Stephen Grosz - ‘Real love is going to hurt’ episode artwork

EPISODE · Oct 8, 2025 · 52 MIN

Stephen Grosz - ‘Real love is going to hurt’

from How To Fail With Elizabeth Day · host Elizabeth Day and Sony Music Entertainment

Warning: this episode may contain MIND-BLOWING moments. Stephen Grosz is a practising psychoanalyst and a personal hero of mine. He has worked with patients for more than 45 years and his first book, The Examined Life, drew on these experiences. When it was published in 2013, it caused a sensation and went straight to number one in the Sunday Times bestseller list. Since then, hundreds of thousands of readers, including me, have taken it to our hearts. Now 12 years on from his debut, Grosz is back with Love's Labour, which asks fundamental questions around how to love and be loved in return, drawing on his almost half a century of clinical expertise. In this episode we discuss why real love causes suffering, why failed marriages are often the best kind, the difference between surrender and submission in relationships, why loss has to be part of being human and how we can be happy. Plus: a fascinating peek into what it’s like to be a psychoanalyst when I get to ask ‘are you ever annoyed by your clients?’ ✨ IN THIS EPISODE: 02:28 Understanding Attachment to Suffering 04:25 The Role of Denial in Our Lives 06:32 Failures and Self-Perception 07:23 Stephen's Childhood 21:46 The Power of Unconscious Signals 25:24 Navigating Change and Loss 26:25 The Anxiety of Letting Go 28:22 The Price of Love 29:23 Writing from the Heart 30:16 Support Systems 32:27 Family Dynamics and Psychoanalysis 36:51 Surrender vs. Submission 45:25 Understanding Pain and Grief 48:25 Final Thoughts and Farewell 💬 QUOTES TO REMEMBER: The aim of life is to see oneself clearly, and the world clearly. Psychoanalysis is two people not knowing - together. We have to figure it out together, and that means both of us will make mistakes and I will get it wrong. These failures brought me embarrassment, unhappiness, and pain. I wouldn't wish them away. Real love is going to hurt 🔗 LINKS + MENTIONS: Stephen’s new book - Loves Labour: www.stephengrosz.com Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 📚 WANT MORE? Dr Nicole LePera - The Holistic Psychologist sheds light on life’s struggles: https://link.chtbl.com/Tlf5L5Jb Emma Reed Turrell - the psychotherapist and author joins Elizabeth to discuss people-pleasing and the art of setting boundaries: https://link.chtbl.com/zthtQyEm Alain de Botton - the famed philosopher on how to love and be loved: https://link.chtbl.com/RBaS4VUy 💌 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 Substack: https://theelizabethday.substack.com/ Elizabeth and Stephen answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: howtofailpod.com 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 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

Warning: this episode may contain MIND-BLOWING moments. Stephen Grosz is a practising psychoanalyst and a personal hero of mine. He has worked with patients for more than 45 years and his first book, The Examined Life, drew on these experiences. When it was published in 2013, it caused a sensation and went straight to number one in the Sunday Times bestseller list. Since then, hundreds of thousands of readers, including me, have taken it to our hearts. Now 12 years on from his debut, Grosz is back with Love's Labour, which asks fundamental questions around how to love and be loved in return, drawing on his almost half a century of clinical expertise. In this episode we discuss why real love causes suffering, why failed marriages are often the best kind, the difference between surrender and submission in relationships, why loss has to be part of being human and how we can be happy. Plus: a fascinating peek into what it’s like to be a psychoanalyst when I get to ask ‘are you ever annoyed by your clients?’ ✨ IN THIS EPISODE: 02:28 Understanding Attachment to Suffering 04:25 The Role of Denial in Our Lives 06:32 Failures and Self-Perception 07:23 Stephen's Childhood 21:46 The Power of Unconscious Signals 25:24 Navigating Change and Loss 26:25 The Anxiety of Letting Go 28:22 The Price of Love 29:23 Writing from the Heart 30:16 Support Systems 32:27 Family Dynamics and Psychoanalysis 36:51 Surrender vs. Submission 45:25 Understanding Pain and Grief 48:25 Final Thoughts and Farewell 💬 QUOTES TO REMEMBER: The aim of life is to see oneself clearly, and the world clearly. Psychoanalysis is two people not knowing - together. We have to figure it out together, and that means both of us will make mistakes and I will get it wrong. These failures brought me embarrassment, unhappiness, and pain. I wouldn't wish them away. Real love is going to hurt 🔗 LINKS + MENTIONS: Stephen’s new book - Loves Labour: www.stephengrosz.com Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 📚 WANT MORE? Dr Nicole LePera - The Holistic Psychologist sheds light on life’s struggles: https://link.chtbl.com/Tlf5L5Jb Emma Reed Turrell - the psychotherapist and author joins Elizabeth to discuss people-pleasing and the art of setting boundaries: https://link.chtbl.com/zthtQyEm Alain de Botton - the famed philosopher on how to love and be loved: https://link.chtbl.com/RBaS4VUy 💌 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 Substack: https://theelizabethday.substack.com/ Elizabeth and Stephen answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: howtofailpod.com 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 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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Stephen Grosz - ‘Real love is going to hurt’

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This episode was published on October 8, 2025.

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Warning: this episode may contain MIND-BLOWING moments. Stephen Grosz is a practising psychoanalyst and a personal hero of mine. He has worked with patients for more than 45 years and his first book, The Examined Life, drew on these experiences....

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