, the organization was launched in January 2019 out of the West End of Toronto and is centered around core values of authenticity, connection, and joy. 

Inspired by childhood memories of a tight-knit community and conversations with her friends, Teshyla created Sis To Sis Toronto to provide a similar safe space for women.

Launching Sis To Sis Toronto: Creating Safe Spaces for Healing and Community Support

Teshyla’s passion for community development and gender equity came from her conversations about life with her childhood friends during recess in grade school. However, conversations about their lived experiences as children took a much deeper meaning later in life.  

With a degree in sociology and a minor in women and gender studies, Teshyla credits her major for allowing her to be able to put to words some of her experiences.

“Something I realized only after joining university was that a lot of our shared experiences were around complex trauma,” said Bailey. “In university, I started to gain the language to really understand oppression and different forms of racism, whether it be on the systemic or personal level. I think that changed the game for me.” 

“It allowed me to start engaging in conversations around these issues and start my own journey in trying to address them. I want to challenge some of these realities and hopefully, end that cycle for other young girls growing up in the city.”

She started applying for women organizations, but while seeking these spaces to gain services, she was unable to identify with those providing the services. 

“They did not look like me,” she said.

“When I finished up school and came back into the city, I started getting together with friends to talk about this transitional period in our lives and the ways in which we wanted to heal and ultimately grow into our next chapter.”

In the quest to replicate the same girlhood pride and girl vibes she and her childhood friends shared but as young women in their mid-20s, they started hosting informal online sessions through social media. The overwhelming positive response led to the launch of Sis To Sis Toronto.

When asked if there were any challenges in launching an organization from scratch, Teshyla mentions how Sis To Sis Toronto was started through mostly in-kind donations and had no funding in its early stages.

“Support came from members of the community offering their time and resources, like food, decorations or a helping hand during events. We had to definitely work hard to pull in resources and get crafty to bring out the first few sessions,” she said.

“Pre-funding stage, it was also really hard to get our messaging out there to create awareness around our organization in the spaces that we were creating. We wanted to capture the stories and strength of everyone present.” 

Launching Sis To Sis was a learning experience for Bailey and she reaped in the knowledge, be it learning how to run an organization, how to manage projects and lead a team, as well as how to be a great team member herself.

Living By Sis To Sis: Teshyla on Personal Development, Self-Awareness and Wellness

Whether it be following through on her workout routine or mindfulness, Bailey is actively engaged in different personal development spaces, such as physical wellness.

“So much of our culture intertwines these wellness aspects and allows us to heal as well. My family is Jamaican and we’re really big on music and dance, so I’ve been really mindful to tap back into that energy,” Bailey said,

“I commit to SoCo Cycle sessions which allows me to listen to music from my culture, like Afrobeats, and allows me to move and release stress,” she said.

Outside of physical development, Bailey is focused on healing practices and mindfulness.

“I do my best to be transparent in my own journey when I’m entering spaces with the Sis To Sis community. Being able to open up not only gives me a sense of relief but allows me to take ownership of the things I’ve gone through and be empowered instead of feeling any sense of shame,” she said.

Advice for Women Leaders and Community Organizers: Start Up or Scale Up Through Self Reflection

When asked what advice she could give to other women actively looking to be leaders in their community, Bailey stresses the importance of self-reflection.

“Take some time to reflect on your personal journey and think about what continues to motivate you. In that way, you’re pulled in the direction of your ‘why’ and you’re able to rely on your lived experiences that propel you forward in your work,” she said.

She credits the strength of Sis To Sis Toronto to each member’s stories and experiences. 

“There’s so much power that comes from our lives, our culture and communities. It’s important to tap into that energy to start or scale up your work.”

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