How To Fail With Elizabeth Day

Latest Episodes:

Dorinda Medley on Grief, Identity and The Real Housewives: ‘I was angry. I was lost. I felt like I got cheated.’ Jul 23, 2025

Show notes

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 Housewives was both painful and necessary. This is a raw, funny, emotional conversation with a woman who’s lived many lives - and isn’t afraid to talk about all the ways they’ve fallen apart.

✨ IN THIS EPISODE:

00:00 Intro

02:12 Life After Reality TV

03:30 Authenticity and Public Perception

06:37 Dealing with Grief and Loss

14:06 Finding Strength in Vulnerability

19:14 The Impact of Fame

21:56 Housewives' First Visit to Blue Stone Manor

23:03 Behind the Scenes Drama

23:32 Staying Connected with Castmates

25:36 Dealing with Trolls and Haters

29:00 Coping with On-Screen Conflicts

31:19 Reflecting on the Housewives Experience

32:48 Blue Stone Manor Tag Sale

35:57 Life Lessons and Moving Forward

💬 QUOTES TO REMEMBER:

“A lot of people mourn by crying. I was angry. I was lost. I felt like I got cheated.” “If you want to love me, great. If you don’t, I’m okay with that.” “There’s a difference between missing Housewives and wanting to do it again.”

🔗 LINKS + MENTIONS:

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
Join Elizabeth at an upcoming one-off show at Cadogan Hall on 21 Sep for her new novel One of Us: ⁠https://www.fane.co.uk/elizabeth-day
Watch How To Fail on YouTube: https://www.youtube.com/@HowToFailPodcast
Instagram: @howtofailpod / @elizabday
TikTok: @howtofailpod / @elizabday
Elizabeth’s Substack: https://theelizabethday.substack.com/

💌 LOVE THIS EPISODE?

Subscribe to How To Fail on Spotify, Apple or wherever you get your podcasts
Leave us a 5⭐ review – it helps more people discover these conversations
Share this episode with someone navigating grief or reinvention

📚 WANT MORE?

Stanley Tucci on grief, identity and the taste of memory https://listen.sonymusic-podcasts.link/pbegMUD1?at=1010l396Y
Miriam Margolyes on fame, failure and finally giving fewer f*cks https://listen.sonymusic-podcasts.link/PJdd42Bp?at=1010l396Y
Mo Gawdat on how to solve for happiness https://listen.sonymusic-podcasts.link/RhEwJYA2?at=1010l396Y

Production & Post Production Coordinator: Eric Ryan

Studio Engineer: Sam Bair

Sound Engineer: Matias Torres

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

Vanessa Williams - ‘It would be hard to be married to me!’ Jul 16, 2025

Show notes

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 adaptation of The Devil Wears Prada.

It’s all a long way from her historic crowning as the first African-American Miss America in 1983 - she was later forced to resign after unauthorised photos taken when she was a student were leaked without her consent.

Vanessa joins us for an honest, hilarious and no-holds-barred conversation about her childhood, her romantic relationships, and - in a How To Fail first - why she regrets sending her daughter to boarding school.

Elizabeth and Vanessa answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content

00:00 Intro

02:47 Overcoming Scandal and Achieving Success

06:24 The Joys and Challenges of Stage Performance

10:31 Reflecting on Miss America

18:30 Family and Personal Reflections

23:40 Looking at Transparency and Shared Struggles

24:11 The Impact of Losing a Mother

26:00 A Mother's Influence on Trust and Relationships

28:51 Navigating High School Friendships and Trust Issues

30:07 Romantic Relationships and Parental Approval

34:58 Coping with Parental Loss and Family Dynamics

43:41 Musical Legacy and Family Bonds

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com

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

Studio & Sound Engineer: Matias Torres

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

Suzi Ruffell - ‘I didn’t know I was gay until I saw Titanic’ Jul 10, 2025

Show notes

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 Bestseller. Suzi opens up about her sexuality, her Kate Winslet obsession and talks about her totally relatable failures in this entertaining and hilarious, but moving episode.

Elizabeth and Suzi answer YOUR questions in our subscriber series, Failing with Friends from a live audience in Cardiff. 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

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

Live Sound Engineer: Will Kontargyris

Studio & Sound Engineer: Matias Torres

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

Pamela Anderson - ‘It wasn’t about being pretty, it was about being brave’ Jul 07, 2025

Show notes

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 was always about being brave.

Together, we unpack the beauty ideals of early 2000s that continue to shape how women view themselves today. Backed by Dove’s Self Esteem Project body confidence science and exercises, this episode dives deep into Pamela reflecting on being the poster girl of an era and shares how she’s reclaimed her image, her narrative and what beauty means to her.

✨ IN THIS EPISODE:

00:00 Intro

02:08 Second Act and Self-Discovery

06:01 Embracing Natural Beauty and Challenging Norms

13:11 Reflections on Beauty and Self-Worth

18:41 Journey to Self-Acceptance

23:16 Relationship with Her Parents and Personal Growth

27:54 The Early Days of Styling

28:35 Creating Iconic Looks

29:10 Rockstar Wife Persona

32:05 Impact of Y2K and Social Media

33:07 Body Image and Self-Acceptance

35:36 The Dove Self-Esteem Project

38:54 Embracing Natural Beauty

42:01 Reflections on Fame and Identity

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com

If you want more support, Dove has created a journal designed to help you reflect, reset, and take control of how you engage with beauty and your body. You can find it at dove.com/why2k.

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

Melinda French Gates - ‘Just because you’re smart doesn’t mean you’re wise’ Jul 02, 2025

Show notes

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 philanthropic organisation. Today, a divorced French Gates heads up Pivotal, which works to advance women’s power and influence in the U.S. and around the world.

Along the way, she has raised three children and written two bestselling books - The Moment of Lift and her latest, The Next Day: Transitions, Change, and Moving Forward.

It is an astonishing journey: from the normality of a middle-class childhood to becoming one of the wealthiest women in the world and one of our most influential philanthropists.

French Gates joins me for an open conversation about her divorce, ensuring her children never became spoiled, being strict about smartphones and surviving the death of a friend. Plus: the importance of empathy in the workplace and whether we should be scared of AI.

Elizabeth and Melinda answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content

✨ IN THIS EPISODE:

00:00 Intro

01:50 Philanthropy and Personal Growth

03:49 Reflections on Grief and Friendship

14:41 Parenting Challenges and Lessons

23:26 Cultural Context in Philanthropy

23:39 Vaccine Distribution Challenges

25:19 Vaccine Shortage and Initial Mistakes

25:39 Treadle Pumps and Cultural Missteps

26:45 Learning from Failures

28:58 Empathy as a Superpower

30:13 Personal Anecdotes and Relationships

32:03 The Power of Friendship

36:33 Microsoft Bob and Technological Failures

39:55 Reflections on AI and Personal Growth

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com

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

Studio & Sound Engineer: Matias Torres

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

1x pre-roll

2x Mid-roll

1x Mid-roll

1x post-roll

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Monica Lewinsky - ‘I would have liked a more normal life’ Jun 25, 2025

Show notes

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 reinterpreted the shocking way she was treated. Her podcast, which launched earlier this year, is called ‘Reclaiming’ and features interviews with guests who are in the process of reclaiming their own narratives, just as she was forced to do. She joins us to talk about her experiences with shame, her perfectionism and why the pain she went through has given her purpose.

Elizabeth and Monica answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content

✨ IN THIS EPISODE:

00:00 Intro

01:32 Early Life and Career

03:12 Reclaiming Her Narrative

06:17 Reflections on Turning 50

11:19 First Memory of Failure

18:40 Struggles After the Scandal

23:12 Navigating Post-Scandal Job Search

23:58 The Fragility and Vulnerability of Public Scrutiny

25:03 Media Obsession and Public Perception

25:59 Surviving the Media Onslaught

27:16 Reflections on Love and Power Dynamics

30:22 The Impact of Betrayal and Somatic Therapy

35:50 The Handbag Business Venture

40:12 Lessons Learned and Final Thoughts

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

AJ Tracey - ‘Buying my mum a house will always be my proudest achievement’ Jun 18, 2025

Show notes

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

🌎 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

How To Cope With A Friendship Break-Up - with Cynthia Nixon - Special Release Jun 12, 2025

Show notes

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

Cynthia Nixon - ‘Being brave is feeling scared and doing it anyway’ Jun 11, 2025

Show notes

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

🌎 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

Christine McGuinness - ‘I don’t want to hold back anymore - I date women! So what?’ Jun 04, 2025

Show notes

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

🌎 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