How To Fail With Elizabeth Day

ON MOTHERHOOD… with Jessie Ware and Francesca Segal

Motherhood is often portrayed purely as a joyful, magical chapter of life – and while it certainly can be – we rarely speak openly about the hard, exhausting and deeply challenging truths. In this episode, singer‑songwriter Jessie Ware reflects on becoming a parent while building a career in the public eye. She talks about the pressure she felt to prove she could do everything at once, the exhaustion that followed and the grounding process of learning to be present rather than perfect. We also hear from novelist Francesca Segal, who shares the story of her twins’ premature birth and the unexpected reality of early motherhood inside a neonatal ward. She describes the chasm between the idealised story of birth and the lived experience many mothers face. I hope this episode brings comfort to anyone navigating the complexities of motherhood. May it remind you that every journey is different, that there is no single right way to parent and that you are never alone in this experience. Listen to Jessie’s full episode of How to Fail here: http://swap.fm/l/8cUuwGs4vc7tAXiPcDab Listen to Francesca’s full episode of How to Fail here: swap.fm/l/MsPtRFvgP8z18GLPgpdL 🔗 LINKS + MENTIONS: Maternal Support: https://maternalmentalhealthalliance.org/ https://mothersformothers.co.uk/ Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Rosamund Pike - ‘Failure Is Pretending To Be Someone You’re Not’

Rosamund Pike! What a woman. Famed for her portrayals of razor-sharp, morally complex and deliciously unpredictable characters, she brings that same intriguing duality to this conversation. Thoughtful and quietly rebellious, she reflects on a career that has defied neat narratives from the very beginning. After taking a year out from studying English at University of Oxford to pursue acting, she graduated and stepped straight into the global spotlight as Bond girl Miranda Frost in Die Another Day. From there came a string of unforgettable movies: Pride & Prejudice, Jack Reacher, A Private War and Saltburn. Her chilling performance in Gone Girl earned her an Oscar nomination and she took home a Golden Globe for I Care a Lot. In 2025, she returned to the stage for the first time in 15 years in the National Theatre’s production of Inter Alia. In this episode, she talks about her ‘failure’ to get married, the realities of raising two sons and her decision not to read a single review of her work for the past 25 years. Plus why she’s ‘constantly in battle’ with her own fear, her failure to be an action movie hero, her miserable attempt to cook a rabbit and whether or not she’s ‘cool’. ✨ IN THIS EPISODE: 00:00 Intro 03:18 No reviews rule 06:57 Early perfectionism and stage craft 07:58 Inter Alia and modern womanhood 10:09 Luminate meditation mask 12:42 Failure to learn Chinese 19:09 Onstage mishaps and acting roles 28:59 What Cool Really Means 29:26 Cool Girl vs Amy 32:21 Failing at Being An Action Star 36:52 Failure to Get Married 45:17 Mothering Two Boys 47:28 Smells and Teen Hygiene 48:44 Rabbit Dinner and Being Enough 💬 QUOTES TO REMEMBER: Failure is usually pretending to be someone you’re not. I don’t think you ever regret having a big love affair - even if goes to shit. I’m quite a coward. I like to play brave people because I’m not. I’m constantly in battle with my own fear. Cool means that you can go your own way. You don't give too many, f***s... you can think originally. I didn’t want to be the sex symbol. 🔗 LINKS + MENTIONS: Inter Alia is on at the Wyndham’s Theatre: 19 March - 20 June 2026 Rosamund’s Meditation App is: www.lumenate.co Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Glennon Doyle - on wildness, the end of people-pleasing and why we can all do hard things swap.fm/l/Nd3ZzVy73FXUMupJ4i1q Phoebe Waller Bridge - on creative control, perfectionism and the fear of being misunderstood swap.fm/l/gTCOCJUmXX9t22mTABSa 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Rosamund answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

SPECIAL EP: On Fertility and Finding Your Family… with Rebecca Coxon

In this one‑off special, Elizabeth sits down with author Rebecca Coxon to discuss family, fertility and the secrets that have shaped her life: after uploading her DNA to an ancestry site, Rebecca discovered that the man who raised her was not her biological father – a revelation that sent her on a remarkable search for the truth about her origins. Her memoir Inconceivable launches Elizabeth’s new imprint, Big Day Books. Rebecca writes with clarity and compassion about being a donor‑conceived IVF triplet, later donating her own eggs and facing fertility treatment herself – a story of family secrets, shame, resilience and deep love. You don’t need personal experience of IVF or DNA surprises to be moved by this conversation. Rebecca is thoughtful, emotionally perceptive and quietly courageous. She speaks about having her identity reshaped overnight, the coexistence of gratitude and grief, and the invisible threads that bind us across generations. This is a discussion about truth, belonging and the ethics and emotions of creating new life – and about redefining family not by biology alone, but through love, choice and understanding. A deeply honest, intimate and ultimately hopeful discussion – and a very special moment for How to Fail. ✨ IN THIS EPISODE: 00:00 Intro 01:15 Donor Conceived Truth 02:52 Test Results Moment 05:26 Endometriosis Reality 07:57 Choosing Egg Donation 08:36 US Donor Market 10:26 Recipient Letter Impact 13:58 Dating And Time Pressure 15:53 James And IVF Collapse 20:50 Meeting Donor Rodney 30:47 Pregnancy After Book 💬 QUOTES TO REMEMBER: The experience of watching your friends have babies. Every milestone in their lives feels like a splinter in mine. I'm still on the shoreline waiting for my time, and I'm standing alongside people who are struggling." — Rebecca describes the mindset she had while finishing her book, just before discovering she was pregnant. 🔗 LINKS + MENTIONS: Rebecca’s new book Inconceivable is available to buy now: www.bigdaybooks.co.uk/inconceivable Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Toni Laites - Love Island Healed My Toxic Dating Patterns

Toni Laites made history last year as the first American to win Love Island, but her journey to the villa was anything but ordinary. Discovered in Las Vegas working as a cabana girl by the show’s creative director, Toni was persuaded to fly 6,000 miles to Mallorca. The rest, as they say, is history. But you don’t need to be a Love Island superfan to love this episode. Toni is funny, emotionally intelligent and disarmingly honest. She opens up about living with the chronic illness Ulcerative Colitis, her pattern of choosing the wrong men in the past, working through anxious attachment and the hard-won strength it takes to forgive yourself. This is a conversation about resilience, self-awareness and what it really means to back yourself - even when the odds (and the public vote) are against you. ✨ IN THIS EPISODE: 03:18 Vegas Sales to Villa Casting 05:36 Saying Yes to Love Island 07:21 Life Inside the Villa 08:33 Votes, Outcasts and Forgiveness 10:57 The Big Three Friendship 14:18 Health Scare and Ulcerative Colitis 28:10 Tourist In London 28:43 Toxic Dating Patterns 32:22 Pressure On Her Relationship 34:57 Fame And Social Media 37:34 Family And Attachment 44:28 Self Criticism And Hate 49:44 Plan For The Future 💬 QUOTES TO REMEMBER: There is value in doing nothing and taking a step back and waiting for good things to come. I always say not all disabilities are visible and people don't really understand what that's like. 🔗 LINKS + MENTIONS: Join the How To Fail community: https://howtofail.supportingcast.fm/#content Elizabeth’s Substack: https://theelizabethday.substack.com/ 📚 WANT MORE? Olivia Attwood - on heartbreak, public scrutiny and building a successful career after Love Island. Jessel Taank - on infertility, identity and The Real Housewives of New York. 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Toni answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

ON AMBITION… With Gillian Anderson and Munroe Bergdorf

Ambition can be a powerful force: it propels us forward, sharpens our focus and pushes us to dream bigger. But it can also whisper that we are only as good as our latest achievement - and these two brilliant former How to Fail guests explore what it really means to live a driven life. Gillian Anderson reflects on her lifelong drive to prove herself, the guilt she feels when stepping back from work and the tension between motherhood and a demanding career. Munroe Bergdorf shares how rejection and gatekeeping in fashion shaped her ambition. Once treated as a token gesture, she has become a leading voice for representation, speaking openly about resilience, self‑worth and creating space for others to follow. An episode about striving and self‑belief – and about whether ambition truly supports us, or whether we end up chasing it at our own expense. Listen to Gillian’s full episode of How to Fail here: swap.fm/l/7NyZMzkfVOpGyDtlB6k0 Listen to Munroe’s full episode of How to Fail here: swap.fm/l/tu153m3gHYreWBZSrcY1 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]