How To Fail With Elizabeth Day - Patrick Radden Keefe - ‘Lying Is More Prevalent Than People Think’

Episode Date: June 17, 2026

What draws an award-winning writer to the darkest corners of human behaviour? Patrick Radden-Keefe is a New York Times bestselling author and staff writer at The New Yorker. He is known for his acclaimed books, including Empire of Pain and Say Nothing - the latter was adapted into a BAFTA and Emmy-nominated drama series. Radden Keefe’s latest book, London Falling, investigates the life and untimely death of Zac Brettler, a North London teenager drawn into the criminal underworld. In this conversation, Patrick reflects on why he is so fascinated by “the bad guys”, how the extraordinary story behind London Falling unfolded and his unconventional writing process. Patrick also talks about the years of rejection that preceded his success and how it has shaped him. I hope you enjoy this conversation with one of the world’s finest narrative journalists (oh, and Patrick). JUST KIDDING. ✨ IN THIS EPISODE: 03:25 Why He Writes Bad Guys 05:12 London Falling Origin Story 08:01 Reinvention and Secret Lives 10:06 Holocaust Legacy and Lying 14:58 Carrying Grief and First Failure 31:47 Parents Read First Drafts 33:13 Family Themes And Fixations 34:22 Chasing The New Yorker Dream 36:49 Rejection Resentment And Drive 41:14 What To Leave Out 43:28 Research Outline 48:13 Screenplays That Never Get Made 50:51 Growth Outside Comfort Zone 💬 QUOTES TO REMEMBER: I tend to look at people, even people who do pretty monstrous things, as human beings... The question for me is always, how did they get there? And usually they got there by degrees. I'd like to think that the sense of who you are as a person isn't contingent on the dopamine hit of people telling you you've done a good job. 🔗 LINKS + MENTIONS: London Falling is out now: www.patrickraddenkeefe.com Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Jon Ronson - another journalistic hero of mine, Jon talked about his love of storytelling, what being bullied at school taught him and why truth-telling is vital: swap.fm/l/3Uwm2GCNCBpHQVZc6dwr Malcolm Gladwell - on being mediocre at running, failing to be a friend and whether prejudice can ever be a force for good: swap.fm/l/CxIsEyNtJcyXROPZQCvh 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Guest bookings for How To Fail only come from official @sonymusic.com emails Elizabeth and Patrick answer listener questions in our subscriber series: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [e-mail] _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices

The legal threats don't scare me, I will say. I get a lot of those. The gangsters never threaten me in a kind of outright way. The people who threaten me are people like the Sacklers, are wealthy people who hire lawyers to send really nasty letters. But at the end of the day, those are just nasty letters, you know. My dad was really disappointed and wouldn't speak to me. He didn't talk to me for about four days.

And he wrote me a letter. This episode of How to Fail is brought to you by Dove Whole Body Deodorant. Hello and welcome to How to Fail. This is the podcast that firmly believes failure is just simply something we have to go through on our path to success. Before we get into this episode, please do remember to like, follow and subscribe so that you never miss a single conversation. This episode is brought to you by L'Oreal Group. Beauty is a powerful force that moves us. That's why L'Oreal Group has built a beautiful.

business that is inclusive at its heart with 100% of its brands, championing diversity. With 25,000 professional opportunities for people under 30 worldwide and 54% of leading positions held by women, diversity is a strength that helps L'Oreal Group create the best beauty products for all people. Visit L'Oreal.com to learn more. Here at the Happiness Lab, we're serving up some hot takes for the summer, big ideas that just might reshape how you think about your well-being, like the radical notions. that we should get rid of small talk completely. We talk about current events.

We talk about what you do for a living, but not do you love what you do for a living. Is this your dream job? For more surprising ideas backed by psychological science, check out our new series, Happiness Hot Takes. Listen to the Happiness Lab with me, Dr. Lari Santos, wherever you get your podcasts. In 2018, I read a book that would change the way I came to think about my life.

It was Say Nothing by Patrick Raddenkief, an extraordinary non-fiction work, telling the story of the abduction and murder of Jean McConville, a Belfast mother of 10 at the height of the Troubles in 1972. Despite having grown up in the north of Ireland, say nothing told me the story of my home in a way I'd never been taught at school. And as a literary work, it bore all the hallmarks of what I would come to understand was classic Radankeef, a rigorous dedication to unpacking moral complexity, an eye for the telling human detail that would illuminate bigger institutional corruptions, and an ability to marshal reams of reported material

into a gripping narrative. But the stories he tells, whether in the pages of the New Yorker, where he's a staff writer, or in any of his award-winning, internationally best-selling books, always have a clear sense of moral purpose. He's especially interested in understanding the rogues at the margins of society who work their way into its centre, but who all too often end up like Icarus flying too close to the sun. His previous work, Empire of Pain, won the Bailey Gifford Prize for nonfiction, and Say Nothing was adapted into a BAFTA and Emmy-nominated drama series. His latest book, London Falling, details the life and untimely death of Zach Pryff. a North London teenager who became enmeshed with the criminal underworld. Radenkeith's understanding of London might mistakenly lead some readers to think in British.

In fact, Radnkeef grew up in Massachusetts and has a clutch of degrees from elite academic institutions, including Cambridge, the LSE and Yale. He is the recipient of a Guggenheim Fellowship and just as importantly, a former model for J.Crew. Every time he tells me a new story idea, I feel like I have a mini heart attack, his wife, Justina, said in a recent newspaper profile. Oh, geez, another litigious asshole or murderous criminal. Can't you do a celebrity profile or something? But Patrick is intrigued by all of the bad guys. Patrick Radinkeef, welcome to How to Fail. I'm so happy to be here.

I'm so happy you're here, and I'm so happy that I quoted your wife in that introduction, not knowing that she would also be. be here today. Yeah, indeed. Shout out to Justina. Why are you so compelled to write about bad guys? I don't know. It's funny. I think people sometimes wonder if there's some rosebud moment in my past, some family secret of my own. But it's not that. I think it's just something about transgression, kind of the ways in which people deviate from conventional morality. and I tend to look at people, even people who do pretty monstrous things as human beings. And I kind of wonder how it's not a situation where I look at those types of people. And I think I could never be that person.

They're sort of fundamentally different from me. The question for me is always, how did they get there? And usually they got there by degrees. And I'm interested in self-delusion, the kind of the stories that we tell ourselves about the decisions we make. And so all those stories have always been intriguing to me. I don't know why, but I come back to them again and again. Do you think it's fair what I said in the introduction about your books having a sense of moral purpose? Yeah, I do.

I mean, I think my mother is a retired professor of philosophy and somebody who, you know, talk to us about ideas and big ideas and sort of wasn't shy about engaging her kids in questions about more. morality and ethics and so forth. And it's not that I think of myself as a particularly righteous grown-up, but I am attuned to those kinds of questions. So if a celebrity did something terribly bad, then you might do a celebrity profile. Then I'm in. Yeah, absolutely. I'm just waiting. I'm waiting for that to happen because as we all know, celebrities never do anything bad. Well, quite. So I'm very interested in what you say there about delusion and the narratives that we tell ourselves about who we are and who we want to be. And that interest led

you to the story at the heart of London falling, didn't it? Can you tell us a little bit about this book? Yeah. So the book, it came about in this interesting way. I was in London, living in London, in the summer of 2023. We were turning my book, Say Nothing, that you mentioned, into this drama, which is now on Disney Plus. And I was producing the show and a guy plunked down next to me who was a visitor to the set that day. He was a guest of the director.

And we started to chat. And something I often do is I often try to engage strangers in conversation. I think it's... I always did it. I'm a naturally curious person, but I also think it's important for a journalist to kind of be out in the world.

and you never know where a story is going to come from. And in this case, I got to chatting with this guy, and he said, I might have a story for you. I know this family here in London, who I'm very close with. And in 2019, they had this tragic thing happen. They lost a child. They lost their son, Zach, who was 19 years old. And he died in quite mysterious circumstances.

He went off the balcony of a luxury apartment building overlooking the Thames, and he died in the river. And after his death, his parents, whose names are Matthew and Rochelle, were trying to figure out what had happened to him. And they made this astonishing discovery, which is that, unbeknownst to them, their teenage son, Zach, had a secret life. And he had been moving around London pretending that he was the son of a Russian oligarch. And this guy, his name is Andrew, the guy I met that day, told me about that much. I was so intrigued, I knew if the family will talk to me, this is a story I want to tell. Secret Lives is a recurring theme throughout the book.

The Secret Life of London. So in the same way as Say Nothing taught me about where I'd grown up in a way that I'd never understood when I was growing up there. London falling means that I can never look at my city in the same way again, particularly because I live very close to that luxury block of apartments that you mentioned there. and every time I walk near it, I now just see it completely differently. But there's the secret life of the city, there's the secret life of Zach, but in a way so many of the people that you encounter are living these lives of self-construction in a way.

Can you talk to us a little bit about that, about the reinvention of it? So there was a theme that I was really drawn to, which is that this is a story about this kid, Zach, who as an adolescent does something that I think probably a lot of us remember doing from adolescence, right? Which is you kind of don't know exactly who you are and who you're going to be. And sometimes our sense of our identity is quite fluid at that age. I remember myself, there's different types of, you know, what kind of music do I like? What kind of movies do I like? What are my favorite books?

How do I dress, you know, all these kinds of questions? And in Zach's case, he took it to this extreme, which is that he essentially reinvented himself with this alter of the son of an oligarch. But what was intriguing to me as I pushed into the story was that Zach is in the apartment that night, the night that he dies with these two older men who turn out to be men who do not have his best interests in mind. But when you look at their lives, they also had kind of reinvented themselves. And when you push back into the family history, you get all these different people coming to London, often from other places. And it's like a, it's like a blank slate, like a tabula rasa. You kind of decide, well, who am I going to be now? And then there's an even

deeper story, which is about London itself being reinvented really over the last 25 years. I lived here in London between 2000 and 2001. And I've come back pretty much every year since. I've got loads of friends here. It's a city that's very close to my heart. But I've seen it change. And people who are here have seen it change. It's become a much more kind of moneyed, ostentatious, blingy place with the kind of glass and steel architecture and the supercars and Mayfair and all the rest of it. And so I thought that there might be an opportunity to kind of look at these stories of personal reinvention, but then also the reinvention of a place.

You know, this kind of London has the sort of stage in which all these people are assuming these new identities. It was fascinating. The trauma and the idea of re-invention being associated with a kind of intergenerational trauma. So this sense of trying to live a new kind of life was a very compelling theme for me, partly because Zach's grandfathers were both survivors of the Holocaust. They survived it as teenagers. Can you talk to us a little bit about that and the impact that you think that might have had on Zach? Yeah. So, you know, initially this was an article in The New Yorker.

And it was a long piece and a lot of people read it. And there might have been some sense of, okay, I've done it now. But even as I was finishing the article, I knew that there was so much more to this story, there were all these different dimensions. And one of them was that I had learned about, so Rochelle and Matthew were Zach's parents. And I learned about their families. And they both had fathers. They had this thing in common, which is that they both had fathers who'd survived the Holocaust when they were really young.

And they had lost virtually their whole families. And both of those grandfathers, their names were Hugo and Benny, they both arrived here in England as teenagers solo in the world and got here and had to kind of decide who, we going to be? You know, you learn English, you become English. They're both married English women. Benny went into the textile trade in Manchester, and Hugo became a rabbi and actually a very famous rabbi at the West London Synagogue here in London. And Hugo Grin. Hugo Grin, yeah, and a figure who, you know, it was a regular on the BBC and kind of a public intellectual, a really grand figure of his day. And when you look at the history,

particularly with Hugo, there are these fascinating moments. So there's a story that Hugo would tell about arriving at Auschwitz when he was just a boy. He was about 13 years old. And arriving on a train with his family, with his father and mother and his little brother.

And as they got out on the platform, he saw a guy walking towards him The guy was dressed in stripes. There's a Jew in Auschwitz, and he seemed mad. He seemed crazy. And he started walking towards Hugo, and he was muttering in Yiddish. And as he walked by, like a crazy person, he muttered, you're 18 and you have a trade. You're 18 and you have a trade.

So the family got into this line to be processed. And they were waiting, waiting, and finally they get to the front of the line. And an Nazi asked Hugo, how old are you? And he said, I'm 18. And they said, and do you have a trade? And he said, yes, I'm a carpenter and joiner. And they said, okay, we'll go and go over there. And they sent him in the direction where they sent people who were able to work.

And Hugo's little brother, who couldn't tell the lie, was sent to the other line and was killed. And I should say that, you know, I think it was important to Rochelle, because this is a story about her father and her son, to make clear that Hugo died before Zach was born. You know, I think she would sort of push back against the notion that there was any sort of trait in this family towards lying. I tell the story not to suggest that that was the case, not to suggest that Zach was sort of fated into becoming a fabulous by the story of his grandfather. More to underline the fact, well, two things really. One, that I think lying is much more prevalent than people generally acknowledge. I think these stories are very, very prevalent. And the other is that I think it's often.

the case that the lies that people are telling are these kind of situational lies where in Hugo's case, if he hadn't told that lie, there would be no Zach, there would be no Rochelle, there'd be no family, he would have been killed. And there are other lies, including in Hugo's life, where there are these little situational lies. And I think that Zach had a kind of you fake it till you make it approach to the world, which there's a history of that, you know, going back in this family. But again, it's not exclusive to this family at all. I think that this kind of behavior is, in fact, incredibly common. And actually very relatable.

I mean, I know Zach took it to an extreme. And in a way, how talented that he was able to take it to that extreme. But that concept of a teenage boy looking for his place, particularly in the modern world. and being hypnotized by wealth and the access that he sees around him is intensely relatable. I know that you're the father of teenage sons. And I also read that when you were researching and writing this book is the first and only time you've gone into therapy. So I wanted to ask how you carry these stories that are so painful.

You know, you're sitting down with these parents who've undergone the worst grief that a parent can experience. where do you put that pain? It's hard. It's a strange aspect of what I do, and I should say, but it's one that feels like a privilege to me that I quite often over the course of my career end up in these situations where I am sitting down with people and I'm asking them to recount the worst thing that's ever happened to them.

Generally speaking, part of the reason I went into therapy for the first time while working on this book, part of the reason was the first time at almost 50, is that I'm generally on a pretty even emotional keel. So there have been some stories over the years where I just found it hard to shake emotionally what I was taking in.

I wrote a big piece years ago about a death penalty lawyer who was representing the surviving bomber in the Boston Marathon bombing case. And there were, weeks and weeks of testimony from people talking about the experience of that bomb blast. And in some cases, their own children being killed and maimed. And that was, I had young kids at the time.

And it was, it was hard for me to shake that. I felt myself quite emotionally affected by the experience. But I should say, you know, as a journalist, I think it's funny, I want to be emotionally affected by the stories that I tell. I think I need to be open to that. I think that when you sit down, you need to be objective to some degree. I think of objectivity as kind of almost a process on the page, but not so objective that you're cold to what is happening. And so, you know, sometimes I'll hear stories. Sometimes people will tell me stories and I, you know, I'll start crying.

And I suppose there might be a part of me that would think, you know, you should be a grown-up, you should be dispassionate, You should be a professional. This isn't about you. It's about them. You know, you have a job to do here. But there's another part of me that feels as though the last thing I want to do is kind of seal off that part of me. Because if the story affects me, just in hearing it, hopefully it will affect the reader. Hopefully I can find a way to make that affect the reader.

And in this case, I think the challenge is that, as you put it beautifully, Zach was an exceptional kid, unusual, a fabulous. he took it to a crazy extreme. But in another respect, Zach was an adolescent and he was going through a series of changes that I think a lot of people would recognize from their own adolescence or if they have adolescent kids. There's a friend of mine, a mentor of mine,

who at one point I was talking about how my kids don't want to talk to me anymore and think I'm a loser. Do they know that you model for J-Crew? Yeah, please, please come. catalog model. What do they care? Yeah. And my friend said this beautiful thing. He said, he said, you know, what happens is that you have to think of it as an orbit. And for part of their orbit, they're on the other side of the moon. And they're kind of on the dark side of the moon. And they're going to come back around, if you're lucky. And I think that the challenge with

Zach is that he didn't, he kind of never came out the other side. And I spent two years talking to these parents who have been grieving that long. and thinking about things they could have done differently that might have meant that he was still alive. And when you're parenting your own adolescence, the thing that I struggled with, and great credit to Justina, he mentioned, my wife, because I think her feeling was,

it's also not fair to catastrophize. Like, it's not fair to the children. It's not fair to the family. That you sort of worry so much about your kids, that when they start doing knuckleheaded stuff that anybody does in adolescence, that I did, that you did, that as a parent, you're, you know, you're so kind of primed to be terrified of losing them, that you overreact. And that was the thing that I kind of had to work on, but I did.

You're fixed. I mean, I don't know if I'm fixed, but I found it extremely helpful to talk, to be able to talk with somebody. I'm not generally an inhibited person, so I'll actually tell anybody about my, you know, Great for me. My deepest yell, please, I'm here. I'm an open book. It's all very close to the surface.

But nevertheless, to talk with somebody who's kind of very good at thinking these things through was really helpful for me. I know that I have to get onto your failures. There's just so many things I want to ask you about how you write and the work that you've produced, but I'll content myself with one for now before we get onto your failures,

which is, are you scared? Because in London falling, you're dealing with the criminal underworld. in say nothing, you're dealing with the IRA and you effectively solve an unsolved murder through the course of that book. In Empire of Pain, you're dealing with the Sackler family. Those are just your books, let alone your New Yorker articles.

Do you get scared? I mean, I think I'm not cavalier about this stuff, and I think it would be irresponsible for me to be cavalier. I have a wife. I have children. there are times when I get a little nervous about meeting certain people or how certain things that I write are going to go over with people who sometimes are impulsive and violent. It's a constant conversation at home with Justina about what makes sense,

what doesn't? There are some stories while she'll say, no, I'm exercising my marital prerogative telling you that that is not a story that I want you to write, and I respect that. And there are others where I just try to be as careful as possible. The legal threats don't scare me. I will say I get a lot of those. The gangsters never threaten me in a kind of outright way. Nobody in the IRA ever threatened me.

The people who threaten me are people like the Sacklers, are wealthy people who hire lawyers to send really nasty letters. But at the end of the day, those are just nasty letters, you know. So I'm pretty careful. I mean, you told this story. I think I listened to you on a podcast talking about your first meeting with Andy Baker, who is this kind of criminal underworld figure, a very senior figure. And when you first met him, he knew your dead dog's name asked after your sons by name.

Which, as you say, it's not an open threat, but it is a mark there. There's a chilling mark. But that's the way people like that work. I mean, Andy, you know, we met. I was, I had taken great precautions when I went to meet him because he's a dangerous guy. And he had never talked to a journalist before. And I didn't really know what I was getting into. He was a long time associate of this guy, one of the main characters in the book, this gangster known as Indian Dave.

And I felt like I got real insight in that moment into Indian. in Dave because what Andy Bicker did was he shook my hand, big smile, unbroken eye contact, kind of unblinking, and he kind of came in close. You know, he's sort of all very jovial, but also very kind of in my personal space, and asked after my wife and kids by name. And he really wasn't threatening me. And I think he would probably, if he were here with us today, he would take issue with the suggestion that he would ever do anything like threaten somebody in their family.

I think it's more just he was letting me know. You know, we stayed in touch. Andy Baker's back, back in prison now, I regret to say. But we stayed in touch and he calls me from prison. He's in prison in Wales. I always know it's him because you get, you know, when somebody calls you from prison, you get a pre-recorded thing saying you are being called from a prison. This call is being recorded.

And when Andy calls me, I answer the phone and I get the long pre-recorded message, but it's in wealth. Okay. The only time when I pick up the phone to a pre-recorded message in Welsh, I know it's handy on the line. Is he just shooting the shit with you? Yeah. I mean, he called, very sweetly, he called on the day the book came out to congratulate me.

And then we've had one chat since then. And a plan is afoot to have me come and do a reading at the prison. How amazing. Which I'm very happy to do. He's having some of the young folks in the prison read my work. Which on the one hand, I find very charming. On the other hand, I sort of wonder how compulsory this feels to some of these young guys. I often find myself late at night scrolling after a long day when I suddenly spot something I need.

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With Wayfair, there's no what if. Just style you love and quality you can trust. Visit Wayfair. Way, fair, every style, every home. Okay, let's get on to your failures. Your first failure, you describe it and say that in retrospect, it turns out to have been a big moment in your life. And you had been sent to a very competitive private school by your parents.

And in one term, you didn't do particularly well. And then what happened? I was probably about 13. I was at this pretty elite school, which was expensive. and my parents were paying for it, but they were working really hard to afford to be able to do that. And I kind of blew off school. And at the end of the term, I guess my grades came back.

And my dad was really disappointed and wouldn't speak to me. He didn't talk to me for about four days. And he wrote me a letter. And the letter was all about privilege and the kind of the abuses of privilege and the idea that I had been afforded this incredible privilege that many other people would give a lot to have and that I was behaving as though it was my birthright. And it was kind of mind to squander. And he basically gave me an ultimatum and he said, you know, you'd better get your act together or you're out of that school. at the end of this term. At the time, I was really furious, and I think I was really hurt.

I'd never felt that kind of sort of emotional coldness from him, the idea of just days going by in which he couldn't address me. And it's a thing I think about a lot. I mean, I've thought about it in the context of this book because, you know, there's a lot in this book about Zach going to school and these questions of kind of competitive schools and parental sacrifice and parental love and how you parent and adolescence.

In my case, it sort of worked spectacularly in the sense that I ended up doing well. I wonder, it would be interesting to wonder what my dad would say now, I should ask him. Yes. Because I think, I mean, to me, the downside would be that it, I think there was a kind of, if I had done years and years of therapy, I think what we would have arrived at, which I already know for free, is that. Classic New Yorker writer. Yeah, there you go. Is that it sort of conditioned. And there was a kind of implicit sense that love is conditioned on success.

The good thing and the bad thing for somebody coming out of a situation like that is that I became somebody who sought and has received a lot of affirmation from the world. Like I'm in the business now of writing things and putting them out in the world. And people review my books and readers engage with my articles and books and write me lovely notes. And it's kind of all worked out so far because I get that, that, like, drip, drip, drip of positive affirmation. And that, I think, drives me to work very hard. But I think that I think it's also probably a pretty, probably not the best foundation for one's sense of self. In the sense that if I met with real failure or if I wrote a book and nobody read it or I wrote book and it was completely panned, I'd like to think that I'd have, that I, that I would still be me.

Yes. And that the kind of sense of who you are as a person isn't contingent on the sort of dopamine hit of people telling you you've done a good job on something. I'll bet if my father were with us right now, he would say, job done, mission accomplished, you know, my tough love parenting when you were 13. paid off. I don't know on the question of sort of my sense of self. I will say that in terms of sort of opening my eyes

at a pretty early age to how lucky I was and that being given a privilege is also being given a responsibility and that you should recognize that and be sensitive to how good you've got it and not squander it. I think those are all good lessons. I relate a lot to what you just said about external validation

and the fear that my internal sense of self is so shaky without it. And you have to be careful with that because at some point, I suppose the question will be, is this enough? Like, when do I stop? Yeah. Do you think you will ever reach that point? Or do you think that you will want to do more work,

more diverse work, rack up those modelling campaigns? Do another podcast, do another book. Do you think you will ever sate that interior beast? Well, okay. I mean, I guess there's two things I would say. One is that if I'm only doing this to chase validation or affirmation, it's pretty deeply buried because the truth is that I love the work. I love the work for what it is.

Like if I have an issue at home with my family, it's that I love the work so much that it doesn't feel like work and that I will just work all the time. Occasionally people will say, oh, you're a workaholic. And I always think that that sort of misunderstands me because I'm not doing this out of any sense of obligation. I'm doing it because it's like cake.

It's fun. I love it. In terms of the kind of the sort of hamster wheel of it, it's not a sense of, oh, God, I can't stop. It's that I would sort of get bored. Like, I get bored at the beach. I love the beach for a day. And my wife loves the beach for a week.

And every time it's a bit of an argument about how long are we going to do this because I will be going mad by day two. I guess the only other thing I would say is I wrote a big piece for the New Yorker about Anthony Bourdain before he died. And there were some respects in which I really identified with him and other respects in which I didn't. And I think a big part of his history in his life was that he had, you know, he had a very addictive. personality and he had a lot of demons and he was a very depressed person in ways that I didn't even fully appreciate when I knew him, but I understand better now. And one of my big questions for Tony over the year that I spent working on that piece was I kept saying, like, why are you still moving at this tempo? You don't need to be. He had this brilliant television series,

but he'd been doing it for so long that he started to go back to places that he'd already been. I think there was a sense with Tony that he was afraid of what would happen, like what he'd get up to if he stopped moving. And I think as I get older, that's something I want to be mindful of

just because I think that ultimately, you know, we're all going to get old. Hopefully. Yeah. And sort of at a certain point, you slow down. And I'd like to think that there's, you know, that you have enough of a sense of who you are and what matters outside the four corners of your job. Have your parents ever said that they're proud of you?

Oh, yeah, all the time. Oh, that's nice. Have they read your work? Oh, my parents. I have an incredibly close relationship with my parents. I realize I've just made my poor father sound cold and withholding. My mother's the cold and withholding one. The, no, they...

Your mother's a legend. Oh, she's amazing. A philosopher of psychiatry. What a cool job. She's written more books than I have. Yeah, she's great. My parents are both in their 80s. I talk to them all the time.

They read my work before. I'm basically my wife and my parents read my work before anybody else does. I feel very, very lucky to have a very close relationship with them. So they're great. I'm just chuckling because I was just in Ireland on book tour. And I met a woman. I met a woman who's a bookseller in Cork. This was in Galway, but she'd come to this event.

And I said, oh, my parents love Cork. My father's his Irish citizenship, and my parents had spent a month, you know, staying in an Airbnb in Cork last year. And I said, my parents were in Cork, and she said, oh, I know. Your father would come into our bookstore and announce that he was your father.

I was so mortified. She didn't even need, you know, as soon as she said he would come into the bookstore, I sort of, I knew, oh, God, it kills me. Anyway, so probably too proud. Yeah. No such thing. So many of your books are about families, which might be a really trite thing to say because ultimately everything is kind of about a family. Yeah. But are you aware of that linking thread?

And do you think your interest in families and do you? dysfunction and loss has changed how you show up in your own family. Oh, interesting. I mean, I'm aware of it for sure. Not in a sense of, I never go into stories. When I'm looking for stories, I don't have a list of ingredients in mind. The only thing that I go by is whether if you start telling me a story, do I feel myself leaning forward?

It's almost physiological. I think I've gotten better over the years at listening to my own gut. And if I feel really compelled when you're telling me something, that's usually a good indication that A, it'll be a fruitful thing for me to spend time on a B, I can make it compelling for readers. It's only in retrospect when I look back that I realize that I have these fixations. And one of them for sure is family. Let's move on to your second failure, which is that you knew from the age of 16 or 17 that you wanted to write for the New Yorker. but it took a long, long time for you to get there and a lot of rejection. Tell us this story.

So I started reading The New Yorker in high school. I discovered it in the kind of what we called the periodicals room of my high school library. I was really taken with it. I was taken with the articles themselves and the stories and all the rest of it, the cartoons, the whole package. But I was also sort of taken with the idea of the New Yorker writer as a cultural archetype. and decided that that was what I wanted to do. And when I got to college, I was a research assistant to Simon Shama, who at the time was the art critic for The New Yorker,

and that only intensified the sense in which I was kind of just obsessed with the magazine and the lore and all of it. And I actually started pitching the New Yorker myself in college to no avail. And pitched and pitched and pitched. I started and I have a rejection letter on my wall at home framed from 1998. Went to grad school, went to law school, was pretty convinced that it wasn't going to happen for me. The whole reason I what the law school was to have a proper job in case the writing thing didn't work out. Finally, they accepted a pitch in 2005, so it had been seven years of pitching.

piece came out in 2006 and I thought I've arrived ready for the rest of my life I was 30 I'd just turn 30 they said no no no you haven't arrived we're not going to make you a staff writer you're not good enough not yet you are good enough that we'll do one freelance piece a year and so for the next six years I wrote one big article for the New Yorker a year and I did all kinds of other stuff to make ends meet. I wrote screenplays. I had a job with a think tank. I did all kinds of other things. And it was, it was tough. It was a, it was a long process. And they finally, they only actually offered me a full-time job when somebody else offered me a full-time job. Yeah, you were offered a full-time job by the New York Times and then they finally gave you one. I want to come back to

that, but I want to ask first of all, I'm very intrigued by when someone decides, to quit. Because sometimes if you decide to quit, it's the most powerful thing you can do, and sometimes it is just giving up. So was there ever a point during this very, very long process where you thought, what am I doing? I mean, yeah, constantly, because, and for a couple of reasons, like, part of it was that it didn't make any economic sense, that I was sort of hustling and I was doing all this other stuff. There were times where I felt like I'm doing all this other. stuff to subsidize the New Yorker, in effect, because I was spending all this time writing, you know, my big project was always the article that I was working on. It just wasn't paying me

very much. And if I'm being really honest, some of it was that I felt indignation because I felt like the work was good. So the message I was getting back was you're not ready, and I really felt like I was ready. And I should say, I'm not somebody who wildly overrates his, it's not a situation where I always think that I have it figured out. And there are certain things I'm not as good at. And I know it, usually. And so it felt unfair. You say that you still have resentment about that long audition process. I do. Here I am talking about it. I love it. I love hearing this. I do. I mean, I don't, I don't, I have a, it's funny because Justina, my wife and I were very different in a lot of ways. And then in some ways we're really similar. And one of the ways in which we're really similar is that we both did. And remember the slights forever. Yeah, it does so, by the way. And it's just, and, you know, it can be a small thing. And it's not that I, most of the time the people whose slice I remember, they don't even

know it because I would never mention it, but I always remember. What I think I would have eventually gotten to with my shrink is that if you're somebody who's seeking affirmation and feels as though you just have to work a little harder to get the affirmation that eludes you. you do end up in this kind of crazy situation, which is that if there's some entity out there, be it a parent or a magazine or an editor who keeps withholding it, you will continue to just find greater reserves of energy

to work that much harder because the thing kind of keeps escaping you. There may be some paradoxical sense in which it was good for me. Do you think that you have proved yourself now? Do you think that you are getting the approval? Yeah. At the New Yorker specifically? Yeah. Okay.

Yeah. How do you feel about your New Yorker cartoon of your face? Oh, I mean, not great. I don't think it's weird. You would think that I would have a face that would sort of lend itself to caricature. Yes. But most characters are bad. In a good way.

In a good way. I feel as though most of the, anytime people, it hasn't been that many times, but like the three or four times when somebody has done a kind of artist rendering of my face, I always feel like it looks like Dugie Houser without a nose, you know. Has any part of your ambition ever been about being the editor of the New Yorker? No. Would you, if it were offered to you, would you say yes? I mean, it's not being offered is the thing. This is a question that comes up periodically because there was a period of time where David Remnick was talking. about how he was going to not be at the magazine forever.

And this parlor game started where people started to throw out names. And mine was one of the names, but there were many names. And I think that David probably won't be there forever. But I also think that he's a, he's a, just a once-in-a-generation figure. And I want him to stay. I want him to stay for longer than he'd probably, going to want to stay. It's all just, you know, it's academic, ultimately. I mean, I love doing what I'm doing and I feel very lucky to do it at David's New Yorker. What happens next? I have no

idea. I'm so delighted with the status quo. I want it to last as long as possible. Okay, fine. Kendall Roy. Okay. So when you're crafting a piece for the New Yorker, how much is it what you leave out that makes it good? What a great question. I love this question. It's everything is what you leave out. Everything. Distillation.

The whole thing. What a great question. Because I feel as though it took me a while to realize that reporting is so hard. Finding some detail, getting some little side story. some amazing quote, some statistic, that I think that there's a mistake that a lot of writers make, which is they look at the thing

and they're thinking about their own kind of sweat equity and obtaining it, and that's the basis on which they decide whether or not something should go in the article. And that turns out is lunacy because you're not thinking about the reader and what the reader actually needs and can handle.

I was just, so I was just in Galway last night trying to speak in a diplomatic way because there were a lot of Irish writers in attendance about my frustrations with the literature of the troubles and what I was trying to do differently with say nothing. And one of my frustrations is that there's so many great stories in Ireland that there is a kind of storytelling tendency in which everybody is just like cramming. It's like they give you the whole buffet. And there's not enough. selection that happens. And it's partially because all the characters are great characters. All the stories are great stories. But sometimes just saying, I'm going to give it all to you, I think is really counterproductive because it's like a cognitive load problem for readers. I think this was always true. I think it's even more true now that we all have these phones that have broken our brains. And so to me, telling a story is all about what you leave out. And in terms of my research, what you're getting is three percent of it.

Because you do hundreds, sometimes thousands of interviews. Well, never thousands on a single thing, but hundreds for sure, yeah. With London falling, you had this depth of material. How do you craft it and draft it? Like, just get really technical with me. Yeah. What's the process? So I don't, I, the vast majority in terms of time of my work is research.

I write quickly. at the end. And for me, it's really helpful to write quickly. I feel like on the good days, there's a kind of velocity as it goes onto the page. And when it's really working, I feel like the reader, I can just transmit that to the reader. And you can sort of feel that velocity. I want you turning the pages. I want you absorbed. I'm getting all these wonderful notes from people who've read the book and they say they've read it in two or three days. And I love that. That's what I want to hear. It's not that I do tons of research and then I sit down on a blank page and at the end, I crank it out very quickly.

It's what actually happens is I start outlining really early. So I'll be doing the research and pretty early on in the research I do this thing. For me, it's, I always use the back of an envelope. I'll just say, what are the big beats in this story? What are the big hinge moments? And usually it starts with just kind of seven or eight beats. And the helpful thing about doing that early is that it directs my research is that I don't waste as much time as I used to. where I'll kind of encounter some fascinating side character

and spend four days doing all this research only to then decide this is actually kind of extraneous to the story I'm telling. Do you literally do it on the back of an envelope? I do, yeah. That's what starts. What size of envelope? Just a kind of standard manila, you know,

I'll do it. I mean, the best is doing it on the back of a hotel stationer. Nobody has hotel stationer anymore, but it sort of goes back to that idea that I was, as a teenager, I was in love with the New Yorker, but I was also in love with the sort of romantic archetype of the New Yorker writer. So, you know, give me a, I'm the guy who, like, stays at the Chateau Marmont and steals all the stationary. I expect station at Marmont or the Sunset Tower.

Exactly. Final question on this failure before we rattle through your final one. But do you have a point with every manuscript where you think, I am the world's worst writer, what am I doing? This is terrible. I've lost all of my skill. Asking for a friend. Or because of the nature of the material, do you not have that? Because you're just too in it and getting through it.

I'm too in it. Yeah. I mean, it's, you know, bracket that thought because I think on the third failure, we will be able to get into that kind of, that kind of self-doubt. On this kind of writing, I don't. I mean, I don't, this may seem like a kind of cheeky or evasive answer, but I, these days I don't take on a piece of nonfiction writing unless I know I can make it. So no, I realize that maybe it's kind of an obnoxious answer, but no, on this kind of stuff, I don't have those moments. It's more I'm actually, I'm enjoying it.

And in a way, I think what you're too humble to say is that you are in service to the story. So maybe you feel it's less about you as a writer, even though you're an exceptional writer. And the way that you write is so compelling and so riveting. But maybe it's that thing that we started off talking about having a clear and moral purpose. You're doing it for other people. and other people's stories. Sort of. Like, I didn't write this book for Matthew and Michelle Brettler. You know, it was a good story. And that was what drew me to it initially. It does have some kind of, I think,

pretty profound moral bones to it, which is part of what's interesting to me. But I had to be very clear to the Brettlers from the outset that I, and I always am with people I write about, I'm not writing this for you. You know, that we will, I want you to share with me as much as possible,

but you need to know that when I sit down and write, you're not the audience I have in mind because I think if you do that, I think you're cooked as a writer if you do that. People will sometimes say that there are, you know, there are twists in my stories, right? As if this is some kind of cheap, like, genre fiction gimmick that I'm introducing.

And the truth is that there are twists in life. And when I am writing in these big reversals, part of what I'm trying to do is capture how crazy it is to be alive and to kind of encounter these types of, you know, at the end of say nothing when I identify the murderer, that was one of the most shocking moments of my whole life to make that discovery of myself. All I want to do is capture for the reader the sense of just like heart hammering, you know, hair on your arms, standing straight up shock that I've felt. Well, you do it brilliantly. Your final failure, and I don't know if you know this, but there's one other person who has chosen exactly this failure. Really?

Yes, during the course of How to Fail. Who? John Ronson. Oh, John Ronson. So this specific failure is your failure to write movies. Well, not to write them, but to get them made. Yeah, yeah. Oh, I've written plenty of them.

Yeah, yeah. This is what you were doing to sort of make a living during all of those years of New Yorker rejection. Yeah. During those years when I was a freelancer, I started getting jobs writing screenplays for, I think, my first thing. I wrote a couple of pilots for HBO. This is almost 20 years ago. And then started writing feature scripts for studios.

And at the time, you know, I was a freelancer. This was big money. And they would fly me first class and put me up at nice hotels in L.A. It was very glamorous. I got health insurance, which I didn't get through the New Yorker from the Writers Guild. None of the movies got made and none of the shows got made. It was one of those interesting things where at times I have wondered whether I'm just not good at it. I'm definitely good enough to keep getting the jobs.

But I struggle with screenwriting. I think I'm pretty good at it after all these years. I'm still doing it now. I'm writing something for HBO right now. But it's different in the sense that I don't have the same facility where when I sit down to write nonfiction, it just kind of pours out of me. It doesn't take a lot of agony. I mean, to go back to your earlier question, it's like I don't have those kind of moments of profound self-doubt. But I wonder, because you're a novelist and you mentioned having that feeling.

I think the difference for me is when I'm doing fictional screenwriting, it's the sort of paralysis. of you can do anything? Yes, the paralysis of possibility. Yes. Yes. It's that. And then the amount of other people who are involved. Oh, God.

Yes. Let's talk about that. Yes, that was the worst bit. It's the worst. So you have experience with this, right? I'll never do it again. Yeah, I've had moments where I've asked myself, why am I still doing this?

Because I don't need the money in a way that I used to. And I find it difficult. And on some level, the time I spend writing a script, that may or may not get produced, is time when I could be writing an article or a book that I know is going to be a fact in the world. I know it's going to come out. In a weird way, maybe it all goes back to my first failure.

You know, maybe on some level, the fact of this thing that's just kind of just outside my grasp is part of what keeps me going and keeps me sort of trying. But I also think there's another thing, which is that I think it's good. I'm turning 50 in a few weeks. there are things that I do that I know I do well and I love doing them.

I also like being outside my comfort zone. I sort of like the vertigo. And so I think maybe part of what's happening with the screenwriting is that it's that I think it's actually kind of healthy for me to struggle with work in a way that I don't struggle with my day job. I do think that there's something really important there

about being engaged. in the work. And as you say, challenging yourself, not just doing the things that you already know you can do. That's growth. I think it is growth. I think there's a danger in a certain kind of mastery. I think it's very often the case that somebody figures out how to do a thing and do it well. And then the world actually tells them, you know what, it would be great, is if you just keep doing that again and again forever. And I think I would find that quite boring and stifling. But also, I think that what ends up happening is that you sort of stop to grow, you stop growing as a person. And at a certain point, you're just kind of, you know, you're just sort of going through the motions.

And I don't want that. I can't imagine that happening to you. Never stop growing, never stop writing. Thank you so much for coming on how to fail. Thank you so much for the gift of your books. Thank you. And happy birthday. Thank you.

Thank you. It's a big one. Thank you so much for listening and watching. 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.

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