ON HEARTBREAK... With Alain de Botton and Jay Shetty

ON HEARTBREAK... With Alain de Botton and Jay Shetty

Author: Elizabeth Day and Sony Music Entertainment September 8, 2025 Duration: 15:17
Welcome to this brand-new concept for How to Fail – where I dive into the back catalogue of the How to Fail archives, highlighting specific themes each week to bring you bitesize takeaways! Hopefully these episodes can bring some clarity on similar issues you’re facing or great stories that you might find comfort from. This week we’re looking at heartbreak. You’ll hear a highlight from my conversation with philosopher Alain de Botton, originally released in October 2019, who shares wise and insightful advice on how to process and understand heartbreak. Secondly, we hear from Jay Shetty, whose episode originally broadcast in May 2023, and gives incredibly validating advice and support for anyone who might have experienced heartbreak of any kind. I hope that this episode will be a beacon of light to anyone who has been or is currently going through this! Listen to Alain de Botton’s full episode of How to Fail here: https://link.chtbl.com/RBaS4VUy Listen to Jay Shetty’s full episode of How to Fail here: https://link.chtbl.com/-nR18lfT 🔗 LINKS + MENTIONS: Jay Shetty’s book – 8 Rules of Love www.8rulesoflove.com Elizabeth’s upcoming one-off show at Cadogan Hall on 21 Sep for her new novel One of Us: ⁠https://www.fane.co.uk/elizabeth-day 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

There's a quiet revolution happening in how we think about success, and How To Fail With Elizabeth Day is right at the heart of it. This isn't about schadenfreude or wallowing in misfortune. Instead, Elizabeth Day has created a space where the most interesting conversations begin with a simple, radical premise: our lowest moments are often our greatest teachers. Each episode, a guest-from celebrated artists and thinkers to everyday people with extraordinary stories-sits down to examine three significant failures from their own life. The magic lies in the excavation, as Elizabeth guides the discussion toward the unexpected wisdom and resilience that emerged from those setbacks. You'll hear the raw honesty in their voices, the laughter that comes with hindsight, and the profound clarity that failure can uniquely provide. This podcast, presented by Elizabeth Day and Sony Music Entertainment, digs into the messy, human stuff of life that connects us all, transforming shared vulnerability into a source of collective strength. It’s a reminder that the path to any meaningful achievement is rarely a straight line, but a series of instructive detours. The show actively invites listeners to reflect on their own stories, fostering a genuine community around the idea that we can all succeed better by understanding where we've previously stumbled. Tune in for conversations that are as comforting as they are challenging, and which might just change your perspective on what it means to live a well-lived life.
Author: Language: English Episodes: 100

How To Fail With Elizabeth Day
Podcast Episodes
ON WRITING... With Salman Rushdie and Kazuo Ishiguro [not-audio_url] [/not-audio_url]

Duration: 24:18
Welcome to another special edition of How to Fail, where I revisit conversations from the How to Fail archives. Each week, we shine a light on a particular theme, hopefully offering inspiration, perspective and comfort t…
ON GRIEF… With Mo Gawdat and Bonnie Tyler [not-audio_url] [/not-audio_url]

Duration: 13:28
Welcome to the newest evolution of How to Fail! Each week, I’ll be diving into the archives to spotlight key themes that have come up throughout my conversations with How to Fail guests. I’ll be sharing bite-sized takeaw…
Robin Wright on ageing, confidence and the myth of being ‘too late’ [not-audio_url] [/not-audio_url]

Duration: 49:50
‘I didn’t think I had that confidence, so I turned those roles down.’ Robin Wright is the legendary star of The Princess Bride, Forrest Gump, House of Cards, and Amazon’s gripping new thriller The Girlfriend. An Emmy-nom…
Tom Ellis - Fatherhood, Surrogacy and Years of Therapy [not-audio_url] [/not-audio_url]

Duration: 49:40
You may know Tom Ellis as the devilishly charming lead in Netflix’s Lucifer, or as the lovable Gary in the BBC sitcom Miranda. He's also made waves in the U.S., starring alongside Gina Rodriguez in Players, and appearing…
Failure Throwback: Jameela Jamil [not-audio_url] [/not-audio_url]

Duration: 58:34
Jameela Jamil is an actor, activist, and founder of the I Weigh movement. From teaching English to starring in The Good Place, Jameela shares the highs, lows, and radical honesty that define her journey. This episode fir…
Failure Throwback: Glennon Doyle [not-audio_url] [/not-audio_url]

Duration: 1:07:01
Author of Untamed and fierce truth-teller Glennon Doyle joins me for a raw and revelatory episode, first recorded in July 2020. We dive into: Why we chase approval instead of trusting our inner voice Her struggles with b…
Failure Throwback: Chimamanda Ngozi Adichie [not-audio_url] [/not-audio_url]

Duration: 1:08:02
This week we revisit one of my all-time favourite guests: Chimamanda Ngozi Adichie, recorded in July 2021. Best known for Americanah and her globally resonant TED Talks, Chimamanda opens up about the profound grief of lo…
Sir Tony Robinson - ‘I learned comedy as a defence mechanism’ [not-audio_url] [/not-audio_url]

Duration: 49:45
Recorded with a live audience in Cambridge, this captivating conversation delves deep into the life and career of a cultural force of the last half-century. Known of course for his iconic role as Baldrick in Blackadder,…