How To Fail With Elizabeth Day

Elizabeth Day and Sony Music Entertainment
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Jun 25, 2025 • 48min

Monica Lewinsky - ‘I would have liked a more normal life’

Monica Lewinsky, an activist and podcaster known for her role in a major political scandal, dives deep into her journey of reclaiming her narrative. She discusses the impact of public shaming and how it shaped her identity and purpose. Lewinsky shares insights on overcoming trauma and embracing transformation in her 50s, highlighting the importance of acceptance and resilience. The conversation also touches on the creative process and the lessons learned from failure, ultimately celebrating personal growth and wellness.
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Jun 18, 2025 • 51min

AJ Tracey - ‘Buying my mum a house will always be my proudest achievement’

Rapping phenomenon and Tottenham Hotspur superfan AJ Tracey joins us this week to talk about supporting his mum through her cancer journey, the pressures of staying an independent artist and what football has taught him about failure. AJ Tracey has been rapping since the age of four. He dropped out of his Criminology degree at London Metropolitan University and started uploading tracks to SoundCloud in 2011, achieving five Platinum singles and over two billion Spotify plays as an independent artist. His first studio album debuted at number three in the UK Albums chart and his breakthrough hit, Ladbroke Grove, became the unofficial summer anthem of 2019. Now, after a three-year hiatus, marked by leaked songs and pandemic delays, Tracey has just released his third album, Don't Die Before You're Dead. It’s his most vulnerable and personal work yet and as well as being a love letter to the UK, the album fuses grime, garage, and R&B with themes of trauma, mental health, faith and love. ✨ IN THIS EPISODE: 00:00 Intro 01:11 Early Life and Career 03:04 The Making of 'Don't Die Before You're Dead' 07:10 The British Influence in AJ's Music 09:00 School Days and Influential Teachers 12:34 The Challenges of Being an Independent Artist 18:18 Faith and Personal Mission 23:02 Family and Personal Struggles 24:52 Mom's Health Scare and Recovery 25:40 Proudest Moment: Buying Mom a House 27:44 Growing Up with Responsibility 30:53 Struggles and Sacrifices 33:46 Name Change and Fresh Start 38:12 Grenfell Tragedy and Community Impact 41:58 Reconciliation with Dad 43:43 Football, Family, and Life Lessons Elizabeth and AJ answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://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 All episodes in June are brought to you by @arlalactoFREE - all the taste, easier to digest. Listen to our bonus episode brought to by ArlaLactoFREE with Vicky Pattison here: https://link.chtbl.com/VickyPattison 🌎 Get an exclusive 15% discount on your first Saily data plans! Use code [howtofail] at checkout. Download Saily app or go to to https://saily.com/howtofail ⛵ I have an upcoming one-off show at Cadogan Hall on 21 Sep for my new novel One of Us. Full show details here: https://www.fane.co.uk/elizabeth-day Production & Post Production Coordinator: Eric Ryan Mix Engineer: Matias Torres Studio Engineer: Gulliver Tickell Assistant Producer: Suhaar Ali Senior Producer: Hannah Talbot Executive Producer: Carly Maile 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
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Jun 12, 2025 • 27min

How To Cope With A Friendship Break-Up - with Cynthia Nixon - Special Release

Cynthia Nixon joins Elizabeth to answer YOUR questions and failures including: whose failures would you most like to hear (dead or alive) how to cope with a friendship break up and how to know when to have kids. Elizabeth then takes a moment to reflect on meeting Cynthia, and everything they covered. To hear Cynthia tackling your failures join our community of subscribers here: https://howtofail.supportingcast.fm/#content Do you have something to share of your own? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Mix Engineer: Matias Torres Studio Engineer: Sam Bair Senior Producer: Hannah Talbot Executive Producer: Carly Maile 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
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Jun 11, 2025 • 52min

Cynthia Nixon - ‘Being brave is feeling scared and doing it anyway’

Whilst Cynthia Nixon’s versatility is beyond question, it's fair to say that she has become permanently associated with one character, Miranda Hobbs, in Sex and the City and its companion piece, And Just Like That. She won an Emmy for her performance and a generation of fans who identified with the ambitious type-A lawyer whose cynicism disguised as vulnerability has grown markedly through the decades. Nixon is also a political activist and vocal advocate for progressive causes. She even met her wife at an education rally in 2002. In 2018, she ran unsuccessfully for the governorship of New York. More recently, she has repeatedly spoken out in support of a permanent ceasefire in Gaza. Nixon's political conscience recalls perhaps the legacy of her journalist Father Walter, who won awards for his coverage of the Civil Rights Movement. An uplifting, smart and enlightening woman - what a joy it was to meet her. ✨ IN THIS EPISODE: 00:00 Intro 03:12 Miranda Hobbs and Lessons on Failure 04:53 Controversial Storylines in 'And Just Like That' 12:38 Political Journey 15:43 Running Against Andrew Cuomo 18:03 Gender and Politics 21:34 Early Political Influences 26:58 Missed Opportunities in Acting 28:24 Influence of Family on Career 30:18 Quiz Show Memories 32:22 Truth and Pretense in Acting 35:15 Filming Amadeus 40:10 Thanksgiving Preparations 44:58 Family Dynamics 48:52 Gratitude and Hope for the Future Elizabeth and Cynthia answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have something to share of your own? Click here to get in touch: howtofailpod.com All episodes in June are brought to you by @arlalactoFREE - all the taste, easier to digest. Listen to our bonus episode brought to by ArlaLactoFREE with Vicky Pattison here: https://link.chtbl.com/VickyPattison 🌎 Get an exclusive 15% discount on your first Saily data plans! Use code [howtofail] at checkout. Download Saily app or go to to https://saily.com/howtofail ⛵ Production & Post Production Coordinator: Eric Ryan Mix Engineer: Matias Torres Studio Engineer: Sam Bair Senior Producer: Hannah Talbot Executive Producer: Carly Maile 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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Jun 4, 2025 • 51min

Christine McGuinness - ‘I don’t want to hold back anymore - I date women! So what?’

TW: discussions around anorexia and sexual abuse. In an incredibly powerful episode (and a How To Fail first), Christine McGuinness speaks publicly about her sexuality for the first time. She reveals she had a long-term relationship with a woman before her marriage to comedian Paddy McGuinness and that she’s now dating women again. She refuses to label her sexuality - as she puts it: ‘I want love for me’. What an honour to be part of Christine’s journey to live her truth! You will already know Christine as a TV personality, author, businesswoman and prominent autism advocate. The mother of three autistic children, she has made critically acclaimed documentaries including Our Family and Autism, with her then-husband, as well as penning a series of autism-inclusive children’s books and launching a range of sensory-positive clothing. Despite serious adversity (her father was a heroin addict, she endured bullying at school and suffered sexual abuse at the hands of a family member), Christine is a total inspiration and has achieved so much. She’s about to launch her first podcast, Situationships, in which she and her co-host Sophie Gravia delve into listeners’ dating and relationship dilemmas. ✨ IN THIS EPISODE: 00:00 Intro 00:52 An Inspiring Journey 02:30 Challenges and Triumphs of Motherhood 05:01 Raising Neurodivergent Children 08:03 The Importance of Asking for Help 12:52 Reflecting on Childhood and Autism 20:23 The Journey of Self-Discovery 23:41 Navigating Public Attention 24:35 Discussing Divorce and Public Perception 26:07 Challenges of Sexuality in the Public Eye 28:09 Living Authentically 31:13 Reflections on Relationships 41:40 Friendship and Trust Issues 43:28 Motherhood and Personal Growth 45:47 Concluding Thoughts and Future Hopes Elizabeth and Christine answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have something to share of your own? Click here to get in touch: howtofailpod.com All episodes in June are brought to you by @arlalactoFREE - all the taste, easier to digest. Listen to our bonus episode brought to by ArlaLactoFREE with Vicky Pattison here: https://link.chtbl.com/VickyPattison 🌎 Get an exclusive 15% discount on your first Saily data plans! Use code [howtofail] at checkout. Download Saily app or go to to https://saily.com/howtofail ⛵ Production & Post Production Coordinator: Eric Ryan Mix Engineer: Matias Torres Studio Engineer: Gulliver Tickell Assistant Producer: Suhaar Ali Senior Producer: Hannah Talbot Executive Producer: Carly Maile 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 you Learn more about your ad choices. Visit podcastchoices.com/adchoices
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Jun 2, 2025 • 56min

Vicky Pattison - ‘You don't become old and wise if you haven't been young and daft’

Vicky Pattison, a reality TV star and author, reflects on her transformative journey from Geordie Shore fame to self-acceptance. She candidly discusses her struggles with PMDD, societal pressures, and the impact of an alcoholic parent on her life choices. Vicky shares insights on balancing a hectic lifestyle with downtime, navigating public scrutiny, and the importance of communication in personal relationships. Through her experiences, she advocates for empathy towards others’ challenges, emphasizing that growth often comes from past mistakes.
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May 28, 2025 • 57min

Dannii Minogue - ‘I hit low points where I thought: “I just can’t take this any more.”

Dannii Minogue, the talented Australian singer and TV personality, opens up about her journey through fame since age 10. She candidly discusses the pressures of being compared to her sister Kylie and the heartbreak of a difficult divorce. The conversation touches on her advocacy for the LGBTQ+ community and the importance of authenticity. Dannii also reflects on navigating public scrutiny during her time on The X Factor and how personal experiences have reshaped her views on success, self-acceptance, and resilience.
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May 21, 2025 • 53min

Julia Stiles - ‘I ran in the other direction from fame’

Julia Stiles, celebrated actress and director known for her roles in '10 Things I Hate About You' and the 'Bourne' series, shares her journey from teen star to filmmaker. She discusses the pressures of body image in the industry, emphasizing the importance of self-kindness and acceptance. Stiles reflects on navigating fame, finding authenticity, and the challenges of balancing career and motherhood. Her personal anecdotes reveal the transformative power of friendships and creativity in her life, making for an engaging and relatable conversation.
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May 14, 2025 • 55min

John Bishop - ‘I’ve always wanted someone to say: you’re good enough’

John Bishop, a highly acclaimed stand-up comedian, reflects on his journey from aspiring footballer to comedy icon. He discusses the highs and lows of stand-up, including the thrill of audience reactions and the struggle with imposter syndrome. John shares how comedy saved his marriage and touches on the emotional weight of past disappointments. He also delves into the importance of philanthropy, personal growth through challenges, and even offers skincare tips, humorously relating laughter to intimacy.
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May 7, 2025 • 60min

Simon Cowell - ‘I often think: what gives me the right to judge people?’

Simon Cowell, the entertainment mogul known for his role in shaping modern talent shows like Pop Idol and Britain’s Got Talent, reflects on his journey. He candidly discusses his biggest failures, including a near-death experience and the emotional toll of bankruptcy. Cowell shares valuable insights on resilience, fame, and the sometimes harsh public perception. He humorously examines the complexities of success in a social media-driven world and why he believes in the need for another Brexit referendum.

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