Podcast Summary

How To Fail With Elizabeth Day

Episode: On Navigating Your 20s… With Phoebe Waller-Bridge and Lily Allen
Date: October 5, 2025
Host: Elizabeth Day
Guests: Phoebe Waller-Bridge, Lily Allen

Episode Overview

In this special episode, Elizabeth Day revisits favorite conversations with Phoebe Waller-Bridge and Lily Allen, focusing on their tumultuous, formative 20s. Both women reflect with brutal honesty and wit on mistakes, heartbreak, the pressures of gender expectations, and difficult moments in their careers. Their shared stories celebrate "failure" as a path to growth, creativity, and ultimately, wisdom. The episode is both entertaining and deeply human—a source of comfort and insight for anyone navigating their own messy decade.

Key Topics & Insights

1. Failing at Relationships & Growth Through Messiness ([03:34]–[06:20])

• Phoebe Waller-Bridge laughs at her “glorious” failures in romance, describing painful breakups, awkward one-night stands, and how these foster personal creativity:

  • “I think fighting so hard to be so in love with someone with all that passion in your 20s… then it not working, or like there being so much pain… that is the stuff that so much creativity comes out of.” — Phoebe Waller-Bridge ([03:41])
  • Recalls a hilarious mishap singing “At Last” after a failed date: “He was like, ashen-faced and shaking. And I was like… Oh God, no. God, no, no. That was pretty dire.” — Phoebe Waller-Bridge ([05:03])

• Would she relive her 20s?

  • “You couldn’t pay me to be 20 again… I’d really like to have the skin from my 20s, but I prefer my heart and my guts now.” — Phoebe Waller-Bridge ([05:59])

2. Self-Image, Society, and Female Rebellion ([06:27]–[08:43])

• Phoebe humorously discusses aging, beauty standards and how media pressures women to self-loathe:
  • “There’s a message from society and billboards… teaching us to sort of hate ourselves. And I’ve always felt like that was a kind of way of controlling us. The moment I realized that, I was like, oh, you’re just trying to control me. Then that flicked my rebellious switch more. Now I just feel way more fierce than I ever did in my 20s.” — Phoebe Waller-Bridge ([06:42])
• On patriarchy and media narratives:
  • “I can’t imagine that women en masse… would want to peddle the same message…I have faith that we will [break the habit], as more women climb higher up that pole, dance, swing higher up that pole… we reclaim the pole.” — Phoebe Waller-Bridge ([07:28])

3. Fleabag & Connection Through Authenticity ([08:08]–[10:12])

• Phoebe reflects on the impact of Fleabag:
  • “It’s not about advice or wisdom. It’s about people feeling seen and people feeling heard…what has spoken to women, in particular, is the front that we have…and underneath, we have no idea what’s going on…we have dark, perverted thoughts and we sanitize them, even for ourselves.” — Phoebe Waller-Bridge ([08:43])
  • “If this fails, then it essentially means that we’re alone…so the fact that it caught on and people could relate to it made us all feel less lonely. And me too.” ([09:49])

4. Lily Allen: Career, Postnatal Depression & Public Perception ([10:12]–[12:15])

• Sheeza’s Album & Feeling Like a Failure:

  • Lily describes public and personal perceptions of her third album, Sheeza’s:
    • “The tabloids were writing about me as if I was a massive failure at the time…when everybody’s saying, ‘Haha, you used to be this successful and now you’re half as successful, so you’re a failure.’” — Lily Allen ([10:31])
    • “It’s the first time I’d approached a record as a means to an end…what came out 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.” — Lily Allen ([11:03])
  • Describes the effects of postnatal depression, loss of faith, pressure to get in shape, and resulting struggles with alcohol and drugs.

• On Fast-Tracking Life:

  • “I have lived life to the extremes from a very young age…and I think I maybe sort of had my midlife crisis in my late 20s.” — Lily Allen ([11:54])

5. Touring, Motherhood, and Feminine Expectations ([12:27]–[15:38])

• Lily discusses the challenges of being on tour away from home and kids, and how touring exacerbated personal crises:

  • “I’m a real home person…to be taken out of that and be on a tour bus in the middle of nowhere without that sounding board…yeah, I just became very lost.” ([12:47])
  • Touring throws up existential questions: “All I need is a backpack and a phone…don’t need the house. I certainly don’t need all the stuff that’s in it…it’s all just…yeah.” ([13:43])
  • On industry pressures after streaming devalued recorded music: “Streaming has completely devalued the product. The one way to make money is to tour…the other way is branding—which is easier if you subscribe to the gym bunny makeup game.” — Lily Allen ([14:23])

• Hard lessons learned:

  • “You’re a mum and an artist and you’ve got to be really strict with the people around you…because if you don’t make that clear, nobody else is going to take that into account.” ([15:18])

6. Balancing Art, Kids, and Vulnerability ([15:38]–[17:19])

• On her fourth album ‘No Shame’ and writing the song “Three” for her daughter:
  • “I struggled, when I came back from tour, to connect…I knew that I wanted to have a song 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. They keep saying, like, when are you going to write another one?” — Lily Allen ([16:37], [17:21])

Notable Quotes

• “A sticky one night stand is the best expression ever… The next day’s stickiness, as you get back into the knickers.” — Elizabeth Day ([04:20])
• “The gloom of self-loathing that was supposed to grow around us as we get older and start fearing that our value is diminishing has been the opposite experience for me.” — Phoebe Waller-Bridge ([06:42])
• “Touring throws up all these weird sort of existential questions anyway…all I need is a backpack and a phone.” — Lily Allen ([13:43])
• “If you don’t make it clear [that both jobs—mum and artist—have to be done and done well], nobody else is going to take that into account.” — Lily Allen ([15:18])

Notable Moments & Timestamps

• [03:34] Phoebe Waller-Bridge on glorious failures in relationships
• [05:03] Phoebe’s dire post-hookup “At Last” misunderstanding
• [06:42] Realizing beauty standards are a tool of control
• [08:43] On Fleabag and the power of being seen
• [10:31] Lily Allen on being labeled a failure by press during Sheeza’s
• [11:03] Postnatal depression and feeling lost in her career
• [13:43] Lily’s existential reflections during touring
• [15:18] Assertiveness in balancing motherhood and artistry
• [16:37] Lily on writing vulnerably about motherhood in her music

Episode Tone

Warm, witty, candid, self-deprecating, and empowering. Both guests blend laugh-out-loud stories with moments of heartfelt sincerity and hope.

Takeaway

This episode offers invaluable reflections on navigating uncertainty, societal pressures, and self-doubt in your 20s. Both Phoebe Waller-Bridge and Lily Allen embrace their failures, revealing how vulnerability, humor, and honesty can lead not only to great artistry but to deeper self-acceptance. Elizabeth Day’s compassionate hosting brings out the best in both guests, making this a must-listen—or read—for anyone seeking comfort or solidarity in the chaos of figuring things out.