#90 - Ryan Holiday: Stillness, stoicism, and suffering less
This episode features Ryan Holiday, bestselling author, discussing Stoic philosophy's influence on his life and work. He shares strategies for developing stillness, avoiding ego, jealousy, and anger, and finding balance in a hyperconnected world.
Deep Dive Analysis
16 Topic Outline
Impact of a Hyperconnected World on Our Lives
Consequences of an Overly Secure Life and Misconception of Unlimited Time
Stoicism 101: Definition, Origins, and Core Virtues
Seneca's Moral Compromises and the Dangers of Political Proximity
Ryan Holiday's Career Transition: Writing and Marketing Insights
The Upside and Downside of Storytelling and Self-Narrative
Motivation for Success: Craving vs. Fullness
Ego vs. Confidence: Identifying and Counteracting Destructive Ego
The Challenge of Finishing a Book: Knowledge is Not Static
Stillness: What It Is, Obstacles, and Its Relationship to Meditation
Ryan's Morning Routine and Managing Technology
The Perils of Jealousy and Envy
Living in the Moment and the Concept of 'Dying Well'
Fatherhood's Impact on Stillness and Presence
Strategies for Cultivating Stillness in Daily Life
Anger: Stoic Perspectives and Its Destructive Nature
5 Key Concepts
Stoicism
An ancient Greek philosophy that posits we don't control the world around us, but we control how we respond. It is built around four virtues: courage, justice, temperance (moderation), and wisdom, aiming for a virtuous life rather than simply abstract thought.
Ego vs. Confidence
Confidence is knowing what you're capable of, backed by evidence and self-awareness of strengths and weaknesses. Ego, however, is an association of our identity with external results or things, often stemming from insecurity and leading to self-sabotage or an inflated sense of importance.
Enough vs. Craving
This mental model explores whether high achievement must come from an insatiable desire for more (craving) or if it can be sustained from a place of satisfaction, passion, and appreciation (fullness). The latter is suggested to be more sustainable and less prone to misery.
Stillness
A philosophical approach to living in the real world, not merely synonymous with meditation or solitude. It involves reducing expectations, extracting the unnecessary, and fully engaging in the present moment, even amidst daily chaos and responsibilities.
Dying Well
This concept, rooted in Stoic philosophy, suggests that to philosophize is to learn how to die. It's about living in a way that culminates in a graceful and principled end, recognizing death as a continuous process of life and using this awareness to prioritize and live more intentionally.
10 Questions Answered
While connectivity offers benefits like navigation, it has also led to an 'optimization point' where we have too much, eroding freedom and creating an artificial sense of urgency and constant tethering to devices, which was foreign to human DNA until recently.
An overly secure life leads to an assumption of unlimited time and an inflated sense of control over our existence, fostering arrogance and a lack of presence. This 'survivorship bias' makes us shocked by death and less appreciative of the quality of our current life.
The central precept of Stoicism is that we don't control the world around us, but we control how we respond to it. It emphasizes controlling one's own reactions rather than external events or other people.
Signs of ego include feeling that everything rests on you, experiencing paranoia that people are 'out to get you,' tying your identity and worth to external results or status, and comparing yourself to other people instead of your own standards or intentions.
Learning continuously, adopting a 'student's mindset' (humility embodied), and embracing the idea that as knowledge grows, so does awareness of ignorance, can help counteract ego. This fosters curiosity, openness, and less rigidity.
Knowledge is not static; authors continuously learn new things, making it hard to 'kill the book' and release it, knowing that new insights will emerge after submission. The challenge is to accept the book as the best one was capable of in that specific moment.
Stillness is presented as a broader, more comprehensive philosophical approach to living in the real world, rather than just a specific practice like meditation. While meditation can be a tool, stillness focuses on integrating quiet and presence into daily life amidst responsibilities, rather than relying on temporary retreats.
Reliable strategies include daily walking (without distractions like phones or music, focusing on the experience), journaling to process thoughts, and engaging in hobbies that are not goal-oriented or willpower-driven, like gardening or certain sports, to provide restorative, non-work activities.
Fatherhood can unexpectedly bring stillness by forcing parents to slow down and be present in simple, often mundane activities that captivate children, such as digging in dirt or getting a haircut. This shift in perspective helps one appreciate the 'now' and reduce the need for constant activity.
Stoics are generally against anger, viewing it as destructive and rarely a solution to problems. They distinguish between moral outrage (being upset about injustice) and temper (being jerked around by reactions). Anger is seen as counterproductive, especially in serious, high-stakes situations that require discipline and rational thought.
45 Actionable Insights
1. Control Your Reactions
Focus on controlling your response to external events and other people, as these are the only things truly within your power, rather than trying to control the world around you.
2. Live Virtuously
Strive to live a life guided by the four Stoic virtues: courage, justice, temperance (moderation), and wisdom, as these form the essence of a good life.
3. Embrace Memento Mori
Adopt the Stoic view that time passed is ‘dead time’ and you are ‘dying all the time’; this fosters urgency and intentionality in how you spend your finite time, as every second is unrecoverable.
4. Question Life Quality
Regularly ask yourself if you are afraid of death because you won’t be able to continue your current activities, to assess and improve the quality of your present existence.
5. Cultivate a Sense of Enough
Develop a clear understanding of what ’enough’ means for you, allowing you to appreciate what you have and perform from a place of fullness rather than constant craving or dissatisfaction.
6. Identify and Combat Ego
Distinguish between healthy confidence and destructive ego, recognizing ego as tying your identity and self-worth to external results, status, or comparisons with others.
7. Ego Audit: Watch for Paranoia
Audit your internal state for paranoia, the feeling that people are ‘out to get you’ or ‘holding you back,’ as this is often a sign of ego at play.
8. Ego Audit: Prioritize Truth
Prioritize seeking the truth over merely being ‘right,’ especially in disagreements, as being more interested in winning an argument than understanding is a strong indicator of ego.
9. Adopt a Student Mindset
Cultivate humility by embracing a student mindset, recognizing that true mastery is a continuous learning process and you cannot learn what you think you already know.
10. Avoid Absolute Certainty
Recognize that certainty is the enemy; strive for a softer, more balanced, and nuanced tone in your beliefs and communication, as certainty is often what you regret in retrospect.
11. Seek Stillness in Daily Life
Actively find ways to access stillness within the demands of your normal, real-world life, rather than relying on temporary retreats that don’t address underlying chaos.
12. Reduce Overcommitment
Avoid committing to more than you can conceivably handle, as overactivity and insatiable demands are significant obstacles to achieving stillness.
13. Minimize Unnecessary Noise
Reduce both internal (mental chatter) and external (environmental) unnecessary noise in your life to create space for stillness.
14. Establish Positive Routines
Break bad habits and establish positive routines and limits, as a lack of structure is a major obstacle to stillness.
15. Keep Phone Out of Bedroom
Do not sleep with your phone in the room; keep it in another room to avoid immediate morning distractions and start your day proactively.
16. Delay Phone Checking
Gradually extend the time you go without checking your phone in the morning to prevent starting your day reactively and allow for focused, intentional activity.
17. Use Technology Intentionally
Strive to ‘be using the phone rather than be used by the phone,’ ensuring your interaction with technology is deliberate and serves your purpose, not the device’s.
18. Prioritize Deep Work
Structure your morning to prioritize your main tasks or deep work before engaging with reactive communications like email, to ensure important work gets done without distraction.
19. Practice Quiet Solitude
Practice sitting quietly alone, as many problems stem from an inability to do so, and much of our activity is driven by an avoidance of solitude.
20. Set Boundaries for Subtle Asks
Be vigilant about setting boundaries against subtle, small asks, as their cumulative effect can be as disruptive to your time and focus as larger, more obvious demands.
21. Embrace Parental Presence
Embrace the inherent stillness of simply ‘being’ with your children, allowing for unstructured, simple activities like playing with dirt, rather than constantly ‘doing’ or orchestrating events.
22. Design Your Ideal Day
Reflect on your ‘perfect days’ (e.g., a relaxing Saturday) and intentionally make deliberate choices and compromises to design your life to incorporate more of those elements.
23. Make Intentional Financial Choices
Make financial choices, such as buying a house you can easily afford, that support your desired lifestyle and presence, rather than creating obligations that force you away from it.
24. Say No to Non-Essential Opportunities
Practice saying no to opportunities that, while potentially appealing or prestigious, do not align with your desired lifestyle or priorities, to protect your time and focus.
25. Actively Reset Your Norm
Actively reset your life to a desired ’normal’ after intense periods (e.g., a book launch), as things won’t automatically return to normal; you have to make it happen.
26. Walk Daily for Reflection
Incorporate daily low-impact walks, primarily for mental and reflective benefits, intentionally bringing your attention back to the present sensory experience if your mind wanders.
27. Journal Regularly
Engage in regular journaling as a philosophical practice for self-reflection, clarity, and processing thoughts, similar to how Stoics used it.
28. Cultivate Non-Work Hobbies
Develop hobbies that are distinct from your work, not focused on winning or effort-based outcomes, and are restorative, to provide balance and prevent burnout.
29. Resist Over-Optimization
Resist the urge to over-optimize all aspects of your life, allowing for unstructured downtime and ‘just doing nothing’ to foster genuine rest and presence.
30. Age and Die Gracefully
View aging and dying well as a natural culmination of living by sound principles throughout life, rather than clinging to past roles or achievements out of compulsion.
31. Learn from History’s Mistakes
Study history, such as the Cuban Missile Crisis, to understand the potential for unintended consequences and to approach complex problems with deliberation and consultation.
32. Use Time as a Tool
Actively use time as a tool for deliberation and problem-solving, rather than passively letting it pass or using it as a ‘couch’ for procrastination.
33. Be Decisive, Yet Flexible
Be decisive about your desired outcomes but remain flexible and open to various methods of achieving them, understanding that there are many paths to a goal.
34. Beware of Anger’s Excuses
Be wary of making excuses for anger, as it is rarely productive; reflect on past instances to realize its lack of positive outcomes.
35. Distinguish Moral Outrage from Temper
Differentiate between constructive moral outrage (seeking change for wrongs) and destructive temper (uncontrolled emotional reaction), ensuring your actions are not merely ‘jerked around’ by reactions.
36. Act Without Anger
Pursue justice or take action from a calm, calculated place, not out of immediate anger, to avoid self-inflicted harm or irrational decisions.
37. Observe Others’ Anger
Observe the immaturity and ineffectiveness of anger in others to gain perspective on your own potential for it and to avoid succumbing to similar reactions.
38. Self-Observe Your Anger
Use self-observation, such as looking in a mirror when angry, to confront the unpleasant reality of your own anger and motivate yourself to change.
39. Avoid Rigid Compromise
Avoid rigid adherence to principles that prevent necessary compromise, as an inability to make things work in less-than-perfect scenarios can lead to worse outcomes.
40. Align Passion with Market
For creative work, find the intersection of what you can’t stop thinking about and what people can’t stop saying they need, as this overlap creates powerful results.
41. Communicate to the Uninterested
Find ways to adapt and deliver your ideas to people who are not initially interested in your topic, rather than only speaking to those already engaged.
42. De-Risk with Timeless Models
De-risk creative projects by modeling them on timeless stories or concepts with proven endurance, rather than solely relying on entirely new ideas.
43. Avoid Living a Performance
Avoid living your life as if performing for an imaginary audience, as this detracts from actually living in the moment and can lead to an egotistical existence.
44. Recognize Suffering
Be aware that you might be suffering unknowingly, even if accustomed to it, and actively seek to identify and address sources of misery in your life.
45. Question Posthumous Fame
Question the cost of pursuing external validation like posthumous fame on your present happiness and quality of life, as you won’t be around to appreciate it.
9 Key Quotes
I have enough. You know, I have a sense of what enough is.
Joseph Heller (as recounted by Ryan Holiday)
Most of our time already belongs to death. The time that has passed is dead.
Seneca (as recounted by Ryan Holiday)
Comparison is the thief of joy.
Theodore Roosevelt (as recounted by Ryan Holiday)
All of humanity's problems stem from our inability to sit quietly in a room alone.
Blaise Pascal (as recounted by Ryan Holiday)
You can't learn that which you think you already know.
Epictetus (as recounted by Ryan Holiday)
As your island of knowledge grows, so does the shoreline of ignorance.
John Wheeler (as recounted by Ryan Holiday)
People who long for posthumous fame forget, first off, that the people in the future are just as dumb as the people who are alive right now. And second, you're not going to be around to appreciate it.
Marcus Aurelius (as recounted by Ryan Holiday)
We've got to use time as a tool and not as a couch.
John F. Kennedy (as recounted by Ryan Holiday)
Of all the seven deadly sins, envy is the only one that's no fun.
Joseph Epstein (as recounted by Ryan Holiday)
2 Protocols
Ryan Holiday's Morning Routine
Ryan Holiday- Wake up early (6-7 AM), often without an alarm or with the phone in another room.
- Do not touch the phone for at least two and a half hours (current goal, started with 10 minutes, then 30, then an hour).
- Engage in non-phone activities like taking son for a bike ride, having breakfast, journaling, or going straight into writing for the day.
- Use the phone only when needed for specific tasks (e.g., directions, photos), not for reactive checking of messages or social media.
Cultivating Stillness
Ryan Holiday- Go for a daily walk: Be outside, without a phone or music, and focus on the sensory experience, returning attention to the present if the mind wanders.
- Journal regularly: Engage in a word-based writing process for self-reflection and to process thoughts, similar to how Stoics used journaling.
- Engage in a hobby that is not work-related and where effort does not necessarily equal outcome: Choose activities that are restorative and not willpower-driven, such as gardening, certain sports, or creative pursuits, to provide balance and a sense of control.