How To Fail With Elizabeth Day

Emilia Clarke, Emmy‑nominated actor best known as Daenerys Targaryen, talks about her rise to fame, learning Russian for Ponies, and producing for the first time. She reveals her terrifying aneurysm recoveries and founding Same You. She reflects on imposter syndrome, grief for her dad, and navigating fame and beauty culture.

Aline Brosh McKenna, screenwriter and director best known for The Devil Wears Prada and co-creator of Crazy Ex-Girlfriend, reflects on a career that flipped at 38. She chats about writing bold, brash characters, revisiting Miranda for a sequel, her scrappy on-set craft, failed magazine dreams that nudged her to screenwriting, and the hard-won confidence to ask for what she wants.

Richard Gadd, writer, actor and comedian behind Baby Reindeer and Half Man. He talks about sudden global fame and its effect on self-worth. He explores transforming physically and psychologically for roles. He discusses rebuking shame, sexuality beyond labels, and how workaholism, family and survival shaped his storytelling.

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 podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Emma Grede, entrepreneur and investor who co-founded Good American and helped launch SKIMS, talks ambition, hustle and resilience. She reflects on her East London roots, work-life trade-offs and a fearless work ethic. She also opens up about parenting, fertility choices and learning from public business setbacks.

Sophie Habboo, podcaster, model and co‑founder of JamPot who features in the Disney+ film Raising Chelsea. She talks candidly about overwhelm and wedding anxiety, a late ADHD diagnosis, struggles with people‑pleasing and boundary‑setting, and the fears and realities of new motherhood. Conversations are frank, warm and often surprising.

A lively dive into Richard III’s tangled legacy, from alleged murders and Tudor propaganda to surprising legal reforms. They trace the real-life drama of Bosworth, the sensational discovery of his remains under a Leicester car park, and why cultural storytelling keeps reshaping his reputation. Short takes on mystery, revival, and how history turns failure into fascination.

Amy Jackson Westwick, Liverpool-born Bollywood star and podcast host. She recounts rising from pageants to international films. She talks about growing up fast, being drawn to controlling partners, breaking patterns and building a blended family. Short, candid and personal.

Miranda Hart, British comedian who married at 51, shares a charming first-date tale. Celeste Barber, Australian comedian and actress, recalls meeting her husband young and navigating stepparenting while pursuing comedy. Glennon Doyle, American author and activist, talks about leaving a marriage for love, co-parenting and setting firm family boundaries. They discuss meeting love at different life stages with humour and warmth.

Chris Appleton, celebrity hairstylist and memoirist, reflects on a life of red carpets, viral looks and hard-won resilience. He talks about shame and coming out, imposter feelings driving his work, identity expressed through hair, social media pressure, and how personal healing and relationships shaped his story.