What happens when the systems that are supposed to help people aren’t built for everyone? What could exist that would meet the needs of more people and leave fewer aspiring business owners and dreamers behind. It’s a question Shannon Pestun, a Calgary-based entrepreneur and social advocate who works towards closing critical gaps in the financial system, is trying to answer. 

She got her start growing up in Calgary, a curious and sometimes rebellious child in a very large and connected family. At five, she started wondering about her purpose, and a few years later she experienced sexual abuse. She withdrew inward, struggling to find her place in the world and her trauma. 

Early on, Pestun was a teacher’s pet who loved school and wanted to teach, lining up her teddy bears for lessons after school. Learning delighted her but the joy was swallowed by tragedy, her grades dropping to F’s until she couldn’t bear failing any longer. Miles behind, unable to catch up, she left school, her sense of self shaken and desire to learn stifled by pain. 

Strong family support helped her overcome challenges and she learned to trust her gut but she left home at sixteen, struggling with suicidal thoughts and surrounded by the wrong crowds. Fortunately, incredible role models came into her life to help her find success. 

Her first job was mucking stalls at a nearby ranch at eleven years old, toiling to get to ride at the end of the day. It’s where she could be herself, connect with animals as spiritual beings and enjoy the land. After dropping out of school, she worked at a makeup company, dressing up and expressing herself while making minimum wage. 

Life took a turn at a hot dog stand when she was handed a nightclub flyer. She looked older made up and could go there and dance. One day, the hotdog stand vendor needed someone to take over and Pestun took charge, elevating the experience by suggesting new premium toppings. Selling makeup by day and hot dogs by night, a conversation in the mall food court changed her path again. 

A leader helped her see her forgotten potential and return to school for her GED. Back to straight A’s and driven to succeed, she went on to Mount Royal University and University of Lethbridge for a business degree. 

She started marketing in the finance industry, became a business lender, and her journey took another turn. She helped others launch businesses with financing, realizing she could really help people. At the same time, Pestun saw how the system left some people behind. She wanted to change that. 

She started contracting with the Women Entrepreneurship Knowledge Hub, supporting research, policy recommendations, best practices, all to help Indigenous women entrepreneurs get ahead. She recently launched a financial literacy company to help entrepreneurs have empowered financial conversations and change the narrative around money. Clients learn to read financial statements and make decisions to create the lives and impacts they craved. Working with Indigenous financial institutions, Pestun’s looking at creating micro loans to bridge market gaps.

Pestun’s time is full of emails and emotional labour so she starts her day with a gratitude practice. Working with government, researchers, financial institutions and those trying to understand how to shift these systems to align with truth and reconciliation, she sees daily positive change and brings Indigenous perspective to her work. Her childhood dream of teaching came true, but differently than she imagined.

She sees how youth are expected to know what they want to do and where they want to go to school, a big ask at that age. “Life is this combination of all of our experiences, and when you find what you're passionate about, it takes learning, it takes like knowing what feels good and seeing different things and watching different people. Don't limit yourself, stay open to the possibility but really know what feels good, what feels in alignment to you,” she recommends to youth struggling with those choices. 

Pestun encourages youth to recognize everyone has unique gifts and has choices to make around how to present those gifts to the world. She advocates for confidence in declaring one’s purpose without comparison to others and seeing the value of those precious gifts.  

Reflecting on her hopes for the future, she shares how she doesn’t have a business plan because it feels like she’s still learning and deciding. Overall, she hopes to feel her spirit in the work she does, connecting to purpose and giving more to see it come back from the universe. Pestun wants to keep doing meaningful work, to keep talking about and participating in changing the systems for the future. 

“I'm hoping our kids and grandkids will look back at this time and see a lot of the work that we did, just as we have to recognize a lot of the work that our ancestors did,” she shares, thinking about her impact seven generations from now.  

In closing, she says, “The world is going to hand you different things. Sometimes you're gonna feel like you're at one and everything is working well. Sometimes you're gonna feel like you're fighting with the world. Sometimes you're gonna feel like you're fighting with yourself and I guess my encouragement as somebody who knows that life can be really dark, it can be really, really hard… You just never know how that can turn around. You also never know when you will become an inspiration for other people.”

At certain points in her life, Pestun wasn’t living in an aspirational way, out of alignment and moving too fast as she was young and struggling. What she’s learned is, ”Anyone can turn a story around. There's always something around the bend. Trust that process. Life is just a process. It's just a series of moving through a shared experience.”

Now back in alignment, moving at a comfortable pace, she’s grappling with the questions… What happens when the systems that are supposed to help people aren’t built for everyone? What could exist that would meet the needs of more people and leave fewer aspiring business owners and dreamers behind? Shannon Pestun, as an entrepreneur and social advocate working towards closing critical gaps in the financial system, is trying to find those answers and she’s sharing what she’s learned along the way.  

Thanks to Alison Tedford Seaweed for authoring this article.