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Diary of a CEO · 2021-04-19

Elizabeth Day Opens Up About Heartbreak, Miscarriage & Failure | E77

Elizabeth Day on how failure, heartbreak, miscarriage and shedding social expectations led her to redefine success and self-worth.

Elizabeth Day Opens Up About Heartbreak, Miscarriage & Failure | E77
The guest

Elizabeth Day: Best-selling author, journalist, and host of the 'How to Fail' podcast; author of the memoir 'How to Fail', 'Failosophy', and the novel 'Magpie'.

What this episode covers

Stephen Bartlett interviews author and podcaster Elizabeth Day about how societal expectations conditioned her to feel like a failure after divorce, IVF, and miscarriage in her thirties. She reframes failure as simply 'what happens when life doesn't go according to plan' and argues self-worth must come from within rather than external validation. The conversation explores people-pleasing, communication and love languages in her relationship with her husband Justin, vulnerability as the source of human connection, and the toll of social media criticism. They also dig into nuance, cancel culture, personal responsibility, race, and the importance of curating a small, healthy social context.

The guest's own work

BookBy the guest

How to Fail: Everything I've Ever Learned from Things Going Wrong

Elizabeth Day

“you've written this amazing book about called philosophy about failure”— Elizabeth Day
BookBy the guestISBN verified

Failosophy

Elizabeth Day

“the definition i came up with in philosophy is that failure is what happens when life doesn't go according to plan”— Elizabeth Day
BookBy the guestISBN verified

Magpie

Elizabeth Day

“i've got a novel out my new novel is out in september and it's called magpie”— Elizabeth Day

Big reveals from this episode

  • At 36, divorced and childless after emotionally devastating fertility treatments and her first miscarriage, Elizabeth felt like a failure.
  • She realized that exam approval had become a substitute for self-worth, leaving her outsourcing her identity to external validation.
  • A Times article called her infertility advocacy a 'mishap' she was exploiting for a career, prompting the one time she publicly responded to defend her integrity.
  • She and her husband Justin nearly didn't meet; she went on a Hinge date she almost cancelled.
  • Stephen's chapter-20 conclusion: you never become intrinsically 'less' or 'more' enough, so real ambition must be intrinsically driven.
  • Mo Gawdat told Stephen how, after his son Ali died at 21, he retrained his grief by adding 'yes, but he also lived' to his morning thought.
  • Elizabeth reveals she is still determined to become a mother and would not share a future pregnancy publicly out of respect for women facing infertility.

Worth remembering

  • Elizabeth defines failure as 'what happens when life doesn't go according to plan.'
  • She advocates shrinking your 'context' to four or five trusted people in an age of social-media comparison.
  • Her self-protection tactics include muting critics, unfollowing, and keeping her phone on airplane mode in the mornings.
  • She was in back-to-back monogamous relationships from age 19 to 36, with gaps as short as a month.
  • She and Justin took the love-languages quiz; his is acts of service while hers shifted from words of affirmation to quality time.
  • Stephen says he has been a Huel fanatic for four years and credits it for being in the best shape of his life.
  • Elizabeth notes a memoir 'cannot be intersectional' because it speaks only from one person's lived experience.
  • After a serious breakup she googled how long heartbreak lasts and found accepting a roughly six-week timeline made it easier.
  • She praises Angela Merkel for publicly apologizing for an overturned Easter lockdown ruling.