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 researcher and author, 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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