From beauty queen to CEO: embracing my past and empowering my present

Jennifer Stewart Miss Universe Canada pageant
Jennifer Stewart as a finalist in Miss Universe Canada

At the age of 19, I found myself thrust into a world light years away from the corporate boardrooms and entrepreneurial ventures I now navigate on a daily basis. Little did I know that participating in the Miss Universe Canada pageant would become a pivotal chapter in my life, shaping my journey toward becoming a successful female executive and entrepreneur.

Reflecting on this seemingly incongruent part of my past, I realize the valuable lessons and skills that it bestowed upon me.

As an entrepreneur and CEO in my late 30s, admitting that I was once a beauty pageant contestant isn’t exactly a conversation starter in professional circles.

The traditional image of a successful businesswoman rarely aligns with the glitz and glamour of the pageant world. Yet, as I’ve matured and grown, I’ve come to appreciate the strength and resilience it took for my 19-year-old self to step into that spotlight.

Jennifer Stewart backstage at Miss Universe Canada

One of the standout moments during the pageant was undoubtedly the nerve-wracking interview round. Seated in front of a panel of five people, I was grilled on various topics ranging from global issues to personal beliefs.

Surprisingly, I found myself excelling, securing the first position in the interview segment amidst 30 other women, many seven and eight years my senior. It was a humbling experience, and looking back, I realize how crucial it was in shaping my ability to think on my feet, articulate my thoughts, and face challenging questions head-on — skills that are invaluable in the business world.

Jennifer Stewart interviewing The Right Honourable David Johnston

The confidence required to strut across the stage, answer impromptu questions, and navigate a highly competitive environment filled with media scrutiny, interviews, and fashion shows was unparalleled. Little did I know that those very qualities would become the bedrock of my success as a CEO.

The pageant experience taught me to be comfortable in the spotlight, to embrace challenges, and to project confidence even in unfamiliar territory — skills that have proven essential in the corporate landscape.

In the cutthroat world of beauty pageants, where competitors are often judged not just on their physical appearance but also on their intellect and charisma, I learned the art of balancing grace with substance.

This balance has been a guiding principle in my journey as an entrepreneur and executive, where the ability to present oneself with confidence while maintaining a strong foundation of knowledge is paramount.

Jennifer Stewart inteviewing Melissa Farrell, President and CEO, Halton Healthcare

As I approach my 40s, I find myself looking back at 19-year-old Jennifer Wilson (my maiden name at the time) with a sense of pride and admiration. Back then, she navigated a world that often seemed at odds with the path she would later take. The unwavering belief she had in herself, the courage to embrace challenges, and the resilience to overcome stereotypes have become pillars of my success today.

It’s funny how perspectives on experiences change over time. What was once a source of embarrassment has transformed into a reflection of pride. I’m proud of the young woman who defied expectations and ventured into uncharted territory.

The lessons learned on that glittering stage continue to resonate in my professional life, reminding me that strength, resilience, and self-belief can transcend any preconceived notions or societal expectations.

So here’s to you, 19-year-old Jennifer Wilson — for having the courage to break moulds, for embracing challenges, and for setting the stage for the empowered and successful CEO that I am today. Cheers to the journey, the lessons learned, and the growth that comes from embracing every facet of our past.


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