When Penny Cromwell became a BIG through her work, she saw firsthand how important it was for young people to have someone that looked like them to offer guidance and an ear to listen.  

Through her work’s partnership with Big Brothers Big Sisters of Toronto, she was given the opportunity to mentor young people to develop skills that would help them land jobs. As a confident, black, single mother, Penny was matched with two young girls, both people of colour.  

“They would not have felt comfortable to say what they said or share what they said if it was someone that didn’t look like them,” Penny said. “I think it’s so important that we make sure that we pair young people with somebody that looks like them – someone that understands them.” 

At the time, Penny recalls that there weren’t a lot of mentors that looked like her. She stood out.  

Penny was an award-winning hip hop artist, an accomplished business woman on Bay Street in Toronto, and living comfortably in the Mississauga/Oakville are of Ontario.   

Coming from a place of high accomplishment, Penny had a wide skillset that she could offer her Littles. What started out as support for working in their professional lives, including tips on crafting a resume and education about clothing in professional business settings, turned into a supportive and caring relationship. 

“I mentored her, I had her call me every day, we would meet up every other week,” said Penny. The value she offered extended well beyond her business knowledge, “my value was giving them the opportunity to find whatever was in them.” 

In spending more time together, Penny worked to understand her Littles better in order to offer them the support and guidance that they needed.  

“Being a BIG…showed me that it was so important to not just try to fix the shell, but to be intentional and to hear and to understand what somebody else has gone through.” 

Penny believes that because her Littles were able to identify with her, she was able to get to know them better, and offer support that not all mentors could. She claims that despite not growing up in the same area, she was able to understand her Littles because she’s faced similar circumstances in her life. That allowed her to open up levels of dialogue that deepened her relationship to her Littles.  

“It was learning for me, learning how to communicate and understand,” said Penny. “Sometimes we’re in a bubble. It gave me this opportunity to come outside of this bubble. I understand them because I understand the community. I could talk to both girls”  

Through always offering a listening ear and being careful not to insert herself beyond what was necessary, she was able to provide unparalleled support to these girls. She recalls that watching them grow had an incredible impact on her as well.  

“I grew from watching them blossom, watching them turn into who I knew they could be,” said Penny taking great pride. “It’s so important when you’re touching someone’s life to acknowledge that you’re a little part of that person’s personal journey and path.” 

Reflecting on her experience, Penny paused, “your words matter. Your actions matter. Your non-actions matter. Now she’s married [one of her Littles], she’s got a couple of children, she’s in a good job.”