Overthinking About Failure

Overthinking About Failure

June 24, 2026 · 42 min

About this episode

Amanda Montell and guest Jane Marie Chen discuss the fear of failure and its impact on personal growth and self-worth.

Why does failure feel so much bigger than it actually is? This week, Amanda is joined by entrepreneur, author, and leadership coach Jane Marie Chen (@janemarie.chen) to spiral about failure: why we're so terrified of it, why we avoid it at all costs, and why it often hurts so much more than the thing that actually happened. Together, they explore perfectionism, rejection, burnout, imposter syndrome, and the childhood experiences that shape our relationship to failure long before we ever encounter it. And what if failure isn't evidence that we're unworthy? What if it's simply the price of catching bigger waves? A reflective spiral about risk, resilience, and learning to love yourself even when things don't go according to plan. Further Reading: Like a Wave We Break by Jane Marie Chen - 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…

People in this episode

Host: Amanda Montell

Guest: Jane Marie Chen

Topics covered

Keywords

Sponsors

Whatnot

Mentioned in this episode

Organizations: Magical Overthinkers Club, Magical Overthinkers Substack

Books & works: The Age of Magical Overthinking: Notes on Modern Irrationality, Like a Wave We Break

More episodes of Magical Overthinkers

Explore listener stats, chart rankings, contacts and more on the Magical Overthinkers podcast page.