How To Fail With Elizabeth Day - On Navigating Your 20s... With Phoebe Waller Bridge and Lily Allen

Episode Date: October 5, 2025

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 [e-mail] Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

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This episode is all about your 20. 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're just bringing you entertainment, that's fine too. First up, Phoebe Waller Bridge. 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 20s 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 Claritie.

and courage, and I promise you'll be glad you listened. Let's get into it. Do you think you failed at relationships in your 20s? 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, and 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 20s and teens and then throwing everything at it and then it not working or like there being so much pain or 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 a sticky one night stand is the best expression ever The next day is stickiness as you get back into the knickers. Can you think of the worst date you've ever been on or the worst one night stand? Let me flick through my diary. Your rolodex or extensive roller decks. I wish I had a date diary. And that actually would be proved very useful now.

The worst date I ever had. There's just the ones where you just don't click at all and you feel yourself just sort of falling slowly into a little. a chasm of boring the other person to tears. I don't know. There was one when I, 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 is at last. I'm always singing like it. 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. And like, my love has come along. And when we caught to the bottom stairs, he was like ashen faced and like shaking. And I was like, what? And he was like, I didn't realize this had meant so much to you. I was like, oh God, no, God, no. No, that was pretty dire that led on to a very, an awkward breakfast.

I mean, they all sort of feel gloriously. I'll see if I can think of another one as we go along. Are you glad that you don't have to live your 20s again? 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 20 again. And then I think Lena Jones character says,

well, they don't pay me anything at all to be in my 20s. I love that line so much. Yeah, I feel like I did it. I committed to it. I'd really like to have the skin from my 20s, but I prefer my heart and my guts now. 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. Do you remember when we got quite busy up one night and I was going, I used to have a porcelain forehead. Alabaster. Alabaster. But then even that kind of stuff, like women can be so haunted by or hunted by as they get older, because we're taught to be hunted 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 we're supposed to grow around us as we get older. start fearing that our value is diminishing has been the opposite experience for me actually 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 realized that I was like oh 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 20s. When you say it's a question of control, do you think it's control that stems from men having been in charge? Yeah, yeah, absolutely. I mean, I can't imagine that women on mass 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 that 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 do you feel dance swing higher up that pole as we do

we reclaim the pole do you feel because Fleebank has been so totemic for so many women particularly young women in their 20s didn't say pole

she said totem so much classier way I've been swinging my body around that totem as much as I possibly can. 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 20-somethings feeling a bit lost, coming to you for advice or wisdom. And I wonder if you feel the pressure of that. 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 to say, oh, that's like me. Because to be honest, when I was writing it and with, you know, my theatre company, dry-write and with five of us women creating that show, the producer and the stage manager and is my sister, the composer, and Vicky to 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 me too. This brings us on to talk about Sheezers, which. which was your third album. 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? 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,

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 atal depression, and it's the first time that I had 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. 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 a long period 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 don't talk about that. 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 up 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. And then alcohol became an issue and drugs and sex. 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 20s. And I think I maybe sort of like had my midlife crisis in my late 20s, you know. life as a female pop star is actually quite short anyway so it kind of makes sense that they don't tend to last throughout their 30s so I guess if you applied that career to any other normal person then yeah your late 20s sits about right in terms of midlife crisis 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? 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.

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 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 book it 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 going to need for that, you know, a 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 going to pay off your mortgage in a house that you can't live in unless you're not living in it.

If that makes any sense. 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 22 and a half hours a day until you get on stage for an hour and a half then it's all over. 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. Yeah. And also because I guess 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 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 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. But it wasn't like that with Jesus. It was an experiment and it was a really fucking hard one, you know. I learned a lot from it, which was your 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 it. account. They just want to get you around whichever country you're touring in the cheapest way

possible, the most profitable way. There's a great song on your fourth album, No Shame, which I absolutely laugh. 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 lots of people. And then did the embarrassing fangirl thing of tweeting about it. And then Lily Allen liked my tweet. Yay. Yay. But part of the reason I love it. I love it. But part of the reason I love that album so much, it's 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, there's one song there, 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, mum, but you weren't around to see it. And it's such a beautiful song. Is that where it all came from, from this experience? There's a book, actually. I might be at here somewhere called How to Listen So Kids Will Talk and Talk So Kids Will Listen. Much so I wanted to have kids, I've not really been around many children.

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. I was relatively young when I started trucking them out. I guess because I had personal 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. They love it. Oh, do they? That's nice.

But they keep saying, like, when are you going to write another one? 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.