How To Fail With Elizabeth Day

Sophie Habboo - I Wish I Had More Boundaries

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 Laing in 2017. The two began dating - and then launched a media empire. Their podcast, NearlyWeds was an instant hit and was rebranded as NewlyWeds when they got married in 2023. Habboo now runs the hugely successful JamPot podcast production company with her husband and the two served as executive producers on Raising Chelsea, a new three-part Disney+ documentary following the couple as they face the messy, scary and comic reality of becoming parents for the first time. In this episode Sophie talks openly about her feelings of overwhelm and anxiety in the run up to their wedding, her ADHD diagnosis, the challenges of being a new mum and the importance of setting boundaries. ✨ IN THIS EPISODE: 03:50 Family Roots And Motherhood 06:39 Ziggy Bay And Marathon Madness 08:35 Failure One: No Boundaries 10:23 One Day Office Job Disaster 16:01 Wedding Overwhelm And ADHD 20:52 Insecurities and Social Situations 21:53 Anxiety and Imposter Feelings 23:05 Therapy and Psychic Rituals 24:18 Sponsor Break The Testaments 26:12 Motherhood and Fear of Failing 29:36 Love Story With Jamie 33:54 A Surprise Voice Note 💬 QUOTES TO REMEMBER: I do always have imposter syndrome and maybe even as a mother... I really struggle with ‘mum guilt’. Had I been diagnosed with ADHD earlier, I would've been able to understand and have more compassion for myself. 🔗 LINKS + MENTIONS: Raising Chelsea is available to watch now on Disney+ The Testaments, a new Hulu original series, streaming April 8 exclusively on Disney+ Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Jamie Laing - on anxiety, insecurity and the pressure of fame. Plus his ‘failure’ to have a long-term relationship [spoiler alert: it all worked out just fine!]: swap.fm/l/QXKrzzpg5hULgBpXWMBY Dorinda Medley - on young widowhood, dealing with anger and what The Real Housewives of New York taught her: swap.fm/l/Q3MPl0zGn9MShaUdGEi4 💌 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: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Sophie answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless 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 [https://podcastchoices.com/adchoices]

Elizabeth's New Show: History’s Greatest Fails

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 the reality-TV-style discovery of his remains under a Leicester council car park in 2022.  To listen to the full mini-series, head to This is History: History’s Greatest Fails wherever you listen to podcasts and on YouTube.  And more about this episode: In many ways, Richard’s alleged ‘failures’ — which include allegedly killing the Princes in the Tower and overseeing the demise of Plantagenet rule — overshadow Richard III as the reformer that also existed. He introduced trial by jury and translated many laws into English. But those facts are not often what’s associated with him. He’s more likely to be seen as the villainous caricature of Shakespeare’s Richard III.  He died at the Battle of Bosworth in 1485. And we haven’t been able to stop talking about him since.  Yes, it’s time to consider the story of England’s last Plantagenet king, Richard III — a centuries-old tangle involving alleged murder, Shakespeare, vanquish and one mighty rediscovery.  – A Sony Music Entertainment production.  Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts [http://sonymusic.com/podcasts]  To bring your brand to life in this podcast, email podcastadsales@sonymusic.com [podcastadsales@sonymusic.com]  Learn more about your ad choices.  Visit megaphone.fm/adchoices  –– Presented by Dan Jones and Elizabeth Day  Producer - Alan Weedon  Senior Producer - Dominic Tyerman Executive Producer - Simon Poole  Executive Producer for Daylight Productions - Elizabeth Day   Executive Producer - Dan Jones Production Manager - Jen Mistri  Production coordinator - Eric Ryan  Head of content - Chris Skinner  Special thanks to Alex Lawless, Hannah Talbot, and Selina Ream Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Amy Jackson Westwick - I Was A Magnet For Narcissists

Amy Jackson Westwick is a major Bollywood film star with some 14 million followers on social media. Yet she grew up in a working class family in Liverpool. So how did a teenager from Merseyside become one of the most recognisable British actors working in Bollywood? Today on How To Fail, she tells us her story. We discuss growing up too fast, how she broke free from a cycle of narcissistic relationships and how she now manages a blended family (Amy has two sons - one with her husband, the actor Ed Westwick, and one from a previous partner). Plus: what she learned from her years in Bollywood and why she’s ’a petty cow’. ✨ IN THIS EPISODE: 00:00 Intro 03:13 Chasing Security Not Fame 04:08 Finding Yourself Again 06:35 Growing Up Too Fast 06:50 Liverpool Childhood Roots 11:27 Pageants to Bollywood Break 24:04 Perfect Family Fantasy 25:21 Romanticising Love 26:40 Back To Back Relationships 27:30 People Pleasing Patterns 29:06 Narcissists And Boundaries 31:53 Leaving And Healing 36:39 Blended Family Reality 39:52 Step Parenting Rules 47:05 Listening To Yourself 💬 QUOTES TO REMEMBER: Security comes in so many different forms - and for me it's peace of mind. If it doesn't feel right, then it's not right... you've got to actually know how you're feeling and not be afraid to voice it. [On narcissistic relationships]: I confused controlling behavior for somebody who was loving and caring, and in actual fact it was the complete opposite. 🔗 LINKS + MENTIONS: Amy’s podcast ‘What’s the Tea Amy?’ is out now The Testaments, a new Hulu original series, streaming April 8 exclusively on Disney+ Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Lily Allen - on early fame, mistakes, relationships and motherhood: swap.fm/l/8Otj3tpmbH5SF4xjVHTJ Gillian Anderson - on body image, rebellion and refusing to fit in with other people’s expectations: swap.fm/l/7NyZMzkfVOpGyDtlB6k0 💌 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: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Amy answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless 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 [https://podcastchoices.com/adchoices]

ON FINDING THE ONE… With Miranda Hart, Celeste Barber and Glennon Doyle

This is a special episode, sponsored by Bumble, taking a look at all the different ways we can meet someone: whether you meet young, in your 50s, or post-divorce. The three women in this episode (and four if you count me!) - are here to show us that finding the love of your life isn’t always straight-forwards, or linear. First up, you'll hear from the brilliant and hilarious Miranda Hart, who got married when she was 51, and talks through her first date with her now husband. Then Australian comedian Celeste Barber talks about meeting her ‘hot husband’ young, and quickly becoming a step-mum to two young children. Finally, American author Glennon Doyle talks about leaving her marriage for the love of her life, Abby – and co-parenting her three children with her ex-husband in a blended family. I hope this episode brings you as much laughter, reassurance and warmth as each of those guests have brought me. And hopefully it inspires you to refresh your Bumble profile, or download Bumble now! Listen to Miranda’s full episode here: swap.fm/l/oTScN30b80GflJtO4rgu Listen to Celeste’s full episode here: swap.fm/l/qLmwfjyeSolWuFeaHGdt Listen to Glennon’s full episode here: swap.fm/l/Nd3ZzVy73FXUMupJ4i1q 🔗 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 [https://podcastchoices.com/adchoices]

Chris Appleton - ‘I Felt Shame Before I Felt Love’

Celebrity hair stylist Chris Appleton has a slew of devoted clients including Kim Kardashian, Kris Jenner and Martha Stewart, as well as millions of Instagram followers and a regular slot offering advice on The Drew Barrymore Show. His memoir, Your Roots Don’t Define You, is a New York Times bestseller. But growing up was hard on Appleton: he was the middle of five children and struggled with undiagnosed dyslexia at school. He was bullied by his classmates for being gay - something he didn’t yet understand about himself. At 16, he left school to work full-time and began a serious relationship with his colleague, Kate. By 19, he was a father. In this episode we discuss imposter syndrome, the darkest moments of his life, shame and the work he’s done to overcome the hurdles he’s faced. And, of course, we talk about the Kardashians. ✨ IN THIS EPISODE: 02:33 Imposter Syndrome as Fuel 04:24 Red Carpets and Online Pressure 05:27 Hair as Celebrity Identity 07:15 Memoir and Health Wake Up 08:48 Dash the Dog and Comfort 11:02 Shame Coming Out and Healing 22:26 Kids First After Divorce 23:05 Holiday Triggers and Boundaries 24:31 Success Doesn't Heal 25:18 Inner Child Healing Work 27:22 Envy Into Mentorship 30:08 Kardashians on Failure 31:25 Hair Identity and Change 35:18 Comparison and Social Media 💬 QUOTES TO REMEMBER: It’s okay to make mistakes, but I love learning from them and understanding why we make those decisions. Hair is such a big part of people's identity. It tells who you are. You can externally excite yourself... But if you're not aligned internally, you still have that sad and lonely feeling. I think imposter syndrome to an extent is healthy... It keeps me turning up to jobs prepared. I treat every job like it's the first time I've done it. 🔗 LINKS + MENTIONS: Chris Appleton’s book Your Roots Don’t Define You, is out now Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Rylan Clark - on public breakdowns, surviving divorce and rebuilding his sense of self. Dawn French - on comedy, adoption and finding confidence later in life. 💌 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: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Chris answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless 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 [https://podcastchoices.com/adchoices]