#128 Ryan Holiday: A Stoic Life
Ryan Holiday, a prolific author and modern philosopher, discusses his writing and reading processes, the value of journaling, and the four virtues of Stoicism. He shares how Stoicism can guide decisions and help manage emotions.
Deep Dive Analysis
17 Topic Outline
Introduction to Stoicism: Philosophy for the World
Ryan Holiday's Prolific Book Writing Process
Integrating Reading and Writing into Daily Routines
The Hidden Costs of Saying Yes and Opportunity Costs
Defining Success and Legacy in Creative Professions
Decoupling Success Metrics: Sales, Criticism, and Personal Pride
Core Teachings of Stoicism: Control and Virtue
Learning from Flawed Individuals and Steel-Manning Arguments
The Paradox of Extraordinary Success and Unbalanced Lives
Prioritizing Longevity and Sustainability Over Immediate Gains
Decision Making: The Power of Momentum and Avoiding Stalling
Accepting What Cannot Be Controlled and Aligning with Reality
Managing Anger and the Corrosive Nature of Passions
The Importance of Pausing Before Responding
Cicero's Opportunism and Lack of Commitment
Journaling for Self-Awareness and Reflection
The Four Stoic Virtues: Courage, Temperance, Justice, and Wisdom
6 Key Concepts
Stoicism
An ancient philosophy originating in Athens, Stoicism is a practical guide for active professionals, helping them navigate the world and make decisions. It emphasizes focusing on what is within one's control and using challenges as opportunities to practice virtue.
Dichotomy of Control
This is a primary Stoic exercise that distinguishes between what is 'up to us' (our thoughts, opinions, actions, beliefs) and what is 'not up to us' (external events and circumstances). The philosophy teaches that any energy spent on things outside our control is wasted.
Steel-Manning
Instead of creating a 'straw man' caricature of an opponent's argument, steel-manning involves understanding and articulating their position as strongly and charitably as possible. This practice not only reveals potential validity in their views but also strengthens one's own argument by preemptively addressing its strongest counterpoints.
Opportunity Cost
The value of the next best alternative that was not chosen when a decision was made. It highlights the hidden cost of saying 'yes' to one thing, as it inherently means saying 'no' to another, often with long-term implications for quality and focus.
The Passions (Stoicism)
Emotional states like envy, lust, anger, fear, pain, and worry that lead individuals away from rational thought. Stoicism views these passions as corrosive forces that contribute to mistakes and hinder clear, strategic decision-making.
The Four Stoic Virtues
These are the cardinal virtues in Stoicism: courage, temperance (self-discipline), justice, and wisdom. Every situation presents an opportunity to practice one or more of these, with wisdom serving as the guiding virtue that determines when and how to apply the others effectively.
9 Questions Answered
Stoicism is an ancient philosophy that originated in Athens, designed for active professionals to guide their decisions and actions in the real world. It's relevant today because it provides a framework for understanding what's within our control and how to respond virtuously to challenges.
Ryan Holiday achieves this by writing every single day, always having the next book idea and contractual deadline set, and continuously reading to generate material. This creates a perpetual system where he is always in motion and focused on his creative output.
Saying 'yes' to distractions, even lucrative ones, incurs significant opportunity costs and can dilute the quality of one's core work over time. Success generates more inbound requests, making it crucial to decline most to protect the focus that led to success in the first place.
Success should be measured internally against one's own potential and continuous improvement, rather than externally against others. Comparing oneself to others in creative fields is often a recipe for misery due to varying goals, timelines, and external factors.
Acceptance is not about approving of an event, but acknowledging it as a fact that has already happened and cannot be undone by objection. Mentally assenting to reality allows one to move past the event and focus energy on what can still be influenced.
An idealistic preoccupation with how things *should* be, rather than how they *are*, puts individuals at odds with reality and makes effective change less likely. Real progress requires starting with the world as it is and aligning with its realities to create momentum.
Most mistakes stem from 'the passions'—emotional states like anger, envy, lust, or fear—which override rational thought. Avoiding them involves cultivating a pause before responding, allowing for reflection and strategic thinking instead of instinctive reactions.
Journaling serves as a conversation with oneself, fostering self-awareness and self-criticism by reflecting on experiences and translating them into actionable insights. It also provides a safe space to process emotions, preventing impulsive reactions and improving decision quality by allowing for rational review.
The four cardinal Stoic virtues are courage (putting oneself on the line), temperance/self-discipline (the standard one holds oneself to), justice (treating others fairly and doing the right thing), and wisdom (the intuitive sense of how and when to apply the other virtues effectively).
36 Actionable Insights
1. Cultivate Stoic Virtues
Actively cultivate the four cardinal Stoic virtues—courage (putting yourself on the line), temperance (self-discipline and moderation), justice (treating others fairly), and wisdom (applying the other virtues appropriately)—as a framework for ethical living and personal excellence.
2. Practice Dichotomy of Control
Regularly distinguish between what is within your control (thoughts, opinions, actions, beliefs) and what is not, directing your energy only towards the former to avoid wasted effort.
3. Control Your Response
Focus on controlling your response to events, rather than the events themselves, as this is where your agency truly lies.
4. Implement Pause Before Responding
Before instinctively responding, especially when overcome by passion, implement a brief pause to allow for rational thought and prevent irreversible actions or words.
5. Journal for Self-Awareness
Engage in daily journaling as a conversation with yourself to reflect on your aspirations, evaluate your current progress, and identify areas for improvement in becoming the person you want to be.
6. Reflect for Deeper Learning
After experiences, actively reflect on them by asking what variables mattered, and how to digest, process, and distill the information, as this reflection is key to true learning and creating actionable abstractions.
7. Practice Saying No
Consciously say ’no’ to most requests and opportunities, understanding that every ‘yes’ to one thing is a ’no’ to another, often more important, activity like your core creative work.
8. Consider Opportunity Costs
When evaluating new commitments, actively consider the opportunity costs—what you are giving up by saying ‘yes’—to make more informed decisions about your time and energy.
9. Prioritize Deep Work Mornings
Reserve mornings for high-concentration tasks like book writing, as this period offers the freshest energy and focus required for demanding creative work.
10. Default to Creative Work
Treat creative work (writing, reading, thinking) as the default activity when your calendar is empty, recognizing that scheduled appointments disrupt this flow and demand a pivot.
11. Daily Consistent Work
Show up and work on your craft every single day, as consistent daily effort naturally produces output over time.
12. Continuous Reading Fuels Creation
Maintain a habit of continuous reading, as it generates new material and ideas that can fuel future creative projects, keeping your system in motion.
13. View Obstacles as Virtue Practice
Reframe every challenge or event as an opportunity to practice virtue and excellence, transforming obstacles into pathways for personal growth.
14. Accept Reality to Change It
To effectively change the world, you must first accept and understand it as it truly is, rather than being preoccupied with how you wish it were.
15. Commit Fully to Core Principles
Avoid ‘channel surfing’ for opportunistic angles; instead, commit fully and unwaveringly to core principles, character, or a long-term vision, as this commitment is a hallmark of admired individuals.
16. Self-Assess Anger’s True Cost
Honestly evaluate the true costs and benefits of anger in your life, recognizing that it is often a corrosive force that leads to regret and mistakes, rather than a positive driver.
17. Guard Against Passions
Be vigilant against the ‘passions’ (envy, lust, anger, fear, pain, worry), as these emotional states often lead to mistakes by overriding rational thought.
18. Practice Self-Control Small Moments
Cultivate self-control and thoughtful responses in minor, everyday situations, so that when major challenges arise, you have already developed the habit and can respond instinctively with composure.
19. Cultivate Calm Philosophical View
Strive to view all situations ‘in the calm light of mild philosophy,’ cultivating a rational, empathetic, and unhurried temperament, especially in positions of leadership.
20. Sleep on Important Decisions
For important decisions, write them down at night and revisit them in the morning to engage your rational mind (System 2) and ensure clarity and soundness before acting.
21. Draft Emotional Communications
When feeling emotional or upset, draft emails or letters but delay sending them, allowing time for reflection and revision to ensure your communication is problem-solving, not just venting.
22. Analyze Past Actions Objectively
Regularly review your past actions and experiences from a distance, like watching game film, to objectively break them down, identify triggers, and understand what could be done differently next time.
23. Journal to Process Emotions
Use journaling as a safe outlet to write down frustrations, strong emotions, or negative thoughts, allowing the ‘ferocity of that feeling’ to dissipate before engaging with others.
24. Recover from Mistakes Gracefully
When you make a mistake, acknowledge it and commit to not repeating it, but avoid throwing away all progress; instead, get back on track and learn from the error.
25. Plan Next Project Early
Before finishing a current project, already have the next idea or project lined up to avoid existential angst and maintain continuous momentum.
26. Use Deadlines for Accountability
Establish contractual obligations or deadlines for projects to maintain honesty and ensure consistent output.
27. Integrate Reading into Daily Routine
Integrate reading into various parts of your day, such as during lunch, in the afternoon, before bed, and on weekends, to ensure consistent engagement with material.
28. Visible Reminder to Say No
Place a visible reminder, like a sign with ‘NO’ in capital letters, in your workspace to reinforce the importance of declining non-essential requests.
29. Selectivity in Opportunities
Be highly selective about the opportunities you pursue, much like a baseball player is defined by the pitches they don’t swing at, to conserve energy and focus on what truly matters.
30. Avoid Half-Assed Work
Recognize that saying ‘yes’ to too many things can lead to a decrease in quality across all your work, which is an unseen but significant opportunity cost that erodes long-term success.
31. Focus on Internal Scorecard
Measure success against your own potential and continuous improvement rather than comparing yourself to others, as external comparisons can lead to misery and are often based on different games or timelines.
32. Prioritize Personal Pride in Work
Evaluate your work based on whether you are proud of it and if you achieved your intended goals, rather than external metrics like sales or critical reception, which are often unrelated to quality.
33. Learn from All Sources
Be open to learning from anyone, regardless of their perceived character or reputation, as valuable insights can come from unexpected sources.
34. Steel-Man Opposing Views
To strengthen your own arguments and understanding, actively try to articulate and argue opposing viewpoints better than their proponents, rather than creating straw-man caricatures.
35. Cooperate with Reality
Align yourself with how the world works and let it teach you, rather than fighting against its realities, to avoid unnecessary headwinds and learn valuable lessons.
36. Recite Alphabet to De-escalate
When provoked or angry, recite the letters of the alphabet before acting or speaking to create a mental pause and prevent impulsive reactions.
7 Key Quotes
Everything you say yes to is saying no to something else.
Ryan Holiday (recalling advice he received)
The irony of success is that there are infinitely more distractions from that success. And as you get more successful, the higher the price or bribe attached to those things is.
Ryan Holiday
Everything that happens is an opportunity to practice virtue.
Marcus Aurelius (quoted by Ryan Holiday)
I shall never be ashamed of citing a bad author if the line is good.
Seneca (quoted by Shane Parrish)
The social organizer has to start with the world as it is for what it is, if they want to change it.
Saul Alinsky (quoted by Ryan Holiday)
Paper is more patient than people.
Anne Frank (quoted by Ryan Holiday)
I want to look at everything in the calm light of mild philosophy.
George Washington (quoted by Ryan Holiday, attributed to Cato)
2 Protocols
Ryan Holiday's Book Writing Process
Ryan Holiday- Show up and write every single day to ensure consistent output.
- Always have the next book idea and contractual deadline set before finishing the current one to avoid existential angst.
- Continuously read to generate material for future books, keeping the creative system in constant motion.
- Dedicate morning hours (e.g., 8:30 AM to 11:30 AM) specifically to book writing, as it demands fresh concentration and energy.
- Break down writing into smaller, manageable pieces to maintain momentum and a sense of progress.
- If stalled on a difficult chapter or section, pivot to easier, subsequent chapters and return to the challenging part later, rather than stopping progress.
Athenodorus's Advice for Managing Anger
Athenodorus (quoted by Ryan Holiday)- When provoked or feeling angry, recite every letter of the alphabet before taking any action or responding.