MAGICAL OVERTHINKERS

MAGICAL OVERTHINKERS

Overthinking about failure

This week's Magical Overthinkers ep... a day early and ad-free!

Jun 23, 2026
∙ Paid

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

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