How To Fail With Elizabeth Day - ON HEARTBREAK... With Alain de Botton and Jay Shetty
Episode Date: September 7, 2025Welcome 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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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?
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
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,
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
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.
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,
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.
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
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
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,
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,
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
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,
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
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.
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
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 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
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.
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.
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