- 51 minutes 21 secondsAline Brosh McKenna - The Rom Com Queen Who Wrote The Devil Wears Prada
Aline Brosh McKenna is the brilliant writer behind some of the most iconic films and TV of our time: The Devil Wears Prada, 27 Dresses, Morning Glory and Crazy Ex-Girlfriend. Now, she’s back with The Devil Wears Prada 2.
Before Hollywood, Aline studied literature at Harvard and worked as a freelance magazine writer in New York. She was 38 when everything changed with the release of The Devil Wears Prada - and she’s been creating sharp, funny, deeply relatable stories ever since.
In this episode, we talk about writing for Meryl Streep (no biggie) the acting and magazine career that never happened and what life as an award-winning screenwriter *really* looks like. Plus: the motivating advice every single woman needs to hear.
✨ IN THIS EPISODE:
00:00 Introduction
03:15 27 Dresses and People Pleasing
04:24 Learning Not to Smallify
07:09 Writing Bold Characters
08:11 Devil Wears Prada Two Return
12:35 ‘Failed’ Acting Dreams
17:31 Working With Great Actors
23:20 Writing Meryl’s Big Speech
25:35 Scrappy Creativity Mindset
26:34 ‘Failed’ Magazine Career
29:00 Screenwriting Doors Open
32:07 Comedy Cred And Awards
35:23 Nine Pilots No Series
41:57 Ask For What You Want
💬 QUOTES TO REMEMBER:
I wasn't taught to “smallify” myself by my mother, and that's maybe one of her greatest gifts.
If it becomes necessary to apologise to get what you want, I think that’s okay. As long as you're aware that you're doing it... as a tactic or a strategy.
Learning to withstand and be amused by failure is so key and so critical.
🔗 LINKS + MENTIONS:
Devil Wears Prada 2 is in cinemas now!
Join the How To Fail community: www.howtofail.supportingcast.fm/#content
Elizabeth’s Substack: www.theelizabethday.substack.com
📚 WANT MORE?
Stanley Tucci - A DWP cast member no less! The iconic Nigel…sorry, Stanley came on HTF and talked about dealing with the loss of his late wife, surviving cancer, finding love again and…failing to swim: swap.fm/l/WCW054IGNZnSnTzEXPTN
Dawn French - Another genius comedy writer who talks about heartbreak, humour, adoption and meeting Jennifer Saunders: swap.fm/l/NJDrzxLKhyi6icOrxmHT
💌 LOVE THIS EPISODE?
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👋 Follow How To Fail & Elizabeth:
Instagram: @elizabday
TikTok: @howtofailpod
Podcast Instagram: @howtofailpod
Website: www.elizabethday.org
Guest bookings for How To Fail only come from official @sonymusic.com emails
Elizabeth and Aline 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
6 May 2026, 4:00 am - 49 minutes 43 secondsRichard Gadd - On Shame, Sexuality and Success
Richard Gadd is the creative talent behind Baby Reindeer - the Netflix show which won six Primetime Emmys, two Golden Globes and garnered 84.5 million views within its first 45 days.
Gadd began in stand-up, and by 2016 he’d won a Perrier Award at the Edinburgh Fringe. His work became known for its compulsive storytelling, blending dark comedy with a kind of philosophical kink for asking audiences the most uncomfortable questions.
Now Gadd returns with Half Man, a six-part drama co-production between HBO and the BBC, which Gadd created, wrote, executive produced and stars in.
In this episode we talk through his childhood, how it felt to be abruptly catapulted into being the most googled man on the planet following the release of Baby Reindeer and the complexity of identity and sexuality.
✨ IN THIS EPISODE:
03:13 Fame and Self Worth
05:37 Writing Dark Truths
06:52 Baby Reindeer Explosion
08:00 Becoming Ruben
09:40 Half Man Meaning
10:57 Workaholism Origins
23:58 Family Support After Trauma
24:30 Comedy Meets Abuse Healing
26:13 Rebuking Shame
27:51 Fame And Re Triggering
29:12 Stubbornness And Casting Martha
33:03 Sexuality Beyond Labels
36:15 Grudges Empathy Forgiveness
40:13 Athlete Failure And Closing
💬 QUOTES TO REMEMBER:
I never wanted fame. I just liked the idea that one day I would make a piece of art that was culturally important because then maybe I would learn to like myself.
It doesn't matter your intelligence, where you come from, your upbringing, anything… it’s about the hours you put into it. Hard work trumps everything.
I think actually that we have but scratched the surface of sexuality in a way... there are so many complications to it.
🔗 LINKS + MENTIONS:
You can watch Half Man on BBC iPlayer every week
Join the How To Fail community: www.howtofail.supportingcast.fm/#content
Elizabeth’s Substack: www.theelizabethday.substack.com
📚 WANT MORE?
Stephen Merchant - the actor, writer and director on turning 50, failure in stand-up and what he learned from Ricky Gervais when he co-wrote The Office: swap.fm/l/Lta5mlFbVnPHyFb8R1n2
Phoebe Waller-Bridge - the creator of Fleabag talks about ambition, doubt and creating bold work: swap.fm/l/gTCOCJUmXX9t22mTABSa
💌 LOVE THIS EPISODE?
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👋 Follow How To Fail & Elizabeth:
Instagram: @elizabday
TikTok: @howtofailpod
Podcast Instagram: @howtofailpod
Website: www.elizabethday.org
Guest bookings for How To Fail only come from official @sonymusic.com emails
Elizabeth and Richard 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
29 April 2026, 4:00 am - 51 minutes 31 secondsRita Wilson - ‘I’m 69. I’m At My Most Unfiltered.’
The acclaimed actor, singer and producer was born in Los Angeles to a Greek mother and a Bulgarian father who emigrated to the United States in 1949.
You might know her from early roles like Bosom Buddies, where she met her future husband Tom Hanks, and from standout turns in films including Runaway Bride, It's Complicated and her unforgettable scene-stealing in Sleepless in Seattle.
Behind the camera, she helped bring My Big Fat Greek Wedding and Mamma Mia! to the big screen.
Alongside her film career, Wilson has built a powerful musical voice, releasing albums since 2012 and collaborating with artists like Elvis Costello and Willie Nelson. She now returns to her solo work with her sixth album, Sound Of A Woman, released on 1st May.
In this episode, we talk about growing up in a traditional, private family but later living in the public eye, bringing My Big Fat Greek Wedding to the screen, her friendships with Nora Ephron and Bruce Springsteen - and how her experience of breast cancer reshaped her life and friendships.
✨ IN THIS EPISODE:
02:39 Sleepless In Seattle Scene Secrets
04:32 Finding Her Voice
07:53 Labels and Late Blooming
13:07 Privacy to Speaking Out
14:56 Greek Wedding Breakthrough
17:43 Drama School Rejections
27:57 Proving Them Wrong
29:03 Onscreen Friendship Magic
31:03 What Friendship Means
32:12 Breast Cancer and Blame
35:07 Honoring Her Father
39:55 Family Secrets and Privacy
45:50 Building Family Values
47:20 Fired as Ticket Taker
💬 QUOTES TO REMEMBER:
I’ve come to a stage in my life where I’m only now just finding my voice, both metaphorically and literally.
We spend so much of our lives shedding those identities that don't work for us anymore until we get to a place where I am now, which is literally the most unfiltered place you can be when you get to a certain age where you just don’t care what anybody thinks and you can tell the truth more fully.
🔗 LINKS + MENTIONS:
Sound Of A Woman is out on 1st May
Join the How To Fail community: www.howtofail.supportingcast.fm/#content
Elizabeth’s Substack: www.theelizabethday.substack.com
📚 WANT MORE?
Ruth Wilson – on refusing Botox, being rejected from Oxford and living with her father’s Alzheimer's: swap.fm/l/ZbkfbAmZFOX0zB2u1iiC
Melanie Chisholm – the former Spice girl on mental health, identity and navigating fame: swap.fm/l/OAU4TwoXfjVLvCdrcSYY
Gloria Steinem – my personal hero: on activism, ageing and redefining success: swap.fm/l/WbcOneXzQpdLfYriAQXE
💌 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
Guest bookings for How To Fail only come from official @sonymusic.com emails
Elizabeth and Rita 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
22 April 2026, 4:00 am - 54 minutes 1 secondEmma Grede - ‘Ambition Is Something I Am Entitled to’
Today’s guest is a female billionaire: the co-founder and CEO of the Good American inclusive fashion brand and a founding partner of SKIMS, the shapewear and loungewear company. Emma Grede’s close working partnerships with the Kardashian family have led her to become an advocate for empowering women through business.
Now, she’s publishing her first book, Start With Yourself, in which she explores everything from building personal resilience to developing self-forgiveness.
In this episode we discuss her East London mindset, her famously controversial (!) attitude towards work-life balance, being a mother of four (her twins were born via a surrogate) and her experience of miscarriage. Female ambition, fertility, the discomfort of hard work…I’m so grateful to Emma for opening up on subjects that are so often shrouded in silence.
✨ IN THIS EPISODE:
03:02 Ambition Loves Discomfort
05:57 Growing Up East London
07:31 ‘Too Ambitious’
08:34 East London Business Code
11:15 An Employee Mindset
19:13 Work-Life Balance Myth
26:34 Fearless Hustle Mindset
27:53 ITB Rise and Influencers
29:08 LA Office Ego Crash
31:40 Parenting as a Team
32:56 Fertility Reality Check
38:19 Good American Expansion Misstep
46:25 Mother’s Influence
💬 QUOTES TO REMEMBER:
I have always thought about ambition as something that I am entitled to as long as I work for it.
If you want to be extraordinarily successful… Then extraordinary work is required.
You become confident because you know you can get through things and you know what's on the other side of failure.
🔗 LINKS + MENTIONS:
Emma’s debut book ‘Start With Yourself’ - is available to buy now
The Testaments, a new Hulu original series, streaming exclusively on Disney+
Join the How To Fail community: www.howtofail.supportingcast.fm/#content
Elizabeth’s Substack: www.theelizabethday.substack.com
📚 WANT MORE?
Melinda French Gates - another extraordinarily successful female philanthropist, who co-chaired the Bill & Melinda Gates Foundation, the world's largest private charitable organization, for 24 years: swap.fm/l/Zr3OTH30YZpvPRiXIkeX
Mo Gawdat - an incredible guest who has been on How to Fail FOUR times - most recently in December last year to talk about the most common mistakes we make in love: swap.fm/l/Daw9T2DZbicGt0aOZZVX
💌 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 Emma 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
15 April 2026, 4:00 am - 47 minutes 18 secondsSophie 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
8 April 2026, 4:00 am - 33 minutes 51 secondsElizabeth'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
To bring your brand to life in this podcast, email [email protected]
Learn more about your ad choices.
Visit megaphone.fm/adchoices
––
Presented by Dan Jones and Elizabeth Day
Producer - Alan Weedon
Senior Producer - Dominic TyermanResearcher - Phoebe Joyce 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 ReamLearn more about your ad choices. Visit podcastchoices.com/adchoices
7 April 2026, 4:00 am - 55 minutes 17 secondsAmy 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
1 April 2026, 4:00 am - 24 minutes 32 secondsON 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 [email protected]
Learn more about your ad choices. Visit podcastchoices.com/adchoices
29 March 2026, 11:00 pm - 45 minutes 10 secondsChris 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 [email protected]
_________________________________________________________________________
Learn more about your ad choices. Visit podcastchoices.com/adchoices
25 March 2026, 5:00 am - 1 hour 19 minutesMel Schilling - ‘She was the embodiment of vibrant life’
I never thought I would have to write these words, but here we are. In the wake of my dear friend’s passing, I wanted to reflect on the life of one of the most radiant people I’ve ever met: Mel Schilling. I never quite understood the truth of the phrase ‘she lights up a room’ until I met Mel. It wasn’t just the sparkling smile or the sequins she loved wearing or the glittery eyeshadow; it was deeper than that: she wanted others to shine, to feel special and to be loved. To believe themselves worthy of love.
To be in Mel’s company was to feel anything was possible.
I wanted to re-release this very special episode of How to Fail because it shows so much of the woman she was. It was also the first time I met Mel in person after admiring her for years from afar on our TV screens. I’m so lucky to have known her.
Please enjoy getting to know my friend Mel.
And if you want to hear more of her extraordinary insights and wisdom, you can listen to her on How To Date [link here: swap.fm/l/92EWhbCOZtcpVjwW1ZhD].
👋 Follow How To Fail & Elizabeth:
- Instagram: @elizabday
- TikTok: @howtofailpod
- Podcast Instagram: @howtofailpod
- Website: www.elizabethday.org
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How to Fail is an Elizabeth Day and Sony Music Entertainment Production.
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24 March 2026, 4:30 pm - 20 minutes 45 secondsON STARTING OVER AFTER GRIEF… With Stanley Tucci and Geri Halliwell-Horner
Starting over can feel heartbreaking and overwhelming, especially after losing a loved one, and the idea of rebuilding a life can seem impossible. In this episode, Stanley and Geri show us that sometimes moving forward isn’t about letting go of the past, but learning to carry it with you in a way that allows life to continue.
Stanley Tucci speaks with brave honesty about the death of his first wife, Kate – the guilt he felt as he tried to move on and the difficult choices he faced while creating a new life for his children.
Geri Halliwell Horner reflects on losing her father as a teenager, how that loss shaped her ambition and how writing her novel unexpectedly helped her make sense of long‑held grief.
This episode explores love, loss and the resilience that allows us to keep going after such events. I hope it brings you a sense of solidarity or confirmation that we don’t need to erase what came before; sometimes, it becomes the very force that helps us begin again.
Listen to Stanley’s full episode of How to Fail here: http://swap.fm/l/WCW054IGNZnSnTzEXPTN
Listen to Geri’s full episode of How to Fail here: swap.fm/l/a7i32bvmHld3JFuDmShl
🔗 LINKS + MENTIONS:
Bereavement support: https://www.cruse.org.uk/
Elizabeth’s Substack: https://theelizabethday.substack.com/
Join the How To Fail community: https://howtofail.supportingcast.fm/#content
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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 [email protected]
Learn more about your ad choices. Visit podcastchoices.com/adchoices
23 March 2026, 12:00 am - More Episodes? Get the App