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

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

Author: Elizabeth Day and Sony Music Entertainment October 6, 2025 Duration: 17:15
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 podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

There's a quiet revolution happening in how we think about success, and How To Fail With Elizabeth Day is right at the heart of it. This isn't about schadenfreude or wallowing in misfortune. Instead, Elizabeth Day has created a space where the most interesting conversations begin with a simple, radical premise: our lowest moments are often our greatest teachers. Each episode, a guest-from celebrated artists and thinkers to everyday people with extraordinary stories-sits down to examine three significant failures from their own life. The magic lies in the excavation, as Elizabeth guides the discussion toward the unexpected wisdom and resilience that emerged from those setbacks. You'll hear the raw honesty in their voices, the laughter that comes with hindsight, and the profound clarity that failure can uniquely provide. This podcast, presented by Elizabeth Day and Sony Music Entertainment, digs into the messy, human stuff of life that connects us all, transforming shared vulnerability into a source of collective strength. It’s a reminder that the path to any meaningful achievement is rarely a straight line, but a series of instructive detours. The show actively invites listeners to reflect on their own stories, fostering a genuine community around the idea that we can all succeed better by understanding where we've previously stumbled. Tune in for conversations that are as comforting as they are challenging, and which might just change your perspective on what it means to live a well-lived life.
Author: Language: English Episodes: 100

How To Fail With Elizabeth Day
Podcast Episodes
Rita Wilson - ‘I’m 69. I’m At My Most Unfiltered.’ [not-audio_url] [/not-audio_url]

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The acclaimed actor, singer and producer was born in Los Angeles to a Greek mother and a Bulgarian father who emigrated to the United States in 1949. You might know her from early roles like Bosom Buddies, where she met…
Emma Grede - ‘Ambition Is Something I Am Entitled to’ [not-audio_url] [/not-audio_url]

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Today’s guest is a female billionaire: the co-founder and CEO of the Good American inclusive fashion brand and a founding partner of SKIMS, the shapewear and loungewear company. Emma Grede’s close working partnerships wi…
Sophie Habboo - I Wish I Had More Boundaries [not-audio_url] [/not-audio_url]

Duration: 47:18
This week we are joined by podcasting royalty, Sophie Habboo! Habboo found fame on Made In Chelsea, E4’s structured-reality show following the lives of affluent 20-something Londoners where she met fellow cast-mate Jamie…
Elizabeth's New Show: History’s Greatest Fails [not-audio_url] [/not-audio_url]

Duration: 33:51
In this debut preview episode of History’s Greatest Fails, Elizabeth Day and Dan Jones argue that the story of Richard’s rise and fall (and rise again) is much more modern that you’d first believe. Not least because of t…
Amy Jackson Westwick - I Was A Magnet For Narcissists [not-audio_url] [/not-audio_url]

Duration: 55:17
Amy Jackson Westwick is a major Bollywood film star with some 14 million followers on social media. Yet she grew up in a working class family in Liverpool. So how did a teenager from Merseyside become one of the most rec…
Chris Appleton - ‘I Felt Shame Before I Felt Love’ [not-audio_url] [/not-audio_url]

Duration: 45:10
Celebrity hair stylist Chris Appleton has a slew of devoted clients including Kim Kardashian, Kris Jenner and Martha Stewart, as well as millions of Instagram followers and a regular slot offering advice on The Drew Barr…
Mel Schilling - ‘She was the embodiment of vibrant life’ [not-audio_url] [/not-audio_url]

Duration: 1:19:57
I never thought I would have to write these words, but here we are. In the wake of my dear friend’s passing, I wanted to reflect on the life of one of the most radiant people I’ve ever met: Mel Schilling. I never quite u…