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!

For the full transcript of our conversation, click here: https://drive.google.com/file/d/16X6L...  

Important Links:

X (Twitter) – https://x.com/catehall?lang=en

Astera – https://astera.org/team/cate-hall/

Website – https://www.catehall.com/

LinkedIn –   / cate-hall-9a81a35  

Substack – https://substack.com/@usefulfictions

Show Notes:

(00:00) Guest Introduction

(00:24) The Edge Between Rampant Optimism and Crushing Pessimism

(03:34) Misguided Compromises & Imaginary Boundries

(08:40) The "I Must Win" Mindset Is Short-term Thinking

(11:24) Writing a List of Fears

(13:40) Belief in God

(23:27) Poker & Reading People

(29:57) Distracting Ourselves From Uncomfortable Truths

(33:54) Introspection Without Self-flagellation

(37:05) Confronting Negative Thoughts

(42:54) Aella, and Crossing The Boundaries

(44:53) Seeking Rejection

(49:24) Agency vs Addiction

(54:38) Slow Change Instead of Breakthroughs

(57:13) Luck