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EPISODE · Jul 22, 2026 · 43 MIN

Overthinking About Starting Over

from Magical Overthinkers · host Amanda Montell & Studio71

This week, Amanda is joined by entrepreneur, former supreme court attorney and professional poker player, and author of You Can Just Do Things, Cate Hall, to unpack why starting over feels so terrifying and why it might be the very thing that leads us toward a more authentic life. Together, they chat about the fear of quitting, the sunk cost fallacy, why we crave a tidy life story, and how to tell the difference between running away from something and running toward yourself. They also answer listener thought spirals about toxic jobs, divorce, changing careers, moving across the world, getting "too old" to begin again, and whether it's ever really too late to start over.Further Reading: You Can Just Do Things by Cate Hall with Sasha Chapin - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. - Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. - If your glasses are overdue for a refresh, now is the time. Use code PODCAST15 for 15% off your first order at ⁠⁠⁠bit.ly/3OdtU5X ⁠- Download Whatnot today and get $20 Off and free shipping on your first purchase. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Episode metadata supplied by the publisher feed · Published Jul 22, 2026

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Overthinking About Starting Over

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