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Ryan Holiday: How to Win the War with Yourself

Nov 26, 2024 1h 43m 60 insights
Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal missteps to famous entrepreneurial gambles, this episode is a deep dive into the art of learning from experience, knowing when to listen, and the cost of stubbornness. Plus, Holiday revisits his roots to discuss how Stoic principles can guide you in navigating feedback, balancing ambition with self-awareness, and understanding the fine line between determination and delusion. Holiday is a New York Times bestselling author. He has written over 10 books, covering both the fundamentals of Stoicism as well as key elements of modern-day marketing and media. His most recent release is Right Thing, Right Now. Holiday has been a guest on the podcast twice before. Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/ -- Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠https://fs.blog/membership/⁠⁠ and get your own private feed. -- Follow me: ⁠⁠⁠⁠⁠⁠⁠⁠https://beacons.ai/shaneparrish⁠⁠⁠⁠⁠⁠⁠⁠ -- Watch on YouTube: https://www.youtube.com/@tkppodcast
Actionable Insights

1. Control Your Response

Understand that while you cannot control external events, you always control your response to them, which is the core of Stoicism and allows you to orient your actions with virtue.

2. Heed Life’s Whispers

Pay attention to the subtle messages and feedback life sends you, as ignoring them can lead to more severe consequences later, allowing you to choose your ‘rock bottom’ rather than having it forced upon you.

3. Distinguish Signal from Noise

Learn to differentiate between helpful, valid feedback (the ‘whisper’) and mere noise or doubt, especially after past successes that came from ignoring conventional wisdom, as blindly ignoring all feedback can lead to a ’tough spot.’

4. Journal for Self-Conversation

Use journaling as a practice to have an ongoing conversation with yourself about your thoughts, beliefs, values, and actions, similar to how meditation is central to Buddhism.

5. Reflect Post-Emotion

Engage in reflection and examine the causes of a situation only after strong emotions about it have dissipated, to ensure a clearer and more objective learning process.

6. Separate Cause from Present Action

When facing a difficult situation, separate how you got there from your current reality. While examining causes for learning is important later, in the moment, focus on the immediate choice of what to do about it, rather than getting distracted by blame or dissection.

7. Manage Emotions with Stoicism

Employ Stoic exercises and practices to understand and process your emotions, aiming to not be ruled by them, rather than suppressing or denying them entirely.

8. Distinguish Emotion from Action

Learn to differentiate between feeling an emotion (e.g., anger, sadness) and acting out of that emotion (e.g., doing something out of anger, falling into despair).

9. Preface Interpretations Carefully

When interpreting someone’s words or actions, preface your statement with ‘what I make up about that is’ or ’the story I’m telling myself about that is.’ This acknowledges your interpretation as subjective, inviting correction and reducing judgment.

10. Invite Correction with ‘Story’

Use the phrase ’the story I’m telling myself is…’ to invite others to correct your interpretation, as it’s less threatening than direct judgment and encourages them to inform you of the truth.

11. Challenge Upsetting Opinions

Recognize that it’s not external events themselves that upset you, but rather your opinions or interpretations about those events, which helps you realize you are ‘bringing a lot to this’ and making things up.

12. Define Your Rock Bottom

Consciously decide what level of negative consequence is unacceptable for you, rather than waiting until you’ve lost everything, empowering you to act before situations become dire.

13. Patience Prevents Lost Time

Avoid rushing comebacks or recoveries, as a lack of patience often leads to losing more time in the long run than if you had just followed the initial ‘prescription’ for rest or recovery.

14. Cultivate Patience for Better Outcomes

Recognize that a lack of patience can negatively alter outcomes, especially when trying to ‘get rich quick’ instead of following a clear, slow, and steady path.

15. Make Haste Slowly

Adopt the principle of ‘fastina lente’ (make haste slowly), understanding that looking for shortcuts often takes longer than a steady, deliberate approach.

16. Accept Reality, Maximize Hand

Do not argue with or complain about the reality of a situation or the hand you’ve been dealt; instead, focus on playing that hand to the best of your ability.

17. Train Mind for Conscious Response

Actively train yourself to slow down your reactions and become more conscious of your responses to events, rather than being a slave to immediate impulses.

18. Transform Challenges into Lessons

When faced with unavoidable challenges (like traffic), reframe them as teaching moments, especially when others are present, to practice making the best of a situation and model positive responses.

19. Learn by Teaching

Actively teach others, as the Stoics believed that you learn and reinforce your own understanding and skills in the process of teaching.

20. Practice Private Self-Discipline

Cultivate self-discipline as a personal virtue, focusing on what you insist upon yourself and do when no one is watching, rather than discipline imposed externally.

21. Self-Discipline: Emotional Control

Understand that self-discipline extends beyond physical acts to include the ability to remain calm, keep your head, and manage your emotions in stressful situations.

22. Discipline: Balance and ‘No’

Redefine discipline as prioritizing balance and the ability to say ’no’ to excessive commitments, rather than constantly pushing yourself to say ‘yes’ to more.

23. Daily Habits for Consistency

Commit to a daily habit (e.g., going to the gym every day) rather than intermittent ones, as the ’everydayness’ removes the choice and makes consistency easier to maintain.

24. Do a Little Something Daily

Aim to do a ’little something’ related to your goals every day, as this consistent effort is more effective than postponing tasks to start ’next month.’

25. Combat Compulsive Overworking

Actively fight against the compulsive tendency to overwork, especially when it means sacrificing personal time for arbitrary goals, to avoid burning out or validating an unhealthy self-perception.

26. Question Compulsive Beliefs

Interrogate the underlying belief that ‘if you don’t do it, things will fall apart’ when dealing with compulsive tendencies, as these beliefs are often unfounded.

27. Seek Genuine Rewards

Be aware if your motivation for working comes from avoiding a negative self-perception (‘see, you’re not a piece of shit’) rather than genuine pride or impact, as this is an unhealthy feedback loop.

28. Ignore Peers’ Paths

Cultivate indifference and ignorance towards what your peers are doing, as this allows for a healthier mindset and a clearer focus on your own path and goals (euthymia).

29. Stay in Your Own Lane

Focus on your own goals, stroke, and lane, avoiding distractions from competitors, as looking over can lead to losing by ‘milliseconds.’

30. Balance Competition for Focus

Recognize that while competition can be healthy and motivating, too much of it can be disorienting and self-defeating, so find a balance that supports your focus.

31. Physical Practice for Mental Discipline

Engage in a regular physical practice (e.g., endurance sports, cold plunge) to cultivate mental and cognitive discipline, as the act of doing something hard strengthens your resolve.

32. Seek Hard Things for Discipline

Intentionally engage in uncomfortable or hard activities, even if their external benefits are questionable, purely for the mental discipline gained from doing something difficult.

33. Build Character Privately

Focus on building your character through what you do when no one is watching, understanding that character is distinct from your public reputation.

34. Practice Virtue Through Action

View virtue as a verb, not a noun; become a more virtuous person by consistently performing virtuous actions, just as one becomes a better musician by playing their instrument.

35. Virtue: Small Daily Decisions

Understand that living virtuously is not about grand moral choices, but a continuous series of small, daily decisions and practices, like any other discipline.

36. Protect Your Character

Safeguard your character, as it is the one thing no one can take from you, even amidst injustice or criticism. Resist the urge to let anger, feeling mistreated, or collapsing willpower compromise it.

37. Avoid Radicalization Post-Scandal

When facing public criticism or ‘cancel culture,’ strive to emerge from it without becoming a radicalized caricature of yourself, preserving your core character despite external pressure.

38. Acknowledge Goal Trade-offs

Understand that every decision and goal involves inherent trade-offs, and you cannot combine disparate elements from different paths; choosing one goal means not choosing others.

39. Choose One Strategy

Define your strategy by clearly choosing specific objectives and deliberately not choosing others; attempting to straddle two different strategies will lead to self-destruction.

40. Drill Down on Success Reasons

Avoid taking superficial ‘business book headline’ narratives of success or failure; instead, deeply analyze the actual, underlying reasons why something worked or didn’t work to gain genuine understanding.

41. Write Memos Before Meetings

Adopt the practice of writing a detailed memo outlining the agenda and purpose of a meeting, and have it edited by others, before the meeting takes place, as this clarifies thoughts and ensures preparedness.

42. Paper Clarifies Meeting Purpose

Make it essential to put your thoughts, agenda, and the purpose of any discussion or meeting down on paper, as this act itself clarifies thinking.

43. Write to Persuade

Approach writing as a ‘hostile act’ where you aim to convince someone to adopt your perspective, requiring immense skill to meet people where they are and guide them to your desired conclusion.

44. Cultivate Uninterrupted Focus

Develop the belief in your ability to achieve clarity and insight through uninterrupted focus and concentration, especially when tackling complex problems.

45. Develop AI Bullshit Detection

In the age of AI, cultivate a strong sense for ‘bullshit’ and the ability to push back, examine, and verify information generated by AI, as it can be prone to inaccuracy or telling you what you want to hear.

46. Acquire Expertise to Challenge

Gain sufficient domain expertise in your field so that you can effectively challenge and push back against information, whether from AI or human experts, ensuring you get to the truth.

47. Use AI as Personal Tutor

Use AI as a personal tutor by first creating your own reasonably good work, then asking the AI to identify weak points or offer feedback, rather than having it generate content from scratch.

48. AI Generates Better Prompts

Leverage AI to generate its own prompts (e.g., asking it to summarize content to create a better prompt for further interaction), as this can result in more effective and refined inputs than you might create yourself.

49. Learn AI Limitations, Master Prompting

Actively learn the inherent limitations and underlying logic of AI, and develop strong prompting skills, as these are crucial for effectively using AI as a tool rather than a replacement.

50. Strive for Excellence

Recognize that the cost of mediocrity is increasing, so strive for excellence in your chosen domain to remain relevant and valuable in a world where technology eliminates average performance.

51. Pursue Singular Excellence

Identify the specific area where you can achieve excellence and be prepared to be ‘somewhat unbalanced’ in its pursuit, as this singular focus is often required to reach the highest levels.

52. Keep Emails Concise

When sending emails, especially to people you don’t know, keep them concise (ideally under five sentences) to increase the likelihood of them being read and not deleted.

53. Develop AI Detection Skills

Cultivate the ability to distinguish between AI-generated content and human-generated content, as this skill will become increasingly important in daily communication.

54. Define Success: Autonomy, Schedule

Define success as having autonomy and control over your schedule, allowing you to prioritize what truly matters, such as spending time with your children, without needing external permission.

55. Avoid Upward Social Comparison

Refrain from constantly comparing yourself to those who are more successful, as this can perpetually make you feel inadequate and destroy your satisfaction.

56. Re-evaluate Past Success Definitions

Periodically reflect on how you previously defined success, as this can provide perspective and help you appreciate your current achievements and values.

57. Appreciate Your Own Problems

Recognize that most people, given the choice, would still prefer their own problems over someone else’s, fostering a sense of appreciation for your current circumstances.

58. Counter Jealousy with Trade-offs

When feeling jealousy, remind yourself that you cannot selectively pick aspects of someone else’s life; to have what they have, you would likely need to trade your entire life or career for theirs, revealing the true cost.

59. Cultivate Resilient Joy

Strive for a more resilient form of joy and happiness that isn’t solely dependent on external circumstances, allowing you to flourish even amidst life’s challenges.

60. Write to Clarify Thoughts

Put your thoughts on paper, as they often make sense in your head but reveal their inconsistencies or lack of clarity when externalized, providing a different lens for understanding.