How To Fail With Elizabeth Day

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Stephen Grosz - ‘Real love is going to hurt’

Oct 8, 2025

Guest

Stephen Grosz

In this engaging conversation, Stephen Grosz, a seasoned psychoanalyst and author, discusses the intricacies of love and loss after nearly fifty years in practice. He explores how early family experiences shape our attachments and the role of denial in relationships. Grosz delves into the painful yet essential nature of real love and how failed marriages can lead to deeper connections. His insights into surrender versus submission reveal how intimacy can flourish or falter. Listeners will gain a profound understanding of grief as a catalyst for desire.

52:23

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INSIGHT

Attachment To Familiar Suffering

Early family patterns can create an 'attachment to suffering' that feels safer than happiness.
Stephen Grosz warns that unconscious familiarity can direct life choices unless made into a story.

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ADVICE

See Your Part In Failure

Do try to see your own role in failures rather than placing blame externally.
Stephen Grosz says the aim of life is to see oneself and the world clearly, and denial blocks that.

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ANECDOTE

Childhood Among Survivors

Grosz describes growing up with Holocaust survivors in his community and a cousin from Auschwitz.
He recalls a therapist who told her she met him not because she was mad but because she lived in a mad world.

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How childhood stories shape adult suffering

04:07 • 2min

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How does denial shape our life story?

06:24 • 3min

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Growing up with Holocaust-survivor family dynamics

09:38 • 3min

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Why analysts need their own analysis

What failures taught me about seeing clearly

15:13 • 51sec

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Why analysis is two people not knowing together

16:04 • 2min

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When patients unconsciously test the analyst

17:42 • 3min

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Do analysts feel anger or boredom with patients?

20:35 • 3min

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What unconscious signals reveal in therapy

How is love built around loss?

29:10 • 4min

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How writing as myself replaced writing like an analyst

32:48 • 2min

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How family made me less austere as an analyst

35:06 • 2min

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Does success and praise matter to you?

What's the difference between surrender and submission?

41:23 • 5min

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Why failed marriages can lead to true remarriage

46:34 • 2min

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What is a proper psychological marriage?

49:03 • 52sec

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How should someone handle breakup grief and hope?

• Mentioned in 23 episodes

The interpretation of dreams

Sigmund Freud

In this seminal work, Freud introduces his theory of the unconscious with respect to dream interpretation and discusses what would later become the theory of the Oedipus complex. He argues that dreams are forms of 'wish fulfillment' and are influenced by unconscious forces and censorship. The book differentiates between the manifest content and latent content of dreams and explores the mechanisms of dream formation, including displacement and the 'dream-work'. Freud uses his own dreams and those of his patients to illustrate his theories, providing a deeply personal and insightful look into the human psyche.

Love's Labour's Lost

William Shakespeare

Love's Labour's Lost follows the King of Navarre and his three companions as they attempt to swear off women for three years to focus on study and fasting. However, their resolve is quickly tested when they encounter the Princess of France and her ladies-in-waiting. The men eventually abandon their vow and pursue the women, leading to a series of comedic misunderstandings and ultimately, a year-long wait to prove their love. The play explores themes of love, loyalty, and the complexities of relationships.

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• Mentioned in 3 episodes

The Examined Life

How We Lose and Find Ourselves

Stephen Grosz

In 'The Examined Life', Stephen Grosz shares a series of poignant and insightful essays based on his experiences as a psychoanalyst. The book explores how people lose and find themselves through their struggles and transformations, offering a compassionate and intelligent perspective on human psychology. It has been praised for its clarity and depth, drawing comparisons to Chekhov and Oliver Sacks.

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?

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Production & Post Production Coordinator: Eric Ryan

Sound Engineer: Matias Torres

Assistant Producer: Suhaar Ali

Senior Producer: Hannah Talbot

Executive Producer: Carly Maile

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