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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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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As a climate scientist, Dr. Britt Wray has a front row seat to the terrifying unknowns of our planet’s future; as a young mother, she has developed very specific coping strategies for staying sane through the eco-anxiety. Britt’s choice to have a child was a central thread in her bestselling and critically-acclaimed book Generation Dread. Her thought-leading work at the intersection of mental health and climate change makes her the best person to listen to in the midst of another scorching, wildfire-plagued summer. In this encouraging and surprisingly hope-filled conversation, Britt Wray offers thoughtful perspective and frank advice about managing the most existential uncertainty of all: the future of life on earth.

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The host of the wildly successful TED podcast How To Be A Better Human, comedian Chris Duffy infuses every conversation with thoughtful curiosity, wit and enthusiasm—including this one! Chris and Gill talk about his determination to help us all bring more laughter into our lives; why humour is such a potent stabilizer in the midst of uncertainty and change; the wisdom he learned from his students when he taught fifth grade; and why we should all take ourselves less seriously, especially now. Plus an early peek at some of the strategies Chris shares in his upcoming book on how to get better at being funny and finding the comfort and joy of humour wherever you look.

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Outspoken, passionate and endlessly creative, Jann Arden is a model of courage in the face of unknowns. As she was finishing work on her latest book and preparing to tour her new album, Mixtape, Gill & Jann caught up about her unexpected viral hit of Canadian pride; how she’s staying grounded in the face of political turbulence; how she developed the confidence to face down whatever challenge she encounters, and what her late mother’s battle with Alzheimers’ taught Jann about handling uncertainty.

Jann performs at Massey Hall in Toronto June 9 and10 as part of her Mixtape tour.

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As a federal cabinet minister, Lisa Raitt walked the corridors of power. All that was snatched away when her partner got a diagnosis of young-onset Alzheimer's. With extraordinary candour, Lisa shares with Gill what it’s been like to watch her beloved slip away before her eyes; how she managed the out-of-left-field change to her personal and professional life; what she has learned about what strength and power really looks like; and how sometimes painful experiences can bring us closer to feeling truly alive.

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For decades, Ian Brown has written his way through the unknowns of life. His international bestseller The Boy in the Moon was his way of trying to understand the rare genetic condition his son was born with; his decades of Globe & Mail newspaper columns make sense (and good fun) of the world around us. As he enters some of his final decades, Brown’s powers of observation and wonder are sharper than ever (a point he might dispute). His critically-acclaimed book Sixty examined the unknowns of aging. And now he is working on his next memoir - Seventy. Gill and Ian’s conversation is full of his signature humour, thoughtful reflections on the inevitability of change, and the encouraging sense that getting older is in fact getting better.

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An iconic legend of Canadian television comedy, a published author, a high-profile spokesperson for mental health advocacy and a loyal Newfoundlander to the end—from the outside, Mary Walsh appears to have it all together. But in this wide-ranging conversation, the deeply intelligent and relentlessly funny Walsh is candid about the sea of unknowns she faces as a mother, a recovering addict, and an independent artist; and about the hard-won wisdom that helps keep her feeling positive in the face of hard things.

Mary is nominated for two Canadian Screen Awards this year: Best Performance in a Supporting Role, and Best Lead Performer In A Comedy. You can catch Mary later this year on the upcoming MGM series The Institute, based on the Stephen King novel.

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