

How To Fail With Elizabeth Day
Elizabeth Day and Sony Music Entertainment
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
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
Mentioned books

Aug 6, 2025 • 50min
Sir Tony Robinson - ‘I learned comedy as a defence mechanism’
Sir Tony Robinson, famed actor and writer known for his role as Baldrick in Blackadder, shares his captivating journey with humor and wisdom. He reflects on fatherhood's transformative power and the daunting experience of writing his novel. The conversation delves into the impact of Blackadder, personal insecurities, and the emotional challenges of caregiving for a parent with Alzheimer's. Robinson candidly discusses lessons learned from failure, emphasizing vulnerability and the importance of meaningful connections in life.

Jul 30, 2025 • 44min
Fern Brady - ‘I make more money in comedy than I ever did from stripping‘
In a candid conversation, stand-up comedian and author Fern Brady dives into her experiences with autism and the raw realities of her working-class upbringing. She shares how social masking affected her identity and recounts her time stripping to support her education. Fern also reflects on her success in comedy, the challenges of writing her memoir, and the pressure of fame in the entertainment industry. With her trademark humor, she addresses themes of feminism, authenticity, and the complexities of navigating university life as a neurodiverse individual.

Jul 23, 2025 • 44min
Dorinda Medley on Grief, Identity and The Real Housewives: ‘I was angry. I was lost. I felt like I got cheated.’
Dorinda Medley, an author and former Real Housewife of New York, shares her journey of grief and identity after losing her husband. She candidly discusses feelings of anger and disillusionment following fame and her departure from the show. Addressing the challenges of authenticity in reality TV, Dorinda emphasizes the importance of vulnerability and self-acceptance. She reflects on unique friendships formed during filming, her nostalgic memories at Bluestone Manor, and how embracing 'no' can foster personal growth.

Jul 16, 2025 • 51min
Vanessa Williams - ‘It would be hard to be married to me!’
Vanessa Williams, a celebrated recording artist and actress, opens up about her journey from being the first African-American Miss America to achieving Grammy fame. She candidly discusses the challenges of her romantic relationships and her surprising regret about sending her daughter to boarding school. With charm and humor, Vanessa reflects on the significant influence of family, the emotional nuances of grief, and her recent return to the stage in 'The Devil Wears Prada,' celebrating resilience and personal growth along the way.

Jul 10, 2025 • 48min
Suzi Ruffell - ‘I didn’t know I was gay until I saw Titanic’
Comedian Suzi Ruffell, known for her sellout runs at the Edinburgh Fringe and appearances on Live at the Apollo, shares her journey of self-discovery. She reveals how iconic films like Titanic influenced her understanding of her sexuality. As she discusses the intersection of comedy and identity, Suzi reflects on the pressures of the stand-up scene, her experiences with anxiety, and the importance of genuine connections in her life. With humor and candor, she encourages embracing authenticity and individuality.

Jul 7, 2025 • 53min
Pamela Anderson - ‘It wasn’t about being pretty, it was about being brave’
In a candid conversation, Pamela Anderson, actress, model, and author, shares her journey of self-acceptance and redefining beauty. She discusses the pressure of early 2000s beauty ideals and how she's reclaimed her narrative. Pamela emphasizes bravery over prettiness, exploring the importance of authenticity and self-discovery. She reflects on navigating fame as a sex symbol, the significance of familial bonds, and the shift toward a makeup-free lifestyle. This insightful dialogue highlights her evolution and the collective importance of self-worth.

24 snips
Jul 2, 2025 • 50min
Melinda French Gates - ‘Just because you’re smart doesn’t mean you’re wise’
Melinda French Gates, a leading philanthropist and advocate for women's power, shares her inspiring journey from Microsoft executive to heading Pivotal. She discusses the emotional challenges of divorce, parenting with responsibility, and the pain of friendship breakups. Delving into tech evolution, she emphasizes a cautious approach to AI and culture-centric health solutions. Through personal anecdotes, Melinda highlights the significance of empathy, vulnerability, and learning from failures in both personal and professional realms.

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.

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

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