How To Fail With Elizabeth Day

It was a privilege to have Bonnie Tyler on How to Fail back in 2024 - and we are heartbroken to hear of her passing today.

Bonnie was open, funny and moving when she joined me on How to Fail. Total Eclipse of the Heart made her a global star, and at the time of this recording, she managed to squeeze in an hour on How to Fail between gigs and the release of her new album, In Berlin. It was also her first ever podcast interview.

You might want to bring the tissues for this one, as we have a bit of a weep when Bonnie talks about losing her amazing mum. We also touched on miscarriage and a childfree life. Plus her failure at elocution lessons, the fascinating story behind her friendship with Tina Turner, performing for Putin (no, really), being a bit of a hoarder and the secret to a 50-year marriage.

We love you Bonnie Tyler, rest in peace.

Production & Post Production Coordinator: Lily Hambly

Engineer: Gulliver Tickell and Josh Gibbs

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

Guest bookings for How To Fail only come from official @sonymusic.com emails

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

In this episode, I sit down with bestselling author‑illustrator Charlie Mackesy, whose work – The Boy, the Mole, the Fox and the Horse – has become a global touchstone for kindness, vulnerability and hope.

Yet Charlie’s path was anything but straightforward: he grew up feeling inherently at fault, shaped by the pressures of competitive schooling and the emotional weight of carrying the painful stories readers now share with him.

He talks about failing his driving test four times and the devastating loss of his best friend, Jamie, in a car crash – a grief that propelled him to London and sparked the first moment he began drawing compulsively, with music as solace.

Charlie reflects on not achieving what he calls “conventional success” through marriage or children, the underrated importance of friendship and the power of kindness and self‑compassion.

We also explore his years of not earning a living as an artist – a period he now sees not as failure, but as an essential process. Charlie urges us to create without fear, to let go of perfection and to live fully in the imperfect present.

✨ IN THIS EPISODE:

00:00 Intro

03:44 Feeling at Fault

04:30 Outsider and School Years

05:55 Carrying Others Stories

13:57 Animals and Ducklings

17:08 Driving Test Failure

18:06 Loss and Aftermath

20:05 Grief Fuels Art

23:14 Bottling Emotions

25:07 Remember Mothers Word

28:28 Mum’s Tactile Reading

29:44 Dementia and Story Comfort

33:21 Redefining Success

37:46 Friendship Essentials

40:37 Kindness and Self Talk

46:09 Failing as an Artist

💬 QUOTES TO REMEMBER:

“When people tell you their weight, their sadness, anything, their failings, whatever it is they tell you, treat it like they’re giving you gold.”

“I just wrote a book about a mole who likes cake and friends who are journeying in a difficult way with each other… but I think people just want to be heard and seen.”

“None of us get out of here alive, so why not try? What have you got to lose?”

🔗 LINKS + MENTIONS:

Charlie’s latest book, Always Remember: The Boy, the Mole, the Fox, the Horse and the Storm, is available from all major UK booksellers.

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

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Jacqueline Wilson - this episode explores how Jacqueline Wilson’s life and career never followed a predictable path. She didn’t become a bestseller until her 40s and the setbacks she faced helped shape the writer she became. It reflects on the imagination and resilience behind unforgettable characters like Tracy Beaker, her ability to reinvent herself, most recently with The Primrose Railway Children and the creativity and determination that have sustained a career spanning more than 100 books. Ultimately, it’s about a woman interrogating creativity, perseverance and the determination required to keep going: swap.fm/l/PawxjS1dFBaohoKZXfpL

💌 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 Charlie answer listener questions in our subscriber series: 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

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

Anastacia has released eight albums and sold over 50 million records worldwide. She has collected a total of 227 gold and platinum certifications and counts Elton John as one of her biggest fans.

In 2000, she released "I'm Outta Love", her debut single, which quickly topped charts worldwide and paved the way for her first album, Not That Kind. This year sees her embark on a major arena tour to celebrate that album’s 25th anniversary.

In this episode we talk about her experience with breast cancer - she underwent a double mastectomy in 2013 after being diagnosed for the second time, dealing with sexism in the music industry and being a mother beyond the traditional sense.

✨ IN THIS EPISODE:

00:00 Intro

02:32 Brodie Joins the Studio

03:15 Day Jobs Before Fame

04:16 Not That Kind at 25

05:31 Finding Her Sound

08:25 Celebrity Gig Stories

11:34 Failures Tech and Glasses

26:04 Dream Glasses Partnership

26:57 Tinted Lenses Origin Story

28:31 Sexism and Image Pressure

31:45 Redefining Femininity

32:32 Cancer Advocacy Fire

37:40 Self Care Birthday Hack

41:44 Writing Singable Songs

44:22 Mothering Beyond Biology

💬 QUOTES TO REMEMBER:

Give yourself a self-care birthday - go and get a mammogram

There are so many different ways to be a mother

 So the word cancer, I didn't like it, but I looked at the first three letters

🔗 LINKS + MENTIONS:

Anastacia is celebrating 25 years since the release of her debut album ‘Not That Kind’ and is taking her #NTK2026 on the road

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Shania Twain - took us back to her childhood, where she felt she grew up too fast, singing in smoke-filled bars at a young age. There are some real similarities between these two episodes - see what you think: swap.fm/l/JyU54nvq2muyBpNFq3B9

💌 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 Anastacia answer listener questions in our subscriber series: 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

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

Welcome to the FIRST EVER How To Fail Roundtable - a format we enjoyed so much we might just keep it. Today, Elizabeth is joined by broadcaster, actor, author and comedian Mel Giedroyc, and presenting powerhouse AJ Odudu for a candid conversation about body confidence, midlife reinvention and self-acceptance. Brought to you by Dove Whole Body Deodorant, they discuss navigating public scrutiny, aging, personal experiences of the menopause and the importance of friendship. 

Together, they explore how honesty, resilience and everyday rituals can help us feel more confident and comfortable in our own skin.

✨ IN THIS EPISODE: 

00:00 Intro

02:39 Mel on body confidence

05:50 AJ on self appreciation

06:53 Freshness and shoot day hacks

09:08 Mel career and live TV

11:46 Screen scrutiny and representation

18:05 Midlife reinvention begins

22:15 The Power of Invisibility

23:51 Slowing Down to Go Deeper

24:58 AJ on Reinvention and Grief

27:32 Daily Rituals as Survival

28:45 Perimenopause Reality Check

30:47 HRT and Finding Relief

33:46 Owning ‘No’ and the Crone Era

35:42 Women Supporting Women Finale

💬 QUOTES TO REMEMBER:

Mel: Body confidence, to me, is literally getting closer to the mirror.

AJ: We don't worship ourselves and honour our bodies in the way that we should. 

Elizabeth: Everything is data acquisition about the thing that went wrong… you can do better next time or make different choices.

🔗 LINKS + MENTIONS:

Dove Whole Body Deodorant: www.dove.com/uk/collections/whole-body.html

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

💌 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

Production & Post Production Coordinator: Eric Ryan  

Engineer: Matias Torres

Assistant Producer: Shania Manderson

Senior Producer: Hannah Talbot

Executive Producer: Alex Lawless

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

In a career spanning four decades, Dame Kristin Scott Thomas has become one of Britain’s most celebrated actors: Four Weddings and a Funeral, The English Patient, The Horse Whisperer, Tell No One and Slow Horses, alongside acclaimed stage work including her Olivier‑winning performance in The Seagull.

Yet her path was far from straightforward: discouraged at drama school, she moved to Paris as an au pair and rebuilt her training from scratch. Her childhood had already been shaped by profound loss after the deaths of her father and stepfather in near‑identical accidents. She has now channelled these experiences into her directorial debut, My Mother’s Wedding, which she also co‑wrote and stars in, alongside Scarlett Johansson, Sienna Miller and Emily Beecham.

We talk about her early grief, the emotional armour she built as a teenager, the chaotic experience of filming with Prince, making My Mother’s Wedding, the power of women writing women, her unforgettable Fleabag monologue and the joy and clarity she has found in her 60s.

✨ IN THIS EPISODE:

00:00 Intro

03:15 Reclaiming a Tragic Narrative

04:59 Joy in her 60s

06:22 Co Writing With Her Husband

07:03 Animation and Childhood Memory

09:07 Casting and Creative Reunions

12:23 Failure One: Prince Film Debut

17:06 Fame Theater and Radical Roles

24:09 Under the Cherry Moon Lessons

25:28 Failure Two: Teenage Grief

26:24 Childhood Losses

27:58 Eldest Sibling Burden

28:37 Acting Through Sadness

29:59 English Patient Reflections

33:19 Four Weddings Role

36:39 Therapy and Healing

43:41 Grief Advice and Faith

45:45 Football and Identity

49:16 Aging and Gratitude

💬 QUOTES TO REMEMBER:

“I wanted to take my past and make it into something positive.”

“If people enjoy what you do, it’s not bad.”

“Having children allowed me to see where I’d gone wrong and where I was beating myself up.”

🔗 LINKS + MENTIONS:

Kristin’s directorial debut, My Mother’s Wedding, is now available in UK cinemas and streaming platforms such as Amazon Prime and Apple TV

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Rosamund Pike - this episode explores how her career has resisted tidy narratives, how she’s navigated fame without reading reviews for 25 years and how her so‑called “failures” – not getting married, struggling with fear, raising two sons while working, even a disastrous attempt at cooking a rabbit – have shaped her. It’s ultimately about a woman interrogating identity, courage and the stories she tells herself:http://swap.fm/l/tePOA4HZ2PoaBBwudnv7

💌 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 Kristin answer listener questions in our subscriber series: 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

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