The Daily Stoic: The 3-Step Formula for Difficult Conversations

Host: Ryan Holiday
Guest Excerpt: Jefferson Fisher
Date: July 6, 2025

Episode Overview

In this episode, Ryan Holiday explores the Stoic approach to handling difficult conversations and people. Drawing inspiration from a recent conversation with lawyer and viral communicator Jefferson Fisher, Ryan features an excerpt from Fisher's book The Next Conversation, which lays out concrete communication strategies for when kindness and empathy aren’t enough. The episode provides listeners with practical, step-by-step tools—grounded in Stoic philosophy and real-world legal experience—to manage conflict without abandoning respect for themselves or others.

Key Discussion Points & Insights

The Stoic Foundation for Handling Difficult People (00:43 - 03:27)

• Ryan Holiday sets up the episode by discussing the inevitability of dealing with difficult people. He references Marcus Aurelius’ teachings:
  • "You can't let these people implicate you in ugliness and you're made to work with them. You are made to work together." (01:22)
  • Dealing with difficult people is central to Stoic practice—it's where theory becomes reality.
• Ryan introduces Jefferson Fisher and his communication framework as a means to navigate tough interpersonal scenarios.

Real-Life Case Study: Conflicted Sisters (03:27 - 08:13)

• Jefferson Fisher shares a story of two sisters in a legal dispute over a shared business, illustrating the emotional complexity and high stakes of conflicts with close relations.
• When negotiations devolve into personal attacks, Fisher advises:
  • "You always play nice…that doesn't mean you play soft. You don't need to push back. You just can't be pushed over." (05:08)
• The pivotal moment:
  • The hostile sister lashes out: "And I've never liked you. You're dead to me anyway."
  • Fisher’s client responds after a pause: "I need you to repeat that." The sister cannot, marking a shift in power and tone.
  • The client then asserts: "I'm getting off this rollercoaster. If you want to get off with me, do it now. And I've always loved you." (07:16)
• Takeaway:
  • Empathy is important but not always possible. When compassion is exhausted or exploited, new strategies are needed.

When Push Comes to Shove: Standing Up for Yourself (09:50 - 14:00)

• Fisher outlines the common responses to persistent disrespect: withdrawal or escalation. Instead, he advocates a third path:
  • Use assertive responses that are bold but not disrespectful.
  • Key Principle:
    • "You have to know and consciously decide if the person standing in front of you is one who means something to you. To assertively disagree and stand up for yourself is both an art and a skill." (10:45)

The 3-Step Formula: Deflecting Insults & Belittling (11:30 - 18:30)

• Fisher explains why people insult or belittle: pursuit of the dopamine rush from controlling the situation or provoking a reaction.
• Three-Step Response to Insults:
  1. Pause:
     • "The long pause gives their words a chance to echo back to them...the silence takes away their dopamine." (13:01)
  2. Echo/Repeat:
     • Slowly repeat what was said, e.g., "I need you to repeat that." This places the responsibility back on the aggressor and removes the satisfaction (“dopamine”) from their attack. (16:43)
  3. Breathe/Control:
     • Focus on deep, steady breathing to preserve your composure and keep emotions in check.
• For belittling or condescending remarks:
  • Ask them to repeat it: Throws off their expectations and draws attention to the remark’s impropriety.
  • Ask outcome-based questions:
    • "Did you want that to hurt?"
    • "Did you want that to embarrass me?"
    • "Was that supposed to make me feel small?"
    • "Did that feel good to say out loud?" (17:44)
  • Reply with silence:
    • Let the awkwardness hang in the air; typically, the other person will retreat or backtrack.

Notable Quotes & Memorable Moments

• Ryan Holiday:
  • "Dealing with difficult people is where meditation starts." (01:10)
  • "It is not inevitable that we have to be difficult." (02:58)
• Jefferson Fisher:
  • "Kindness alone doesn't always work. No amount of patience or gentle explanation makes a difference. The person is committed to misunderstanding you." (09:51)
  • "Your value is too high for such low behavior." (14:50)
  • "Let their poor behavior linger as your silence shows you to be the one with control and composure." (18:25)
• Pivotal Client Moment:
  • "I'm getting off this rollercoaster. If you want to get off with me, do it now. And I've always loved you." (07:16)

Timestamps for Key Segments

• 00:43 – Stoic context for dealing with difficult people
• 03:27 – Fisher's case study: Family business dispute
• 05:08 – On being nice but not soft
• 07:16 – The transformative conversation
• 09:50–10:45 – When kindness isn’t enough, standing up for yourself
• 11:30–13:01 – Why people belittle and insult others
• 13:01 – Step 1: The Power of the Pause
• 16:43 – Step 2: Repeat/Echo their words
• 17:44 – Step 3: Outcome-based questions
• 18:25 – Let silence be your reply

Final Thoughts

The episode blends Stoic wisdom with legal and psychological tactics for handling conflict without sacrificing one’s values or self-respect. Jefferson Fisher’s 3-step formula—Pause, Echo, Breathe—is a practical guide for listeners hoping to maintain composure and assertiveness in the most trying conversations.

Useful for:
Anyone facing regular conflict at work, in families, or in relationships, and for those seeking to apply Stoic principles to modern life’s interpersonal challenges.

For further reading:
The Next Conversation by Jefferson Fisher.
Watch Ryan’s full interview with Jefferson Fisher on YouTube.