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 📚 WANT MORE? 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? 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 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
