Arlene Dickinson is an enigma who wears her heart on her sleeve — a striking duality of two seemingly distant traits.
She is well-known for her accepting and assertive approach on Dragon’s Den Canada, where she is the longest-standing female dragon.
Dickinson is a decorated businessperson. She has won more than one Lifetime Achievement Award and a Queen Elizabeth II Diamond Jubilee Medal.
Dickinson was also named on Canada’s Most Powerful Women: Top 100 Hall of Fame by the Women’s Executive Network.
Her shining portfolio neatly co-exists with her humbleness — a pattern surely shaped by the dysfunction and struggle of her early life.
Childhood challenges
Dickinson’s brand is thoroughly Canadian. Amidst the political controversy with the US, she has been advocating for Canada’s independence and distinct identity.
She is originally from South Africa and was raised Mormon. Dickinson’s parents moved their three children to Calgary, AB, Canada in 1959 when she was 3.
In an interview with Chatelaine, Dickinson described the extreme poverty her family faced.
“By the time we landed in Canada, my parents had only $50 to their name. They’d given up everything to come here, and we lived a very hand-to-mouth existence,” she stated.
Her father, a struggling electrician, walked to work to save the 15-cent bus fare. At 6 years old, she vividly remembers when her father sold her mother’s wedding ring for a run-down vehicle. A deep sadness hung in the air.
Grocery shopping was not a regular activity. Buying food was a luxury enjoyed when there was enough money to go around. Heated arguments and palpable tension filled their home with money being the greatest point of contention.
Identity crisis
Life became more difficult at 13 when her parents divorced, leading to her social ostracization at school and church where she was bullied for coming from a broke and broken home.
To cope, Dickinson learned to stay under the radar as much as possible to remain unnoticed, unproblematic and unimposing.
Her story arch is incredible considering where she is now — in the spotlight, which she clearly earned and claimed.
Dickinson graduated early at 16 and took it as an opportunity to escape her chaotic household and immediately enter the workforce.
She “didn’t feel smart enough to go to university,” despite having an impressive academic history.
“That broke my father’s heart. He was a teacher, education was his reason for living, and I remember him telling me I’d be barefoot and pregnant the rest of my life if I didn’t have a degree,” she told Chatelain.
Ironically, her father’s comments iterated what her Mormon upbringing taught her — to create a happy, loving family.
“ Women of my generation were very much encouraged to marry young and to believe that our role in life was to raise children. Having a career didn’t even cross my mind.”
Yet Dickinson always held a job from being a secretary, sales clerk, bill collector.
Motherhood
Arlene Dickinson married at 19 and gave birth to her first of four children at 21. Money continued to be a problem but she was determined to make it work.
“We had no money and had to do a lot of it ourselves, everything from hanging wallpaper to shingling the roof — I acted as my own general contractor when I was seven months pregnant!”
When her husband decided to go back to school, Dickson picked up full-time work while taking care of the house and children.
However, the fulfilment of being a wife and mother that her upbringing promised wasn’t complete.
”Part of it was how my husband treated me, part of it was feeling I couldn’t live up to the Mormon standard, and part of it was simply that growing up, I’d always felt inadequate,” she said.
A life-altering affair
Miserable in her marriage and sense of self, Dickinson sought more elsewhere. She began having an affair when she was 30.
When her husband found out, a series of losses and traumatic experiences followed. The pair divorced after a humiliating and invasive interrogation by the church.
Most devastating, she lost primary custody of her children. This is what pushed Dickinson to level up her life, her income and her self-confidence.
Only one year post-divorce, while sleeping on her father’s couch, she became a partner at Venture and her life completely transformed.
Without going back to school or training, Dickinson helped accelerate the growth of the small start-up marketing agency into one of Canada’s largest independent marketing firms.
Her trick to the trade? “I learned how to be persuasive without being aggressive, and I convinced key people to back me and give me a chance,” she told Chatelain.
“But let’s face it, I had the best motivator in the world: I wanted to get my kids back,” she added. Which she most definitely did.
Hatching a Dragon
Dickinson’s greatest obstacle was her self-perception. It took time, fortitude and perseverance to reshape how she saw herself.
It boiled down to practice and figuring out what you can offer in a situation versus only what you will get out of it.
Her practice became a profession. Arlene Dickinson is widely recognized as one of Canada’s greatest entrepreneurs.
On Dragon’s Den, she is known for her assertive and compassionate approach — a sharp contrast with the more cutthroat and profit-focused Kevin O’Leary.
Dickinson genuinely admires the hard work, dedication and creativity demonstrated by guests on the show.
At the same time, she doesn’t stray from asking hard questions and challenging them to step up to the plate.
The financial strain and internal conflict she endured for the first half of her life didn’t determine her destiny.
Dickson shares more of her story and her insight into mastering the business world in her book Persuasion: A New Approach to Changing Minds.
For more about her incredible story, click here.
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