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Reading about Stoicism won’t change your life—practicing it will.

In this conversation with Donald Robertson, one of the world's leading Stoic authors and cognitive-behavioral therapists, we explore a major misconception: Stoicism isn’t just a philosophy to study—it’s a way of life to train.

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What if another person could act as a mirror for your mind? 

In this thought-provoking conversation with philosopher Donald Robertson we delve into Socrates' timeless insights on wisdom, self-awareness, and the art of questioning. Discover how Socrates used deep dialogue to uncover life’s most fundamental truths and what he meant by an eye that can see itself.

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In this lesson, I speak to Stoicism expert Donald Robertson about how to apply the Socratic method. 

Discover the timeless wisdom of Socrates and his groundbreaking two-column technique—a simple yet profound method for improving critical thinking, questioning assumptions, and making better decisions. This ancient approach to self-improvement has inspired philosophers like Epictetus, Seneca, and Marcus Aurelius, and remains a powerful tool for modern personal growth.

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How do you know when to speak up and when to stay silent? When to push forward and when to step back? In this conversation with Donald Robertson, we explore the concept of coping flexibility—the ability to adapt your response based on the situation.

Drawing from Stoicism, cognitive behavioral therapy (CBT), and martial arts, we discuss:

📌 Key Topics in This Interview:

- What is coping flexibility, and why does it matter?
- The Stoic skill of picking your battles wisely.
- Epictetus’ lesson: How do you know if you can fight a lion?
- Why even Marcus Aurelius practiced martial arts.
- The role of self-knowledge in decision-making.
- How to build practical wisdom for facing adversity.

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Modern Stoicism often focuses on self-control and resilience, but what if we’ve overlooked its most important lesson? 

True Stoicism is about strength through compassion. Marcus Aurelius believed that anger is weakness and that true power comes from brotherly love and justice. Yet today, Stoicism is often misrepresented as cold, emotionless, and distant.

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In this episode, we explore practical strategies to manage challenging relationships, including high-conflict individuals and those with personality disorders. Drawing from Stoic philosophy and modern psychology, we cover:

• Why ancient Stoics emphasized handling insults and toxic people.
• The distinction between caring and caretaking—and why caretaking can harm you.
• Empathy vs. compassion: understanding the psychological and emotional differences.
• Communication frameworks like the "I" Model, DEAR MAN, and Nonviolent Communication (NVC).
• Tools for setting boundaries effectively without escalating conflict.
• Grey Rock technique: when and how to use it in abusive dynamics.
• Tactical empathy and the power of tone, labeling, and mirroring for conflict de-escalation.

If you've ever struggled with navigating tense relationships, setting boundaries, or balancing compassion without burning out, this episode is packed with insights and actionable advice.

Key Takeaways:

1. The Caretaking Trap: Caring is healthy, but overextending yourself to meet others' needs while neglecting your own is not. Learn how to protect your emotional well-being.
2. Empathy vs. Compassion: Empathy can be hijacked and lead to poor decisions. Cultivate compassion instead—a detached yet intentional approach to helping others.
3. Boundary Setting Basics: Boundaries are about what you do, not controlling others. Learn practical methods to uphold boundaries with confidence.
4. Communication Tools: Techniques like the "I" Model, DEAR MAN, and NVC help you express yourself assertively and resolve conflicts constructively.
5. Grey Rock Strategy: Make yourself uninteresting to toxic people by limiting engagement and avoiding emotional responses.
6. Tactical Empathy: Use tone and labeling to de-escalate tense situations and foster collaboration.

Resources Mentioned:

• The Compassionate Mind by Paul Gilbert
• Against Empathy by Paul Bloom
• Stop Caretaking the Narcissist or BPD by Margalis Fjelstad
• Never Split the Difference by Chris Voss
• Not Nice: Stop People-Pleasing, Staying Silent, & Feeling Guilty by Dr. Aziz Gazipura

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In this episode, I sit down with Donald Robertson, renowned author, psychotherapist, and expert in ancient philosophy, to dive deep into the life, methods, and lessons of Socrates. Donald brings his unique perspective, blending cognitive behavioral therapy (CBT) and Stoic philosophy, to explore why Socrates remains a pivotal figure in philosophy—and what we can learn from his methods today.

Donald’s new book, How to Think Like Socrates, is out now!
📖 Get the book here
🎧 Listen to the audiobook here

🎙️ Episode Highlights

1. Socrates’ Legacy

• Socrates shifted philosophy from nature to ethics, asking: How should we live?

2. The Socratic Method

• Mastering the art of questioning, he emphasized critical thinking over rigid beliefs.
• His two-column technique parallels modern CBT tools.

3. Emotional Resilience

• Socrates taught that setbacks, like failure or loss, can lead to growth and wisdom.
• “Injustice harms the perpetrator more than the victim.”

4. Xanthippe: His Wife

• Known for her temper, Socrates viewed her as a challenge to cultivate patience:
  “Xanthippe’s thunder is always followed by rain.”

5. Ancient Self-Help Critique

• Socrates critiqued passive self-help, urging active engagement and self-reflection.

6. Philosophy in Action

• His life, trial, and death embodied the examined life.

📖 Get Donald Robertson’s new book:

• How to Think Like Socrates
• Audiobook

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In this episode of our series on crafting a Stoic daily routine, we focus on how to build effective work rituals. These rituals are designed to help you find deeper meaning and purpose in whatever form of work you do—whether it’s a formal job, creative endeavor, or a personal project like martial arts. Here are the key highlights from the episode:

Episode Notes:

1. Broadening the Definition of Work

• Work doesn’t have to be limited to a traditional career. We explore how to recognize anything you spend time on and take seriously as your “work”—whether it's drawing, studying martial arts, or any passion project.

2. Pre-Work Ritual: Six Key Points

• Inspired by John Yates' "The Mind Illuminated," we dive into a six-step preparation ritual that helps set the stage for a successful work session.
• Key elements include defining your motivation, setting specific goals, acknowledging expectations, committing to diligence, addressing potential distractions, and preparing your work environment.

3. Finding Enjoyment in Your Work

• We discuss the importance of enjoying the process rather than seeing work as a box to tick off your list. Finding ways to enjoy your work not only makes it more sustainable but also enriches the entire experience.

4. The Power of a Performance Statement

• Develop a performance statement as an affirmation to keep you on track. For example: “Every time I get distracted, I will make a note of the distraction and return to the task.” This simple tool helps reinforce positive behavior and mindfulness during work.

5. Work as Meditation

• Applying a meditative mindset to work helps you stay present and focused. Just like mindfulness meditation, when you lose focus, gently redirecting yourself back to the task at hand can transform your productivity and mindset.

6. Post-Work Reflection

• Reflecting on what went well after each work session is crucial. Focus on three positive outcomes to reinforce growth and keep yourself motivated.

7. Working with Others: The EAR Acronym

• Good communication during collaboration can be broken down into Empathy, Assertiveness, and Respect (EAR). This simple framework helps improve how you navigate work relationships and difficult dynamics.

8. Premeditation of Adversity

• Inspired by Marcus Aurelius, we explore the Stoic practice of **premeditating potential obstacles** to remain calm and composed during challenging moments at work. It’s not about being negative but about being prepared

Resources Mentioned:

• John Yates' "The Mind Illuminated"** – The inspiration behind the six-point pre-work ritual.
• Three Pillars of Skillful Communication Cheat Sheet – A quick primer to help you improve communication and navigate work relationships effectively.
  
  Related Links:
• 10-Day Course: Stoic Survival Guide for Navigating Troubled Relationships – A course designed

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In this episode, we dive into the power of a structured morning routine inspired by Stoic philosophy. We'll explore practical steps you can take to start your day with clarity, purpose, and resilience. From reflecting on Stoic quotes and mindful journaling to incorporating meditation and even cold exposure, this episode offers a comprehensive guide to building a morning routine that sets a positive tone for the rest of your day.

Episode Highlights:

• [02:15] Reflecting on a Stoic Quote: Start your day by reading and contemplating a Stoic quote. This simple practice helps align your mindset with Stoic principles right from the moment you wake up.
• [05:30] The Power of Stoic Journaling: Learn how to use journaling to cultivate gratitude, anticipate obstacles, and set a clear intention for the day.
• [12:00] Meditation for Mindfulness: Discover the benefits of starting your morning with a brief meditation session to cultivate presence and awareness
• [16:40] Reading Stoic Texts: Incorporate Stoic readings into your routine to fortify your mind against daily challenges and deepen your understanding of Stoic principles.
• [20:30] Embracing Cold Exposure: Understand how integrating cold showers into your morning can build resilience and enhance mental discipline.
• [24:15] Death Meditation: A reflective practice to remind yourself of life's impermanence and motivate you to live fully.
• [28:10] Dressing with Intention: Explore how your clothing choices can reflect your values and help you live more authentically.
  
  

Resources Mentioned:

• Meditations* by Marcus Aurelius
• Letters from a Stoic* by Seneca
• Atomic Habits* by James Clear

Enjoyed this episode? Subscribe to the podcast and leave a review! Don’t forget to share this episode with someone who could benefit from creating a more intentional morning routine.

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In this guided meditation, you are encouraged to transform feelings of judgment towards others into opportunities for self-reflection and personal growth. Drawing on the wisdom of Marcus Aurelius, the meditation leads you through a process of recognizing your own faults, practicing self-compassion, and extending empathy towards those you might judge. By reflecting on the lessons these situations offer, you can deepen your understanding and commitment to your own growth, fostering greater wisdom and compassion in your daily life.

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