S2 Ep3: The Brutal Truth About FAILURE You Need To Hear | Elizabeth Day

Aug 5, 2025

Elizabeth Day, a bestselling author and journalist known for her insightful podcast on failure, dives into the transformative power of embracing setbacks. She shares poignant stories from her childhood in Northern Ireland, revealing how rejection has become her superpower. Elizabeth discusses the importance of practical self-compassion and offers strategies for those feeling lost. She also opens up about her personal experiences with miscarriage and fertility struggles, emphasizing that our failures can redefine our identities and ambitions.

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INSIGHT

Failure Shapes Growth

We live in a culture chasing impossible perfection that obscures growth from mistakes.
Elizabeth Day argues failures shape who we become and teach essential lessons over time.

ANECDOTE

From Outsider To Confident Performer

Elizabeth grew up in Northern Ireland and felt like an outsider which sharpened her observer skills.
Boarding school and debating taught her that confidence is a muscle to be practiced.

ADVICE

Value Depth Over The Race

Spend time getting to know yourself and value depth above noise; life is not a race.
Treat fallow periods as gestation where the next thing grows rather than proof of failure.

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No one teaches you how to embrace failure, but what if that’s the only way to truly succeed?

Today, I’m sitting down with Elizabeth Day, bestselling author, journalist, and host of the How To Fail Podcast, the hit podcast that’s changed how millions of people think about setbacks.

Elizabeth opens up about the moments that shaped her: growing up in Northern Ireland, feeling like an outsider at school, the pursuit of confidence, and how repeated rejection eventually became her greatest superpower.

She also shares the deeply personal stories behind her success, from boarding school struggles to navigating miscarriage, online hate, and public life, and why your ability to fail well might be the most important skill you’ll ever learn.

If you’ve ever felt like you're behind, broken, or not enough, this one’s for you.

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0:00 Introduction
1:40 Elizabeth & Chris’ experiences with IVF struggles
7:00 Self doubt in your 20s
9:55 Elizabeth’s early years
15:40 “Confidence in a muscle you can flex”
16:55 Elizabeth’s first job at 12
20:30 Gossip columnist
23:20 “Just do the hard thing over and over again”
24:50 Introverted Vs Extrovert
31:00 Understanding failure
35:20 If you're feeling lost watch this
39:15 Thoughts on Ozempic
41:15 How to balance it all
49:30 Elizabeth's IVF story
59:40 Sally Phillips opens up about failure
1:03:30 Kate Winslet opens up about failures
1:05:30 Psychic readings
1:13:30 Failing in your 20s
1:16:00 5 year plans
1:21:00 The importance of friendship
1:23:00 Work addiction
1:26:50 Conflict avoidant
1:29:20 Stop being a people pleaser
1:32:00 How to set boundaries
1:35:00 How to deal with negative opinions
1:40:20 Justin Baldoni & Blake Lively court case
1:44:50 Elizabeth being a CEO & Founder

Follow Chris: https://www.instagram.com/chrisdonnellyofficial/
Follow Elizabeth: https://www.instagram.com/elizabday/
Pre sale link: https://lnk.to/OneOfUsElizabethDay