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Charlie Mackesy
You know, I had a brilliant therapist once who was actually an ex Franciscan monk and he said when people tell you their, their weight, their sadness, anything, their failings, whatever it is they tell you, treat it like someone's they're giving you gold.
Charlie Mackesy (alternate or reflective voice)
And my best friend at the time,
Charlie Mackesy
silence I suppose in my heart was Jamie who, who was killed in his car I think six months late. And he just looked at me and he had tears pouring down his face and I looked at him and then I had tears pouring down my face and I held his hand and then gave him a hug and we never spoke.
Elizabeth Day
This episode of how to Fail is brought to you by Dove Whole Body Deodorant. Welcome to how to Fail with Me, Elizabeth Day. This is the podcast that believes failure is simply the what makes us human. Before we get into this episode, please do remember to like follow and subscribe so that you never miss a single conversation.
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Elizabeth Day
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Elizabeth Day
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Elizabeth Day
Online for details if you haven't met my guest today in person, the chances are you are familiar with his work on the pa. Perhaps you saw one of his illustrations during the pandemic on phone screensavers and hospital walls and Instagram grids. Perhaps you remember his familiar handwriting, shaping the question what's the bravest thing you've ever said? And the answer Help. Or perhaps you've read his books with their tales of a curious boy, a cake obsessed molecule, an anxious fox and a sage old horse, and you've been forever changed by their accessible wisdom. Their author is Charlie Macassie, whose outdoorsy childhood in Hexham, Northumberland, later informed his love of nature and wildlife. He briefly attended university twice, but left on both occasions within a week. He started out as an illustrator and a cartoonist for the Spectator and Oxford University press, but in 2019, shortly before turning 60, Mackersey's life changed overnight when a book he had written and illustrated, the Boy, the Mole, the Fox and the horse, spent 152 weeks in the Sunday Times bestseller list. It was translated into over 40 languages, sold more than 10 million copies, and was turned into an Oscar winning animated film in 2022. Three years later, Makassi published the sequel Always Remember, which became the UK's Christmas number one. While his work has helped thousands of readers, many of whom come up to him at book signings and tell Makasi he saved their lives, it hasn't necessarily helped him feel better about his own perceived flaws. That's been my feeling most of my life, he says. Somewhere deep within me, most of the time the feeling is, yeah, I'm in trouble somewhere. It's my fault. I did it. Charlie McAssee.
Charlie Mackesy
Did I say that?
Elizabeth Day
You did say that.
Charlie Mackesy
That's true.
Elizabeth Day
Welcome to how to Fail.
Charlie Mackesy
Thank you for having me.
Elizabeth Day
Are you feeling it now?
Charlie Mackesy
I'm mainly feeling quite sweaty because isn't it the Hottest day in 100 years?
Elizabeth Day
It's the hottest day of the year. And because we're in a studio and the audio quality is important, we can't put on the aircon. So this is like a Bikram podcasting session. Apologies.
Charlie Mackesy
Does the temperature affect the sound? That's a thing?
Elizabeth Day
No. The sound of the egg or the whir of the fan? The whir of the fan, the temperature affects the quality of the interview. I'm going to Get. When can you first remember feeling like that, that you must be at fault in some way?
Charlie Mackesy (alternate or reflective voice)
I'm not sure.
Charlie Mackesy
It's a bit like when you are a bit uncomfortable with something and you realize at some point that it's a song that you don't like is playing.
Elizabeth Day
Mm.
Charlie Mackesy
So it happens, we go, oh, that. Yeah.
Charlie Mackesy (alternate or reflective voice)
So when.
Charlie Mackesy
I don't know, but I think is this kind of.
Charlie Mackesy (alternate or reflective voice)
It's an undercurrent, isn't it?
Elizabeth Day
Yes.
Charlie Mackesy (alternate or reflective voice)
Someone somewhere is really annoying.
Elizabeth Day
It's interesting because I have the same thing.
Charlie Mackesy
Do you?
Elizabeth Day
Definitely.
Charlie Mackesy (alternate or reflective voice)
You always had.
Elizabeth Day
That's actually a really difficult question to answer, isn't it?
Charlie Mackesy (alternate or reflective voice)
Yeah, exactly. There you go.
Elizabeth Day
I think I've always been quite aware of it.
Charlie Mackesy
Have you?
Elizabeth Day
Yes. The answer I tend to reach for is that aged four, my family and I moved to the north of Ireland and as you can hear, I speak with a very English accent. And so even though it was my home, I didn't feel necessarily that I belonged. And so I think there was an observational quality to a lot of my experience. And I think being an observer is closely linked to feeling like an outsider. So that sense of not fitting in and having. Being slightly wrong probably dates from that point.
Charlie Mackesy
Yeah. Like the sound of you is wrong.
Elizabeth Day
Yes, exactly.
Charlie Mackesy
Yeah.
Elizabeth Day
Because you got sent to boarding school. I wonder if it started there.
Charlie Mackesy
Yeah, I don't know. Yeah, probably.
Charlie Mackesy (alternate or reflective voice)
I think the way the system was set up was very much you're in
Charlie Mackesy
competition with each other, which is a strange way of going about things. Like, there's a corridor of constant test results for various subjects and you could always seeing where you were on the list. And of course, I was always 8th equal or 12th or bottom. And so you're constantly being reminded that you're not what you could be.
Charlie Mackesy (alternate or reflective voice)
But, yeah, then I went to a brilliant Geordie school in Hexham, and then again with a posh voice, and that
Charlie Mackesy
wasn't easy, but they were so gorgeous. But in the end, I had no reason to feel anything but. But loved.
Elizabeth Day
We were talking before we started recording about the fact that you've just come back from a trip to a book festival. You often do these events because your work is so important to people. And although I think you'll shrivel at my saying this, you are a beloved and popular author.
Charlie Mackesy
I'm shriveling slightly.
Elizabeth Day
Okay. We can't tell. It's all internal shrivel. And you have come back from this event and many, many people in the audience shared their experiences with you, their trauma with you, their survival. With you. And I wanted to ask you how you feel about carrying those stories.
Charlie Mackesy
Carrying them. It's a really good question. I thought you're going to say, how do you feel about hearing them? Which is a privilege. Carrying them is different. I think normally what happens is I listen to those things and often get really moved, cry with a good number of people, and then afterwards it feels like a train is slowly hitting me. And then I go. Go back to where I'm staying and sit on the bed and look out the window and try to look at something, anything that takes my mind off because I can't. It's too much sometimes.
Charlie Mackesy (alternate or reflective voice)
And then I think I try to. There was a moment in lockdown.
Charlie Mackesy
I always remember it in those days. Those days I had a lot of people messaging me all the time and listen, I'm no sage. I just wrote a book about a mole who likes cake and friends who are journeying in a difficult way with each other and feeling uncomfortable about things.
Charlie Mackesy (alternate or reflective voice)
But I don't really have. You know, I think people just want
Charlie Mackesy
to be heard, probably and seen. And so they were saying, ah, I'm a nurse in a ward and my two friends have died and, you know, help. And I remember pushing my bike through a field one morning with Barney.
Elizabeth Day
Your dog.
Charlie Mackesy
Yeah. In the basket. And just suddenly stopping and feeling. It was almost like someone turning on taps in my head. And I just. It was just. And I was just. Just weeping and weeping and weeping, standing there for. And then lay down. And I was thinking, you know, when something happens, it's almost passive. I didn't choose it, wondering what it was. And I suppose as the body needs to let go of stuff, right?
Elizabeth Day
Yes.
Charlie Mackesy (alternate or reflective voice)
Maybe my subconscious saying, you're not going
Charlie Mackesy
to do this, so we're going to do it or something. But I cried for a good half an hour and lay down and then felt better for it.
Charlie Mackesy (alternate or reflective voice)
But, yeah, it's a very good question and I don't think I carry it
Charlie Mackesy
very well, but I do see it as a privilege. I had a brilliant therapist once who was actually an ex Franciscan monk. And he said when people tell you their weight, their sadness, anything, their failings, whatever it is, they tell you, treat it like they're giving you gold. Receive it like they're giving you gold. And I always think of that line when someone's telling me they've been in rehab for three years and a drawing has helped them, and I just imagine them doing that.
Elizabeth Day
Yes.
Charlie Mackesy
You know, and I find it really overwhelming to see it that way.
Charlie Mackesy (alternate or reflective voice)
So in a Sense, it's a privilege.
Charlie Mackesy
But to carry it. We can't really.
Elizabeth Day
You said something that I'm going to disagree with about the feeling that you don't think you carry it well. And actually, I think you are such an empath and a feeler that the feeling is. It is the message. The feeling is the thing. And so actually it's the most beautiful way I think you can respond. And there is something quite monk like about it, actually, now that I think about it.
Charlie Mackesy (alternate or reflective voice)
That's a lovely thing to say. I mean, I think I'm usually lost
Elizabeth Day
for words because you're feeling it.
Charlie Mackesy (alternate or reflective voice)
You feel it.
Charlie Mackesy
And sometimes there's a long silence where someone just says something and you look at them.
Charlie Mackesy (alternate or reflective voice)
The first time it happened was when I first started doing these drawings and
Charlie Mackesy
I put on an exhibition in the gallery and didn't think anyone would really come. You know, my mum, maybe and my sister and friends might turn up. And it was quite scary. And I remember a girl bringing her boyfriend to see me and he was huge. He looked like he played rugby for Ireland, you know, number eight or something. And she said, this is whoever. And I said, hello, you have. Johnny said hi. And he looked at me and I was sitting down and he just looked at me and he had tears pouring down his face and I looked at him and then I had tears pouring down my face and I held his hand and then gave him a hug and we never spoke. Wow. Yeah.
Charlie Mackesy (alternate or reflective voice)
And I had no idea. I didn't need to know.
Charlie Mackesy
It wasn't my business to know. But it was plenty for him to. There was a lot he said a lot.
Elizabeth Day
I think all the most profound human experiences lie beyond words.
Charlie Mackesy
Yeah.
Elizabeth Day
And words are the closest approximation we can get to in this fallible.
Charlie Mackesy (alternate or reflective voice)
They're an attempt.
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Elizabeth Day
And I think you're probably asked quite a lot, like, why you think your work resonates. And I'm not going to ask you that because I don't think you need to put words to it. But I would like to ask you about your characters and whether you feel that your characters are facets of you. Talk me through how you see them.
Charlie Mackesy
I didn't know that for a long time.
Charlie Mackesy (alternate or reflective voice)
I generally don't know a lot. And I usually am retrospective if I
Charlie Mackesy
do and go, oh, that's why I ran naked through a field.
Charlie Mackesy (alternate or reflective voice)
You know, it's always that kind of
Charlie Mackesy
thing where I have no idea what I'm doing till afters.
Charlie Mackesy (alternate or reflective voice)
And in similarly with this journalist for the Independent on in, just after the book came out, said of course, you
Charlie Mackesy
know, we understand what you're doing there for different parts of you. And I was sort of, oh, yes, you're right.
Charlie Mackesy (alternate or reflective voice)
So I think, yeah, in. They are all different facets of maybe
Charlie Mackesy
being human or sort of. We can't be too clear about it, but generally speaking, we have different ways of operating and coping mechanisms and various things about us. And those four characters are definitely how I have operated a lot of my life, I think.
Elizabeth Day
How do you describe them? What are their characteristics?
Charlie Mackesy (alternate or reflective voice)
Well, the boy usually has all the
Charlie Mackesy
questions, is anxious pretty much about everything and probably thinks he's in trouble or too ordinary or what happens if. Or, you know, one day you'll discover I'm ordinary and all these things. He feels the fox is sort of that wounded side that can't trust and is sort of wryly observing people, relationships, connections and going, you know.
Charlie Mackesy (alternate or reflective voice)
And then the mole is the bit
Charlie Mackesy
of me that, as, you know, when things are tricky, I'll reach for the crisps, cheese and onion. Usually snacks. It just lunges for things to comfort.
Charlie Mackesy (alternate or reflective voice)
But underneath it all, I think, you
Charlie Mackesy
know, the mole is the addictive sort of personality. And then the horse is probably the deepest part of us.
Elizabeth Day
Now, why isn't there a cat?
Charlie Mackesy
Would you like one?
Elizabeth Day
Yes, please. I love cats.
Charlie Mackesy
Do you?
Elizabeth Day
Yes. I mean, I love all animals, but I love that.
Charlie Mackesy (alternate or reflective voice)
I mean, there are many animals to squeeze in.
Elizabeth Day
There are.
Charlie Mackesy (alternate or reflective voice)
There are similar ducklings. I mean, I just left.
Charlie Mackesy
I came from Suffolk this morning and I've been looking after some ducklings whose mother was killed in April. And I'm their mother or father or something.
Charlie Mackesy (alternate or reflective voice)
And they're just. Ducks are just basically, ducklings are hamburgers
Charlie Mackesy
until they can fly.
Charlie Mackesy (alternate or reflective voice)
They're just wandering around saying, I'm a snack anyone. You know, they've got nothing. Their beaks are like soft lolly sticks
Charlie Mackesy
and they're surrounded by this terrifying.
Charlie Mackesy (alternate or reflective voice)
Like the pond next to my cottage
Charlie Mackesy
is literally like a stage on which is played this terrifying
Charlie Mackesy (alternate or reflective voice)
three part drama every night.
Elizabeth Day
Have you protected them all so far?
Charlie Mackesy (alternate or reflective voice)
Well, I didn't protect the mum because she was taken.
Elizabeth Day
Oh, gosh.
Charlie Mackesy (alternate or reflective voice)
But they can. The 12, was it two or three days ago. They.
Charlie Mackesy
When they can fly, they're okay because they've escaped danger and they flew across the pond. Oh, I filmed it by accident.
Elizabeth Day
What a mo. This was yesterday.
Charlie Mackesy
Three days ago.
Elizabeth Day
Yeah, three days ago. What a moment.
Charlie Mackesy (alternate or reflective voice)
But I was just filming. They were sitting and then they all decided and they came straight. I mean, just. And then when they land, it's like potatoes landing. They just don't know how to land. It's like, oh, God, what are we doing? Okay, then. But it's very moving that.
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Elizabeth Day
Your first failure for today is that you failed your driving test four times.
Charlie Mackesy
I did, yeah. Yeah.
Elizabeth Day
Why do you think that was?
Charlie Mackesy
Probably didn't listen enough to what was being asked. Too nervous, anxious. And also the worst one was the fourth one where I was quite hungover, aged 18, and without indicating, I pulled the car over onto a pedestrian pavement, opened the door and threw up.
Charlie Mackesy (alternate or reflective voice)
And I remember throwing on.
Charlie Mackesy
You know how you throw your eyes watering. And then I looked across at the examiner.
Charlie Mackesy (alternate or reflective voice)
He had his thing.
Charlie Mackesy
He was just. Look, he gave me. It's just, you know.
Charlie Mackesy (alternate or reflective voice)
And so, yeah, so it was interesting because actually, in retro, I'm quite sorry. Good. I think, you know, they're there for a reason, these tests.
Charlie Mackesy
Right. And if I'd passed, I may well not have been sitting here, you know what I mean? Like, I was a reckless boy.
Elizabeth Day
Yes.
Charlie Mackesy (alternate or reflective voice)
And my best friend at the time,
Charlie Mackesy
silence, I suppose, in my heart was Jamie, who was killed in his car, I think, six months later. And it was those moments where I remember Thor was lowered him into this hole. And I remember looking into the hole and thinking, well, what do we do now? Everything's different now. There's a red line drawn now. You could feel it. Nothing will ever be the same now. And then I went mad for a while.
Elizabeth Day
I'm so sorry that you went through that and I'm so sorry that Jamie's no longer here in a physical sense. Can you tell me about him? What was he like?
Charlie Mackesy (alternate or reflective voice)
He was amazing because I.
Charlie Mackesy
Well, he was funny and kind and also was quite. I was often prone to lows. I wouldn't go through quite lows. And he would see them and often would pull me out of them in this sort of, stop moping, let's get on and do something. And it would annoy me for 10 minutes and then it worked. You go and feed some sheep or do something.
Charlie Mackesy (alternate or reflective voice)
And I think he was, you know,
Charlie Mackesy
one of those people that we love music, played the same songs, just, you know, talked about girlfriends, failed at them, ate together, drank together. So, yeah, he was. I was at school with him.
Charlie Mackesy (alternate or reflective voice)
But I definitely like the loss of him. You know, we all have.
Charlie Mackesy
Everyone has losses. And I. I think part of you goes the bit that you.
Charlie Mackesy (alternate or reflective voice)
I think we're different with every.
Charlie Mackesy
Every person we're close to with, they see a different side of us. And so that was, you know, I think him a lot still.
Charlie Mackesy (alternate or reflective voice)
And.
Charlie Mackesy
But what's interesting about that was this sort of. You have these sort of salient, cataclysmic moments in your life, right, where something happens. And I then, for some reason ended up, you know, getting a lift to London, never been before, and then staying on floors and seeing an ink pen on a table three or four days after the funeral, maybe, and picking it up and asking if I could borrow it. And I walked out into the street, it was in Battersea, and sat down and started drawing the street without even thinking about it. And then I did that drawing. So that went into Battersea park and drew again. And I thought, oh, I like this. And what was happening was I had borrowed these headphones with a tape and I was really moved when I was doing it and the combination in it, I started crying and the Music and the drawing helped me and I haven't really stopped since.
Charlie Mackesy (alternate or reflective voice)
So really,
Charlie Mackesy
that's what happened.
Elizabeth Day
Goodness.
Charlie Mackesy
Yeah. It's mad. But think about it.
Charlie Mackesy (alternate or reflective voice)
When you trace your steps back, there's always these little things, aren't there?
Charlie Mackesy
It could be a word or a
Charlie Mackesy (alternate or reflective voice)
sentence or a friend or something.
Charlie Mackesy
And it was that pen on that table and I liked the look of it and it just made marks that were interesting. And
Elizabeth Day
what was the music you were listening to, Joanna?
Charlie Mackesy
Trading.
Elizabeth Day
This is. I don't want this to come across as an insensitive question. Be insensitive, because obviously I wish Jamie Owen were alive today. Do you think you had to go through the grief to get somewhere, to get here?
Charlie Mackesy (alternate or reflective voice)
You know, it's impossible to answer, but, I mean, I think for me that without it, I would have been very different.
Charlie Mackesy
That broke me in half.
Charlie Mackesy (alternate or reflective voice)
And then actually, those years were hard.
Charlie Mackesy
He wasn't the only one I lost.
Charlie Mackesy (alternate or reflective voice)
So there was a series of them.
Charlie Mackesy
And of course, it's just like being buffeted. Yeah.
Elizabeth Day
And young as well.
Charlie Mackesy (alternate or reflective voice)
Yeah.
Charlie Mackesy
18, 19, 20.
Charlie Mackesy (alternate or reflective voice)
And so I think I. Then also, what's strange about it is I think when those things happen, in a way gives you the confidence, you just go, well, so what then?
Charlie Mackesy
What have you got to lose? Start. People go, oh, don't be an artist. Nightmare. You know, you never. You'll never succeed at that. It's impossible or bit risky, or, come on, mate, get a proper job. But because of that, you think, no, just do what's in your heart and listen to it. Because guess what? We're all. We're all. None of us get out of here alive. So why not try, then? What do you got to lose? I think.
Elizabeth Day
Were you talking to anyone about how you were feeling?
Charlie Mackesy
Such a good question. No, I wasn't. I didn't really know how to verbalize it then. Age 18, in those days, people drank a lot, so I think I just put it into ink and music and, you know, crying with a Walkman on and then just carrying on. It's a good question,
Elizabeth Day
because I know you. You speak very lovingly of your parents.
Charlie Mackesy
I do.
Elizabeth Day
And I'm also aware that we're talking about a different generation where prior to books like yours and podcasts like mine, these sort of conversations about emotion and vulnerability were just not happening.
Charlie Mackesy
No.
Elizabeth Day
But do you think your parents were worried about you?
Charlie Mackesy (alternate or reflective voice)
That's a good question.
Charlie Mackesy
I don't know.
Charlie Mackesy (alternate or reflective voice)
I remember saying to my dad, because they were the war generation, so they'd been through
Charlie Mackesy
horrors. You know, Mum lost her Father on the Normandy beaches, my dad's father, you know, they all went through. And so I suppose, you know, they just stoically carried on.
Charlie Mackesy (alternate or reflective voice)
But for me, I remember saying to
Charlie Mackesy
my dad, I think of the third friend had died. I said, is this normal? He was on the phone, he said, charlie, this is not normal. I promise you that. And it was a lovely.
Charlie Mackesy (alternate or reflective voice)
It was heart. The way he said it was really heartfelt. But, yeah, I think it may be me.
Charlie Mackesy
I think I probably just did bottle things up quite a lot.
Elizabeth Day
You've also said this thing that I read in an interview about your mother when she was getting you ready for school.
Charlie Mackesy
Yeah.
Elizabeth Day
Buttoning up your clothes and saying something to you. Saying one word.
Charlie Mackesy
Yes.
Elizabeth Day
What would she say to you?
Charlie Mackesy (alternate or reflective voice)
Well, it's more that she would. In fact, she was quite good at that.
Charlie Mackesy
Even in her last year, whenever I
Charlie Mackesy (alternate or reflective voice)
saw her, she'd say, well, hello.
Charlie Mackesy
Said them all.
Charlie Mackesy (alternate or reflective voice)
But in those days, she'd always say, remember.
Charlie Mackesy
Always remember. And if I was going to school, she'd say, you are here. You know, you're all right. You can come back, you can start again. I love that idea. The idea of starting again. It's a new day tomorrow. Just remember, we love you. And actually nothing really else matters, I don't think.
Elizabeth Day
Yes.
Charlie Mackesy
Ultimately, nothing really is any consequence whether you succeed or don't, except whether love is it really. I think, ultimately, isn't it?
Elizabeth Day
Yes. And there's so much in that single word, remember. There's so much love and history and tenderness.
Charlie Mackesy (alternate or reflective voice)
Yeah.
Charlie Mackesy
Because we forget. So a tendency to. Especially in times of panic. I forget everything when I'm in a tight place or things are a nightmare. I do forget those things. So important you.
Elizabeth Day
I'm sorry. Because I feel like I'm just sort of bringing up these catastrophic losses in your life. But over the last few years, you lost your beloved mum and your beloved Barney, your dog. How do you remember them? Is it a sort of practice that you.
Charlie Mackesy
That's a really good question.
Elizabeth Day
Thank you.
Charlie Mackesy
You're very good. No wonder everyone loves your podcast
Charlie Mackesy (alternate or reflective voice)
different ways. A different Barney.
Charlie Mackesy
Because he'd never left my side.
Charlie Mackesy (alternate or reflective voice)
I often sort of sense him. And I actually. Barney came to me because I had another dog and good friends of mine had Barney.
Charlie Mackesy
And so we shared him, really, from 18 years ago. And so it's lovely. Cause I can talk to them about him. He came to stay and then stayed for 18 years or whatever it was.
Charlie Mackesy (alternate or reflective voice)
And that's quite good to chat about
Charlie Mackesy
his ways and cry and going. Yeah.
Charlie Mackesy (alternate or reflective voice)
And Mum with my Sister.
Charlie Mackesy
We send each other photographs of Mum doing funny things.
Charlie Mackesy (alternate or reflective voice)
So I think, you know, processing with
Charlie Mackesy
others really helps if you can. And
Charlie Mackesy (alternate or reflective voice)
I think for me, I think with Mum, there was such a tenderness
Charlie Mackesy
and a humor and a lightness. And she really loved the drawings and she stuck them all over her walls and that you couldn't see the. The walls for the drawings. And I love that.
Elizabeth Day
Yes.
Charlie Mackesy
You know, and when she had the book, she wore out the COVID with her fingers.
Charlie Mackesy (alternate or reflective voice)
She would read like this and she'd.
Charlie Mackesy
And then.
Charlie Mackesy (alternate or reflective voice)
And so the embossing, the words were off. I've still got the word.
Charlie Mackesy
There's nothing left.
Charlie Mackesy (alternate or reflective voice)
And sometimes she would hold the book
Charlie Mackesy
open and she would, with her fingers, run over the drawings and to feel them.
Charlie Mackesy (alternate or reflective voice)
And the only place I've ever seen
Charlie Mackesy
that before was in a place called the Dragonfly Unit, which was a hospital for teenagers who are struggling mentally. And I covered in lockdown. It was empty. I covered the corridors and other rooms with the drawings and never met any of them. But I hear from them indirectly. And one lady who works has said, there's a girl who's been here a year who's. It's a miracle she's even still here. But she runs her fingers. She's wondering where she runs her fingers over. And they can barely see the drawing anymore on the wall because she just looks at it and likes to connect with it. And I think that's what Mum was doing. Like, when you feel something like that, you like to. There's something comforting about it. So Mum did that. And I have that book and I look at. I just. I walk past it every day and I look at it and think of
Elizabeth Day
her, because I know she had dementia. So I wonder if there's also something about. There's something so profoundly beautiful about holding onto the words and the stories, but ultimately, by holding onto them, they disappear. But then having the physical object of
Charlie Mackesy (alternate or reflective voice)
that book, it's a really interesting idea, this whole of the physicality of written words and connecting with them physically. It's almost like if you. It's like sculpture.
Charlie Mackesy
You want to touch it or hold it or something, if you feel something.
Charlie Mackesy (alternate or reflective voice)
But my sister was. She lived next to my sister and family.
Charlie Mackesy
And so I went there every day
Charlie Mackesy (alternate or reflective voice)
to see them, and I'd often find
Charlie Mackesy
my sister reading the words to her.
Charlie Mackesy (alternate or reflective voice)
And I think I hear from a lot of people who have someone with
Charlie Mackesy
dementia in the family, and sometimes they say that the book, because of the
Charlie Mackesy (alternate or reflective voice)
drawing, the simplicity, that they connect through
Charlie Mackesy
it, there's something in it and you
Charlie Mackesy (alternate or reflective voice)
asked me what it was.
Charlie Mackesy
I don't know really what it is. And it doesn't work for everyone. How could it? But I'm glad it does for some, you know.
Elizabeth Day
Yes. It's honest. So failing your driving test four times, you do pass it. Do you drive now?
Charlie Mackesy (alternate or reflective voice)
You know what the weird thing is? Less and less, I like trains.
Elizabeth Day
I love trains.
Charlie Mackesy
Do you love a train train?
Charlie Mackesy (alternate or reflective voice)
Me too.
Elizabeth Day
I'll always choose the train over a car.
Charlie Mackesy
Me too.
Charlie Mackesy (alternate or reflective voice)
So this morning, just now, I came two hours sitting on a train, you know, I bumped into someone I met on the train three weeks ago. We had a good chat.
Elizabeth Day
Don't like that.
Charlie Mackesy (alternate or reflective voice)
I didn't mind it. I was saying, I'm going to see you. And she said, oh, I love Elizabeth Day. Oh, yeah. So actually I love that. Love that. So, yeah, for me, they're quite stressed cars. I don't know.
Charlie Mackesy
I don't know anymore.
Elizabeth Day
Yeah,
Charlie Mackesy
some people love them, that's fine. But you know trains.
Elizabeth Day
Yes. I find cars just inimically terrifying.
Charlie Mackesy (alternate or reflective voice)
Terrifying.
Elizabeth Day
I'm constantly thinking about things that could go wrong and then I have to actively make myself imagine the positive outcome that's going to happen if I'm at the wheel now. Yeah. Yes. Actually, it's the first time I've admitted that out loud because I feel like there's something about being an adult where you're just meant to be able to drive, but it's actually terrifying.
Charlie Mackesy (alternate or reflective voice)
You're in a metal box spinning along a road with other metal boxes with other people missing you by feet.
Elizabeth Day
Yes. What I know. And they haven't all had the data acquisition of four failed tests. Some of them are less good drivers.
Charlie Mackesy (alternate or reflective voice)
True story.
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Charlie Mackesy (alternate or reflective voice)
Let's go.
Elizabeth Day
Your second failure is I haven't achieved conventional success. So many people have asked me through
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life, when I'm having kids, I why
Elizabeth Day
am I not married?
Charlie Mackesy
Yeah, all the time, why aren't you married? Why haven't you got kids?
Charlie Mackesy (alternate or reflective voice)
And I don't come out with some erudite, clear answer.
Charlie Mackesy
I just go. I usually ask them a question back something.
Elizabeth Day
Why are you married? Why do you have kids?
Charlie Mackesy (alternate or reflective voice)
Or just, you know, why don't you plant more trees? But, you know, like, it's something that I've wanted to do, but I've never
Charlie Mackesy
wanted to do it for the sake of it. And I feel like I've helped lots of friends with their kids, you know.
Elizabeth Day
Well, I mean, beyond friends, I think you've helped the world with their children in terms of encouraging people.
Charlie Mackesy
Yeah, that's a moving thought.
Charlie Mackesy (alternate or reflective voice)
I do get a lot of
Charlie Mackesy
packages of books that have been made by kids with the characters, but with their own words. And that breaks me up because they're so honest. Will I ever not be ugly? Said the mole. You're beautiful. Said, you know all this stuff, you're going,
Elizabeth Day
yeah. I mean, perhaps, if I may, your role in this lifetime, your purpose was not to have children in order that you could parent in this way.
Charlie Mackesy
Yeah, maybe I don't.
Charlie Mackesy (alternate or reflective voice)
I don't.
Charlie Mackesy
I don't think about it too hard about why I just.
Charlie Mackesy (alternate or reflective voice)
I tend to just play what's in
Charlie Mackesy
front of me, if you know what I mean by that. Like, life presents itself and you just take each day and do your best. And I think for me, there could have been times, but there weren't. It hasn't, and that's fine. And you are right. I think maybe I wouldn't have had the time,
Charlie Mackesy (alternate or reflective voice)
you know, because actually making those books and the journey to making
Charlie Mackesy
them is not simple and you have to become pretty obsessive. And, you know, I not see people for ages, and these other writers, I'm sure you're not like that. But for me, I did disappear and my main connections were with Instagram, where I'd say, here's a drawing and hear back from them. That was really moving.
Elizabeth Day
Yes. And that's very interesting because social media comes in for so much warranted criticism.
Charlie Mackesy (alternate or reflective voice)
Warranted. Yes.
Elizabeth Day
But one of the things that I have always valued about it is that sense of community. And often when you feel lonely or isolated, if you put something on Instagram and people see you for what you're putting out there. It's incredibly profoundly connective.
Charlie Mackesy (alternate or reflective voice)
The number of people who've put a
Charlie Mackesy
comment on a post, and then there are 60 ensuing comments saying, oh, are you okay? Where are you? Do you wanna meet for a cup of tea? You know, I'm sitting in the hotel in a hospital corridor. My dad's had a heart attack and been sitting here for seven hours. And then they all bring a conversation
Charlie Mackesy (alternate or reflective voice)
that I'm only a small part of.
Charlie Mackesy
And that, for me, where people are drawn to something that they feel they can have some kind of belonging to is great. I love that.
Elizabeth Day
Can I ask you why? Why you think people feel they can ask you that question? Because I think not. I think it's interesting.
Charlie Mackesy
Yeah.
Elizabeth Day
Because we are so conditioned to accept and expect life to travel a certain path.
Charlie Mackesy (alternate or reflective voice)
Yes.
Elizabeth Day
That so many people feel emboldened to ask you, why are you not married? Why do you not have children?
Charlie Mackesy (alternate or reflective voice)
Yes. As if you've made a terrible mistake
Charlie Mackesy
or you somehow failed society.
Elizabeth Day
Yeah. Is it hurtful when people ask you, or did it used to be?
Charlie Mackesy (alternate or reflective voice)
It might have been. I don't. I can't really remember, but I. I
Charlie Mackesy
find it quite funny as well, because there's so many other questions you could ask.
Elizabeth Day
Yes.
Charlie Mackesy (alternate or reflective voice)
But also, people look at me and
Charlie Mackesy
they go, well, he's quite scruffy and he lives. He's. He's eccentric. No wonder. It's no surprise that he's.
Charlie Mackesy (alternate or reflective voice)
He doesn't even know.
Charlie Mackesy
He doesn't wear the same socks and.
Charlie Mackesy (alternate or reflective voice)
But I have deep friends.
Elizabeth Day
Yes.
Charlie Mackesy (alternate or reflective voice)
Deep.
Elizabeth Day
But I want to talk about.
Charlie Mackesy (alternate or reflective voice)
Friends die for.
Elizabeth Day
Let's talk about friendship.
Charlie Mackesy (alternate or reflective voice)
Yeah.
Charlie Mackesy
I think it's one of the most underrated loves. We do spend a lot of time, quite rightly so, thinking about romantic love
Charlie Mackesy (alternate or reflective voice)
and maybe because I lost my best
Charlie Mackesy
friend very early on, so I've always felt the depth of what they can be. And you have them for life.
Charlie Mackesy (alternate or reflective voice)
I think I remember when I realized that.
Charlie Mackesy
That whole idea of someone. Of daring to say to someone, this is how I feel, who I am, what I'm going through. This is a storm I'm really in. Because we're all in storms most of the time. And for it to be met with. Oh, yeah, me too. That's incredible. Yeah. I'm so grateful for my friends and they tolerate me.
Elizabeth Day
I'm sure they're so grateful.
Charlie Mackesy
I love them a lot. Yeah.
Elizabeth Day
For you, too. This poet laureate of friendship. You clearly have such a gift for friendship. What do you think great friendship must entail. Are there sort of five qualities?
Charlie Mackesy
Oh, my days. You asked me to list five qualities.
Elizabeth Day
Well, I've thought a lot about this because.
Charlie Mackesy (alternate or reflective voice)
Go on, you tell me.
Elizabeth Day
I've written a book about friendship purview. Yes.
Charlie Mackesy (alternate or reflective voice)
Why. Why aren't you doing all the talking?
Charlie Mackesy
You're asking me the questions.
Charlie Mackesy (alternate or reflective voice)
How about you?
Elizabeth Day
Well, I think it's extremely individual and I. I'm so pro having conversations like the one that we're having because so many people don't talk about what friendship means to them, and that can lead to misunderstanding. So there'll be certain people who want a daily phone call as part of their friendship. I'm not one of those people. And, and. And I think it's really helpful to work out the things that you value and to have the conversation with your friend about that and see where you meet.
Charlie Mackesy
Yeah.
Elizabeth Day
So the things that I value, you hit on it there. Generosity of spirit is my number one quality because I want them. I want to feel that they're thinking the best of me in any given situation.
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Elizabeth Day
Even if I am rubbish on the phone and we haven't seen each other for two months because life is hectic, that when we do see each other, we can hit that relational depth quickly because there's no guilt associated with it. That's my number one quality.
Charlie Mackesy
Generosity of spirit.
Elizabeth Day
Generosity of spirit.
Charlie Mackesy
Love that. Yeah.
Elizabeth Day
Curiosity. That's just one of my favorite human characteristics.
Charlie Mackesy
That's amazing, isn't it? That's why you love cats. Yes, among other reasons.
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Yeah.
Elizabeth Day
You really have to have a cat character.
Charlie Mackesy
Okay, thank you. Okay.
Elizabeth Day
Anyway, do you agree with those qualities?
Charlie Mackesy (alternate or reflective voice)
Yes, very much so.
Elizabeth Day
Okay, great, great. There we go.
Charlie Mackesy (alternate or reflective voice)
I think kindness, you know, I think kindness is a. Yeah. The word is used a lot these
Charlie Mackesy
days, but it's such a crucial facet to a friendship.
Charlie Mackesy (alternate or reflective voice)
And I think, you know, I remember meeting someone.
Charlie Mackesy
Not meeting, but my neighbor, one of my neighbors and someone Suffolk. And she said to me, you know, when are you going to make another book? And I said, I don't know, really. This is two or three years ago, I always remember. And she said, you know, I teach kids sometimes who have come from really tough backgrounds, and your book gave them permission to be kind.
Charlie Mackesy (alternate or reflective voice)
And I'll always remember that for many.
Charlie Mackesy
But for many reasons, not least the fact they needed permission.
Elizabeth Day
Yes.
Charlie Mackesy
To be kind, as if it was something they shouldn't do because it's not cool or it's weak or. And kindness is
Charlie Mackesy (alternate or reflective voice)
such a strength. In the same breath, you know, I did hear I'm banging about stories, but I did hear once of a tiny
Charlie Mackesy
act of kindness shown by a teacher to a pupil who had decided. She decided to not live anymore. And this was her last lesson. And 20 years, 15, 20 years later, she was back at the school. He was retiring. She had a child at the school. And she said to him, do you remember me? And he said, I'm not sure. And she reminded him who she was. And she said, I just want to say thank you because you did a tiny thing that was enough to keep me here. You were kind for 10 seconds.
Charlie Mackesy (alternate or reflective voice)
And so I've always thought that kindness
Charlie Mackesy
can be fleeting or huge and all of these different ways of being so important. And I would love to be kinder. I would love to. You know, we're all on a journey of
Charlie Mackesy (alternate or reflective voice)
kind to others and to myself. That's a big journey.
Elizabeth Day
Oh, that's a huge one. Yes. Self compassion, I mean, and self acceptance. Because that's really what we're talking about.
Charlie Mackesy (alternate or reflective voice)
It's self acceptance. Then I think you can accept others more easily anyway. So I think, you know, I think this whole journey is uncomfortable of being
Charlie Mackesy
human and beautiful and difficult. And I think kindness and love, all these things help us on that journey. But particularly I think for me at least, and I know others, that to
Charlie Mackesy (alternate or reflective voice)
learn to speak, you know, I lose so many things and I lost my favorite mug yesterday.
Elizabeth Day
I'm sorry.
Charlie Mackesy (alternate or reflective voice)
Yeah, it's an ancient mug.
Elizabeth Day
I love mugs.
Charlie Mackesy (alternate or reflective voice)
Yeah, me too. It's just beautiful mug. I drunk tea and I just was berating myself.
Charlie Mackesy
I was really relaying into myself what you done with what?
Charlie Mackesy (alternate or reflective voice)
You know, this is after I come back from Ireland.
Charlie Mackesy
I was so cross with me and
Charlie Mackesy (alternate or reflective voice)
which is normal, but I just think
Charlie Mackesy
I could have been a bit kinder.
Elizabeth Day
I relate to this very deeply and I've had various therapists over the years and one of the things that they will say to me when I recount a similar episode is, whose voice is that? Whose voice?
Charlie Mackesy (alternate or reflective voice)
Ah, good question.
Elizabeth Day
Whose voice is it for you?
Charlie Mackesy (alternate or reflective voice)
It's not one particular voice, I don't
Charlie Mackesy
think, but it's an intolerant, impatient, critical voice.
Elizabeth Day
Judgmental. Oh, yeah, yeah. It's interesting, isn't, is when I'm asked that question, I always say, it's my voice.
Charlie Mackesy (alternate or reflective voice)
Who do you think it is then?
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Elizabeth Day
I don't think it would be so much easier if I could hang it on the hook of an individual who was mean to me, but I can't. That doesn't feel.
Charlie Mackesy (alternate or reflective voice)
Yeah, maybe you're right. Maybe I'm wrong, you know.
Elizabeth Day
No, I think you're right. I think you're right.
Charlie Mackesy (alternate or reflective voice)
No, I think it probably is me.
Elizabeth Day
And no one in real life would be as unkind to you.
Charlie Mackesy
Wouldn't say that.
Elizabeth Day
I don't think so. Definitely no one I've spoken to about Charlie Makassi. You are so beloved, truly, and I think it's really important. Thank you for my. To say that and for you to hear it, even if you don't feel it. The hearing of it is important.
Charlie Mackesy (alternate or reflective voice)
I mean, I feel so grateful in my life. Like if today was my last day, I would feel nothing but gratitude
Charlie Mackesy
for everything, including the losses, pains, mistakes, failures, everything. And the love and my friends and people I'll never ever meet, who I felt or had messages from. They're the heartbreaking ones. So I do hear it and I'm grateful.
Charlie Mackesy (alternate or reflective voice)
But there's always the bit of me going, ah, but you don't really know me. No. Do you know what I mean, though?
Elizabeth Day
But that's what stops you from being insufferable. So that's actually a character strength.
Charlie Mackesy (alternate or reflective voice)
My cottage has piles of clothes in
Charlie Mackesy
it and half finished things and I
Charlie Mackesy (alternate or reflective voice)
don't know,
Elizabeth Day
but I love that. Yes, it's very human and it's very accessible. Anyway, that would have been a beautiful note to end the entire interview on. But we do have one more failure. We have one more failure, which is that you failed at being an artist for most of your life. If. And you wrote to me, and this is such an astute point, because failure. We were talking before recording about how it's such a diffuse, vague term for very complicated, nuanced. But you say if failure means making a living, you've failed at being an artist for most of your life.
Charlie Mackesy (alternate or reflective voice)
Being an artist is a strange idea
Charlie Mackesy
anyway, because everybody is. We're all making things in different ways, whether it's a pie or love or a shirt or making someone's day. That's artistry in itself. So I don't know about all this. Artist would.
Charlie Mackesy (alternate or reflective voice)
But for me, you know, now, like when I go in my house, it's rammed with drawings and the ones in frames have all been exhibited and haven't sold. So I'm surrounded by work that hasn't sold. And I used to see it as work that hasn't sold. Now I just see it as a
Charlie Mackesy
really important part of the process of
Charlie Mackesy (alternate or reflective voice)
you were on a journey somewhere and you have to make these to get somewhere else.
Charlie Mackesy
It's what you have to do. So, like breathing to get to the door, you got to breathe eight times. So it's the same idea that keep breathing, keep making mistakes, keep trying and you get somewhere else, you move. And for me now, making art is not about anything other than trying and enjoying it and
Charlie Mackesy (alternate or reflective voice)
not putting the pressure
Charlie Mackesy
on yourself to sell, not putting the pressure on yourself to achieve some.
Charlie Mackesy (alternate or reflective voice)
Just enjoy it and be free to
Charlie Mackesy
make the mistakes that you learn from.
Charlie Mackesy (alternate or reflective voice)
And I think the fear of not coming up to standard you would like prevents us often from doing anything at all. People say to me often, I wish
Charlie Mackesy
I could, I just don't let myself because I can't bear to see what I'll do. Say, well just think you're five years old because five year olds don't give a monkey. So just have a bin and do them and put them in the bin and I guarantee the one you do after that will be more pleasurable than this one.
Charlie Mackesy (alternate or reflective voice)
And da, da, da. And I think that's the journey of
Charlie Mackesy
life is to be in a house, surrounded metaphorically with all your half assed attempts. Brilliant.
Elizabeth Day
Your noble failures.
Charlie Mackesy
Yeah, there you go.
Charlie Mackesy (alternate or reflective voice)
But I think that the process is an end in itself.
Charlie Mackesy
I don't think we're all trying to
Charlie Mackesy (alternate or reflective voice)
get now, is it? There's nothing else now, right, the second where we all are now, is it? And this is our process. We're now half finished.
Charlie Mackesy
Messy, brilliant, vulnerable, awkward states.
Charlie Mackesy (alternate or reflective voice)
Is beautiful and it's enough. And we're always going, oh well, tomorrow
Charlie Mackesy
I'll be the ex, just be in it now. And you're spectacular.
Charlie Mackesy (alternate or reflective voice)
I mean, I should say this to
Charlie Mackesy
myself, I'm saying it to me included.
Charlie Mackesy (alternate or reflective voice)
And one day, as I always say,
Charlie Mackesy
you'll look back and realize how hard it really was. But how well you did. I really think that
Elizabeth Day
just everything. That was just everything. Thank you so much.
Charlie Mackesy
Was it?
Elizabeth Day
Yeah. I want to end when I do my research for these interviews, I tend to note down particular quotes that someone has said before that have meaning for me. And generally it's sort of two or three with you, Charlie. I've just got pages and there's one in particular which really spoke to me and I'd love to draw us to a close by talking about it. And it is. I don't think even the river knows where it's going until it reaches the sea. So it speaks so truthfully to what you've just said there that you have to be the river without questioning where you're ending up. Do you feel that in this lifetime in this human shell that you're inhabiting that you are living your purpose?
Charlie Mackesy (alternate or reflective voice)
Well, I mean, that's a good question, a hard question.
Charlie Mackesy
I hope so.
Charlie Mackesy (alternate or reflective voice)
I mean, purpose is such a central
Charlie Mackesy
thing for all of us. To have such is crucial to feel like we have purpose.
Charlie Mackesy (alternate or reflective voice)
And I think having been very aware
Charlie Mackesy
of my own failings
Charlie Mackesy (alternate or reflective voice)
and being as
Charlie Mackesy
honest as I can about them, if that has helped someone feel less of a failure, then maybe we haven't failed.
Charlie Mackesy (alternate or reflective voice)
For me, this idea that if I can be in a little room making
Charlie Mackesy
inky marks on paper somewhere and they go out into the world and they make someone in Australia, in a town somewhere they'll never go, feel better about their day and more hopeful and less alone and it gives them some kind of voice. They didn't think anything like that or they choose to stay when they were thinking about not. And that for me is. That is purpose, isn't it?
Elizabeth Day
Charlie McAssee, thank you so, so much for your work, for who you are, for what you are, for coming on how to Fail. I feel the rivers of our joint experience have been leading to this moment in some way.
Charlie Mackesy (alternate or reflective voice)
I agree. I think you're incredible. And your book's beautiful and vulnerable and so honest and so necessary and so
Charlie Mackesy
human and funny and keep saying and doing what you're doing is a very important thing.
Elizabeth Day
Thank you. Well, you have been the most perfectly imperfect guest. Thank you.
Charlie Mackesy
Thank you for having me.
Elizabeth Day
Thank you so much for listening and watching. This episode has been brought to you by Dove Whole Body Deodorant. Please do follow how to Fail to
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Elizabeth Day
Thank you so much for listening.
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Air date: July 8, 2026
Host: Elizabeth Day
Guest: Charlie Mackesy
Duration: ~55 min
This episode of How To Fail features bestselling author and illustrator Charlie Mackesy, whose gentle wisdom and evocative art have touched millions worldwide. Charlie joins Elizabeth Day to explore how failure, grief, and vulnerability have shaped his creative journey. Central themes include the experience of feeling an outsider, the transformative power of loss, the weight of community expectation, and, above all, the everyday courage to begin again. The conversation is candid, empathetic, and often quietly profound.
[08:00–12:57]
“I listen ... often get really moved, cry with a good number of people, and then afterwards it feels like a train is slowly hitting me.” – Charlie Mackesy (08:25)
“A brilliant therapist once... said when people tell you their weight, their sadness, their failings – whatever it is – treat it like they’re giving you gold.” – Charlie Mackesy (10:38)
“To carry it... we can’t really. But to see it as a privilege, yes.” – Charlie Mackesy (11:22)
“He just looked at me... had tears pouring down his face and I looked at him and then I had tears pouring down my face and I held his hand and then gave him a hug and we never spoke.” – Charlie Mackesy (12:22)
[05:20–07:39]
“Somewhere deep within me, most of the time the feeling is, yeah, I’m in trouble somewhere. It’s my fault. I did it.” – Charlie Mackesy (04:53) "Being an observer is closely linked to feeling like an outsider." – Elizabeth Day (06:13)
“There’s a corridor of constant test results for various subjects... I was always 8th equal or 12th or bottom. And so you’re constantly being reminded that you’re not what you could be.” – Charlie Mackesy (07:02)
[19:16–24:50]
“It was those moments where... Thor was lowered him into this hole. And I remember looking into the hole and thinking, well, what do we do now? Everything’s different now. There’s a red line drawn now.” – Charlie Mackesy (20:17)
“After the funeral... picked up an ink pen... sat down and started drawing the street without even thinking about it. And... I was really moved when I was doing it... the music and the drawing helped me and I haven’t really stopped since.” – Charlie Mackesy (22:15–23:28)
“That broke me in half... I think when those things happen, in a way it gives you the confidence, you just go, well, so what then?... Just do what’s in your heart and listen to it.” – Charlie Mackesy (24:23–24:50)
[27:14–32:56]
“She’d always say, remember. And if I was going to school, she’d say, ‘You are here. You know, you’re all right. ...you can start again. ...Just remember, we love you. And actually nothing really else matters, I don’t think.’” – Charlie Mackesy (27:26)
“With Mum, there was such a tenderness and a humor and a lightness. ...She really loved the drawings and she stuck them all over her walls and you couldn’t see the walls for the drawings. I love that.” – Charlie Mackesy (30:17)
“There’s a girl... It’s a miracle she’s even still here. ...She runs her fingers over... can barely see the drawing anymore on the wall because she just looks at it and likes to connect with it. And I think that’s what Mum was doing.” – Charlie Mackesy (31:51)
[35:50–40:10]
“Why aren’t you married? Why haven’t you got kids?” – Charlie Mackesy (35:59)
“I tend to just play what's in front of me... Life presents itself and you just take each day and do your best.” – Charlie Mackesy (37:33)
“Packages of books that have been made by kids with the characters, but with their own words. And that breaks me up because they’re so honest.” – Charlie Mackesy (36:49)
[40:14–45:47]
“Daring to say to someone, this is how I feel... and for it to be met with, ‘Oh, yeah, me too.’ That’s incredible.” – Charlie Mackesy (40:40)
“Kindness is such a strength.” – Charlie Mackesy (44:07)
“She said, ‘Your book gave them permission to be kind.’” – Charlie Mackesy (43:47)
“That’s the journey of life is to be in a house, surrounded metaphorically with all your half-assed attempts. …The process is an end in itself.” – Charlie Mackesy (50:51–51:04)
[48:55–51:56]
“I used to see [unsold art] as work that hasn’t sold. Now I just see it as a really important part of the process... keep breathing, keep making mistakes, keep trying and you get somewhere else, you move.” – Charlie Mackesy (49:17)
“Just enjoy it and be free to make the mistakes that you learn from.” – Charlie Mackesy (50:20) “We’re now half finished, messy, brilliant, vulnerable, awkward states. …It’s beautiful and it’s enough.” – Charlie Mackesy (51:19)
[52:00–54:33]
“I don’t think even the river knows where it’s going until it reaches the sea.” – Elizabeth Day, paraphrasing Mackesy (52:00)
“If I can be in a little room making inky marks on paper somewhere and they go out into the world and... make someone... feel better about their day and more hopeful and less alone... that for me is... purpose, isn’t it?” – Charlie Mackesy (53:27)
The conversation is gentle, contemplative, warm, and deeply empathetic. Elizabeth Day’s questions are searching but openhearted; Charlie Mackesy responds with humility, candidness, and often a wry humor about his own foibles. The discussion is rich in metaphor and reflective moments but never pretentious—always grounded in lived experience.
Charlie Mackesy’s How To Fail episode is a powerful meditation on the meaning of failure, the grief that can spark healing creativity, and the bravery required to simply continue, with feeling, in a world demanding answers. Through stories of loss and moments of profound connection, the interview models the kind of vulnerable, honest presence that underpins both great art and great living.