ON NAVIGATING YOUR 20s... With Phoebe Waller-Bridge and Lily Allen

Welcome back to this How to Fail special where we journey through the archive to uncover insight and revisit powerful conversations. Each week, I hand-pick moments that speak to our shared challenges - hopefully offering comfort, clarity, and a renewed sense of perspective for whatever life might be throwing your way. Your 20s are notoriously a time of instability, during which you attempt to find yourself and figure out who you are. Which is why I wanted to bring you this episode! We hear from Phoebe Waller-Bridge who speaks about her rollercoaster 20s and the wisdom that hindsight has afforded her. Then the singer and actor Lily Allen shares her experiences of that decade which she lived out in the unforgiving glare of the public eye. Whether you're navigating this chapter yourself or walking alongside someone who is, I hope this episode offers a sense of solidarity, understanding and light in the darker moments. Listen to Phoebe Waller Bridge’s full episode of How to Fail here: https://link.chtbl.com/Vmnz_IXz Listen to Lily Allen full episode of How to Fail here: https://link.chtbl.com/7f_TpEQ6 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Elizabeth Day?

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• 0:45Elizabeth Day?

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• 0:57Elizabeth Day?

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• 1:42Elizabeth Day?

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• 2:09Elizabeth Day?

  Welcome to How To Fail with me, Elizabeth Day. Today, I'm diving back into the archive to bring you a curated selection of some of my favourite conversations, moments that are honest, hilarious, and most importantly, deeply human. This episode is all about your twenties, that rollercoaster decade of discovery, chaos, heartbreak, joy, and figuring out who you are, or at the very least, who you're not. Whether you're in the thick of it, about to enter it, or reflecting with it in your past, I hope these stories bring you either a little comfort or insight. Maybe they just bring you entertainment, that's fine too. First up, Phoebe Waller-Bridge.

• 2:52Elizabeth Day?

  She speaks candidly and hilariously about one-night-stands, disastrous dates, and why you couldn't pay her to relive that chapter of her life. It's messy, honest, and full of the kind of wisdom that only Fleabag can offer. Then, we hear from Lily Allen, whose twenties were far from ordinary. From releasing sheezers to battling postnatal depression, navigating a breakdown while on tour, and facing the collapse of her marriage, it's raw, real, and utterly compelling. Lily shares it with clarity and courage, and I promise, you'll be glad you listened. Let's get into it.

• 3:35Elizabeth Day?

  Do you think you failed at relationships in your twenties?

• 3:38Speaker 01

  Oh, yeah, yes, gloriously. I mean, I think even when you first said to me, "This is a podcast about failure", I could feel, because you're such a positive person, I could already feel the glory of what you meant there, like, what's the glory in failure? And I think fighting so hard to be so in love with someone with all that passion in your twenties and teens, and then throwing everything at it, and then it not working, or like, there being so much pain, and that is the stuff that so much creativity comes out of. So, out of those painful breakups or miscommunications, or just horrible, sticky one-night-stands, or whatever it is, something, you grow in those moments, and so I value them all.

• 4:20Elizabeth Day?

  A sticky one-night-stand is the best expression ever.

• 4:26Elizabeth Day?

  The next day's stickiness as you get back into the knickers.

• 4:31Elizabeth Day?

  Can you think of the worst date you've ever been on or the worst one night stand?

• 4:35Speaker 01

  Let me flick through my diary.

• 4:37Elizabeth Day?

  Your rolodex, your extensive rolodex.

• 4:39Speaker 01

  I wish I had a date diary and that actually would be proved very useful now. The worst date I ever had.

• 4:46Speaker 01

  There's just the ones where you just don't click at all and you feel yourself just sort of falling slowly into a chasm of boring the other person to tears. I don't know, I'm trying. There was one when I, um, there was a guy I'd, we had a couple of dates and then he'd stayed over and the next morning. It was quite clear to me that like this wasn't going to go anywhere and I think for him as well. But a song that I really love is Etta James's At Last. I'm always singing it like, it's just the earworm that I always have. And I remember I was walking, I was living in a flat that was really on like a fifth floor or something. I was walking down the stairs and I was walking in front of him as we were going to go for breakfast or whatever. And I was singing At Last all the way down the stairs.

• 5:31Speaker 01

  And like, my love has come along. And when we got to the bottom of stairs, he was like ash and faced and like shaking. And I was like, what? And he was like, um, I didn't realise this had meant so much to you. I was like, oh God, no, God, no, no. Um, that was, that was pretty dire. That led on to a very, uh, an awkward breakfast. I mean, they all sort of feel gloriously muddy. See if I can think of another one as we go along.

• 5:55Elizabeth Day?

  Are you glad that you don't have to live your twenties again?

• 5:59Speaker 01

  Yes, like there's a brilliant line in Girls when she goes, you couldn't pay me to be, one of the characters in the first series says, you couldn't pay me to be twenty again. And then I think Lena Dunham's character says, well, they didn't pay me anything at all to be in my twenties. I love that line so much. Yeah, I feel like I did it. I committed to it. I'd really liked to have the skin from my twenties, but I prefer my heart and my guts now.

• 6:21Elizabeth Day?

  I mean, your skin's amazing. That sounds like such a creepy thing for me to say right now. But you're bathed in the evening sunlight of East London.

• 6:28Speaker 01

  Do you remember when we got quite pissed off one night and I was going, I used to have a porcelain forehead.

• 6:33Elizabeth Day?

  Alabaster.

• 6:34Speaker 01

  Alabaster. Alabaster, but then even that kind of stuff, like women can be so haunted by or hunted by as they get older. Cause we're taught to be haunted by it as we get older. There's so much humour in that and there's so much life in that kind of stuff. And it's the gloom of self-loathing that was supposed to grow around us as we get older and start fearing that our value is diminishing. It has been the opposite experience for me, actually. You know, as, as all that kind of stuff comes and you realise, actually, no, this is just, there's a, there's a, I feel like there's a message from society and billboards and all that kind of stuff that is teaching us to sort of hate ourselves. And I've always felt like that was a kind of way of controlling us. And the moment I realised that, I was like, oh,

• 7:15Speaker 01

  you're just trying to control me. And then that flicked my rebellious switch even more. And now I just feel way more fierce than I ever did in my twenties.

• 7:23Elizabeth Day?

  When you say it's a question of control, do you think it's control that stems from men having been in charge?

• 7:29Speaker 01

  Yeah, yeah, absolutely. I mean, I can't imagine that women en masse, operating at that level, would want to peddle the same message. So I think so, but I think it's something we've become so used to. I think that's the problem. I don't think that it's every man in the world saying that this is an impossible standard that women should live up to. I think actually, I mean, it's probably like sinks in somewhere because it's something that we're so conscious of all the time as women. And probably on some level men are as well. But I feel like it's just a habit that we need to break. And I have faith that we will as more women climb higher up that pole.

• 8:03Elizabeth Day?

  Do you feel?

• 8:04Speaker 01

  Dance, swing higher up that pole as we do.

• 8:06Elizabeth Day?

  We reclaim the pole. Um, do you, do you feel, because Fleabank has been so totemic for so many women, particularly young women in their twenties.

• 8:16Speaker 01

  Didn't say pole, she said totem. So much classier way. I've been, I've been swinging my body around that totem as much as I possibly can.

• 8:24Elizabeth Day?

  We've heard they're both phallic symbols and we should rethink the whole phallocentricity of this conversation, but it's patriarchy. What can we do? We're operating within the system. But it is totemic and I imagine you get lots of twenty-somethings feeling a bit lost, coming to you for advice or wisdom. And I, I wonder if you feel the pressure of that?

• 8:44Speaker 01

  I don't feel the pressure of it because I feel like it's not about advice or wisdom. It's about people feeling seen and people feeling heard. And it's more people coming up and going, I am Fleabag or I understand that. And it's men as well. But I feel like it's the duality of that character that has spoken to women in particular, which is the front that we have, which is we're totally in control and we have our nice haircuts and our red lipstick. And underneath, like, we have no idea what's going on. We contradict ourselves relentlessly. We have dark, perverted thoughts and then we sanitise them even for ourselves. And we have impulses that are very similar to the narrative of male impulses and yet they're not spoken about so much. I felt it was cathartic for me to have so many people say, oh, that's like me. Because to be honest,

• 9:30Speaker 01

  when I was writing it and with, you know, my theatre company, Dry Right, and with five of us women creating that show, through the producer and the stage manager and Izzy, my sister, the composer, and Vicky, the director, it felt so relevant to all of us and so funny for all of us. Like every time that I'd be like playing around with something, if they laughed, I was like, okay, I'm not alone. And it was a conversation that we had just before it went up to Edinburgh. And I was like, if this fails, keeping on point, if this fails, then it essentially means that we're alone. Because it feels so right for us. And so the fact that it caught on and people could relate to it made us all feel less lonely and, and me too.

• 10:12Elizabeth Day?

  This brings us on to talk about Sheezers, which was your third album.

• 10:17Speaker 02

  Yep.

• 10:18Elizabeth Day?

  And I hesitate to talk about it in the context of failure because, not that it wasn't a great album, but I think how you perceived of it, definitely in the book, was something of a failure because you didn't feel you were being true to yourself. Is that right?

• 10:32Speaker 02

  Well, I think there's a bit of that, but then also I think that the tabloids were writing about me as if I was a massive failure at the time. So it's only so much telling yourself that you're doing okay when everybody's saying, "Ha ha, you used to be this successful and now you're half as successful, so you're a failure." I do think, when I was writing that record, I probably was suffering with, well, I was suffering with personal depression. And it's the first time that I'd approached a record in terms of it being a job and a means to an end. That hadn't happened before. And what came out in terms of the material was, I think it was decent, but it just wasn't great. And everything I'd done before was great.

• 11:15Speaker 02

  So, yeah, I don't know. I just lost faith in it halfway through. And I think there were a lot of contributing factors to that. I think, you know, I was struggling with being away from my kids for long periods of time when I'd spent a good three years just focusing on them and having them, you know? And then suddenly it was like you're yanked away and all, "Don't talk about that." People, because you're a pop star, people don't really want to hear about babies and vaginas and things like that. So, yeah, let's keep that to a minimum. And you should be back in shape as well, you know, which was hard. Basically meant sort of starving myself, so I was a bit mad from not eating. Then alcohol became an issue and drugs and sex.

• 11:56Speaker 02

  Yeah, I just, I think I have lived life to the extremes from a very young age and I achieved a lot in my early twenties. And I think I maybe sort of had my midlife crisis in my late twenties, you know? Life as a female pop star is actually quite short anyway, so it kind of makes sense that.

• 12:16Elizabeth Day?

  Yeah, it does.

• 12:17Speaker 02

  They don't tend to last throughout their thirties, so I guess if you applied that career to any other normal person, then yeah, your late twenties sits about right in terms of midlife crisis.

• 12:28Elizabeth Day?

  During this time, your marriage was breaking down, and I wonder if, as someone who historically identifies as a codependent. You were trying to end it in ways that you didn't have to confront it, so you were going out and having sex with people. Do you think that's what was going on?

• 12:48Speaker 02

  I'm not sure. I mean, I've just come back from tour in America, which is where I was when things went wrong with me and Sam. And the same thing happened in my current relationship, you know, I mean, I didn't take loads of drugs and have lots of sex with other people, but I think that people deal with touring and stuff differently, and I'm a real home person, you know, I love my home comforts and I, you know, love my children and I love routine, and so to be taken out of that and be on a tour bus in the middle of nowhere without that sounding board and that person to talk to every day, yeah, I just became very lost. Touring throws up all these weird sort of existential questions anyway, you know, like when you're getting ready to go on tour, it's all about packing, making sure you've got everything that you're possibly gonna need

• 13:32Speaker 02

  for that, you know, long period of time away, and then two or three weeks into it, you're like, well, what am I doing here? I'm here because this is my job and this is how you're gonna pay off your mortgage in a house that you can't live in unless you're not living in it.

• 13:51Speaker 02

  If that makes any sense.

• 13:52Elizabeth Day?

  Yeah.

• 13:53Speaker 02

  But a couple of weeks later, you're like, well, actually, all I need is a backpack and a phone, like, I don't need all the other stuff, don't need the house, I certainly don't need all the stuff that's in it, like, it's all just, yeah. Because you're basically sitting on a bus for twenty-two and a half hours a day until you get on stage for an hour and a half.

• 14:10Elizabeth Day?

  I've never even thought about it in those terms, like how, yeah, how messed up that is. If I think just from my own perspective of how exhausting travel is, just a flight, a long haul flight is. And then to layer on top of that, all of this other stuff.

• 14:24Speaker 02

  Yeah. And also because I guess like since streaming and stuff and since making an album and putting it out there is not enough now. You can't live off of that. Streaming has completely devalued the product. So the one way in which to make money is to tour and the other way is branding. And the branding thing is a lot easier if you subscribe to the Jim Bunny makeup game. And the touring thing is not well suited to being a mother of two small children. It just isn't. When you're planning a tour and you're rooting a tour, and certainly on the she's this thing. I mean, it was better this time around because I had experienced it the wrong way. But this time around, we built the tour around the kids' half term so that they could come out to see me in New York. And it wouldn't be six weeks away. It was only going to be two and a half weeks and then on each side.

• 15:08Speaker 02

  But it wasn't like that with she's this. It was an experiment and it was a really fucking hard one, you know? I learned a lot from it, which was you're a mum and you're an artist. And you've got to be really strict with the people around you in terms of making it clear that both jobs have to be done and be done well. Because if you don't make that clear, nobody else is going to take that into account. They just want to get you around whichever country you're touring in the cheapest way possible, the most profitable way.

• 15:39Elizabeth Day?

  There's a great song on your fourth album, No Shame, which I absolutely love. And we were chatting before we started this podcast about whether I'd listened to the album before I read the book. And I had, just for my own pleasure and recommended it to lots of people. And then did the embarrassing fangirl thing of tweeting about it. And then Lily Allen liked my tweet.

• 15:58Speaker 02

  Yay.

• 16:00Elizabeth Day?

  But part of the reason I love that album so much is not only the quality of the sound, there's just something about the way you sound and the samples you use that I love. But the lyrics are amazing. And there's one song, you know, there's one song there, um, I've listened to it so much, Lily, honestly. Three, which is all about your then three-year-old daughter. About how you haven't had a chance to get to know her friends properly, how her social life is more full than yours, and how today she made a papier-mache fish mom, but you weren't around to see it. And I, it's such a beautiful song. Is that where it all came from, from this experience?

• 16:37Speaker 02

  Um, there's a book, actually, it might be here somewhere, called like How to Listen So Kids Will Talk and Talk So Kids Will Listen. Much as I wanted to have kids, I've not really been around many children. I don't have, well, I do have cousins, but they live in Wales and I wasn't around when they were little. And my peers hadn't started having kids yet, you know, I was relatively young when I started chucking them out. I guess because I had postnatal depression and I was spending long periods of time away from them. I struggled with when I came back from tour to connect. Yeah, I just ended up in the studio writing one day and I knew that I wanted to have a song on the album about my kids, but I didn't know that it was going to come out like that from their perspective. But I love that song. And they love it.

• 17:20Elizabeth Day?

  Oh, do they? That's nice.

• 17:22Speaker 02

  They keep saying like, when are you going to write another one?

• 17:27Elizabeth Day?

  Please do follow How to Fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.