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Elizabeth Day
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Jay Shetty
Foreign.
Elizabeth Day
Welcome to how to Fail Now. I started this podcast back in July 2018. That's a whole seven years ago. Can you believe it? 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 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 heartbreak. First, you'll hear an extra from my conversation with philosopher Alain de Botton, who shares wise and insightful advice on how to process and understand heartbreak. Secondly, we hear from Jay Shetty, 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.
Elizabeth Day (Host)
Which brings us on to another of your failure concepts, and I'm so glad you're going to talk about this, which is that breakups, romantic breakups, are not a tragedy.
Alain de Botton
Yes.
Elizabeth Day
So it's the idea that a relationship.
Elizabeth Day (Host)
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.
Alain de Botton
Well, we tend to imagine that the only viable relationship 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. You know, 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 is going to go on forever. And the notion of outgrowing someone is again seen in very dark terms. 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, now that's not a tragedy. If a parent, the whole basis of parenthood is, 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 you know, 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 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, for most of human history didn't live longer than 22. You spent 22 years with someone, that's amazing. And 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. Psychotherapists 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 never 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.
Elizabeth Day (Host)
My problem is 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, 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.
Elizabeth Day
Very hard to deal with.
Elizabeth Day (Host)
And it feels like even though I can make the effort to do everything that you're saying and to think that way, it feels like I'm the one making the effort again and the other person's just sailing off with a lack of consciousness.
Alain de Botton
Look, I think an important thing to bear in mind in those situations is they're going to be miserable lots of the time. No, no, I mean, it's a very important thing when we're in situations of envy. If I can be brutal and say this, 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' 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 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 fallen 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 on in our minds. Our minds are intermittent. Often they're sort of in a daze. Often they're quite unhappy. Weird stuff goes on in 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 that. And the reason is that we always edit ourselves for other people without meaning to show off or deceive anyone. 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 prob. More like you than they're like anybody else. I often find 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. 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 blissful happiness with somebody else are almost zero. They will have all the moods that you have with your own new partner, let's say moments of ambivalence, moments of jealousy, moments of longing for other people. All these things will continue because that's the way way in which life goes. So we need to stop torturing ourselves with idealized images of what the lives of other people are like. The lives of other people are basically like your life. And that means bit up and down.
Elizabeth Day (Host)
Do you think the earliest men and women fell in love?
Alain de Botton
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, 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 romanticism, what we know is romanticism, which is a whole set of ideas embodied in poetry, in songs, in our cultural language, which crops up in the mid 18th century and has now dominated the world, places romantic love at its center 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. You know, I went out for 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, this would have been fantastic. It's like you've been spared the nightmare of sexual jealousy and love and all the 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 prize. So, total shift in the evaluation of friendship versus love.
Elizabeth Day (Host)
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 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.
Elizabeth Day
That idea that you might be broken.
Elizabeth Day (Host)
Up with, but you're not broken.
Elizabeth Day
Your soul is unbreakable. Can you tell us a bit more about that?
Jay Shetty
Yeah, definitely. So, first of all, I want to say that if anyone's had their heart broken 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 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 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 approach this from a very spiritual point of view in the book, which is what you just mentioned now, and I reference often the Bhagavad 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 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, but it's something you should know inherently and deeply.
Elizabeth Day (Host)
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. I think that's a very meaningful thing for people to hear.
Elizabeth Day
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 and Sony Music Entertainment original podcast. Thank you so much for listening.
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Release Date: September 7, 2025
Host: Elizabeth Day
Guests: Alain de Botton, Jay Shetty
This special thematic episode of How to Fail with Elizabeth Day delves into the topic of heartbreak, featuring philosopher Alain de Botton and author/podcaster Jay Shetty. The episode explores the ways romantic breakups are misunderstood, how we can reframe our pain, and what it means to endure and grow through heartbreak. Both guests offer philosophical and spiritual perspectives on why heartbreak hurts—and how to see ourselves as unbreakable, even when broken up with.
Guest: Alain de Botton
Host: Elizabeth Day
Guest: Alain de Botton
Guest: Jay Shetty
Host: Elizabeth Day
On finite relationships:
“You spent 22 years with someone, that’s amazing... does it need to be a tragedy in the terrible sense? It doesn't need to be.”
— Alain de Botton (05:36)
On the comparison trap:
“We're very good at... conjuring up images of the happiness of others... The lives of other people are basically like your life. And that means bit up and down.”
— Alain de Botton (09:16 – 10:21)
On heartbreak as withdrawal:
“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.”
— Jay Shetty (12:24)
On your “unbreakable soul”:
“There is a you before every relationship, during every relationship and there will continue to be one of you after every relationship.”
— Jay Shetty (14:05)
The discussion is warm, thoughtful, and deeply validating. Alain de Botton brings wit and philosophical depth, deconstructing cultural myths about relationships. Jay Shetty’s approach is gentle and empowering, drawing on science and spirituality to remind listeners of their inherent worth. Elizabeth Day is candid and empathetic, echoing listeners' doubts while guiding the conversation to hopeful, practical wisdom.
If you’ve wrestled with heartbreak, this episode offers both comfort and challenge. Alain de Botton reframes endings as natural, not failures, and questions the cultural myths that fuel our pain and envy. Jay Shetty bridges science and ancient wisdom to affirm your pain and remind you that although heartbreak can feel like it breaks you, your deepest self remains whole.
Takeaway: Heartbreak is not a sign of personal failure, and neither your value nor your future are defined by someone else’s choices. There is an unbreakable part of you that persists—before, during, and after any love.