As Dragon’s Den kicks off its 20th season, how exciting to launch our second season with Arlene Dickinson—arguably the most iconic dragon of all. You know Arlene as a titan of business and venture capital, but as she reveals with remarkable warmth and candour as she talks with Gill, her secret weapon is her honesty about doubts, vulnerabilities and uncertainty. It’s what makes her YouTube show Arlene is Alone so popular. In this conversation she talks about the freedom she finds in being on her own, and about her passion for helping Canada through this critical moment of historic uncertainty. Arlene shares deeply personal stories of challenge, lays bare the raw courage it has taken her to keep going through hardship, and reminds us how much strength comes from being willing to accept what we might not know. 

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Gill is loving her summer break!

Launching this podcast was itself a bit of a leap into the unknown, so it has been wonderfully rewarding to hear good things from so many of our listeners. Your stories, your responses and your appreciation of our guests this season have been great encouragement—just the fuel we needed to drive us forward to season 2. We wanted to share some highlights from listener letters. (We do read all your submissions, but we couldn’t read them all on the air…) Keep ‘em coming.

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The future can feel shaky, especially for young people starting out right now. Psychology professor and author Jeffrey Jensen Arnett, Ph.D. changed society's understanding of human development when he coined the term “emerging adulthood.” When adult children are living at home—as many are in this economy— future uncertainty can feel oppressive for everyone in the house. Dr. Arnett gives reassuring context for anxious parents of older children, explaining the social and cultural forces that have changed expectations for young people. He argues that “30 is the new 20” and that parents must learn to be more comfortable with less control, and trust that the kids are, in fact, alright.

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When our health feels uncertain, we turn to our physicians—doctors have all the answers, right? But what about when they don’t? Dr. Kieran Quinn has devoted much of his busy clinical and research time since 2020 to understanding post-Covid syndromes. Though he is considered a top long Covid specialist, it is a condition riddled with unknowns, for which he can offer no remedy, no treatment and very few answers. He talks candidly with Gill—his former patient—about navigating the unstable ground of the unknown, and about what we can all learn about finding purpose when the answers are anything but clear.

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If you’ve ever had a secret dream but been too afraid of failure to dare attempt it, Sue Hincenbergs would like a word. Her debut novel—a dark, funny crime story called “The Retirement Plan”—sparked a publishing bidding war and the film adaptation is already in development. (She’s got her fingers crossed for Brad Pitt in a lead role!) Sue makes the case for staying hopeful and working hard, even in the face of failure and uncertainty. 

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Super successful urban blogger Jen McNeely made a name for herself when she created the popular Toronto site “She Does the City”. But the toll that lifestyle took on her personal life became untenable and eventually led her to rehab. In sobriety, Jen has made one massive change after another, leaving her career and the city behind; rewriting her life in midlife. Jen is honest and inspiring as she explains the courage it took to lean into so much uncertainty, and the rewards that could only have come from being courageous and trusting herself to try new things.

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If you’ve been paying even a little bit of attention to Canadian politics, you know that change and uncertainty have been dominant themes for several months now. Trump‘s tariffs and talk of annexation are fueling a lot of fear about what lies ahead. Author, journalist and cultural commentator Stephen Marche explores it all in his new podcast "Gloves Off ". But really, adapting to change and facing up to huge challenges are familiar themes for Marche, as he explains to Gill in this wide-ranging chat. From rethinking the Canadian identity to calming ourselves down about AI, Stephen Marche brings his trademark cleverness to a whole lot of unknowns. 

The Acast podcast "Gloves Off" is now available wherever you get your podcasts. New episodes drop each week.

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Retirement ain’t what those ‘Freedom 55’ ad campaigns promised. Bestselling author and award-winning journalist Cathrin Bradbury talks openly about her new book This Way Up and the enormous change of this under-discussed life stage: the wild, unexpected and wonderful chapter that opened up in her life when she finally stepped away from the daily grind. Cathrin shares her own reckoning with all the unknowns inherent in retirement, as she leans into the uncertainty of mapping what lies ahead.

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Improvisational sketch comedy offers a master class in how to not just handle uncertainty but lean into it. Superstar improv comedians Matt Baram and Naomi Snieckus make walking the high wire of unscripted performance look easy. A couple both onstage and off, they have navigated huge life changes together, usually with laughs. When both sets of parents died, they set about processing grief—and a lot of inherited possessions— through their work. The result is Big Stuff, a critically acclaimed stage show that sold out an extended run in Toronto before touring Canada in fall 2025.In our conversation they talk openly (and hilariously) with Gill about all the possibilities that open up when you let go of how things are supposed to go, and about how learning to live with uncertainty on stage has helped them navigate the ups and downs of the rest of life.

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Bestselling author Claire Cameron usually writes fiction, including the award-winning The Last Neanderthal, and The Bear. Her latest book, an instant bestseller, tells a different kind of tale—How To Survive A Bear Attack is a memoir of Claire’s rare genetic condition and cancer diagnosis. Weaving her own experience with the haunting story of a rare, fatal bear attack in Ontario’s Algonquin Park, Claire investigates how to thrive in the face of fear and deadly odds.

In this deeply felt conversation, Claire and Gill talk about facing challenges, both internal and external, about how uncertainty makes the present moment feel extra alive, and about all the forms resilience can take.

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