How To Fail With Elizabeth Day

How To Fail With Elizabeth Day

How To Fail with Elizabeth Day is a podcast that celebrates the things in life that haven’t gone right and what we might learn from them along the way. Every week, Elizabeth’s guest explores three failures, and what these failures have taught them about how to grow and succeed, better. We’d love to hear from you! Get in touch with Elizabeth to share your failures, problems or questions - anonymously or otherwise. She'll go through these each week with the help of her very special guests. And remember: a fail shared is a fail halved. https://forms.sonymusicfans.com/campaign/how-to-fail-uk-2023/ An Elizabeth Day and Sony Music Entertainment Original Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts and follow @sonypodcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com

Episodes

Failure Throwback: Glennon Doyle

August 20, 2025 • 67 mins
Author of Untamed and fierce truth-teller Glennon Doyle joins me for a raw and revelatory episode, first recorded in July 2020. We dive into: Why we chase approval instead of trusting our inner voice Her struggles with body image, love, and emotional resilience The failures that shaped her—from family breakdowns to learning self-protection Every moment is unscripted and packed with wisdom. No edits. No filters. Just Glennon, ex...
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Failure Throwback: Chimamanda Ngozi Adichie

August 13, 2025 • 68 mins
This week we revisit one of my all-time favourite guests: Chimamanda Ngozi Adichie, recorded in July 2021. Best known for Americanah and her globally resonant TED Talks, Chimamanda opens up about the profound grief of losing both her parents within a year—and the raw journey of coping in its aftermath. We talk candidly about: Her essay Notes on Grief Being a daughter and the complexities of motherhood Fertility struggles and wr...
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Sir Tony Robinson - ‘I learned comedy as a defence mechanism’

August 6, 2025 • 49 mins
Recorded with a live audience in Cambridge, this captivating conversation delves deep into the life and career of a cultural force of the last half-century. Known of course for his iconic role as Baldrick in Blackadder, Sir Tony's sharp intelligence and dry humour have had a formative influence on generations.  In this candid discussion, he opens up about the unexpected turns and profound challenges that have shaped his extraordin...
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Fern Brady - ‘I make more money in comedy than I ever did from stripping‘

July 30, 2025 • 44 mins
In this searingly funny and deeply affecting live conversation, Elizabeth speaks to stand-up comedian, author and Taskmaster favourite Fern Brady about her autism diagnosis, her working-class roots, and the failures that shaped her award-winning memoir Strong Female Character. Fern opens up about late diagnosis, social masking, and stripping to fund her education - all delivered with the brutal honesty and whip-smart humour that’s...
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Dorinda Medley on Grief, Identity and The Real Housewives: ‘I was angry. I was lost. I felt like I got cheated.’

July 23, 2025 • 43 mins
What happens when the life you thought you’d built - the one with love, money, recognition - seems to slip away? This week, Elizabeth speaks to Dorinda Medley, author, TV personality and iconic former Real Housewife of New York, about reinvention, resilience and learning to be okay with not being liked by everyone. Dorinda opens up about the loss of her husband, the loneliness that followed fame, and why her departure from Housewi...
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Vanessa Williams - ‘It would be hard to be married to me!’

July 16, 2025 • 50 mins
As a recording artist, Vanessa Williams has earned 13 Grammy nominations and racked up over 212 million digital streams over the course of her eight albums. Her most popular hit, Save The Best For Last, was Number 1 for five weeks in 1992. She is also a highly successful stage and screen actor, appearing in Desperate Housewives and Ugly Betty. She is currently starring on the West End stage as Miranda Priestly in the musical adapt...
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Suzi Ruffell - ‘I didn’t know I was gay until I saw Titanic’

July 10, 2025 • 47 mins
In this special live edition of How to Fail, Elizabeth is joined by comedian Suzi Ruffell. Suzi has performed five sellout runs at the Edinburgh Fringe, as well as appearing on live at the Apollo and filming an Amazon special of her show ‘Dance Like Everyone Is Watching’. She was nominated for Best standup show in the National Comedy Awards and has just written her first book Am I Having Fun Now?’, an instant Sunday Times Bestselle...
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Pamela Anderson - ‘It wasn’t about being pretty, it was about being brave’

July 7, 2025 • 52 mins
I can’t believe I get to say this but…PAMELA ANDERSON! ON HOW TO FAIL! The one and only!  A woman I grew up watching on TV, Pamela was an icon of a generation…But the second act of her career has been the most powerful and Anderson joins me for a  vulnerable chat about her long journey of embracing beauty on her own terms, understand her self-worth, embracing self-acceptance and how it was never about being pretty for her - it w...
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Melinda French Gates - ‘Just because you’re smart doesn’t mean you’re wise’

July 2, 2025 • 50 mins
Melinda French Gates studied computer science and economics and completed an MBA before joining a tech start-up called Microsoft, in 1987. She rose through the ranks to become Manager of Information Products and married the boss in 1994. His name was Bill Gates. Together, the couple founded and co-chaired the Gates Foundation, where, for more than two decades, she set the direction and priorities of the world’s largest philanthrop...
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Monica Lewinsky - ‘I would have liked a more normal life’

June 25, 2025 • 47 mins
Monica Lewinsky is an activist, podcaster and producer.  At the age of 24, Lewinsky, a White House intern, found herself in the eye of a global scandal. She was subjected to a mass public shaming -  losing her livelihood, her anonymity and the future she had once imagined for herself. Now, 51 Lewinsky has garnered a new generation of admirers, who with the advent of social media and shifting cultural tides, have rightly reinterpre...
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AJ Tracey - ‘Buying my mum a house will always be my proudest achievement’

June 18, 2025 • 50 mins
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 Plat...
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How To Cope With A Friendship Break-Up - with Cynthia Nixon - Special Release

June 12, 2025 • 27 mins
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 ...
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Cynthia Nixon - ‘Being brave is feeling scared and doing it anyway’

June 11, 2025 • 51 mins
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 ...
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Christine McGuinness - ‘I don’t want to hold back anymore - I date women! So what?’

June 4, 2025 • 50 mins
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 pa...
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Vicky Pattison - ‘You don't become old and wise if you haven't been young and daft’

June 2, 2025 • 55 mins
Vicky Pattison was 22 when her life changed and she was cast in reality TV show Geordie Shore. She was on the show for nine seasons between 2011 and 2014, during which time the cameras followed her falling in love, becoming engaged, then breaking up. Now 37, Pattison has rarely been off our screens - whether it’s as a finalist on Celebrity Masterchef or winning I’m A Celebrity in 2015. She’s a radio presenter on the Heart network,...
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Dannii Minogue - ‘I hit low points where I thought: “I just can’t take this any more.”

May 28, 2025 • 56 mins
In her most revealing interview to date, Dannii Minogue talks openly about the pressures of fame, the relentless comparisons with her sister, Kylie, and navigating a divorce that left her broke. It’s an extraordinary conversation with a woman who found fame as a 10-year-old in her native Australia. As a  teenager Dannii, signed a record deal and acted in Home and Away. In her early 20s her debut album went Gold in the UK, and sh...
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Julia Stiles - ‘I ran in the other direction from fame’

May 21, 2025 • 53 mins
For many of us who grew up in the the 90s, Julia Stiles was an integral part of our coming of age. Her portrayal of the clever, acerbic Kat in 10 Things I Hate About You was a radical reinvention of the blonde teenage female rom-com lead. Her roles in Save The Last Dance and Mona Lisa Smile spoke to our adolescent feminist awakenings and catapulted Stiles to stardom. And, just like the heroines she played, Stiles chose to do things...
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John Bishop - ‘I’ve always wanted someone to say: you’re good enough’

May 14, 2025 • 54 mins
John Bishop has been a hugely successful stand-up comedian for 25 years. Yet that wasn’t his first dream, which was to play football. We discuss his failure to do so professionally, his challenges at school, the working-class upbringing that shaped him and how comedy saved his marriage when he and his wife were at the ‘decree nisi stage’ of divorce. Plus: skincare tips and why making people laugh is like stripping. Yes, really. ...
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Simon Cowell - ‘I often think: what gives me the right to judge people?’

May 7, 2025 • 59 mins
Simon Cowell has built an entertainment empire on his ability to say exactly what he thinks and an uncanny ability to judge the public mood. From launching Pop Idol in 2001, The X Factor in 2004 and the cultural behemoth Britain’s Got Talent in 2007, he has been at the helm of primetime around the world for over a quarter of a century. His TV shows and Syco record label have shaped the careers of everyone from One Direction to L...
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Celeste Barber: the FUNNIEST woman on the internet

April 30, 2025 • 51 mins
My guest today has been an integral part of my feminist awakening. Celeste Barber’s instagram posts - which parody the unattainable standards of the fashion and beauty industry - are both hilarious and revolutionary. Her work has helped a generation of women to feel better about their bodies - and made her a star in the process. (Plus she’s been blocked by a few celebrities. Lol.) Barber began her account in 2015 as a jobbing acto...
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