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
How To Date: BONUS EPISODE - Your dating questions answered… [not-audio_url] [/not-audio_url]

Duration: 39:49
For this bonus episode, Elizabeth and Mel open up the post bag to answer the burning questions YOU have when it comes to dating… And, let’s just say, we cover A LOT of ground. After you’ve listened, you can get all the r…
How To Date: The most important relationship you’ll ever have [not-audio_url] [/not-audio_url]

Duration: 57:48
For the final episode of How To Date (sob!) Mel and Elizabeth look at the most important relationships any of us can have in our lives: the one with ourselves. We unpack what this means in practical terms. How do we nurt…
How To Date: How to cope with heartbreak and rejection [not-audio_url] [/not-audio_url]

Duration: 44:43
Elizabeth and Mel face one of the most challenging parts of dating: heartbreak and rejection. We are joined by life coach and author Michelle Elman who went through a devastating, public break-up after being notified via…
Erin Doherty - ‘Lean Into Your Truth’ [not-audio_url] [/not-audio_url]

Duration: 45:41
To hear more of Erin offering advice on listener failures, join our community of subscribers here: https://howtofail.supportingcast.fm/#content Erin Doherty’s big break came playing Princess Anne in The Crown. She’s now…
How To Date: Taking it to the next level [not-audio_url] [/not-audio_url]

Duration: 49:15
Things are going well… So Elizabeth and Mel are taking it to the next level where they are getting just that little bit more serious. In this episode, Mel and Elizabeth look at exclusivity and commitment and what it take…
How To Date: Red and Green Flags [not-audio_url] [/not-audio_url]

Duration: 57:04
Mel and Elizabeth look at the subtle (and not-so-subtle) signs that can help us understand whether a potential partner is right for us. That’s right, we’re exploring the red flags that should have us running for the hill…

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