Ryan Holiday: "Do The Right Thing, Right Now" | Stoic Practices For Your Daily Life

Ryan Holiday discusses the essence of stoicism and its modern interpretation, emphasizing the importance of integrating compassion and emotion into the philosophy. He reflects on the balance between personal resilience and ethical living, critiquing the superficial adoption of stoic principles by some as an excuse for insensitivity. Holiday shares insights on maintaining authenticity in one's work amidst success and societal pressures, drawing from historical figures like Lincoln and personal anecdotes. He underscores the need for empathy, integrity, and continuous self-improvement, while navigating the challenges of modern life and personal commitments.

• Radical candor is often misunderstood and misused as an excuse to be rude.
• Stoicism includes not just resilience and toughness but also an ethical framework.
• Stoicism's true essence involves compassion, emotion, and justice.

"People talk about radical candor like it is important to be honest, but I think a lot of times people are seeking out these ideas because it's an excuse to be an [__]."

• Radical candor should not be used to justify rudeness; true honesty should be balanced with kindness.

"Stoicism was a philosophy of personal resilience and toughness and endurance and individuality, but it was also an ethical framework for living, and you can't just pick the first parts and ignore these other parts."

• Stoicism encompasses more than just personal resilience; it also includes ethical living.

• Stoicism is often misunderstood as being devoid of emotion and compassion.
• True Stoicism involves balancing personal control with empathy and consideration for others.

"You and I talked about what the Stoics got wrong... where were the Stoics potentially insufficient or what did they get wrong... there is this idea that Stoicism... is about stuffing the emotions down, not feeling them, not caring about anything that doesn't have to do with you."

• Stoicism should not be about suppressing emotions but understanding and integrating them.

"As a decent person going around the world, trying to offend people deliberately, not caring about how your words land on them or about their feelings is not just rude; that is something that you control."

• Deliberately offending others is against Stoic principles, which emphasize justice and consideration for others.

• Being offended is often more about the person taking offense than the offender.
• Stoics believe in controlling their reactions and being considerate of others' feelings.

"Whenever you're offended, you are complicit in taking offense... we are putting labels on this thing that is outside us and we have no control over."

• Offense is a personal reaction and should be managed internally.

"Going through the world intending to be considerate and compassionate and kind and empathetic... is something we control."

• Stoicism encourages intentional kindness and empathy.

• Misunderstanding Stoicism as emotionless can lead to negative behaviors.
• True Stoicism involves empathy, social adeptness, and relational understanding.

"There was this guy in the UK who was fired from his job... he claims that it's religious discrimination because he was a Stoic... that's the opposite of what Stoicism is."

• Misinterpreting Stoicism can lead to justifying inappropriate behavior, which is contrary to its principles.

"If you think of Stoicism as the suppression and elimination of emotion, you're essentially reverting back to an earlier school of philosophy, the Cynics."

• Stoicism should not be confused with Cynicism, which rejects societal norms and emotions.

• Effective communication involves empathy and understanding the audience.
• Tailoring messages to be considerate and impactful is crucial.

"Thinking about the best way to say what it is that you have to say is obviously very important... the difference between the right word and the wrong word is the difference between lightning and a lightning bug."

• The choice of words and delivery significantly impacts the effectiveness of communication.

"The ability to really empathize and think about how what you're doing is going to be perceived and how it will resonate is just like the most important skill that there is."

• Empathy is essential for successful communication and interaction.

• Balancing personal authenticity with audience expectations can be challenging.
• Customizing communication to meet audience needs while staying true to oneself is important.

"Every audience thinks it's very different... but actually, most organizations and people have the same issues... making little bits of effort or little tweaks that make them feel as if this was tailored exactly to them can be incredibly powerful."

• Understanding commonalities among audiences while making personalized adjustments enhances engagement and effectiveness.

• Emphasizing the importance of diverse representation in stories and books.
• Including a wide range of people, cultures, places, and professions to appeal to a broad audience.
• Making efforts to include specific experiences that allow readers to see themselves in the narrative.

"You don't want to just be talking about the same 10 dead white guys from history. You want to have a wide representation of people and cultures and places and genders and whatever so that each of the readers can see themselves in the pages of what you're doing."

• Diversity in storytelling helps in resonating with a wider audience by including varied experiences and professions.

• Balancing preparation and authenticity in media appearances.
• Avoiding the extremes of winging it and reciting a script to bring the best self to media engagements.
• The paradox of being well-practiced yet able to adapt and be authentic.

"If you're winging it, you're probably not bringing your best self to it, and on the other hand, if you're reciting a script, you're probably not being authentic and real either."

• Authenticity in media requires a balance between preparation and spontaneity.

• Analogizing mastery in media to playing multiple instruments.
• The importance of deep understanding and practice in building confidence and adaptability.
• Trusting oneself to handle unexpected situations due to extensive practice and familiarity with the subject matter.

"I have spent 25-30 years learning how to play almost a lot of instruments. It gives me a sense of comfort that I've got range because I've practiced understanding something at a deep level."

• Mastery involves extensive practice and understanding, enabling adaptability in various situations.

• The significance of planning in achieving success, even if specific plans may not always be used.
• The role of preparation in handling unexpected changes during live events or interviews.

"Plans are worthless, but planning is everything."

• Planning prepares one to handle unexpected situations effectively.

• The benefits of thorough preparation for media appearances, even if the actual event deviates from the plan.
• How familiarity with the subject matter and extensive practice can lead to successful and authentic performances.

"I had a very good sense of how the interview was supposed to go, and I get there, and Carson Daly proceeds not to ask any of the questions from the prep. Because I'd practiced so many times, I had things that I knew I could say, and it worked out perfectly."

• Extensive practice allows flexibility and authenticity during media appearances.

• The excitement and authenticity that comes from improvising during live events.
• The ability to adapt and perform well even when things do not go as planned.

"Isn't it fun to play jazz though? It's really electric."

• Improvisation brings a sense of excitement and authenticity to performances.

• The importance of staying focused on the core activity that one loves.
• Avoiding the trap of becoming a caricature or a guru and instead continuing to engage in the primary craft.
• Writing books as a way to stay humble and connected to the core activity.

"My main thing is that I write books. I happen to write books about stoicism, and sometimes about other things, but my main thing is that I am a writer of books."

• Staying engaged in the core craft helps maintain authenticity and humility.

• The challenge of balancing multiple roles and activities while striving for excellence.
• The risk of spreading oneself too thin and losing focus on the primary craft.

"I want to do three things exceptionally well. I think I'm doing seven things okay."

• Balancing multiple roles requires focus and prioritization to maintain excellence.

• The distinction between the act of writing and the process of publishing.
• Staying focused on the act of writing to maintain authenticity and connection to the craft.

"There's a big difference between writing and publishing. The version of me that's staring at a blank page and struggling with it is different from the one who is on stage or in front of cameras answering questions."

• Focusing on the act of writing helps maintain authenticity and connection to the craft.

• The value of continuous learning and practice in maintaining expertise and authenticity.
• The role of ongoing engagement in the craft in staying grounded and humble.

"As long as I'm writing books, I'm still in touch with the main thing as opposed to sitting on top of this series of accomplishments or this audience."

• Continuous learning and practice help maintain expertise and authenticity.

• The danger of becoming a caricature or a guru by focusing too much on the persona rather than the craft.
• The importance of staying engaged in the core activity to avoid this trap.

"You become just the name or the letters and not the person who is still doing the thing."

• Staying engaged in the core activity helps avoid becoming a caricature or a guru.

• The humbling and challenging nature of engaging in the core craft.
• The importance of staying connected to the craft to maintain authenticity and humility.

"The craft of whatever you do is humbling, and the longer you can stay in that, the more authentic and real you'll be."

• Engaging in the core craft helps maintain authenticity and humility.

• Concept of Identity: The discussion emphasizes the importance of not letting one's profession or actions define their entire identity.
• Professional Bondage: The idea that being identified solely by one's job can feel like a form of bondage.
• Freedom of Being a Verb: Emphasizes the value of being defined by actions (verbs) rather than static labels (nouns).

"You are not what you do. You are so big that the thing that you do can never encompass who you really are."

• Explanation: This quote highlights the vastness of personal identity beyond professional roles.

"I surfed, but I was not a surfer. I never want to be in a felt sense of professional bondage."

• Explanation: Differentiating between the action and the label to maintain personal freedom.

"Having the freedom of not being the noun but being the verb is quite simple and really rich."

• Explanation: Emphasizes the richness of defining oneself by actions rather than static identities.

• Paul Graham's Essay: Discusses the idea that larger identities can make people less intelligent.
• Independence: Maintaining personal independence by not over-identifying with groups or labels.

"The more you identify as or with things, the stupider you are."

• Explanation: Over-identifying with groups or labels can limit intellectual openness.

"The difference between being someone who surfs and a surfer is the refusal to accept that you are the identity that someone or some set of habits wants to foist upon you."

• Explanation: Maintaining independence by refusing to be narrowly defined by one’s actions or habits.

• Broism: A term used to describe a superficial and productivity-focused interpretation of stoicism.
• Surface-Level Understanding: The danger of having only a shallow grasp of philosophical ideas.
• Ethical Framework: True stoicism involves a deeper ethical and moral framework beyond just personal resilience.

"Broism has kind of become this term people have used to throw around this kind of male-centric, masculine hustle culture."

• Explanation: Broism is criticized for its shallow, productivity-focused interpretation of stoicism.

"If you have only a surface level understanding of the ideas, it makes you very susceptible to people who are trying to capture that attention for less than good ends."

• Explanation: Superficial understanding makes people vulnerable to manipulation.

"Stoicism was a philosophy of personal resilience and toughness and endurance, but it was also an ethical framework for living."

• Explanation: True stoicism includes a comprehensive ethical and moral framework, not just personal toughness.

• Four Virtues: Courage, Discipline, Justice, and Wisdom.
• Ethical Living: The importance of aligning courage and discipline with justice and wisdom.
• Moral Compass: Stoicism requires a moral compass to guide personal resilience and toughness.

"Stoicism is built around these four virtues: courage, discipline, justice, and wisdom."

• Explanation: The foundational virtues of stoicism.

"If discipline and courage are not pointed towards a North Star of what is right, you're going to end up very far from where you need to end up."

• Explanation: Courage and discipline must be aligned with justice and wisdom.

• Justice and Compassion: The importance of compassion in ethical considerations.
• Fairness: Questioning the concept of fairness as a virtue.
• Personal Integrity: Emphasizing personal integrity, honesty, and keeping one's word.

"The idea that you would be indifferent to the sufferings of other people or the consequences of a policy strikes me as one of the big problems of our time."

• Explanation: Indifference to others' suffering is a significant ethical issue.

"I have a hard time with fairness as a general virtue."

• Explanation: The speaker questions the practicality and presence of fairness in the real world.

"We have to practice our virtues and values in low temperature environments to have access to them in high temperature environments."

• Explanation: Practicing virtues in everyday situations prepares one for more significant challenges.

• Sports as a Metaphor: Sports provide lessons on integrity and honesty.
• Calling Fouls on Oneself: The importance of self-regulation and honesty in sports.
• Building Ethical Muscles: Practicing honesty in low-stakes situations builds the capacity for integrity in high-stakes situations.

"You can win by cheating, but are you really winning and who are you becoming as a result of winning that way?"

• Explanation: Winning through dishonest means compromises personal integrity.

"In sports, you want to win more than anything, but to win by shoving an opponent or tripping them is to lose in a different kind of way."

• Explanation: True victory requires integrity.

"The person who calls the penalty on themselves in a low stakes environment is building the muscle to be able to do it when it really matters."

• Explanation: Practicing honesty in minor situations builds the ability to maintain integrity in critical moments.

• Personal Stories: Examples of practicing virtues in everyday life.
• Courage and Honesty: Stories of individuals demonstrating courage and honesty in their actions.
• Teaching Virtues: The role of education and upbringing in instilling virtues.

"My son noticed that his teacher made a mistake that would have given him an unearned higher grade. He pointed it out to the teacher, who then recognized his honesty."

• Explanation: An example of practicing honesty and integrity.

"His friend noticed a similar mistake but chose to remain silent, benefiting from the error. This highlights the difference between practicing and neglecting virtues."

• Explanation: Contrasting responses to similar situations demonstrate the importance of integrity.

"We have to practice our virtues and values in low temperature environments to have access to them in high temperature environments."

• Explanation: Reinforces the importance of practicing virtues regularly to be prepared for more significant challenges.

• Practicing Virtues: Emphasizes the importance of regularly practicing virtues to build ethical strength.
• Comprehensive Ethical Framework: True stoicism involves a deep ethical framework, not just personal resilience.
• Personal Integrity: The significance of maintaining personal integrity and honesty in all aspects of life.

• Moments of greatness and selflessness in sports and history can be as significant as victories.
• These moments often highlight human decency, honor, and the right thing to do, even in challenging circumstances.

"Regulus to the Romans became as famous as any of their other great conquerors for this moment of selflessness and courage and commitment."

• Regulus is remembered for his selflessness and adherence to his word, even at the cost of his life.

"Cincinnatus is celebrated for the next 2,000 years because 17 days after becoming dictator, he lays down his command and goes back to his farm."

• Cincinnatus exemplified humility and service to the greater good, a model for leaders like George Washington.

• Regulus: His story illustrates the value of keeping one's word and the impact of personal integrity on broader societal trust.
• Cincinnatus: His actions demonstrate the importance of relinquishing power and returning to ordinary life, setting a precedent for future leaders.

• High character moments, such as athletes taking care of their teams, are crucial yet often under-celebrated.
• Historical figures like Galileo, who spoke truth to power, exemplify the importance of integrity and courage.

"One of the athletes in the NBA Finals spent time waiting to make sure he took care of all the people on his team that lost."

• This highlights the significance of small, high-character actions in sports.

"Galileo was basically condemned at the end of his life because he was speaking truth to power."

• Galileo's story underscores the importance of standing by the truth, even when faced with opposition.

• NBA Athlete: This action shows the importance of caring for others and maintaining integrity in competitive environments.
• Galileo: His story serves as a reminder of the value of truth and scientific integrity against prevailing dogmas.

• Having truth-tellers in one's life, such as family and close friends, is vital for personal growth and maintaining humility.
• These individuals provide honest feedback and help keep one grounded.

"My wife is certainly one of those people having children is a great part of this."

• Family members often provide the most honest and impactful feedback.

"James Ray ultimately asked him if he would officiate his wedding, his prison wedding."

• This illustrates the power of forgiveness and the profound impact of personal relationships.

• Wife and Children: They play a crucial role in offering candid feedback and keeping one grounded.
• James Ray's Request: This example shows the depth of forgiveness and the transformative power of personal connections.

• Understanding that feedback is true to the person giving it and recognizing the validity of their perspective is crucial.
• It's important to differentiate between personal feelings and objective criticism.

"When somebody tells you something's wrong with what you're doing, they're right in that it didn't work for them."

• Feedback should be seen as an opportunity to improve, even if it doesn't align with one's own perspective.

"When someone is expressing their feelings, those feelings are true to them."

• Acknowledging the truth in others' feelings helps in understanding and addressing their concerns.

• Feedback Validity: Recognizing the truth in feedback helps improve one's work and relationships.
• Feelings Validity: Understanding that others' feelings are true to them fosters empathy and better communication.

• Historical figures like Abraham Lincoln are admired for their empathy, political astuteness, and moral clarity.
• Lincoln's ability to empathize with both the oppressors and the oppressed while maintaining a firm moral stance is notable.

"Lincoln was uniquely suited to lead America in the Civil War and tackle the Scourge that was slavery."

• Lincoln's leadership during the Civil War and his moral clarity on slavery are key aspects of his legacy.

"Lincoln had a remarkable amount of empathy for the people who were inflicting that wrong as well as for the victims of that wrong."

• His empathy for all parties involved in the issue of slavery is a testament to his profound understanding of human nature.

• Lincoln's Leadership: His leadership qualities and moral stance during the Civil War are exemplary.
• Empathy: Lincoln's empathy for both sides in the slavery debate highlights his deep understanding of human nature and morality.

• Parents often hope their children will find their own paths and passions, understanding both the rewards and costs of being elite.
• Reflecting on life phases, there is a desire to balance intensity with presence and enjoyment.

"I just want them to become whatever they're meant to become."

• The hope for children to find their own paths and passions, rather than imposing specific expectations.

"I'm trying to find the right balance of how do you relax and be present and enjoy without taking it too far."

• Striving for a balance between ambition and enjoying the present moment.

• Children's Paths: Parents' wishes for their children to follow their own passions and paths.
• Life Balance: The importance of balancing ambition with presence and enjoyment in life.

• The struggle to balance discipline with flexibility in daily routines and commitments.
• Understanding the difference between commitment and compulsion is crucial for maintaining healthy habits.

"Deciding hey this is when I start the day, this is my habit, this is my practice."

• The importance of establishing and maintaining daily routines.

"When does commitment become a kind of compulsion and knowing the difference between those two."

• Recognizing when discipline turns into an unhealthy compulsion is essential for personal well-being.

• Daily Routines: The significance of establishing consistent habits and practices.
• Commitment vs. Compulsion: Differentiating between healthy discipline and unhealthy compulsion.

• Expressing gratitude for support and encouragement from others.
• The importance of community and feeling supported in one's endeavors.

"I feel like you're in my corner even though we don't hang on a regular basis."

• The value of feeling supported and encouraged by others in one's journey.

"I appreciate what you stand for and hope the listener is inspired by your work."

• Acknowledging the impact of one's work on others and the importance of community support.

• Support: The importance of feeling supported and encouraged in personal and professional endeavors.
• Community Impact: Recognizing the influence of one's work on the community and expressing gratitude for that support.