How To Fail With Elizabeth Day

• Bella Freud - Learning To Trust Herself

  Fashion icon Bella Freud on abandoning psychics, learning to trust herself and realising that what happens next is entirely up to her. Freud is a designer and creative whose clothes have adorned the likes of Zadie Smith, Kate Moss, Little Simz and…well…me. She’s also a cult podcaster with her hit show, Fashion Neurosis, where guests are invited to examine what clothes mean to them. She’s lived a fascinating life: the daughter of Lucian Freud, the great-granddaughter of psychoanalyst Sigmund and the sister of novelist Esther who wrote the novel Hideous Kinky about their childhood. Now in her 60s, she joins me to explore why she’s always late, why she regrets never joining the circus and what it’s really like carrying the weight of such an instantly recognisable family name. Plus: why she no longer goes to psychics. Bella is so smart, considered and stylish. This free-ranging conversation will make you think, laugh and feel unexpectedly hopeful about getting older. ✨ IN THIS EPISODE: 00:00 Introduction 04:04 The Power of Fashion and Design 06:47 Challenges in the Fashion Industry 11:52 The Significance of Punctuality 17:02 Childhood Memories and Their Impact 22:18 Therapy and Family Loss 26:13 Reflecting on a Peaceful Passing 27:43 Family Dynamics 30:04 The Circus Job That Never Was 32:33 Sibling Relationships and Childhood Roles 36:06 The Legacy of the Freud Name 41:23 Embracing Failures and Life Lessons 46:28 Living Authentically and Joyfully 💬 QUOTES TO REMEMBER: This whole thing about failure of course, is that you can fail and try again What's going happen is what I make happen, so get on with it The key is to stay and finish and then the whole level of reward is so much greater Being late is an incredibly aggressive thing to do 🔗 LINKS + MENTIONS: You can listen to Fashion Neurosis wherever you get your podcasts and it’s also available to watch on YouTube Bella’s photo is by Lynette Garland (2025) Join the How To Fail community: https://howtofail.supportingcast.fm/#content Elizabeth’s Substack: https://theelizabethday.substack.com/ 📚 WANT MORE? Bernardine Evaristo - the Booker Prize-winner talks about persistence, manifestation and making art on your own terms swap.fm/l/PszltDAfnTF5EpG0UmE7 Trinny Woodall - on the setbacks she’s faced in business, single parenthood and fertility swap.fm/l/fJVwewwLr5xEOE1zLroZ Edward Enninful - the former editor of British Vogue and an influential figure in fashion explores his journey through the industry. We talk about his challenges around diversity, identity and health swap.fm/l/NOAt5NDZeBTgX6qZUWpB 💌 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 Bella answer live audience 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: Suhaar Ali 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• ON FRIENDSHIP… With Dawn French and Vogue Williams

  I’ve always been obsessed with friendship - how it shapes us, challenges us and often goes uncelebrated. In this episode, both Dawn French and Vogue Williams get honest about the beauty and the messiness of it all. Despite being surrounded by great friends, Vogue explains why she worries she’s not the best friend back - although she’s definitely working on it. Dawn then reflects on growing up as an RAF kid. Repeated moves meant she learned early on how hard it can be to build and keep connections. She also talks about her iconic friendship with Jennifer Saunders (which did *not* start smoothly) and the people she holds closest today. My fascination with the subject runs so deep that I even wrote a whole book about it! Friendaholic: Confessions of a Friendship Addict explores why friendship matters and how it evolves over our lives. Feel free to buy a copy for you…and all your friends! Listen to Dawn French’s full episode of How to Fail here: swap.fm/l/NJDrzxLKhyi6icOrxmHT Listen to Vogue Williams’ full episode of How to Fail here: swap.fm/l/KdIrVp0y41qgun1oGjfR 🔗 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Alex Hassell - Rivals, Rejection and Taking Acid at Alton Towers

  You might know the star of Rivals for his revealing role in the hit Disney+ show, but did you know about his dramatic allium allergy?! I thought not. Alex Hassell might be best known for his portrayal of the dashing bounder, Rupert Campbell-Black in the Emmy-Award winning TV adaptation of Jilly Cooper’s Rivals but his career spans the Royal Shakespeare Company, a leading role opposite Anya Taylor-Joy in The Miniaturist, HBO’s His Dark Materials and co-founding the pioneering Factory Theatre Company. In this conversation, Alex reflects on the role therapy and his marriage have played in weathering early-career rejection. We talk about his struggle with self-confidence, his unlikely ’failure’ to get into trouble and the rebellious streak that defined his youth - including that time he took acid at Alton Towers. Plus: having to spray tan his own private parts. This episode was recorded live at the Barbican earlier this year. ✨ IN THIS EPISODE: 00:00 Intro 03:17 Season Two of Rivals 04:35 The Challenges of Acting 05:28 Therapy and Self-Reflection 11:17 Overcoming Self-Doubt 13:31 School Experiences and Bullying 20:13 The Factory Theater Company 23:31 Reflecting on Early Career Challenges 23:57 The Onion Allergy Struggle 28:16 Balancing Historical Accuracy and Sensitivity in 'Rivals' 29:30 The Pressure to Be Good 33:12 Family Influence and Personal Growth 40:57 The Actor's Vulnerability and Connection 💬 QUOTES TO REMEMBER: To withstand being an actor, you have to have very, very thick skin. I am really drawn - for some perverse reason - to parts that intimidate me and that I think I'm probably not capable of playing. I think that acting sometimes can be a bit like being in an abusive relationship in that you feel like the most important and the best... And then it's just taken away and no one wants you and they're not interested and it's like you're a piece of shit. 🔗 LINKS + MENTIONS: Join the How To Fail community: https://howtofail.supportingcast.fm/#content Elizabeth’s Substack: https://theelizabethday.substack.com/ Head shot credit: Morgan Robins 📚 WANT MORE? Dame Jilly Cooper - on bonking, class, adoption and the real-life inspiration for Rupert Campbell-Black https://link.chtbl.com/rjl6Slav Andrew Scott - on bad auditions and his failure to be heteronormative https://link.chtbl.com/18dVhMb_ Sharon Horgan - on the impact of divorce and the liberation of being in your 50s https://link.chtbl.com/hR7kycoN 💌 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 Alex answer live audience 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: Suhaar Ali 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• ON PERSPECTIVE… With Adeel Akhtar and Pat Cummins

  Perspective is something we all chase - because when it slips, life can feel chaotic and overwhelming. But when we find it again, everything becomes a little clearer. In this episode, actor Adeel Akhtar reflects on a time when he lost sight of perspective and how becoming a parent helped him rediscover what truly matters. Cricketing great Pat Cummins shares how the loss of his beloved mum reshaped his relationship with sport and why he’s now more determined than ever to put family first. Listen to Adeel Akhtar’s full episode of How to Fail here: swap.fm/l/eWxKBXUJZAAkfovquzwi Listen to Pat Cummin’s full episode of How to Fail here: swap.fm/l/DecJN4jHYh5gSeSUN72t 🔗 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Mo Gawdat - The 3 BIGGEST Mistakes We Make In Finding Love

  I don’t often have repeat guests on How To Fail but Mo Gawdat is the exception. When he first came on this podcast in 2019, he fundamentally changed my mindset and my approach to life. Back then, he was on a mission to make 1 billion people happier. Now, he returns to focus his brilliant philosophical and analytical brain to the perpetual human question: how to find true love, then nurture and sustain it. He joins me to discuss the three most frequent mistakes we make in love - and to explain how AI could be the saving of us. Mo is about to launch a game-changing AI-powered app called Emma that promises to help us all navigate the dating game with compassion and insight. This is the first time Mo has spoken in depth about this revolutionary new app so, yes, that IS a How To Fail exclusive, no biggie. ✨ IN THIS EPISODE: 00:00 Introduction 04:29 Personal Growth and Relationships 05:40 Heartbreak and Grief 10:03 Reflections on Love and Breakups 18:12 The Complexity of Modern Dating 21:45 Introducing Emma: The AI for True Love 29:53 The Mathematics of Dating 30:33 The Law of Large Numbers in Love 32:54 Dating Fatigue and Its Consequences 33:39 Game Theory in Relationships 36:52 AI's Role in Modern Relationships 39:15 The Economics of Love and Relationships 47:52 Finding Contentment Amidst Global Chaos 💬 QUOTES TO REMEMBER: Heartbreak is very similar to a terminal diagnosis, followed by grief. Falling in love is very easy. The trick is how realistic are you about falling in love with the right person? When you go on a date with a mindset that says “It's not going to work”, it's definitely not going to work. 🔗 LINKS + MENTIONS: Check out Mo Gawdat’s new relationship app: emma.love Join the How To Fail community: https://howtofail.supportingcast.fm/#content Elizabeth’s Substack: https://theelizabethday.substack.com/ 📚 WANT MORE? Mo Gawdat - his first appearance on How to Fail (in 2019!) sparked infinite chatter in the HTF space, covering grief, finding happiness and how to cope with a breakup https://link.chtbl.com/fnA5IzTi Alain de Botton - reflects on how to stay human during a crisis, embracing vulnerability, acknowledging grief without comparing pain and “turning on the light” in your fears so they lose their power https://link.chtbl.com/RBaS4VUy Stephen Grosz - argues that real love causes suffering and embracing those painful failures helps us grow, surrender (not submit) in relationships and see ourselves and others more clearly swap.fm/l/1XYvcQR4PRi06YpBC3RA 💌 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 Mo answer YOUR 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: Suhaar Ali Senior Producer: Hannah Talbot Executive Producer: Carly Maile 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

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