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My high school guidance councillor Mr. Dolan made me take a test that was supposed to help map out my future. Everyone in our class had to take it. A series multiple-choice questions assessed aptitudes and interests to determine a career path. I recall seeing my classmates exit the dimly lit, windowless office looking satisfied, each holding a printout that contained practical proclamations for their professions. Teacher, engineer, mechanic, nurse. Mine said…


I asked to take the test repeatedly. Each time entrepreneur was the only recommendation. I asked Mr. Dolan how to become an entrepreneur. He just shrugged. I would have had more luck consulted a Magic Eight Ball.

I enrolled in a business administration program thinking it would be a fast track to my future as an abstract entrepreneur. Thankfully, my mum read a brochure for a communication arts program and insisted I was in the wrong program. Her instincts were better than the career aptitude test, and the decision to switch programs changed my life’s trajectory.

I thrived in communications studies, finding my voice as a writer, earning good grades, and getting involved in student government. I was no closer to becoming an entrepreneur, but at the age of 18 I had an office on campus, an assistant, and supervised a group of student representatives. By the time I finished the program I had served on numerous academic committees, helped write policies and procedures, was a member of a provincial student governance committee, and gave the convocation address at my graduation.

As I entered the business world I knew how to process large amounts of information, supervise people, run a meeting, and navigate politics, but I still had no idea how to become the elusive entrepreneur. So, I went into media.

When exiting my fifth year in television promotions, my boss gave a speech about how I was a wild stallion that could not be tamed. Radio marketing proved a better fit for my skillset. I was encouraged to dream big, and stay within budget.

After hitting a plateau, my boss told me I could go anywhere, and do anything. The next move was all mine. When I left radio it was not for a fancy new job title, a tall office building, or a big paycheck. I was destined to be…an


That Magic Eight Ball of a career assessment test was right all along. This wild untameable stallion was not meant for the confines of an average boardroom. The woman assigned to mentor me at a local business link office recalled meeting me years earlier, She said she felt I was always destined to be in business for myself. When I asked how she knew, she said she had witnessed a tense moment between me and my supervisor after I suggested a different way of doing things. If I recall correctly, the disagreement was about whether a balloon archway was appropriate decor for a business event.

I have now been an entrepreneur for 19 years. It is both challenging and fulfilling, but I would not, and could not change it for any amount of guaranteed advancement, or money. I love working with my clients, tackling complex problems, and building things. I love feeling what I do matters, even if it just matters to me. Entrepreneurship is a constant and evolving learning experience that comes with its share of plot twists – like how to adapt when a global pandemic crushes your previously successful business model.

Some days I feel it would be easier to ask the Magic Eight Ball for direction. In fact, I ordered one while writing this. 

I ripped open the package soon after the Amazon driver deposited it on my doorstep. The first thing I asked was, “Magic Eight Ball, am I headed in the right direction?”

The Magic Eight Ball answered: “Signs point to yes.”