ON MONEY WORRIES… With Fern Brady and Simon Cowell

ON MONEY WORRIES… With Fern Brady and Simon Cowell

Author: Elizabeth Day and Sony Music Entertainment January 5, 2026 Duration: 14:48
Money worries are far more common than we like to admit: from keeping you awake at night to quietly shaping your choices and decisions, financial anxiety affects us all - especially after a season of festive indulgence. In this episode, comedian Fern Brady (recorded live in Edinburgh) speaks about not having enough money to stay at university - and the unconventional ways she earned a living to keep going. Media mogul Simon Cowell reflects on going bankrupt in his late twenties and how he *still* worries about money even now because of the fear that he’ll have to start again from scratch. Together, these conversations explore financial failure, resilience and the belief that setbacks don’t have to define what comes next. We hope they offer reassurance to anyone feeling overwhelmed by money issues right now. Listen to Fern Brady’s full episode of How to Fail here: http://swap.fm/l/cmeompBv7EHK20enmwbS Listen to Simon Cowell’s full episode of How to Fail here: http://swap.fm/l/hSwuCNEuZNgnaG20v0yB 🔗 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 Join Elizabeth Day for a special How to Fail live show at Crossed Wires Festival in Sheffield! Tickets on sale now: https://crossedwires.live/podcast/how-to-fail 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

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
Charlotte Church - ‘I was totally exploited. I was a commodity’ [not-audio_url] [/not-audio_url]

Duration: 45:48
Charlotte Church is currently starring in the first ever series of BBC One’s Celebrity Traitors. But she first found global fame as the young classical singer with the voice of an angel. By 22, she had sold 10 million re…
ON BABY LOSS… With Sara Pascoe and Trinny Woodall [not-audio_url] [/not-audio_url]

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Stephen Grosz - ‘Real love is going to hurt’ [not-audio_url] [/not-audio_url]

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Jilly Cooper: On Failure, Love and Literature [not-audio_url] [/not-audio_url]

Duration: 38:07
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ON NAVIGATING YOUR 20s... With Phoebe Waller-Bridge and Lily Allen [not-audio_url] [/not-audio_url]

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…
Jane Goodall on Optimism, Hope and Conservation [not-audio_url] [/not-audio_url]

Duration: 1:00:28
We said goodbye to Jane Goodall, who passed away yesterday at 91 after a life that inspired millions. I feel so grateful to have had the chance to speak with her back in July 2022, a conversation I’ll never forget. Today…
Letitia Wright - ‘I was bullied… now I’m Black Panther’ [not-audio_url] [/not-audio_url]

Duration: 52:54
You’ll know Letitia Wright from her standout roles in Black Panther, Wakanda Forever, Black Mirror and Top Boy. She won the BAFTA Rising Star award in 2019 and is currently starring in Not Your Superwoman at The Bush The…
ON ADDICTION... With Mae Martin and Marian Keyes [not-audio_url] [/not-audio_url]

Duration: 16:29
Welcome back to this How to Fail special where we revisit conversations from the archive to highlight particular themes and tap into the wisdom they contain. Each week, I select moments that can offer perspective, comfor…
Joe Locke - ‘At 20, I Felt Like I Was Already 35’ [not-audio_url] [/not-audio_url]

Duration: 46:20
Joe Locke shot to global fame as Charlie Spring in Netflix’s Heartstopper, a role that catapulted him overnight from a schoolboy on the Isle of Man to an Emmy-nominated actor with millions of followers. In this candid co…
ON WRITING... With Salman Rushdie and Kazuo Ishiguro [not-audio_url] [/not-audio_url]

Duration: 24:18
Welcome to another special edition of How to Fail, where I revisit conversations from the How to Fail archives. Each week, we shine a light on a particular theme, hopefully offering inspiration, perspective and comfort t…