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
How To Date: BONUS EPISODE - Your dating questions answered… [not-audio_url] [/not-audio_url]

Duration: 39:49
For this bonus episode, Elizabeth and Mel open up the post bag to answer the burning questions YOU have when it comes to dating… And, let’s just say, we cover A LOT of ground. After you’ve listened, you can get all the r…
How To Date: The most important relationship you’ll ever have [not-audio_url] [/not-audio_url]

Duration: 57:48
For the final episode of How To Date (sob!) Mel and Elizabeth look at the most important relationships any of us can have in our lives: the one with ourselves. We unpack what this means in practical terms. How do we nurt…
How To Date: How to cope with heartbreak and rejection [not-audio_url] [/not-audio_url]

Duration: 44:43
Elizabeth and Mel face one of the most challenging parts of dating: heartbreak and rejection. We are joined by life coach and author Michelle Elman who went through a devastating, public break-up after being notified via…
Erin Doherty - ‘Lean Into Your Truth’ [not-audio_url] [/not-audio_url]

Duration: 45:41
To hear more of Erin offering advice on listener failures, join our community of subscribers here: https://howtofail.supportingcast.fm/#content Erin Doherty’s big break came playing Princess Anne in The Crown. She’s now…
How To Date: Taking it to the next level [not-audio_url] [/not-audio_url]

Duration: 49:15
Things are going well… So Elizabeth and Mel are taking it to the next level where they are getting just that little bit more serious. In this episode, Mel and Elizabeth look at exclusivity and commitment and what it take…
How To Date: Red and Green Flags [not-audio_url] [/not-audio_url]

Duration: 57:04
Mel and Elizabeth look at the subtle (and not-so-subtle) signs that can help us understand whether a potential partner is right for us. That’s right, we’re exploring the red flags that should have us running for the hill…

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