Serena Ryder is incredibly comfortable belting her glorious voice into a microphone. A multiple Juno award winner, she sells out concert halls wherever she goes. Songs like “What I Wouldn’t Do”, “Stompa” and more have scored TV soundtracks, and become iconic rallying cries for celebration. But Serena is incredibly courageous about sharing her vulnerable side as well, using her voice to speak up for those who struggle with mental health issues. Serena’s own history with depression and anxiety has taught her a lot about how to face uncomfortable feelings and move through them to heal and grow stronger. In the middle of her “Merry Myths" holiday concert tour, Serena took time to be her most open-hearted self in this conversation with Gill. It’s a beautiful and hope-filled chat—a powerful reminder that even the most successful among us wrestle with uncertainty and challenge. For Serena Ryder it’s all fuel for wonder and learning how to be alive.

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A long-time productivity and self-help writer for The Guardian, Oliver Burkeman catapulted to international renown with his 2021 book Four Thousand Weeks: Time Management for Mortals. In that book, as well as his 2025 follow up Meditations for Mortals, Burkeman jolts our productivity-obsessed culture awake with the reminder that we can’t possibly get everything under control in the short time we have here on earth. It’s a realization that seems terrifying and slightly depressing at first blush, but the more Burkeman talks us through it the more liberating and life-enhancing it feels. In this conversation, Oliver Burkeman expands on imperfectionism ,on the wisdom of not seeing life as a problem to be solved, and the power that comes with letting the future be the future.

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How do you go from a corporate job you don’t actually like to living your creative and professional dream? For Anar Ali the path involved a lot of leaps into the unknown. Anar is creator and producer of Allegiance, the top-rated show on CBC Television. Before that she was a respected author with a multi-book deal at a major publisher. But none of it would have happened without listening to her instincts and trusting in the possibility of uncertainty. Wise, reflective and bracingly candid, Anar shares her remarkable story—including the frightening chapter that changed how she views everything and made her feel most alive in the midst of the uncertainty.

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Waking up each morning to a relentless news cycle of fear and despair, sometimes being hopeful can seem naive. How can we possibly have hope for a future that often feels grim? As award-winning author Andrea Curtis shares in her newest book, hope and struggle actually go hand in hand. The Story and Science of Hope is written for middle-grade readers but the neuroscience behind it offers comfort to us all. In her warm and upbeat style, Andrea explains how hope differs from optimism, and lays out the evidence showing the power we have to develop our sense of hope. This conversation is like a mini-course in how to cultivate an essential, life-enhancing emotion.

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Living in a post-truth world is wildly destabilizing. With so much conflicting information, how can we trust what is real? Timothy Caulfield is Canada Research Chair in Health Law and Policy as well as a popular author. In his latest book The Certainty Illusion: What You Don’t Know and Why It Matters, Caulfield cuts through simplistic misinformation and reminds us why science, in all its complexity, is our best shot at navigating the way forward. As he discusses in this week’s thought-provoking episode, we must learn to get more comfortable with not always having clear answers and control; it is—ironically enough—actually a desire for certainty that has led to the havoc of disinformation and conspiracy theories. 

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New York Times bestselling author Alex Hutchinson wants us to try new things. A science journalist with a focus on human performance, his new book The Explorer’s Gene is a fascinating dive into why humans are actually wired to not just handle uncertainty but to evolve and thrive because of it.  Betting on the path we don’t know about will yield more rewarding results—even if it doesn’t work out the way we had hoped. Nothing ventured, nothing gained. This is a conversation that will buoy the spirits and boost our confidence to explore, in any part of life. With delightful passion, Alex lays out the research-based arguments showing why trying new foods, new music or a new route on our commute makes us more creative and more able to handle unknowns as they arise. The more we lean into the uncertainty the more the world opens up. 

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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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