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
Hannah Murray - ‘Everything Fell Apart’ [not-audio_url] [/not-audio_url]

Duration: 1:01:33
Hannah Murray found fame when she was just 17, playing the self-destructive Cassie in E4’s Skins. She juggled an English degree at Cambridge University alongside playing Gilly in HBO’s Game Of Thrones and went on to film…
Emily Atack - ‘I’ve forgiven people for unforgivable things’ [not-audio_url] [/not-audio_url]

Duration: 1:00:57
*triggers: contains description of physical assault Emily Atack left school at 16, confident she wouldn’t need a GCSE for what she wanted to do: act. It turns out, she was correct. She starred as Charlotte Hinchcliffe in…
Katherine Parkinson – ‘I’m Still Learning How to Be Me’ [not-audio_url] [/not-audio_url]

Duration: 48:41
*triggers: contains description of physical assault Katherine Parkinson is the two‑time BAFTA‑winning actor beloved for The IT Crowd, Doc Martin, Humans and most recently, Rivals, the hit Jilly Cooper adaptation that bec…
Emilia Clarke - ‘I’m A Bad Celebrity’ [not-audio_url] [/not-audio_url]

Duration: 54:46
Emilia Clarke is the Emmy‑nominated actor who became a global cultural icon as Daenerys Targaryen in Game of Thrones, a role that catapulted her from fresh drama‑school graduate to one of the most recognisable faces on t…
Richard Gadd - On Shame, Sexuality and Success [not-audio_url] [/not-audio_url]

Duration: 49:43
Richard Gadd is the creative talent behind Baby Reindeer - the Netflix show which won six Primetime Emmys, two Golden Globes and garnered 84.5 million views within its first 45 days. Gadd began in stand-up, and by 2016 h…
Rita Wilson - ‘I’m 69. I’m At My Most Unfiltered.’ [not-audio_url] [/not-audio_url]

Duration: 51:31
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]

Duration: 54:01
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…