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#128 Ryan Holiday: A Stoic Life

Jan 11, 2022 1h 11m 36 insights
Stoic philosopher and author Ryan Holiday shows us how to use the ancient philosophy to calm our mind and create a foundation for lasting success. Listen as Holiday takes us behind the scenes, revealing how he not only reads books and what he looks for, but his process for writing and retaining information he can later put to use. He also discusses what he writes and reads, why he journals, and the four virtues of Stoicism.   Holiday is a New York Times bestselling author. He has written a combined 10 books, covering both the fundamentals of Stoicism as well as key elements of modern-day marketing and media, and his books have sold more than 2 million copies in 30 languages. His most recent release is entitled Courage is Calling.    -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/ Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/ Follow Shane on Twitter at: https://twitter.com/ShaneAParrish
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.