Arlene Dickinson: Lessons on Reinvention
- Tony Chapman
- Jul 10
- 5 min read
Arlene Dickinson on Reinvention, Resilience, and the Power of Giving Back
Discover the extraordinary journey of Arlene Dickinson, one of Canada’s most respected entrepreneurs and matriarch of CBC’s Dragon’s Den, as she sits down with Tony Chapman on Chatter That Matters. In this inspiring episode, Arlene shares honest reflections on her immigrant roots, the challenges of single motherhood, and her relentless pursuit of purpose and relevance—both in business and in life.
From South Africa to Calgary: Rising From Humble Beginnings
Arlene’s personal story is a testament to the transformative power of gratitude and hard work. Moving to Canada with virtually nothing, she recounts, “We should be grateful for what we had, grateful for being in the country, and we should be generous with whatever we could.” Listeners will hear firsthand how her upbringing shaped her relentless determination to succeed and her deep commitment to community.
Surviving Setbacks, Embracing Reinvention
Arlene candidly discusses overcoming adversity, from weathering the Calgary flood that nearly wiped out her business to becoming a role model for entrepreneurs across the country. “Sometimes the hardest thing you need to do is just get yourself up,” she reveals, highlighting the value of vulnerability and resilience.
Advocacy, Authenticity, and Canadian Identity
Learn how Arlene turned her business setbacks into opportunities for innovation and how her mission to empower Canadian entrepreneurs led her to launch a pioneering venture fund. She explores what drives her as a leader, noting, “I look for authenticity, and I believe that the best relationships start with a genuine curiosity about what the other person’s saying and why they’re saying it.”
Staying Relevant and Redefining Success After 60
Featuring laughs and life lessons, the conversation dives into Arlene’s new YouTube series, Arlene Is Alone, exploring how relevance and self-worth evolve with age and why embracing individuality matters more than ever.
Why Listen to This Episode?
Gain insight into one of Canada’s top business minds
Discover powerful lessons on personal reinvention and giving back
Get inspired by stories of resilience in the face of adversity
Learn about the importance of authenticity, curiosity, and kindness in business and life
Tune in and be inspired by Arlene Dickinson’s unfiltered wisdom—this is an episode every Canadian, entrepreneur, and dreamer should hear.
Listen Now!
Ready to be inspired? Listen now and discover how imagination and determination can change lives—and why supporting this remarkable company is more important than ever.
FAQs - Arlene Dickinson
1. Where did Arlene Dickinson immigrate from, and what was her experience like as a newcomer to Canada? Arlene Dickinson’s family immigrated from South Africa to Edmonton, Canada when she was a young child. Arriving with only $50 and a few suitcases, they faced significant challenges adjusting to life in Canada and starting over in a new country, which instilled in her deep gratitude and resilience.
2. What early life lessons shaped Arlene Dickinson’s values and work ethic? Growing up in a family with limited resources, Arlene learned the importance of gratitude, generosity, and taking responsibility for one’s own circumstances. Her parents’ repeated advice was to be thankful for what they had, to work hard, and to help others whenever possible.
3. How did Arlene Dickinson start her career in marketing? After a difficult divorce at age 31, with four children to support and only a high school education, Arlene needed to reinvent herself. She discovered marketing, leveraging her natural empathy, curiosity, and ability to listen—qualities she believes are just as important as formal qualifications in the field.
4. How did Arlene overcome challenges as a woman in a male-dominated industry? When faced with exclusion and bias as one of the few women—and one of the only representatives from a regional agency—on an industry board, Arlene realized her unique perspective was valuable. She chose to create her own opportunities rather than conform to traditional industry power structures.
5. What role did adversity play in Arlene Dickinson’s entrepreneurial journey? Arlene’s tenacity was tested during the Calgary flood, which severely impacted her business. Despite setbacks, she reinvented her agency and was willing to invest her own money to save it, demonstrating resilience and a commitment to supporting her employees and clients.
6. Why is Arlene Dickinson passionate about supporting Canadian food and wellness entrepreneurs? Inspired by her experiences on Dragon’s Den and witnessing many promising Canadian startups struggle to find support, Arlene founded a venture fund focused on food, beverage, and wellness companies. She believes adding value to Canadian resources and building a strong food industry is vital for economic security and national sovereignty.
7. How does Arlene define relevance and success in her career and personal life? For Arlene, true relevance comes from authenticity, curiosity, and making a positive impact. She values relationships built on genuine care, listening, and mutual benefit—both in her business dealings and personal connections.
8. What new projects is Arlene Dickinson working on? Arlene hosts a YouTube show called “Arlene is Alone,” where she explores life after 60, singlehood, and the empowerment that comes from embracing one’s authenticity, further proving her ability to continually reinvent herself and connect with new audiences.
9. How does Arlene approach leadership and giving back to the community? Arlene’s philosophy is grounded in providing a hand up, not just a handout. She’s committed to empowering others, especially entrepreneurs, and believes in doing transformative work that leaves a legacy, rather than simply transactional exchanges.
10. Has Arlene Dickinson expressed interest in politics or public service? While Arlene hasn’t formally entered politics, she’s passionate about contributing to Canada’s future and advocates for collaboration, civil discourse, and gratitude for the opportunities the country provides. She hasn’t ruled out future involvement in public service.
About Chatter That Matters and Host Tony Chapman
Featuring insights for aspiring founders, entrepreneurs, and anyone craving inspiration with actionable strategies.
Chatter That Matters is one of Canada’s top-rated podcasts, showcasing stories and lessons from a diverse range of guests, including entrepreneurs, industry leaders, and everyday change-makers. Each episode illustrates how individuals transform challenges into triumphs through mindset and resilience.
Hosted by Tony Chapman—a renowned marketing strategist and three-time inductee into the Marketing Hall of Fame—this acclaimed show ranks among the top 0.5% of podcasts globally. Tune in weekly as Tony converses with guests who share invaluable wisdom on living a meaningful life.
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