Charlie Mackesy – ‘Grief propelled me into work that saved me’

8 Jul 2026 · 54 min · 16 chapters

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In short

Charlie Mackesy discusses grief as a driver of creative work, how he holds others’ stories, and why “failure” (including not selling art, not fitting in, and personal setbacks) can lead to purpose, kindness, and connection.

Guest background

Charlie Mackesy is an author/illustrator from Hexham, Northumberland. He worked as an illustrator/cartoonist (e.g., The Spectator, Oxford University Press). His books The Boy, The Mole, The Fox, and The Horse became a major bestseller (152 weeks), translated into 40+ languages, sold 10+ million copies, and were adapted into an Oscar-winning animated film (2022). Always Remember was a UK Christmas number one.

Key claims

A therapist (ex-Franciscan monk) taught him to treat others’ sadness/failings as “gold.” He doesn’t “carry” trauma well afterward; he gets overwhelmed, then needs quiet to recover. His characters reflect coping facets: anxious Boy, wounded/observant Fox, comfort-seeking Mole, and deepest Horse. Purpose is making marks that help others feel less alone—sometimes even helping people stay alive.

Notable examples

He describes crying with a stranger at a gallery opening who silently broke down. He recalls a grief-triggered drawing after his friend Jamie’s funeral (Jamie died in a car accident). He shares how his mother’s dementia-era tenderness and physical interaction with his books (and his drawings on hospital corridors) helped others connect. He also recounts failing his driving test four times and choosing trains over cars due to ongoing fear.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Therapist Wisdom on Sharing Pain

0:00 to 0:43

Learn how to value the sharing of personal struggles as a gift.

“You know, I had a brilliant therapist once, who was actually an ex-Franciscan monk.”

Therapist Wisdom on Sharing Pain

0:48 to 1:51

Learn how to value the sharing of personal struggles as a gift.

“This is the podcast that believes failure is simply what makes us human.”

Introducing Charlie Mackesy

2:51 to 4:54

Explore the journey and achievements of author Charlie Mackesy.

“Perhaps you saw one of his illustrations during the pandemic on phone screensavers and hospital walls and Instagram grids.”

The Feeling of Not Fitting In

4:54 to 6:10

Discussing the impacts of feeling like an outsider from childhood.

“I'm mainly feeling quite sweaty because isn't it the hottest day in 100 years?”

Carrying the Weight of Others' Stories

6:10 to 9:09

How Charlie Mackesy processes and carries the stories shared with him.

“I think I've always been quite aware of it.”

The Power of Non-Verbal Connection

9:09 to 13:14

Exploring the profound connections that exist beyond words.

“But I don't really have, you know, I think people just want to be heard probably and seen.”

Characters Reflecting the Self

13:14 to 14:00

Delving into how Charlie's characters represent different facets of himself.

“the closest approximation we can get to in this fallible universe.”

The Four Facets of Human Experience

14:00 to 17:30

Explore the four characters representing different aspects of Charlie's personality and how they manifest in his life.

“you know, we understand what you're doing, there are four different parts of you.”

Life Lessons from Ducklings

17:30 to 18:18

Charlie shares a touching story about raising ducklings and the life lessons gleaned from observing nature.

“Everything you need to start selling is there from day one, including the moment someone is actually ready to buy from you.”

Reflections on Grief and Loss

18:18 to 24:26

Charlie reflects on his experiences with grief, including losing friends and how it shaped his life and art.

“This summer, Prime Video takes you back before Legally Blonde, before law school, and into the world of Elle Woods in high school.”
Show all 16 chapters

The Influence of Family and Love

24:26 to 28:00

A discussion on the impact of Charlie's mother's words and the overarching theme of love in life.

“I didn't really know how to verbalize it then, age 18, in those days.”

The Impact of Grief and Memory

28:00 to 33:10

Exploration of love and memory in the context of loss and grief.

“Ultimately, nothing really has any consequence, whether you succeed or don't, except whether, you know, love is it really, I think.”

Exploring Friendship and Life Choices

35:50 to 42:00

Discussion on the significance of friendship and societal expectations regarding marriage and children.

“Your second failure is I haven't achieved conventional success.”

The Importance of Kindness in Friendship

42:00 to 48:40

Explore how kindness shapes relationships and personal growth.

“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.”

Redefining Failure as Artistic Journey

48:40 to 51:18

Discuss how viewing failure as part of the creative process can liberate us.

“We have one more failure, which is that you failed at being an artist for most of your life.”

Finding Purpose Through Artistic Expression

51:18 to 53:31

Learn how creating art can provide purpose and connection to others.

“We're now half-finished, messy, brilliant, vulnerable, awkward.”
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Transcript

Automatic transcript. May contain errors.

0:00You know, 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 someone's, they're giving you gold. And my best friend at the time, Salir, I suppose, in my heart was Jamie, 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. This episode of How to Fail is brought to you by Dove Whole Body Deodorant.

0:47Welcome to How to Fail with me, Elizabeth Day. This is the podcast that believes failure is simply 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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2:37And make laundry day easier with two-in-one washer-dryer combo innovation that completes laundry in about 90 minutes. Shop top brand appliances now at The Home Depot. Offer valid June 17th to July at the US only C-Store online for details. If you haven't met my guest today in person, the chances are you are familiar with his work on the page. 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.

3:16Or perhaps you've read his books with their tales of a curious boy, a cake-obsessed mole, an anxious fox, and a sage old horse, and you've been forever changed by their accessible wisdom. Their author is Charlie Mackesy, 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, Macassie'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.

4:08It 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, Macassie 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 Macassie 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.

4:50I did it. Charlie Mackesy. Did I say that? You did say that. That's true, yeah. Welcome to How to Fail. Thank you for having me. Are you feeling it now? I'm mainly feeling quite sweaty because isn't it the hottest day in 100 years? 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 air con. So this is like a Bikram podcasting session. Apologies. Does the temperature affect the sound? Is that a thing? No, the sound of the air called the whir of the fan. The whir of the fan. The temperature affects the quality of the interview I'm going to get.

5:28When can you first remember feeling like that? That you must be at fault in some way? I'm not sure. It's a bit like when you are a bit uncomfortable with something and you realise at some point that it's a song that you don't like is playing. so it happens oh that yeah so when I don't know but I think it's this kind of it's an undercurrent isn't it someone somewhere is really annoying it's interesting because I have the same thing definitely you always have it's actually a really different question to answer isn't it yeah exactly there you go but when I think I've always been quite aware of it.

6:13Have you? Yes. The answer I tend to reach for is that age four, my family and I moved to the north of Ireland. Yes. 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. Yeah. 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 being slightly wrong probably dates from that point. Yeah. Like the sound of you is wrong. Yes, exactly. Yeah. Because you got sent to boarding school. I wonder if it started there.

6:56Yeah. I don't know. Yeah, probably. I think the way the system was set up was very much you're in competition with each other, which is a strange way of going about things. like there's a corridor of of of constant test results for various subjects and you could always seeing where you were on the list and of course i was always eighth equal or twelfth or bottom and so you're constantly being reminded that you're not what you could be and then um but yeah then i went to a brilliant geordie school in hexham and and then again with a posh voice and that wasn't easy, but they were so gorgeous. But in the end, I had no reason to feel anything but loved.

7:39We 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. 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. Hmm, carrying them. It's a really good question.

8:29I thought you were 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 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. And then I think I try to, there was a moment in lockdown, I always remember it, in 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, you know, friends who are journeying in a difficult way with each other and feeling uncomfortable about things.

9:29But I don't really have, you know, I think people just want 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. The dog. 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 and then lay down. And I was thinking, you know, when something happens, it's almost passive. I didn't choose it. I'm wondering what it was.

10:18then I suppose it's the body needs to let go of stuff, right? Yes. Maybe my subconscious was saying, you're not going 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. But yeah, it's a very good question and I don't think I carry it very well. But I do see it as a privilege. You know, 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.

11:07And 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. Yes. you know and i find it really overwhelming um to see it that way so in a sense it's a privilege but to carry it we can't really 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 the, 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.

11:57That's a lovely thing to say. I mean, I think I'm usually lost for words. Because you're feeling. You feel it. And sometimes there's a long silence where someone just says something and you look at them. The first time it happened was when I first started doing these drawings and 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.

12:31And she said, this is whoever. And I said, hello, you love Johnny. I 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. And I had no idea. I didn't need to know. It wasn't my business to know. But it was plenty for him to... There was a lot. You said a lot. Yes. I think all the most profound human experiences lie beyond words. And words are the closest approximation we can get to in this fallible universe.

13:18They're an attempt, aren't they? Yes. And I think you're probably asked quite a lot 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 i didn't know that for a long time i generally don't know a lot and i i usually am retrospective if i do and go oh that's why i run naked through a field you know it's always that kind of thing where i have no idea what i'm doing until after this and in similarly with this, this journalist for The Independent just after the book came out said, of course, you know, we understand what you're doing, there are four different parts of you.

14:03And I was sort of, oh, yes, you're right. So I think, yeah, they are all different facets of maybe being human. 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. How do you describe them? What are their characteristics? Well, the boy usually has all the 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 he'll discover I'm ordinary and all these things he feels.

14:58The fox is sort of that wounded side that can't trust and is sort of wryly observing people, relationships, connections and going, you know. And then the mole is the bit of me that, you know, when things are tricky, I'll reach for the crisps, cheese and onion usually, snacks, it just lunges for things to comfort. But underneath it all, I think, you know, the mole is the addictive sort of personality. And then the horse is probably the deepest part of us. Now, why isn't there a cat? Would you like one? Yes, please. Okay. I love cats. Do you? Yes. I mean, I love all animals, but I have a very special cat.

15:53I mean, there are many animals to squeeze in. There are. There are. Similarly with ducklings. 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. And they're just ducks. Ducklings are hamburgers until they can fly. They're just wandering around saying, I'm a snack, anyone? You know, they've got nothing. Their beaks are like soft lolly sticks. and they're surrounded by this terrifying... It's like the pond next to my cottage is literally like a stage on which is played this terrifying three-part drama every night.

16:43It's exhausting. Have you protected them all so far? Well, I didn't protect the mum because she was taken. Oh, gosh. But they can, the 12, was it two or three days ago, when they can fly, they're okay because they've escaped danger and they flew across the pond. I filmed it by accident. What a moment, this was yesterday? Three days ago, yeah. Three days ago, what a moment. But I was just filming, they were sitting there 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?

17:16Okay. But it's very moving that.

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18:42L-L-L-Y dot com. This summer, Prime Video takes you back before Legally Blonde, before law school, and into the world of Elle Woods in high school. Set in 1995, this Gemini vegetarian knows exactly who she is, until her family moves from Bel Air to Seattle. Packed with iconic fashion, 90s nostalgia, and a throwback soundtrack, Elle proves one thing. Law school was hard. High school was harder. From the world of Legally Blonde, watch Elle, a new original series only on Prime Video. Watch now. Your first failure for today is that you failed your driving test four times. I did, yeah, yeah. Why do you think that was?

19:25Probably 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. And I remember throwing on, you know how you throw your eyes watering and then I looked across at the examiner, he had his thing, he was just, the look he gave me, it's just, you You know? And so, yeah. So it was interesting because actually in retro, I'm quite, it's really quite good. I think, you know, they're there for a reason, these tests, right?

20:07And if I'd passed, I may well not have been sitting here. You know what I mean? Like I was a reckless boy. Yes. And my best friend at the time, Salir, I suppose, in my heart was Jamie, who was killed in his car, I think six months later. and I it was those moments where I remember four of us lowered him into this hole and I remember looking into the hole and thinking well what do we do now? Everything's different now with a red line drawn now you could feel it nothing will ever be the same now and and and then I went mad for a while 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 he was amazing because I he was funny and kind and also was quite I was often prone to lows I went and 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.

21:27And it would annoy me for 10 minutes and then it worked. We'd go and feed some sheep or do something. And I think he was one of those people that we loved music, played the same songs, just talked about girlfriends, failed at them, ate together, drank together. So yeah, I was at school then. But I definitely like the loss of him, you know, we all have, everyone has losses and I think part of you goes the bit that you, I think we're different with every person we're close to, we're basically a different side of us. And so that was, you know, I think him a lot still. but what's interesting about that was you have these sort of salient cataclysmic moments in your life where something happens and I then for some reason ended up 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.

22:46And 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, and I 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. So really, that's what happened. Goodness. Yeah, it's mad really. Yeah. when you trace your steps back there's always these little things aren't there it could be a word or a sentence or a friend or something and it was that pen on that table and I liked the look of it and it just made marks that were interesting What was the music you were listening to?

23:55Joan Armatrading This is I don't want this to come across as a an insensitive question because obviously I wish Jamie were alive today do you think you had to go through the grief to get somewhere to get here you know it's very it's impossible to answer but I mean I think for me that without it I would have been very different it broke me in half and then actually those years were hard he wasn't the only one I lost so there was a series of them and of course it's just like profited yeah and young as well yeah 18 19 20 um and so i think i then also what's strange about it is i think when those things happen it in a way gives you the confidence you just go well so what then what have you got to lose start people go oh don't be an artist nightmare you know you'll never you'll never you'll never succeed at that it's impossible or a bit risky or come on mate yeah 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 your life so why not try then what have you got to lose I think were you talking to anyone about how you were feeling or such a good question no I wasn't.

25:35I 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 um it's a good question because i know you you speak very lovingly of your parents i do and i'm also aware that we're talking about a different generation yeah where prior to books like yours and podcasts like mine these sorts of conversations about emotion and vulnerability were just not happening No. But do you think your parents were worried about you? That's a good question. I don't know. I remember saying to my dad, because they were the war generation, so they'd been through horrors.

26:38You 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. But for me, I remember saying to my dad, I think of the third friend who died, I said, is this normal? It was on the phone. He said, Charlie, this is not normal. I promise you that. And it was a lovely, it was hard, the way he said it was really heartfelt.

27:10But yeah, I think it may be me. I think I probably just did bottle things up quite a lot. You've also said this thing that I read in an interview about your mother, when she was getting you ready for school, buttoning up your clothes and saying something to you, saying one word. Yes. What would she say to you? Well, it's more that she would, in fact, she was quite good at that. Even in her last year, whenever I saw her, she'd say, well, hello, said them all. But in those days, she'd always say, remember, always remember. And if I was going to school, you were here, you know, you're all right, you can come back.

27:50You can start again. I love that idea, the order of starting it. It's a new day tomorrow, just remember we love you. And actually nothing really else matters, I don't think. Ultimately, nothing really has any consequence, whether you succeed or don't, except whether, you know, love is it really, I think. Ultimately, isn't it? Yes. And there's so much in that single word, remember. There's so much love and history and tenderness. Yeah. Because we forget. It's 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.

28:40It's so important. you 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 really good question thank you you're very good no wonder everyone loves your podcast um different ways different um Barney because he'd never left my side,

29:18I often sort of sense him.

29:24And actually, Barney came to me because I had another dog and good friends of mine had Barney. And so we shared him really from 18 years ago. And so it's lovely because I can talk to them about him. He came to stay and then stayed for 18 years or whatever it was. And that's quite good to chat about his ways and crying. And mum and my sister, we send each other photographs of mum doing funny things. So I think, you know, processing with others really helps if you can. and

30:09I think for me I think with mum there was such a a tenderness and a humour and a lightness and she really loved the drawings and she stuck them all over her walls and you couldn't see the walls for the drawings and I loved that yes and when she had the book she wore out the cover with her fingers, she would read like this. And so the embossing, the words were off. I've still got the book, there's nothing left. And sometimes she would hold the book open and she would, with her fingers, run over the drawings to feel them. And the only place I've ever seen that before was in a place called the Dragonfly Unit, which was a hospital for teenagers who are struggling mentally.

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31:02and I covered the, 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 that there's a girl who's been here a year, it's a miracle she's even still here, but she runs her fingers, she's wandering 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. When you feel something like that, there's something comforting about it. So mum did that. And I have that book and I look at it.

31:48I walk past it every day and I look at it and think of her. Because I know she had dementia. So I wonder if there's also 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 that book. It's a really interesting idea, the physicality of written words and connecting with them physically. It's almost like if you, it's like sculpture, you want to touch it or hold it or something, if you feel something.

32:28My sister was born, she lived next to my sister and family. So I went there every day to see them. I often find my sister reading the words to her. and I think I hear from a lot of people who who have someone with dementia in the family and sometimes they say the book because of the drawing the simplicity that they connect through it there's something in it and you asked me what it was, I don't know really what it is and it doesn't work for everyone, how could it I'm glad it does for some it's honest so fading your driving test four times you do pass it do you drive now you know what the weird thing is less and less i like trains i love trains do you love a train journey i'll always choose the train over a car me too so this morning just now i came yeah two hours sitting on a train you know i just bumped into someone i met on the train and three weeks ago we had a good chat don't like that I didn't mind it I was saying I'm going to see you and she said oh I love Elizabeth yeah so actually oh I love that love that so yeah for me they're quite stressed cars I don't know I don't know anymore yeah some people love them that's fine but you know trains yes I find cars just inimically terrifying terrifying 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.

34:09Now, 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. You're in a metal box spinning along the road with other metal boxes missing you by feet. Yes. What? I know. And they haven't all had the data acquisition of four failed tests. Some of them are less good drivers. True story.

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35:21I, O, let's go! 102 miles ago, the oil light came on. 100 miles ago, you noticed. Now, it's time to head to Take 5. This oil change, fall in love with your car all over again. In just 10 minutes, your dream technician will check your tire pressure, top off fluids, change your oil, and verify with Carfax exactly what your car really needs. All while keeping you in the driver's seat. Take 5, the stay-in-your-car 10-minute oil change. Save up to 30 % on your next oil change to Take 5. Your second failure is I haven't achieved conventional success. So many people have asked me through life, when I'm having kids, why am I not married?

36:02Yeah, all the time. Why aren't you married? Why haven't you got kids? And I don't come out with some erudite clear answer. I just go, hmm. I usually ask them a question back. Something. Why are you married? Why do you have kids? Or just, you know, why don't you plant more trees? But you know, it's something that I have wanted to do, but I have never wanted to do it for the sake of it. And I feel like I've helped lots of friends with their kids. Well, I mean, beyond friends, I think you've helped the world with their children in terms of encouraging people to be kinder. I do get a lot of packages of books that have been made by kids with the characters, but with their own words.

36:59And that breaks me up because they're so honest. Will I ever not be ugly? Said the Ma. You're beautiful. You know, all this stuff. You're going. Yeah. 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. Yeah, maybe. I don't think about it too hard, about why I just, I tend to just play what's in 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 that there weren't. And that's fine. And you are right.

37:55I think maybe I wouldn't have had the time. You know, because actually making those books and the journey to making 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 say, here's a drawing and hear back from them. That was really moving. Yes. And that's very interesting because social media comes in for so much warranted criticism. Warranted, yes. But one of the things that I have always valued about it is that sense of community.

38:36Yeah, man. 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. The number of people who've put a comment on a post and then there are 60 ensuing comments saying, are you okay? Where are you? Do you want to meet for a cup of tea? You know, I'm sitting in a hotel, in a hospital corridor. My dad's had a heart attack and we've been sitting here for seven hours. And then they will be a conversation that I'm only a small part of. And that for me, where people are drawn to something that they feel they can have some kind of belonging to is great.

39:19I love that. Can I ask you why you think people feel they can ask you that question? because I think not, I think it's interesting

39:31because we are so conditioned to accept and expect life to travel a certain path that so many people feel emboldened to ask you why you're not married, why do you not have children? Yes, as if you've made a terrible mistake or you somehow failed society. Yeah. Is it hurtful when people ask you or did it used to be? It might have been. I can't really remember, but I find it quite funny as well. Because there's so many other questions you could ask. Yes. But also, people look at me and they go, well, he's quite scruffy and he's a bit eccentric. No wonder. It's no surprise that he doesn't even know, he doesn't wear the same socks.

40:13But I have deep friends. Yes. Deep. But I want to talk about friends. That I would die for. Let's talk about friendship. it yes i think it's one of the most underrated loves we do spend a lot of time quite rightly so thinking about romantic love and maybe because i lost my best friend very early on so i've always felt the depth of of what they can be and you have them for life i think i remember when i realized that when that whole idea of someone of daring to say to someone this is how i feel who i am, what I'm going through, whatever. This is a storm I'm really in. Because we're all in storms most of the time.

40:57And 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. I'm sure they're so grateful. I love them a lot, yeah. 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? Oh my days, you're asking me to list five qualities. Well, I've thought a lot about this. Go on, you tell me. I've written a book about friendship. Have you? Yes. Why aren't you doing all the talking? You're asking me the question. This is about you.

41:44Well, I think it's extremely individual. And 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 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. So the things that I value, you hit on it there. Generosity of spirit is my number one quality in the group. Because I want them, I want to feel that they're thinking the best of me in any given situation.

42:27Yes. 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 generosity of spirit just love that yeah curiosity that's just one of my favorite human characteristics that's amazing isn't it that's why you love cats yes yeah you really have to have a cat character okay Thank you. Okay. Anyway, do you agree with those qualities? Yes, very much so. Okay, great. Great. There we go. I think kindness, you know, I think kindness is a, you know, the word is used a lot these days, but it's such a crucial facet to a friendship.

43:18And I think, you know, I remember meeting someone, not meeting, but my neighbor, one of my neighbors in 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 and I'll always remember that not least the fact they needed permission to be kind as if it was something they shouldn't do because it's not cool or it's weak. And kindness is such a strength. In the same breath, I did hear, I'm banging on stories, but I did hear once of a tiny act of kindness shown by a teacher to a pupil who had decided to not live anymore.

44:27And this was her last lesson. and 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. She said, you were kind for 10 seconds. and so I you know I've always thought that you know kindness can be fleeting or huge and and all 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 um kind to others and to myself that's a big journey oh That's a huge one.

45:21Yes. Self-compassion. I mean. And self-acceptance, because that's really what we're talking about. Yeah, self-acceptance, then I think you can accept others more easily anyway. Yes. You know, I think this whole journey is uncomfortable of being human and beautiful and difficult. And I think, you know, 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 learn to speak. You know, I lose so many things and I lost my favorite mug yesterday. I'm sorry. Yeah, it's an ancient mug. I love mugs. Yeah, me too. It's just a beautiful mug.

46:06I drank together and I just was berating myself. I was really, really laying into myself. You know, this is after I came back from Ireland. and I was so cross with me. And which is normal, but I just think I could have been a bit kinder. 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? Ah, good question. Whose voice is it for you? It's not one particular voice, I don't think. But it's an intolerant, impatient, critical voice. Judgmental. Oh, yeah. Yeah. It's interesting, isn't it?

46:54It is. When I'm asked that question, I always say it's my voice. Do you think it is? Yes. 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 honest. Yeah, maybe you're right. Maybe I'm wrong, you know. No, I think you're right. I think you're right. No, I think it probably is me. And no one in real life would be as unkind to you. Wouldn't know that. I don't think so. Definitely no one I've spoken to about Charlie Maxey. You are so beloved. Truly. And I think it's really important for me to say that and for you to hear it, even if you don't feel it.

47:35The hearing of it is important. I mean, I feel so grateful in my life. Like if today was my last day, I would feel nothing but gratitude 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. but there's always the bit of me going ah but you don't really know me do you know what I mean though but that's what stops you from being insufferable so that's actually a character strength my cottage has piles of clothes in it and half finished things and I don't know 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.

48:40We have one more failure, which is that you failed at being an artist for most of your life. Yeah. 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 something very complicated and nuanced, but you say, if failure means making a living, you failed at being an artist for most of your life. Being an artist is a strange idea anyway because everybody is. You know, we're all doing, making things in different ways, whether it's a pie or a... or love or a shirt or making someone's day, you know, that's artistry in itself.

49:16So I don't know about all this artist word, 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 really important part of the process of making you're on a journey somewhere and you have to make these to get somewhere else you it's what you have to do so like breathing to get to the door you got to breathe eight times you know so it's the same idea that keep breathing keep making mistakes, keep trying, you know, and you get somewhere else, you move.

50:04And for me now, making art is not about anything other than trying and enjoying it and not putting the pressure on yourself to sell, not putting the pressure on yourself to achieve some, just enjoy it and be free to make the mistakes that you learn from. 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 I could, I just don't let myself, because I can't bear to see what I'll do. I 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.

50:49And I guarantee the one you do after that will be more pleasurable than this one, and da-da-da, and I think that's the journey of life, is to be in a house surrounded metaphorically with all your half-arsed attempts. Brilliant. Your noble failures. Yeah, there you go. But I think that the process is an end in itself. I don't think we're all trying to 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, messy, brilliant, vulnerable, awkward. States is beautiful and it's enough. And we're always going, oh, well, tomorrow I'll be the X, just be in it now.

51:38And you're spectacular. I mean, I should say this to myself. I'm saying it to me included.

51:51And one day, as I always say, you'll look back and realize how hard it really was but how well he did i really think that just everything that was just everything thank you so much yeah i want to i want to end i when i do my research for these interviews i tend to note down particular quotes that someone has said before that okay 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 I really spoke to me. And I'd love to draw a stir 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.

52:37So it speaks so truthfully to what you've just said there, that you have to be the river without that questioning where you're ending up. Yeah. Do you feel that in this lifetime, in this human shell that you're inhabiting, that you are living your purpose? Well, I mean, that's a good question, a hard question. I hope so. I mean, purpose is such a central thing for all of us to have. So it's just crucial to feel like we have purpose. And I think having been very aware of my own failings and being as honest as I can about them, if that has helped someone feel less of a failure, then maybe we haven't failed.

53:31For me, this idea that if I can be in a little room making 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? Charlie Mackesy, 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.

54:25I agree. I think you're incredible and your book's beautiful and vulnerable and so honest and so necessary and so human and funny and keeps hanging and doing what you're doing. It's a very important thing. Thank you. Well, you have been the most perfectly imperfect guest. Thank you. Thank you for having me.

54:46Thank 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 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. Hey, it's Ryan Reynolds here from Mint Mobile. Now, I was looking for fun ways to tell you that Mint's offer of unlimited premium wireless for$15 a month is back. so I thought it would be fun if we made$15 bills but it turns out that's very illegal so there goes my big idea for the commercial give it a try at mintmobile.com slash switch upfront payment of$45 for 3 months $90 for 6 months or$180 for 12 month plan required $15 per month equivalent taxes and fees extra initial plan term only greater than 50 gigabytes may slow when network is busy see terms

From the publisher

In this episode, I sit down with bestselling author‑illustrator Charlie Mackesy, whose work – The Boy, the Mole, the Fox and the Horse – has become a global touchstone for kindness, vulnerability and hope.

Yet Charlie’s path was anything but straightforward: he grew up feeling inherently at fault, shaped by the pressures of competitive schooling and the emotional weight of carrying the painful stories readers now share with him.

He talks about failing his driving test four times and the devastating loss of his best friend, Jamie, in a car crash – a grief that propelled him to London and sparked the first moment he began drawing compulsively, with music as solace.

Charlie reflects on not achieving what he calls “conventional success” through marriage or children, the underrated importance of friendship and the power of kindness and self‑compassion.

We also explore his years of not earning a living as an artist – a period he now sees not as failure, but as an essential process. Charlie urges us to create without fear, to let go of perfection and to live fully in the imperfect present.

✨ IN THIS EPISODE:

00:00 Intro

03:44 Feeling at Fault

04:30 Outsider and School Years

05:55 Carrying Others Stories

13:57 Animals and Ducklings

17:08 Driving Test Failure

18:06 Loss and Aftermath

20:05 Grief Fuels Art

23:14 Bottling Emotions

25:07 Remember Mothers Word

28:28 Mum’s Tactile Reading

29:44 Dementia and Story Comfort

33:21 Redefining Success

37:46 Friendship Essentials

40:37 Kindness and Self Talk

46:09 Failing as an Artist

💬 QUOTES TO REMEMBER:

“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.”

“I just wrote a book about a mole who likes cake and friends who are journeying in a difficult way with each other… but I think people just want to be heard and seen.”

“None of us get out of here alive, so why not try? What have you got to lose?”

🔗 LINKS + MENTIONS:

Charlie’s latest book, Always Remember: The Boy, the Mole, the Fox, the Horse and the Storm, is available from all major UK booksellers.

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Jacqueline Wilson - this episode explores how Jacqueline Wilson’s life and career never followed a predictable path. She didn’t become a bestseller until her 40s and the setbacks she faced helped shape the writer she became. It reflects on the imagination and resilience behind unforgettable characters like Tracy Beaker, her ability to reinvent herself, most recently with The Primrose Railway Children and the creativity and determination that have sustained a career spanning more than 100 books. Ultimately, it’s about a woman interrogating creativity, perseverance and the determination required to keep going: swap.fm/l/PawxjS1dFBaohoKZXfpL

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👋 Follow How To Fail & Elizabeth:

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