Podcast Summary: “Esther Calling - I’m Afraid of Losing More Than Just the Business”

Where Should We Begin? with Esther Perel
Release Date: September 15, 2025

Episode Overview

In this heartfelt episode, a caller seeks advice from Esther Perel about navigating the potential failure of a company she co-founded with a close business partner and later ran alongside her two brothers. Recent business setbacks and deteriorating relationships have left her struggling with guilt, responsibility, anger, and profound sadness. Her main concern is how to reframe her thinking to preserve family and professional ties regardless of the business outcome. The conversation delves into the emotional nuances of family businesses, the interplay of personal and professional roles, and the difficulties of balancing self-fulfillment with loyalty to others.

Key Discussion Points & Insights

1. Background & Caller’s Dilemma

• The caller co-founded a company 10 years ago; her two brothers joined later.
• Three years ago, after personal struggles and a breakdown in her relationship with the business partner, she stepped back from day-to-day management.
• Company performance worsened after her reduced involvement; relationships among her brothers and the partner also declined.
• Facing probable sale or closure, she battles feelings of shame, sadness, responsibility, and anger—particularly over trusting loved ones and the resulting situation.

2. Family Dynamics at Work (04:26–06:21)

• The caller is the middle child and only girl among siblings, describing a happy upbringing.

• Distinction blurred between familial and professional roles; she often feels responsible for the family’s harmony at work.

  • Quote:
    “I seem to have understood that there is something that you bring to the company that mirrors a kind of role that you have had in the family. There’s a kind of a superposition between the role at home and the role at work.”
    — Esther Perel (04:34)

• Tension arises as family relationships complicate objective business decisions.

3. Responsibility, Control, & Guilt (06:21–09:16)

• The caller feels deeply accountable for the company’s success, regardless of official rank.

• Despite wanting no return to a hands-on role, she carries guilt for not preventing failure, especially since she saw warning signs but “let herself be put off.”

• She compartmentalizes her current happiness in her new venture, not sharing successes with her brothers out of sensitivity—describing a mix of guilt and a sense of “betrayal.”

  • Quote:
    “I look back and I see my brothers and the team of the other company having a pretty awful time. And... bringing the two together feels brutal. So I find myself not talking about certain things and not kind of sharing the good times and the excitement with them because it doesn’t feel appropriate.”
    — Caller (08:19)

4. Anger & Unspoken Truths (09:17–11:26)

• The caller is frustrated that her repeated warnings went unheeded, but admits she herself did not want to get involved again.
  • Quote:
    “I’m angry and I can’t say that to them because I know they are working so hard and have never not worked hard. But I’m really annoyed...”
    — Caller (09:37)

5. Why She Stepped Back (11:27–13:53)

• A mix of positive pull (new opportunities) and negative push (business partner’s behavior post-divorces and breakups).
• The close personal relationship with the partner soured during parallel personal crises, changing the partnership’s dynamic.

6. Struggling with Wanting vs. Being Liked (15:44–17:27)

• Esther points out the tension: wanting to do what one desires but also wanting to be liked by others.

  • Quote:
    “It’s very difficult to want to do what you want on a regular basis and to still hope that people will continue to like you.”
    — Esther Perel (16:41)

• The caller recognizes her guilt ebbs and flows with the company’s success: “Now I feel really guilty because I get to keep doing what I want to do and they don’t.”

7. Personal Parallels: The Divorce Analogy (22:13–23:56)

• Caller recognizes a pattern: she left her marriage for personal fulfillment, despite her ex-husband’s reluctance and confusion.
  • Quote:
    “I suppose I sort of, I sort of looked at it as a—again it’s a slightly dramatic way to put it—but it’s like you’re sort of like born alone and you die alone. And fundamentally sometimes you have to make the decisions that are right for you and you cannot carry everyone else’s weight.”
    — Caller (23:34)

8. Working Through Guilt, Responsibility, & Family Boundaries (29:05–34:01)

• Esther highlights the limitation in treating brothers as family first, professionals second. The caller admits this limited her willingness to hold them accountable.

  • Quote:
    “If I used that language, I would find it easier... to hold them to account in a professional way, whereas probably what I’ve done is not held them to account sufficiently in that way, and therefore we find ourselves in a worse position than we would have been.”
    — Caller (29:05)

• Insight: Professional language could have fostered healthier business boundaries.

9. Caretaking & Power Dynamics (32:19–34:01)

• Esther probes the caller’s tendency to “parent” her brothers, questioning whether she truly believes in their capability.
• The caller reflects that this dynamic originated when they first joined the firm inexperienced, but they have long since outgrown that status.

10. Blame, Shame, & Internalized Roles (39:53–42:00)

• Esther distinguishes between responsibility and blame, seeing the caller’s tendency to personalize failure as part of her broader coping strategy.

  • Quote:
    “If it goes well, it’s me, but if it doesn’t go well, it’s also me. There are other people when, if it goes well it’s me and when it doesn’t go well, it’s others, you know.”
    — Esther Perel (40:13)

11. Patterns of Avoidance and Picking: The Need for Candor (46:03–49:04)

• Caller recalls how, in her marriage, irritation and “picking” at her partner surfaced when she wanted out but hadn’t yet acted.

  • Quote:
    “I was picking, right. Everything became source of irritation.”
    — Esther Perel (48:03)

• The marriage therapist’s candor (“there is basically no point you being here because you do not want to be in this marriage”) finally enabled the caller to end things—paralleling the frank reckoning needed in her business situation.

12. Moving Forward: The Real Conversation (49:04–52:50)

• Esther steers the caller to a crucial insight: the conversation with her brothers shouldn’t be just about business or markets, but explicitly about preserving their family bond through this transition.

  • Quote:
    “You matter to me dearly. Companies come and go. You are my brothers for life. And we’re going to go through a difficult transition. What do we need to do as brothers and sisters for us to come through this?”
    — Esther Perel (51:00)

• Esther encourages framing the conversation as a unified goal to maintain their relationship and addressing what each person needs—not just managing logistics but also expressing vulnerability.

Notable Quotes & Memorable Moments

• On Emotional Conflict:
  “I want to do what I want, and that’s not new. And I want to be liked.” — Caller (16:00)

• On Accountability & Language:
  “If I say, ‘oh, my brother’s working really hard, they’re just not performing the role so well at the moment.’ For example, I find it very easy to let them off the hook... I would never in one of my other companies say, ‘oh, my marketing director is working really hard, so even though it’s not working, it’s okay.’” — Caller (30:34)

• On Unspoken Priorities:
  “I want to come out of this as—we’ll always love each other. I want to come out of this as good friends... and I think I’ve never said that that explicitly to them. It feels like maybe a start?” — Caller (50:44)

Important Timestamps

• 00:00–02:11 — Caller introduces her dilemma and asks her central question.
• 04:26–07:07 — Family roles and responsibility in work context.
• 09:03–10:36 — Caller shares deep feelings of conflict, betrayal, and anger.
• 11:50–13:53 — Discussion of what led to stepping back; breakdown in personal/professional relationships.
• 15:44–17:27 — Esther reframes the core conflict as wanting self-fulfillment vs. wanting acceptance.
• 22:13–23:56 — Divorce as an analogy for difficult transitions and guilt.
• 29:05–34:01 — Insight on language and the importance of professional boundaries in family businesses.
• 39:53–42:00 — Blame, responsibility, and internalized roles.
• 46:03–49:04 — Parallels with marriage, “picking” as avoidance.
• 49:49–52:50 — Esther’s guidance on reframing the conversation as about family before business.

Conclusion: Tone, Language, and Takeaways

The episode, in classic Esther Perel style, is compassionate, candid, and exploratory. It offers a vulnerable portrayal of the intersecting complexities of family and business, and the deep work required to separate love from responsibility, and guilt from agency. Both Esther and the caller remain open, self-critical, and often gently humorous (“Don’t make me,” says the caller when Esther prompts her to ask for support).

Takeaway: The path forward isn’t about fixing the unfixable or denying hard feelings, but in opening space for honest conversations about what matters most: maintaining cherished relationships, even as professional chapters close.

“Companies come and go. You are my brothers for life.”
— Esther Perel (51:00)