How To Fail With Elizabeth Day

Episode: Stephen Grosz – ‘Real love is going to hurt’
Date: October 8, 2025
Host: Elizabeth Day
Guest: Stephen Grosz, psychoanalyst and author

Episode Overview

In this deeply insightful episode, Elizabeth Day is joined by renowned psychoanalyst and author Stephen Grosz to explore the transformative power of failure, especially within the context of love and personal growth. Drawing from more than 45 years of clinical experience and two acclaimed books—The Examined Life and Love’s Labour—Grosz delves into failure as a catalyst for self-understanding, authenticity, and genuine connection. Together, Day and Grosz discuss how unconscious scripts shape us, why denial can hinder healing, and the distinction between real and imitative love.

Key Discussion Points

1. The Power of Unconscious Stories

[04:28–06:24]

• How Our Stories Shape Us: Grosz illustrates how people unconsciously internalize and repeat patterns associated with childhood suffering, impacting adulthood satisfaction.
• Attachment to Suffering: He shares an example of a patient more comfortable with misery due to familiarity:

  “There are things from their childhood which they will not remember...they find ways of spoiling what they have, and being unhappy...they have an attachment to suffering...it becomes safer than daring to be happy.” (Stephen Grosz, 05:13)

• Importance of Articulating the Narrative: Understanding and telling one’s story is the first step toward interrupting self-defeating cycles.

2. Denial and Self-Deception

[06:24–08:33]

• Denial as a Deflection: Denial manifests in offloading blame; patients often attribute failure to others, not themselves.
• The Analyst’s Role: Grosz tries to help patients see their part in failure, shifting from “the problem is in the other” to self-examination.

• “Denial is a refusal to...see oneself clearly and the world clearly. It's the insistence that the problem is over there in someone else, not in me.” (Stephen Grosz, 07:30)

3. Influence of Family and Early Trauma

[09:38–12:25]

• Holocaust Legacy: Grosz describes his immigrant family’s traumas—Holocaust survival, assimilation, and unspoken grief—and their indirect psychological impact on him.
• Motivation for Analysis: He reveals how unresolved familial experiences pushed him to want to make sense of his own and others’ stories.

• “I loved my parents, but I didn’t altogether trust them. Part of that was I had a birth defect...my parents thought if we talked about it, it would upset me. So we never talked about it.” (Stephen Grosz, 12:30)

4. The Three Failures:

a. Failure 1: To be a Psychoanalyst is to Fail Every Day

[15:14–23:46]

• Collaboration over Perfection: Grosz learned that analysis is not about omniscience, but two people “not knowing together.”
• Welcoming Mistakes:

  “the psychoanalysis is two people not knowing together. Both of us will make mistakes ...you get it wrong each day, but the other person intuits you're trying.” (Stephen Grosz, 16:14)

• Failure as Experience: Sometimes, patients want to witness the analyst fail, either as a test or to feel understood at an experiential level.
• Limits of Help: Even with best intentions, some analyses seem to fail or are incomplete; “you never know what that child is making use of or not making use of.” (Stephen Grosz, 20:44)

b. Failure 2: Mistaken Identity as a Writer

[33:22–37:50]

• Writing Like an Analyst vs. Like Himself: Grosz admits he initially hid behind psychoanalytic jargon, but personal experiences—falling in love, marriage, fatherhood, supportive friendships—helped him find his authentic voice.
• Fear as the Enemy of Writing:

  “Fear is the enemy of writing. I felt supported. I had a safety net...feeling held, loved...that made me feel, yeah, I can try this.” (Stephen Grosz, 33:51)

• Impact on Practice: Family life and vulnerability made him less austere and more open with clients.

c. Failure 3: Not Understanding the Difference Between Surrender and Submission

[42:13–49:54]

• Submission vs. Surrender: Submission is giving everything in hopes of being transformed by another’s love—a defense against truly letting go. Surrender is mutual, honest vulnerability.

• “Submission...is the belief that if I give you everything...you will love me back and...heal me...Of course, that deal is completely unrealizable and never works. Surrender...is that incredible feeling when two people meet...you can let go to this person and they let go to you.” (Stephen Grosz, 42:34)

• People-Pleasing as Defense: Performing love blocks genuine connection; real love requires risking true self-revelation.
• Remarriage Within Marriage: Many couples only fall in love “properly” after enduring failure and pain together:

  “Some of the best marriages I’ve seen are failed marriages that then there’s a kind of remarriage...if we are able to see clearly, we can really fall in love.” (Stephen Grosz, 47:26)

5. Change, Loss, and Growth

[29:28–32:23]

• Change is Built on Loss: Each stage of life requires letting go—of childhood, of parental ties, of visions of ourselves—to create space for what's new.

• “We love is built around loss. Loss is at the core of love.” (Stephen Grosz, 29:46)

• The Price of Love:

  “If you love someone, it doesn’t end well. It'll either end in divorce or death. Real love is gonna hurt because...at some point there will be loss.” (Stephen Grosz, 32:34)

6. The Value of Feeling Pain

[51:02–53:46]

• Embracing Heartbreak: Grieving loss is essential and a true barometer of the heart’s desires.

• “Those feelings are the most accurate and subtle instrument you have for knowing your heart...If you don't listen to those pains...you have no way of knowing what you desire.” (Stephen Grosz, 51:02)

• Self-Deception and Self-Knowledge: The work of analysis and personal reflection helps undo illusions about self and relationships.

Notable Quotes & Memorable Moments

• On therapeutic failure:

  “To be a psychoanalyst is to fail every day.” (Stephen Grosz, 16:04)

• On relationships:

  “Some of the best marriages I’ve seen are failed marriages…” (Stephen Grosz, 47:26)

• On the reality of love:

  “If you love someone, it doesn’t end well. It’ll either end in divorce or death.” (Stephen Grosz, 32:34)

• On grief and heartbreak:

  “Those feelings are...the most accurate and subtle instrument you have for knowing your heart.” (Stephen Grosz, 51:02)

• On surrender vs. submission:

  “Submission or submissiveness is in fact a defense against surrender...when we are really genuinely surrendered to another person, we're back in the realm of accepting reality.” (Stephen Grosz, 44:03)

Important Timestamps

• Understanding how stories shape us: 04:28–06:24
• Denial and self-deception: 06:24–08:33
• Trauma and family history: 09:38–12:25
• Failure as essential to psychoanalysis: 15:14–23:46
• Change, loss, and the price of love: 29:28–32:23
• The difference between surrender and submission: 42:13–49:54
• Embracing pain after a breakup: 51:02–53:46

Tone and Atmosphere

The conversation is warm, nuanced, and reflective—filled with both vulnerability and intellectual rigor. Grosz is thoughtful and candid, often turning questions back on himself. Day’s admiration and openness foster a space for deep inquiry and shared emotion.

Conclusion

This episode stands as a meditation on the necessity of failure—not just as a route to success, but as the very soil in which love, change, and self-understanding grow. Stephen Grosz, through personal and clinical wisdom, gives listeners permission to embrace pain, question their narratives, and recognize that, ultimately: “All our failures are failures in love.” (Elizabeth Day quoting Iris Murdoch, 54:16)

Recommended Read:
Love’s Labour by Stephen Grosz
The Examined Life by Stephen Grosz

For anyone facing transition, heartbreak, or self-doubt, this episode offers sustenance and hope—a reminder that failure is not just survivable, but meaningful.