How To Fail With Elizabeth Day - ON HEARTBREAK... With Alain de Botton and Jay Shetty

Episode Date: September 7, 2025

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! Hopefull...y 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

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Starting point is 00:00:00 Okay, a breaking news, because I absolutely have to tell you about my new TV obsession, the Real Housewives of London, streaming from the 18th of August only on Hey You. It's going to be the talk of the summer. Trust me, you are not going to want to miss it. I have seen the trailer, I've got the BTS Goss, and let me tell you, if you're already a superfan like me or a newbie, prepare to be totally hooked. You probably already know that I love that. I love the the Real Housewives franchise. My favourites are Atlanta and old school New York. Thanks so much for asking. And the Real Housewives of London is even more special as it's HAU's first original series streaming every week. Why wait when you could join me and everyone else talking about it now?
Starting point is 00:00:48 Sign up for HAYU now to start watching the Real Housewives of London and see the drama unfold. A subscription is required and you'll need to be 18 plus. This episode is brought to you by Squarespace. the all-in-one website platform for entrepreneurs to stand out and succeed online. Squarespace is here to support entrepreneurship and help turn your passion into a business. It does so with cutting-edge design, seamless check-out for customers with simple but powerful payment tools. It helps you turn leads into clients, allowing you to grow and communicate with your audience. Their customers include the dusty knuckle bakery and cafe in East London, and if you know, you know, their bread. is amazing. They're a Squarespace customer and a brilliant example of how to do it right.
Starting point is 00:01:35 Their training program provides young people who've been excluded by society with the basic skills for work and life. Go check them out. Head to Squarespace.com slash fail 10 for a free trial. And when you're ready to launch, use offer code fail 10, that's fail 10, to save 10% off your first purchase of a website or domain. Welcome to How to Fail. Now, I started this podcast back in July 2018. That was a whole seven years ago. Can you believe it?
Starting point is 00:02:14 Where does the time go? That means seven years of a huge archive of brilliant guests. Episodes that contain intriguing insights and compelling life stories and moving moments that make us think about our own life. lives in a different way. With such a rich back catalogue, I wanted to highlight specific themes each week to bring you bite-sized takeaways that may bring clarity or comfort to similar issues you're facing or simply just great stories that you want to listen to. So that's all to say that we are launching a second free weekly episode. You are welcome. And this week we're looking at
Starting point is 00:02:56 heartbreak. First, you'll hear an extract from my conversation with philosopher Alan de Botton, who shares wise and insightful advice on how to process and understand heartbreak. Secondly, we hear from Jay Chetty, who gives some incredibly validating analysis and support for anyone who might have experienced heartbreak of any kind. I really hope that this episode will be a beacon of light to anyone going through something that really, really sucks, a broken heart. you've got this. Which brings us on to another of your failure concepts, and I'm so glad you're going to talk about this,
Starting point is 00:03:33 which is that breakups, romantic breakups, are not a tragedy. Yes. So it's the idea that a relationship ends, not because it's gone badly, but because it's taught you what you need to learn, which I think is such a beautiful and helpful concept. Please explain more. Well, we tend to imagine that the only viable relationship
Starting point is 00:03:53 is one that lasts forever, so that the real success of a relationship is longevity, which is very peculiar. I mean, we wouldn't apply that standard to other things. The best holiday is one that goes on forever, or the best meal goes on forever. There are obviously things that can be valuable but more short-lived. And I think one of the ways to look at relationships is that they are opportunities for us to learn from another person. And we tend to believe that that means that that lesson's going to go on forever. and the notion of outgrowing someone is again seen in very dark terms.
Starting point is 00:04:26 If I say, you know, I've outgrown my partner. People say, oh, how awful. But there's also something potentially rather beautiful and liberating about the idea that someone could be immensely important in one's life and yet not there forever, that they might not be the central person forever. Because in the same way that a child outgrows their family, you know, that's not a tragedy. If a parent, the whole basis of parenthood is,
Starting point is 00:04:50 My child's going to outgrow me, and that's okay. They should outgrow me. There will be a time when my 10-year-old or 12-year-old or 17-year-old is going to find another kitchen to sit in, another group of friends to be with. And that's the way it should be. They'll come back and we'll always have what we had, but they won't be quite the way it is today. And that's not a tragedy. So I think that we can apply the same view to romantic relationships. And there are so many people who torture themselves unnecessarily going, I spent 22 years with somebody, and then, you know, awfully it just ran out of steam. And you want to say, hang on a minute, 22 years, that's an awfully long time. Most people, you know, for most of human history, didn't live longer than 22. You spent 22 years with someone, that's amazing. Presumably you saw and you learned and all these things, yes, yes. So does it need to be, again, a tragedy in the terrible sense? And it doesn't need to be. So much of what we define as a failure is an interpretation of facts. Psychotherapist love this phrase, fear. Your fear is not a fact. It's a way of saying that if somebody's terrified of something, just check in. Does that actually have to be, you know, that noise that you're thinking is a burglar? Is it actually a burglar? That argument does it necessarily mean the beginning of the end or whatever? And I think that we too often apply to situations, interpretations which are really punitive and make us feel terrible for no particular good reason. So when it comes to relationships, we tend to say, that relationship was a failure. They were only together for X time or they know.
Starting point is 00:06:20 have had children together or didn't work out in the end for whatever reason. And that's too punitive. So let's stop torturing ourselves. My problem is that I completely agree with everything that you're saying. And yet because I am imperfect and flawed and everything we've been talking about, I bear a grudge. So if someone has broken up with me, for what I feel are unjust reasons, I feel a tremendous amount of grief, a rage and self-loathing over that. And if that person then goes on to find someone and finds that that person is quote unquote better than me and has a quote unquote more successful relationship that lasts longer. I find that very hard to deal with. And it feels like even though I can make the effort to do everything that you're saying and to think
Starting point is 00:07:05 that way, it feels like I'm the one making the effort again. And the other person is just sailing off with a lack of consciousness. Look, I think an important thing to bear in mind in those situations is they're going to be miserable lots of the time with their new partner. That's all I need. That's what I need to say. No, no, I mean, it's a very important thing. When we're in situations of envy, if I can be brutal and say that it's, you know, we often envy other people, rich people, successful people, famous people, but also people in other relationships. And we just imagine that their life is perfect. And we're very good at that. We have this muscle in our brain that is just fantastic at conjuring up images of the happiness of others. And I think it's tremendously helpful
Starting point is 00:07:43 to keep in mind that almost certainly their level of happiness will be closer to our level of ambivalent mixture of good and bad than it is to some ideal of flawless perfection. And in whatever area it is, the CEO who's riding high, they'll be anxious about a whole host of things, the couple who's just falling in love, they'll be worried about all sorts of things. We don't know what the details are, but they're human. And I think we just forget often that we are made of the same stuff as other people. We only have access to our own minds. This is a fundamental feature of life. We don't know through direct experience what other people are going through. We only know what we're going through. So we end up feeling that we're very weird because from the inside, all sorts of weird stuff goes in in our minds. Our minds are intermittent. Often they're sort of in a daze. Often they're quite unhappy. Weird stuff goes on and our thoughts are odd. We feel quite perverted. We feel weird. We feel odd. And we think, what's up with me? I just met with my mates and there wasn't any evidence of any of that. And the reason is that we always edit ourselves for other people. Without meaning to sort of show off or deceive anyone,
Starting point is 00:08:46 we're constantly presenting edited images of ourselves to other people and seeing edited images of other people in our interactions with them, which gives us a highly distorted picture of how odd we are and how lovely and perfect other people might be. So I think if you want the clearest indication of what another human being is, take it from yourself. They're probably more like, even though they don't let off that many signs of it, they're probably more like you than they're like anybody else. I've found it's a good thing to do when you're hosting someone. When you invite people over for dinner and you're in host position, in other words, you're trying to anticipate and guess what another person wants to do,
Starting point is 00:09:22 people, they lose all sense of reality and they start to cook things that would never eat themselves and try and entertain in ways that they would never feel as entertaining. People do this when they give presents as well. They just forget about themselves. They're forgetting to use themselves as the most accurate guide to somebody else. So the biggest indication of what's going on in the life of an ex or the life of a CEO or the life of a famous person is you. They're probably a bit like you. More than anything else, they're like you, even though the outer circumstances might be a bit different. So the chances of your ex now finding, you know, blissful happiness with somebody else are almost zero. They will have all the moods that you have
Starting point is 00:09:59 with your own new partner, let's say, moments of ambivalence, moments of jealousy, moments of longing for other people. All this thing will continue because that's the way in which life goes. So we need to stop torturing ourselves with idealised images of what the lives of other people are like. The lives of other people are basically like your life, and that means a bit up and down. Do you think the earliest men and women fell in love? I think yes, but the interpretations they put on those feelings would have been very different. So they would, I think, have not seen this as an indication that their whole life was going to be dominated by this person. It might just be a very pleasant feeling that surrounded them one summer with somebody,
Starting point is 00:10:43 or it might be an indication that it would be a good idea to try for a child with that person. But I think that, you know, romanticism, what we know is romanticism, which is a whole set of ideas embodied in poetry, in songs, in our sort of cultural language, which crops up in the mid-18th century and is now dominated the world, places romantic love at its sense. and gives it a very particular spin. It's seen as the pinnacle of what humans are capable of. A huge downgrading of friendship. You know, what's interesting is before romantic love, people spoke about friendship in ways which are totally alien to us now. The notion of being just a good friend, which nowadays seems like a horrible compensation price. I went out for
Starting point is 00:11:24 dinner with somebody and I took them home and they said that they thought we should remain just good friends. This is seen as a terrible disappointment. Like, oh, poor you. In a sort of pre-romantic age, it's sort of been fantastic. It's like you've been spared the nightmare of sexual jealousy and love and all those sort of terrible things that go on in a relationship. Somebody's offered you friendship. You've got, you know, the prize of the century. We'd see it as a consolation price. So total shift in, you know, the evaluation of friendship versus love. Tell us about breakups, because that is one of the things that really affects listeners to this podcast and massively affected me when I was going through.
Starting point is 00:12:03 them because there is no grief quite like heartbreak. It's such a specific and individual thing. And you have some great advice for it. And one of the things that I found most beautiful in this book is that idea that you might be broken up with, but you're not broken. Your soul is unbreakable. Can you tell us a bit more about that? Yeah, definitely. So first of all, I want to say that if anyone's had their heartbroken or has gone through a breakup that was painful because of what someone said or how they treated you. The truth is that it will always hurt because when you look at the science behind heartbreak, it says that we feel the same chemical shift as when someone's trying to detox from cocaine. And so if you think about that, it's like being addicted
Starting point is 00:12:48 to a drug that was fueling you and filling you up. That wasn't good for you, but it was still an addiction. And now that it's been removed from your physical or even emotional presence, you now literally have this feeling of what's craving for another human just as you crave back for cocaine. And so the fact that it hurts is real and true. And we should validate that. You shouldn't feel bad that it hurts or that you're a weak person or that you're someone who doesn't have a backbone or if anyone says to you like, oh, just get over it. The fact that you can't get over it is a very real emotion. We shouldn't just shun it or push it aside. And then to answer your question, I think what we often find is that we believe that someone's love for us is what
Starting point is 00:13:37 makes us lovable. So we believe that if someone values us, then we're valuable. If someone likes us, then we're likable. And so all of our self-belief, self-value, and self-esteem is based on someone else's view towards us. So then when that person leaves, we feel broken because they just took what we so deeply needed. And I approached this from a very spiritual point of view in the book, which is what you just mentioned now. And I've referenced often the Bagu Gita, which is the book that I deeply studied during my time as a monk. And the book is over 5,000 years old. it's originally in Sanskrit, there are some English translations which are beautiful to read and understand. And that book talks about how consciousness or our first self, as I like to call
Starting point is 00:14:33 it, we have so many selves, but our first self is unbreakable, it's insoluble, it's unburnable. And the idea that there's this part of you that existed before this person, during this person, and after this person will always be there. There is a you before every relationship, during every relationship, and there will continue to be one of you after every relationship. And yes, this doesn't solve the heartbreak,
Starting point is 00:15:01 but it's something you should know inherently and deeply. It's very moving that, because you can apply it to so many things, you can also apply it to grief, that there will still be a soul. As you're experiencing this horror, you will get through it, and you will still exist.
Starting point is 00:15:18 I think that's a very meaningful thing for people to hear. Please do follow how to fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music or wherever you get your podcasts, please tell all your friends. This is an Elizabeth Day
Starting point is 00:15:33 and Sony Music Entertainment original podcast. Thank you so much for listening.

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