From left, Honest Talk co-founder Jennifer Stewart, former Ontario premier Kathleen Wynne, Honest Talk co-founder Catherine Clark and Canada's ambassador to the U.S., Kirsten Hillman, at The Women's Summit, presented by RBC and hosted by The Honest Talk at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Arlene Dickinson at The Women’s Summit: Don’t let tall poppy syndrome cut you down
One of the most revealing moments of The Women’s Summit came when famed business leader Arlene Dickinson asked the 400 attendees to raise their hands as high as they could.
Up the arms went, though not quite all the way.
“Now, I want you to raise them a little higher,” she said, scanning the crowd as everyone extended their arms further while seated in the Newbridge Ballroom of the Brookstreet Hotel on Friday.
The entrepreneur and venture capitalist used the exercise to illustrate a simple truth: we often hold ourselves back, even when capable of more. “You did a very Canadian thing: you raised your hands high but looked around… God forbid any of you stood on a table and raised them as high as you possibly could,” Dickinson said.
“And this is what we do to ourselves,” she continued. “We temper our ambition; we don’t want to stand out in the crowd. That’s not going to get you anywhere.”
Failing to make yourself seen or heard can mean missing out on opportunities, she warned. “You’ll always look back and say, ‘I wish I had tried harder,’ ‘I wish I had given myself permission to do this,’ ‘I wish I had gone that extra mile’.”
She accepted that there’s a natural desire for people to want to fit in. “In Canada, we have this ‘tall poppy syndrome’,” she said of the tendency to criticize anyone who dares to reach higher.
Canadian entrepreneur and venture capitalist Arlene Dickinson at The Women’s Summit, hosted by The Honest Talk and presented by RBC, at Brookstreet Hotel. Photo by Caroline Phillips
Dickinson shared fascinating stories. In high school, she was named most likely to be a candlestick maker. “Needless to say, I love reunions,” quipped the self-made multimillionaire.
She spoke candidly about her lifelong struggle with insecurity, joking: “Even though I’ll never be a supermodel, I can buy a supermodel agency.”
She recounted how she reluctantly became a judge on CBC’s Dragons’ Den, persuaded by her children and selected for her combative chemistry with tough guy Kevin O’Leary. Her 17 seasons on the show have given her “a front-row seat” to Canadian entrepreneurs, dreams, challenges and innovation.
On authenticity and vulnerability, Dickinson advised: “If we dare to admit that we’re not perfect, we feel comfortable not being perfect.” She warned against chasing an impossible façade: “People expect perfection, creating this narrative we can’t possibly live up to.”
The topic that moved her most was Canada, and the need to protect it from the United States under President Donald Trump. “Nothing is more important than everyone fighting for our country,” she said of the need to build business, support our communities and defend democracy. “If we don’t step up, who will?”
Canadian entrepreneur and venture capitalist Arlene Dickinson, left, during a discussion with Jennifer Stewart, co-founder of The Honest Talk, at The Women’s Summit, presented by RBC and held at the Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
The Women’s Summit, presented by RBC, was created by Ottawa entrepreneurs Catherine Clark and Jennifer Stewart, co-founders of The Honest Talk podcast and digital platform. Stewart is also the founder and CEO of Syntax Strategic, where Clark serves as strategic counsel while running her own communications firm.
Organizers presented The Honest Talk Leadership Award to Canada’s ambassador to the United States, Kirsten Hillman. The award recognized her ability to navigate some of the world’s most complex and consequential discussions with “intelligence, purpose and a very steady hand,” said Clark. Hillman became Canada’s first female ambassador to the U.S. in March 2020.
This year’s summit, following its successful 2024 debut, sold out months in advance. There are plans to take The Honest Talk on the road to cities across Canada. It’s holding a retreat at Emerald Lake Lodge in Alberta’s Yoho National Park from Nov. 7-9.
Attendees received beautiful lupine-themed pins from RBC, created by Anastasiia Temborska of PINBOX. Her inspiration was Stewart’s favourite childhood book, Miss Rumphius, in which the titular character spreads beauty by planting lupines.
Canada’s ambassador to the U.S., Kirsten Hillman, was awarded The Honest Talk Leadership Award at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
From left, Glenn Sheen, regional director of marketing and citizenship at RBC; Jennifer Stewart, co-founder of The Honest Talk; entrepreneur Anastasiia Temborska, owner of PINBOX; Catherine Clark, co-founder of The Honest Talk; and Erika Whitmee, senior manager of marketing and communications at RBC, at The Women’s Summit, presented by RBC. Photo by Caroline Phillips
With its flowers, candles and pink microphones, the stage was a celebration of femininity. “It made me realize that all of the spaces that we go through and work in every day are not built for us,” Vanessa Vermette, vice president of innovation and skills development with the Canada School of Public Services, told CiTC.
Other attendees shared similar enthusiasm. Hydro Ottawa chief customer officer Julie Lupinacci was joined by a table full of women from her work. “I loved today. This was my favourite conference of all the conferences I’ve attended in the city this year. I loved it because there were so many personal takeaways.”
The day included comedian and mental health advocate Jessica Holmes and a women’s health panel led by CTV Your Morning Ottawa co-host Rosey Edeh with menopause specialist Dr. Ardelle Piper and Christine Harrison (Focus Forward Therapy Group). There were financial wellness insights, delivered in a fun and engaging way, from . There was also a discussion led by Stewart featuring Farhat Ainuddin (Farrah Fine Jewellers) and Emma May (Sophie Grace designs). Delivering the land acknowledgement was Marion Crowe, CEO of the First Nations Health Manager Association.
Personal finance expert Melissa Leong made the subject of financial wellness fun and engaging at The Women’s Summit. Photo by Caroline Phillips
Ziyada Callender (centre),
From left, Jennifer Stewart and Catherine Clark, co-founders of The Honest Talk and The Women’s Summit, on stage to present The Honest Talk Leadership Award to Canada’s ambassador to the United States, Kirsten Hillman. Photo by Caroline Phillips
From left, Ginny Sutcliffe, Caroline Pitfield, Vanessa Vermette and Sarah Plouffe, all with the Canadian School of Public Service, attended The Women’s Summit, hosted by The Honest Talk and presented by RBC, at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Catherine Clark, co-founder of The Honest Talk, on stage with former Ontario premier Kathleen Wynne and Canada’s ambassador to the U.S., Kirsten Hillman. Photo by Caroline Phillips
During the award presentation, Kirsten Hillman drew strength from the positivity and energy in the room. “To be honest, I need all the positivity I can take,” she said to warm applause.
(Hillman was having, as Clark put it, “one heck of a day” at work).
The ambassador acknowledged the mentors who shaped her career, from her mother to a senior male partner in the law firm where she started out, to a former female boss in the public service. She highlighted the importance of leaders who empower teams, value diverse voices and listen more than they talk. Of her champions, she said: “They not only pushed me forward but made the case that I was the right person for the job… I am forever grateful. I would say to all of us: we need to be those people.”
Hillman also voiced her admiration for global artist Taylor Swift as a role model and “kick-ass businesswoman”.
She was joined on stage by former Ontario premier Kathleen Wynne for a discussion led by Clark on such topics as leading with authenticity.
Wynne was not only the first woman to serve as the province’s head of government but also the first openly LGBTQ2+ person to become premier. In addition, she spearheaded the implementation of full-day kindergarten in Ontario when she was the Minister of Education.
It came as no surprise that Hillman had to make a quick exit to “go and save Canada-U.S. trade negotiations,” as Clark phrased it. She left behind a summit that continued to inspire women to raise their hands — and their ambitions — even higher.
Indigenous community leader Marion Crowe, left, and comedian Jessica Holmes, both of whom were featured speakers at The Women’s Summit, at the all-day event, hosted by The Honest Talk and presented by RBC at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Audience members applauded Canada’s ambassador to the U.S., Kirsten Hillman, after she was presented with The Honest Talk Leadership Award at The Women’s Summit, held at Brookstreet Hotel and presented by RBC. Photo by Caroline Phillips
From left, Helen Hirsh Spence, founder and CEO of Top Sixty Over Sixty, and Susan Viner Vered were among the 400 attendees of the sold-out The Women’s Summit, an all-day event hosted by The Honest Talk and presented by RBC at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
From left, Liza Mrak, co-owner of sponsor Mark Motors Group; Jodi Hamilton, operations manager at sponsor Bell Media; Ottawa Board of Trade president and CEO Sueling Ching; and Kathryn Tremblay, co-founder and owner of sponsor Altis Recruitment, at The Women’s Summit hosted by The Honest Talk and presented by RBC at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
From left, Juniper Locilento, CEO of the National Arts Centre Foundation, and Ottawa volunteer and philanthropist Whitney Fox at The Women’s Summit hosted by The Honest Talk and presented by RBC at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Attendees, including Katrin Spencer (left) from Perley Health, mingled during one of the breaks at The Women’s Summit hosted by The Honest Talk and presented by RBC at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Jennifer Stewart, co-founder of The Honest Talk, on stage during The Women’s Summit, held at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
From left, Kristina Logue, chief financial officer at Payments Canada; Colleen O’Connell-Campbell (RBC Dominion Securities); Mila Starodoub, branch manager for RBC Dominion Securities; and Karen Sparks, executive director of Wesley Clover Parks, at The Women’s Summit, held at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Isabelle Lemay, founder and CEO of the caregiving platform Village & Me, in the audience at The Women’s Summit, held at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Canada’s ambassador to the U.S., Kirsten Hillman, was awarded The Honest Talk Leadership Award at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
From left, Soula Burrell, director of business development and membership at event sponsor GOHBA (Greater Ottawa Home Builders’ Association), and Heidi Duchesne (RBC Wealth Management) at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
From left, Altis Recruitment owner and co-founder Kathryn Tremblay, joined by Ian Sherman (2025 Negev Dinner honouree), Erin Benjamin, CEO of the Canadian Live Music Association, and Jennifer Van Noort, chief development officer at The Ottawa Hospital Foundation, at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
From left, Christine Crump, president of Hard Rock Hotel & Casino Ottawa, and her vice president of marketing, Tammy McMullen, at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
Staff and volunteer leaders with the YSB (Youth Services Bureau) Foundation pose for event photographer Lindsey Gibeau at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
Juniper Locilento, CEO of the National Arts Centre Foundation, seen listening to the featured speakers during The Women’s Summit, an all-day event hosted by The Honest Talk, presented by RBC and held at Brookstreet Hotel. Photo by Caroline Phillips
From left, Christine Harrison, founder of Focus Forward Therapy Group, participated in a panel on Women’s Health Redefined with Rosie Edeh, co-host of CTV Your Morning Ottawa, and menopause expert Dr. Ardelle Piper at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
Audience members, including Whitney Fox, left, and Heidi Duchesne, seen applauding featured speaker Arlene Dickinson. Photo by Caroline Phillips
From left, Michelle Crogie, executive director of Pleo — Family Peer Support; Sandy McDonald, regional director of Bell community affairs; Deneen Perrin, director of public affairs, government relations and stakeholder engagement at the Royal Canadian Mint; and Deirdre Freiheit, vice president, senior leadership and executive coach at Pourquoi Pas Coaching, at the late-day Wine Down Reception held at The Women’s Summit. Photo by Caroline Phillips
From left, Jennifer Stewart, co-founder of The Honest Talk, on stage with Emma May, founder and CEO of Canadian brand Sophie Grace, and Farhat Ainuddin, founder and CEO of Farrah Fine Jewellers, at The Women’s Summit, held at Brookstreet Hotel. Photo by Caroline Phillips
From left, Simran Kochar, chair of the Elmwood School Gala and business development and floor division manager at Stone Design Concepts; Ginger Bertrand, co-founder at Neue Theory Wellness and co-chair of The Ottawa Hospital Foundation’s $500-million Campaign to Create Tomorrow; and Tammie Trellert, director of business development for Capital Wealth Partners, at The Women’s Summit. Photo by Caroline Phillips
From left, Syntax Strategic principal Kate Cornick and chief operating officer Jennifer Madigan, alongside Katherine Chowieri (owner of Katasa Groupe + Développement) and her sister Tanya Chowieri (owner of KTS Properties), and Megan Shaw, principal at Syntax Strategic, at The Women’s Summit held at Brookstreet Hotel on Friday, Oct. 24, 2025. Photo by Caroline Phillips
Featured speaker Melissa Leong, who got up close to her audience members, made the subject of financial wellness both fun and engaging at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
From left, Mikka Zeisig, partnership development manager with The Honest Talk, and The Honest Talk’s editor, Lisa Thibodeau, on stage to announce two free year-round passes to GoodLife Fitness hidden in the room (beneath one of the tables). Photo by Caroline Phillips
From left, Rosie Edeh, co-host of CTV Your Morning Ottawa, during a discussion about women’s health with Christine Harrison, founder of Focus Forward Therapy Group, and menopause expert Dr. Ardelle Piper at The Women’s Summit, hosted by The Honest Talk and presented by RBC. Photo by Caroline Phillips
This article is made possible through sponsorship from Star Motors, WCPD, Marilyn Wilson Dream Properties, ExecHealth, Infinity Convention Centre, Altis Recruitment, Bell Canada, First Avenue Investment Counsel, RBC, Welch LLP, Brazeau Seller Law.
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