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
ON FINDING LOVE AT ANY AGE… With Luke Evans and Dolly Alderton [not-audio_url] [/not-audio_url]

Duration: 28:20
We’re taught that love should happen early, and if it doesn’t, something’s gone wrong. But what if that’s not true? In this episode, we hear from past How to Fail guests who found love later, or in their own time. Luke E…
Shabaz Ali - ‘I’ll be a diversity quota as long as I get paid’ [not-audio_url] [/not-audio_url]

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ON FINDING HOPE IN ADVERSITY… With Sir Chris Hoy and Michael Rosen [not-audio_url] [/not-audio_url]

Duration: 19:44
This week we’re revisiting two deeply moving conversations that explore what it means to find hope in the face of profound adversity. First, we hear from the 11-time world champion and a six-time Olympic champion, Sir Ch…
ON THE IMPACT OF EARLY FAME… With Shania Twain and Charlotte Church [not-audio_url] [/not-audio_url]

Duration: 32:09
Fame isn’t always limousines, five star hotels, champagne and private jets. I find this topic totally fascinating and these two past How to Fail guests give us a glimpse behind the curtain as to what becoming famous at a…
Martin Freeman - ‘We should be saying no to our kids’ [not-audio_url] [/not-audio_url]

Duration: 53:44
Martin Freeman is one of the most sought-after actors of his generation. Whether it’s Tim in The Office, John - the mild-mannered porn actor in Love Actually, Watson in Sherlock, Bilbo in The Hobbit, the stressed parent…
ON PANIC ATTACKS… With Jamie Laing and Fearne Cotton [not-audio_url] [/not-audio_url]

Duration: 16:51
Panic attacks are wide-spread in today’s society, and yet remain something we rarely talk about openly. So it’s vital that we normalise an experience so many of us share - because talking about it is often the first step…
Marisa Abela - ‘You never expect to be told you have cancer at 23’ [not-audio_url] [/not-audio_url]

Duration: 53:23
You’ll know Marisa Abela from HBO’s critically acclaimed hit Industry, where her portrayal of Yasmin - a brilliant, volatile young woman with ambition to burn, earned her a BAFTA. She also starred as Amy Winehouse in Sam…
ON MEDITATION… With Kirsty Young and Yuval Noah Harari [not-audio_url] [/not-audio_url]

Duration: 15:12
It’s claimed that meditation can fix everything. If you speak to anyone on the topic, they claim it will reduce your anxiety, make you slimmer, result in you earning more and mean your relationships are all perfect. It m…
Margaret Cho - They Told Me I Was Too Fat To Play Myself [not-audio_url] [/not-audio_url]

Duration: 54:57
This episode contains description of addiction, eating disorders and discussion of suicide. Our guest today is the pioneering comedian, actor and activist Margaret Cho. She began performing comedy as a teenager, opening…