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

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October 5, 2025 • 17 mins

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

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.css-15opob5{left:0;position:absolute;top:0.8rem;} All Episodes

.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}ON NAVIGATING YOUR 20s... With Phoebe Waller-Bridge and Lily Allen