Cate Hall: Crossing The Imaginary Boundaries

Writer and thinker Cate Hall joins me to talk about the tightrope between radical optimism and deep pessimism — and what it actually takes to stay hopeful in a world that doesn’t always reward it. We dig into her widely loved “50 Secrets” post, the kind of people who end up walking that edge, and how she thinks about preserving agency and perspective when the culture around us feels increasingly discouraged. I also reflect on why I consider Cate one of the most hopeful voices of our time, and why these conversations feel especially urgent in 2025. Hope you enjoy!

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