S2 Ep3: The Brutal Truth About FAILURE You Need To Hear | Elizabeth Day
Wake Up with Chris Donnelly
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Balancing Ambition with Presence
They explore ambition's roots, self-awareness of competitiveness, and prioritizing purpose over external validation.
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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.
Sign up to Revolut Business at https://www.revolut.com/rb/wakeup and add money to your account before August 31st, 2025, to receive a £200 / $200 welcome bonus. Subscription fees and T&Cs apply. Available for new Business customers in the UK and US.
US Customers: Revolut is not a bank. Banking services are provided by Lead Bank, Member FDIC. The Revolut USA Prepaid Visa and Prepaid Mastercard are issued by Lead Bank pursuant to licensing by Visa(c) U.S.A. Inc. and Mastercard International for Mastercard cards. Your funds are FDIC insured up to $250,000 through Lead Bank, Member FDIC. See https://www.revolut.com/en-US/ for more details.
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
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.
Sign up to Revolut Business at https://www.revolut.com/rb/wakeup and add money to your account before August 31st, 2025, to receive a £200 / $200 welcome bonus. Subscription fees and T&Cs apply. Available for new Business customers in the UK and US.
US Customers: Revolut is not a bank. Banking services are provided by Lead Bank, Member FDIC. The Revolut USA Prepaid Visa and Prepaid Mastercard are issued by Lead Bank pursuant to licensing by Visa(c) U.S.A. Inc. and Mastercard International for Mastercard cards. Your funds are FDIC insured up to $250,000 through Lead Bank, Member FDIC. See https://www.revolut.com/en-US/ for more details.
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
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