Stoicism’s Lessons on Becoming Wise - Ryan Holiday

In this engaging conversation, the host and guest, Ryan Holiday, explore the challenges and virtues of wisdom, stoicism, and personal growth. Holiday shares insights from his experiences, including the nuances of public speaking and the importance of adaptability and resilience in overcoming unexpected obstacles. They discuss the pitfalls of intelligence, such as ego and the lack of empathy, and emphasize the significance of learning from history and personal experiences. Holiday also delves into the story of Admiral James Stockdale, highlighting the moral complexities and resilience required during his captivity. The discussion underscores the importance of balancing wisdom with humility and maintaining a sense of wonder and purpose despite life's challenges.

• Discusses the importance of taking on arbitrary challenges to grow and learn.
• Emphasizes doing things differently to gain new perspectives and skills.
• Highlights the unpredictability of life and the necessity of adapting to unexpected situations.

"It's good to pick arbitrary challenges and take something that you're good at that you've done a lot of times and just figure out a way to do it the hard way."

• This quote underscores the value of challenging oneself by taking familiar tasks and approaching them in new, more difficult ways to foster growth.

"The lesson in these things is always like you think you need it to go a certain way... you actually find that the thing you were preparing not to for it not to happen actually isn't that bad and it might be better in some ways."

• Highlights the importance of adaptability and finding value in unexpected outcomes.

• Discusses experiences with technical difficulties during public speaking engagements.
• Stresses the importance of being prepared to adapt when things don't go as planned.
• Highlights the ability to deliver content without relying heavily on prepared materials.

"I'm starting and then the guy's like trying to talk to me via the screen, you know? He's like slides comfort. He's like slides slides incoming should be about 10 minutes, you know, and it's like this this is too late, man."

• This quote illustrates the unpredictability of technical issues and the need to adapt quickly.

"If you need it to go a certain way, you're very vulnerable. If you're good with it going effectively anyway, then you'll be all right."

• Emphasizes the importance of flexibility and resilience in the face of unforeseen challenges.

• Discusses the removal of books from the Naval Academy library due to controversial themes.
• Highlights the dangers of censorship and the importance of engaging with diverse ideas.
• Stresses the need for intellectual freedom, especially in elite educational institutions.

"You can't remove books from an elite university because you don't like what's in the books. That's a very different thing."

• Critiques the act of removing books from libraries due to their content, emphasizing the importance of intellectual freedom.

"The irony of like let's remove books that we find to be objectionable and then let's not talk about it and then let's pressure a person from the center of ethical leadership."

• Points out the contradictions in censoring ideas while promoting ethical leadership and intellectual engagement.

• Explores the elusive and multifaceted nature of wisdom.
• Discusses the continuous process of learning and the humility required to gain wisdom.
• Highlights the paradox of wisdom, where the more one learns, the more they realize how much they don't know.

"Wisdom is that it's one of those ones that if you think you have it, you almost certainly don't."

• Emphasizes the humility inherent in true wisdom and the ongoing journey of learning.

"As the island of knowledge grows, so does the shoreline of ignorance."

• This metaphor illustrates the expanding awareness of one's own ignorance as knowledge increases.

• Discusses the concept of unteachable lessons that must be experienced firsthand.
• Highlights the importance of learning from both personal experiences and the experiences of others.
• Stresses the value of recognizing and understanding life lessons early to avoid repeated mistakes.

"You cannot expedite the process of understanding this thing through somebody else's story tale."

• Highlights the necessity of personal experience in truly understanding certain life lessons.

"The fool is not someone who stubs their toe on a rock. It's the person who stubs their toe on the same rock more than once."

• Emphasizes the importance of learning from mistakes to avoid repeating them.

• Discusses the value of stories and historical figures in teaching moral and life lessons.
• Highlights the importance of shared narratives in understanding and applying wisdom.
• Emphasizes the role of biography in illustrating the virtues and flaws of historical figures.

"I write lives. And lives are illustrated by a certain anecdote, a little story, a an utterance of a few words that help you unlock the lesson or the the fatal flaw or the the brilliant genius of this person."

• Highlights the power of storytelling and biography in conveying deep insights and lessons.

"You take back from them little lessons that then yeah, when you're winning a gold medal or you just sold a company... you go, 'Oh, maybe I should.'"

• Emphasizes the importance of applying lessons from stories and historical figures to one's own life decisions.

• The art of impressions involves identifying and imitating key characteristics or quirks of individuals.
• Portable stories or aphorisms can encapsulate complex ideas into memorable, concise forms.
• Original thinking is challenging; thus, simplifying and making existing ideas accessible is valuable.

"In the art of doing impressions of people, there is an unlock. The unlock is this one thing, the way that you speak, the pronunciation of the S, the moving of the fingers, the hands, the face, whatever."

• This quote highlights the technique of identifying a unique trait or gesture that defines a person's character, which is essential for accurate impressions.

"Original thinking is pretty tough and also people way smarter than me and you have already figured stuff out and it's kind of our job to essentialize that and make it accessible."

• This emphasizes the difficulty of original thought and the importance of distilling and sharing existing wisdom.

• Historical stories, whether true or not, often carry moral lessons and values.
• The significance of stories lies in the lessons they impart, not necessarily in their factual accuracy.
• The story of Catis illustrates restraint and selflessness, values that transcend the literal truth of the tale.

"For most people most of the time, the significance of that is the lesson of sort of restraint and selflessness that actually power can be laid down."

• This quote underscores the moral lesson from the story of Catis, highlighting the value of selflessness over historical accuracy.

• Some truths are figuratively true but literally false, serving functional purposes despite inaccuracies.
• Holding modern stories to strict rational standards can overlook their practical or moral utility.

"Something which is literally false but functionally true... like porcupines can throw their quills. No, they can't. But if you treat it like it can, you stay just a little bit further clear."

• This illustrates how figurative truths can guide behavior effectively, even if they're not literally accurate.

• First principles thinking involves questioning assumptions and understanding the fundamental truths of a problem.
• Traditions often solve problems that are no longer remembered, and dismissing them without understanding can be naïve.
• Balancing innovation with respect for tradition is crucial for effective problem-solving.

"And maybe even why it was hard won or how it was hard won you are blowing past and you are ignoring why it was set up this way in the first place."

• This quote highlights the importance of understanding the historical context and reasons behind established practices.

• Wisdom involves understanding the limitations of one's knowledge and being open to learning.
• Humility is a companion to wisdom, as it allows for fewer arguments and a smoother flow in life.
• The pursuit of wisdom is a lifelong journey, requiring continuous learning and reflection.

"Epictetus said one of the signs that you're making progress in the path to wisdom is that you get in fewer arguments."

• This suggests that wisdom leads to a deeper understanding of different perspectives, reducing the need for conflict.

• Experience and learning are essential for developing wisdom and making informed decisions.
• Shortcuts and superficial knowledge cannot replace the depth of understanding gained through experience.
• The story of the Roman with literate slaves illustrates the pitfalls of relying on superficial knowledge.

"You still have to know what questions to ask it. You still have to be able to separate the good answers from the hallucinated nonsensical answers."

• This quote emphasizes the necessity of critical thinking and discernment, even when using advanced tools like AI.

• Innovation should be informed by a deep understanding of existing systems and their reasons for being.
• Outsiders can bring fresh perspectives, but effective reformers respect and understand the status quo.
• Historical reformers like Lincoln and Clarkson exemplify the balance of outsider insight and deep knowledge.

"You have to have this curiosity to go well, these people probably aren't wrong on purpose. So why do they think this?"

• This highlights the importance of empathy and understanding in driving meaningful change.

• Wisdom is not innate but developed through life experiences and challenges.
• Investing in wisdom involves continuous learning and reflection, preparing for future challenges.
• The story of the Roman with literate slaves serves as a cautionary tale against the illusion of knowledge without understanding.

"Wisdom is something you accumulate over time. And so if you're going to want to draw on it in the future, what are the deposits you're making now?"

• This quote stresses the importance of ongoing learning and preparation for future decision-making.

• The importance of not just understanding a concept but being able to explain it in multiple ways and apply it in life.
• Recognizing insights during emotional experiences is crucial for deep understanding.
• There's a difference between initial understanding and true knowledge, which requires repeated exposure and experience.

"I understand and have retained the concept. That's a very good first start because without understanding it and retaining it, you don't know it at all."

• This quote emphasizes the importance of not just learning a concept but retaining it as a foundation for further exploration and application.

"What does it mean to be able to explain it three different ways? What does it mean to be able to apply it in your life?"

• This stresses the need for flexible understanding, where a concept can be articulated in various forms and applied practically.

• The relationship between reading, studying, and experiencing life is cyclical and necessary for unlocking deeper insights.
• Different states of mind can offer new perspectives on the same material, enhancing understanding.
• The abundance of texts today compared to ancient times presents both opportunities and challenges for learning.

"You have to read, have experiences, read again, have experiences because every vantage point that you look at it from, particularly with the passage of time, allows you to unlock something new in it."

• This quote highlights the iterative process of learning, where repeated engagement with material leads to deeper insights.

"There are books that are designed for you to be reading it's not a thing you have done it is a thing you are doing."

• It underscores the ongoing nature of engaging with certain texts, suggesting that some works are meant to be revisited continuously.

• The modern world presents a paradox of choice, leading to challenges in self-identity and purpose.
• Losing everything can be both freeing and destabilizing, prompting a return to formative experiences.
• Journaling is a tool for maintaining a connection with one's past self and preventing existential crises.

"People may have thought they knew who they were and in the modern world have sort of lost themselves."

• This quote addresses the identity crisis faced by many in the contemporary world due to overwhelming choices and changes.

"The purpose of journaling is to keep on nodding terms with who I used to be."

• It explains the reflective nature of journaling, which helps individuals stay connected to their past selves and maintain continuity in their identity.

• The transient nature of emotions and experiences is a central theme in both stoicism and broader philosophical thought.
• The phrase "this too shall pass" serves as a universal truth applicable to all situations.
• Gaining perspective, both personally and historically, helps in understanding the temporary nature of life's challenges and triumphs.

"This is going to end either because it's going to kill you or it's going to go away."

• This stoic perspective highlights the inevitability of change and the temporary nature of suffering.

"The wisest philosopher in the world was asked to find a phrase that's true in any and every situation and always has been and always will be true... and this too shall pass."

• It encapsulates the idea that all experiences, whether positive or negative, are fleeting.

• James Stockdale's experience as a POW in Vietnam is a profound narrative of resilience and moral complexity.
• Stockdale's story is not just about survival but also about holding onto crucial secrets and moral integrity under extreme duress.
• His transformation from a self-focused young man to a leader concerned with the well-being of others is a significant aspect of his legacy.

"Stockdale is in the air the night of the Gulf of Tonken incident... He possesses the most terrible secret that you could possibly possess."

• This quote sets the stage for the immense pressure Stockdale faced, knowing sensitive information that could have been exploited by his captors.

"He begins to beat his face to a bloody pulp with the stool... He basically makes himself unfilmable."

• It illustrates Stockdale's extreme measures to protect sensitive information and his fellow prisoners, demonstrating his commitment and resilience.

• The act of writing is both a personal and professional journey, providing intrinsic joy and fulfillment.
• The balance between celebrating achievements and continuing to pursue one's passion is essential.
• The importance of regulation and maintaining focus on core pursuits is emphasized as a means to achieve personal and professional goals.

"The joy and the fun is not in throwing a party for hitting number one. I like doing it. Like I like writing books."

• This quote reflects the intrinsic motivation and satisfaction derived from the process of writing itself, rather than external validation.

"Regulation is the key to life, right? Getting emotionally regulated. That's what stoicism is."

• It underscores the importance of emotional regulation in stoicism, focusing on managing emotions rather than eliminating them.

• The discussion emphasizes the importance of practicing self-control and deciding "who's in charge" of one's actions and thoughts.
• Physical exercise is used as a metaphor for practicing self-discipline and overcoming feelings of discomfort or reluctance.
• The ability to focus on the present activity and not worry about unrelated concerns is highlighted as a key skill.

"I am feeling tired I am feeling not into it I am feeling cold I am feeling whatever and you're you're saying to yourself but that doesn't matter here's what you're going to do."

• This quote illustrates the practice of overriding immediate feelings with deliberate actions, a core aspect of self-discipline and stoicism.

• Equanimity, or mental calmness, is presented as a crucial trait, especially when paired with intelligence.
• Maintaining equanimity allows individuals to remain regulated and composed, which is essential for effective leadership and parenting.
• The concept is linked to historical figures and philosophies, emphasizing its timeless value.

"The most powerful thing that a leader, a parent, a human being can have, right? Is the ability to sort of be even to be regulated."

• This quote underscores the significance of equanimity as a foundational trait for personal and professional success.

• Empathy is identified as a key component of wisdom and justice, enabling individuals to understand others' perspectives and avoid major historical blunders.
• The ability to see the world through others' eyes prevents misjudgments and enhances decision-making.

"Empathy is like the key to the greatest achievements of western civilization and humanity."

• The quote highlights empathy's role in achieving significant accomplishments by fostering understanding and collaboration.

• The importance of avoiding catastrophic mistakes is discussed, using the mathematical concept of "never multiply by zero" as a metaphor.
• The focus is on preventing major errors that can negate all other efforts and achievements.

"Avoid the major stupid things. And um that idea of okay in the world of business and in the world of sort of objective outward metrics of success I probably should double down on my strengths."

• This quote emphasizes the strategy of focusing on strengths while avoiding critical mistakes to ensure sustained success.

• Ego is identified as a major obstacle to gaining wisdom, as it can lead to complacency and a lack of learning.
• Overcoming ego involves being open to new information and perspectives, which is essential for personal growth.

"Ego is obviously one of the things that makes us very dumb, right? because it filters everything through the lens of what we want to be true or how we see ourselves."

• The quote illustrates how ego distorts perception and hinders the acquisition of wisdom by preventing objective evaluation.

• Wisdom can lead to self-consciousness and cynicism, potentially hindering creativity and enthusiasm.
• The balance between wisdom and maintaining a sense of wonder and hope is crucial for a fulfilling life.

"If wisdom paralyzes you, if wisdom makes you think about everything from every angle, and thus deprives you of the energy or the enthusiasm to do the thing, that can be a real problem."

• This quote highlights the potential downside of wisdom, where excessive contemplation can lead to inaction.

• The discussion includes the importance of learning the right lessons from success and failure.
• Recognizing patterns and avoiding the pitfalls of overconfidence is essential for sustainable growth.

"You watch how smart people learn the wrong lesson from their success. And then you want to make sure that when you experience success or you have these analogous moments in your life, you're like, 'Okay, this is my opportunity in a low stakes, lowkey way to learn the same lesson.'"

• The quote emphasizes the need to critically evaluate successes to avoid complacency and ensure continued learning and adaptation.