
Elizabeth Day Opens Up About Heartbreak, Miscarriage & Failure | E77
Steven Bartlett (host), Elizabeth Day (guest), Narrator, Narrator, Narrator, Narrator
In this episode of The Diary of a CEO, featuring Steven Bartlett and Elizabeth Day, Elizabeth Day Opens Up About Heartbreak, Miscarriage & Failure | E77 explores redefining Failure: Elizabeth Day On Heartbreak, Miscarriage, Authentic Success Elizabeth Day joins Steven Bartlett to unpack how societal expectations around love, motherhood, and success can make people feel like failures even when they’re not. She reframes failure as “what happens when life doesn’t go according to plan,” then challenges where that plan actually comes from. Through candid discussion of divorce, infertility, miscarriage, people-pleasing, online criticism, and heartbreak, she shows how vulnerability and self-inquiry can turn painful experiences into profound personal growth. The conversation also explores social media’s impact on self-worth, the importance of boundaries and communication in relationships, and why sharing our vulnerabilities creates the deepest human connection.
Redefining Failure: Elizabeth Day On Heartbreak, Miscarriage, Authentic Success
Elizabeth Day joins Steven Bartlett to unpack how societal expectations around love, motherhood, and success can make people feel like failures even when they’re not. She reframes failure as “what happens when life doesn’t go according to plan,” then challenges where that plan actually comes from. Through candid discussion of divorce, infertility, miscarriage, people-pleasing, online criticism, and heartbreak, she shows how vulnerability and self-inquiry can turn painful experiences into profound personal growth. The conversation also explores social media’s impact on self-worth, the importance of boundaries and communication in relationships, and why sharing our vulnerabilities creates the deepest human connection.
Key Takeaways
Redefine failure by questioning whose plan you’re following.
Day defines failure as “what happens when life doesn’t go according to plan,” then asks where that plan came from—your genuine desires or inherited scripts (patriarchy, rom-coms, family, class, social media). ...
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Shift validation from external approval to a small, trusted ‘context.’
Both Day and Bartlett describe years of outsourcing self-worth to exam results, money, status, and public praise. ...
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Treat vulnerability as a strength, but share it in the right spaces.
Day’s career pivot—writing and podcasting about failure, infertility, miscarriage, divorce—shows how revealing what you’re ashamed of often has the most universal resonance. ...
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People-pleasing looks kind but ultimately blocks intimacy and progress.
Raised as a ‘nice, pliable girl,’ Day became an inveterate people-pleaser in love and work—never choosing the restaurant, never saying no, taking on all the undesirable work and never asking for a pay rise. ...
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Good relationships rely on explicit communication and understanding love languages.
Day contrasts her old conflict-avoidant marriage (where she turned anger inward and became mildly depressed) with her current marriage, where she and her CEO husband deliberately talk through needs and styles. ...
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Use social media consciously: design how you use it or it will design you.
Both speakers admit that a single negative comment can haunt them for 24–48 hours despite hundreds of positives. ...
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Heartbreak and endings are teachers, not just tragedies.
Day reframes breakups: a relationship is not a failure because it ends; each “failed” relationship taught her something crucial she needed to learn about herself, and cleared space for a better fit. ...
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Notable Quotes
“Failure is what happens when life doesn’t go according to plan.”
— Elizabeth Day
“I realized that my success had become a substitute for self-worth. I was outsourcing my sense of self to everyone else’s opinions of me.”
— Elizabeth Day
“Infertility and miscarriages are not a mishap… for people who experience it, it’s a tragedy over which they have no control.”
— Elizabeth Day
“What you think of as your most personal shame often turns out to have the most universal resonance.”
— Elizabeth Day
“The enough thing is actually bullshit… you never become less, more, or enough. You just are.”
— Steven Bartlett
Questions Answered in This Episode
You distinguish between genuine personal plans and those inherited from patriarchy, media, or family. Practically, how would you advise someone to audit a specific goal—like marriage or homeownership—and decide whether it’s truly theirs or just internalized expectation?
Elizabeth Day joins Steven Bartlett to unpack how societal expectations around love, motherhood, and success can make people feel like failures even when they’re not. ...
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In the moment when that journalist framed you as ‘exploiting infertility’ for a career, what internal dialogue did you have before choosing to respond publicly, and how do you decide which attacks on your integrity deserve a response versus silence?
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You’ve called extreme people-pleasing ‘selfish’ because it withholds your real self. For someone who currently feels their niceness is their only value, what are the first two behavioral experiments you’d set them to begin breaking that pattern without blowing up their life overnight?
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You and Steven both acknowledge that social media criticism can emotionally hijack you for days despite all your insight. If you were designing a ‘social media hygiene’ protocol for high-profile creators from scratch, what specific daily and weekly practices would it include?
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You reframed breakups and miscarriages as experiences that, over time, can carry meaning and teach necessary lessons. Where do you draw the ethical line between finding personal meaning in suffering and implying that all suffering is ‘for a reason’—especially for people whose pain is ongoing or systemic (e.g., racism, poverty)?
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Transcript Preview
(music plays) Elizabeth Day is a world-renowned podcast host. She's a best-selling author, she's a successful journalist.
I felt like a failure, but I probably wasn't. It was what I'd been told to feel. I've had countless failed relationships (laughs) and it sucks. Like, heartbreak, there is no pain like heartbreak. I now realize that I learned something very instructive from each one of those relationships and from the fact that they ended. It taught me something that I needed to know about myself. Infertility and miscarriages are not a mishap. Like, for people who experience it, it's a tragedy over which they have no control, and the idea that I was exploiting it to make a full-time career out of it was so insulting because I know how fucking painful and traumatic it is to go through.
Being vulnerable, something I think we all find it incredibly hard to do. And after hearing my guest's story today, I had tears in my eyes maybe three or four times, and that's because she is willing to be vulnerable and honest and open about her truth, her trauma, and the things she's learned from her most testing times. Elizabeth Day is a world-renowned podcast host. She's a best-selling author, she's a successful journalist, honestly. She's quite frankly one of the most wonderful, smart, lovely people I've ever had the privilege of doing this podcast with. In fact, today, one of the issues I had with this podcast was we agree on so much that it's hard to play devil's advocate with her. It was hard to challenge her views because so many of them represented mine. It felt like she was reading out of my book, and I think that's powerful because she helped me build on my ideas. And some of these ideas are controversial, for some people maybe too controversial. It is remarkable how much societal expectations can cripple your chance of happiness, and I genuinely believe that if we had more people in the world like Elizabeth, who were willing to say what she says today, then maybe that wouldn't be the case. Without further ado, I'm Steven Bartlett, and this is The Diary of a CEO. I hope nobody's listening, but if you are, then please keep this to yourself. One of the things that I wrote recently, which, um, after doing a little bit of reading about your story and your journey, really, really resonated with me, um, was this idea that- that society's expectations of how your life is supposed to be going will fuck you up.
Mm-hmm.
And when I think about, you know, you've wro- written this amazing book about- called Failosophy, about failure, I was thinking, what is... Objectively, like, what is failure? And, um, my conclusion was that failure is like a byproduct of social expectations, um, that's- and as is success. So, could you talk to me a little bit about how social expectations have made you feel like a failure?
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