Ryan Holiday

Quotes are word for word from the source.

• Value of podcasting

  “having a podcast is pretty magical because you get (for free) something that no amount of money in the world could buy: Access to some of the smartest and most interesting people in the world.”

  Our noteRyan explains why hosting a podcast is a unique networking and learning opportunity.

• Attention grabbing placement

  “I put it in the window so the neighbors would see.”

  Our noteRyan explains why he placed a unique Craigslist find in his apartment window.

• Consistency in greatness

  “And that's what the path to greatness almost always looks like: small, ordinary actions, repeated for a very long time.”

  Our noteReflecting on how Lou Gehrig's career was built on simple, reachable habits.

• Managing vocal minorities

  “You NEVER piss off your vocal minority-unless of course, as I discussed early , it is for the benefit of your silent majority.”

  Our noteRyan discusses the risks of offending influential groups like the press.

• Imposter syndrome

  “That the root of all my progress this far had very little to do with myself and everything to do with the false confidence the relationship had given me.”

  Our noteRyan reflects on the self-doubt he felt after a major breakup.

• Rarity of quality

  “First, good content is INCREDIBLY rare. Think of all the sites you read, how many of them actually produce what you read? Most of them are just portals to the people who are the real producers.”

  Our noteRyan discusses the scarcity of original content creators versus aggregators on the internet.

• Unmet quality demand

  “The latent demand for quality is there but the people who can satiate it have fallen down on the job.”

  Our noteRyan points out the gap between the audience's desire for quality and the current supply.

• True goodness

  “Doing what you're supposed to do does not make you a good person.”

  Our noteRyan challenges the idea that following rules equates to moral superiority.

• The Need for Mentors

  “The Stoics knew that life is hard and requires help. "Only beasts can do it alone," Marcus said. We need guidance from those who are further ahead on the path. We need mentors.”

  Our noteRyan explains why seeking guidance from experienced people is essential for personal growth.

• Embracing Uniqueness

  “If you want to improve, Epictetus said, if you want to achieve wisdom, you have to be okay with looking strange or even clueless from time to time.”

  Our noteRyan discusses the necessity of being willing to look foolish in order to grow.

• Power of questions

  “Questions are the key not just to knowledge but to success, discovery, and mastery. They're how we learn and how we get better.”

  Our noteRyan emphasizes that asking simple questions is essential for growth.

• The root of urgency

  “It comes from not being able to understand how someone can be so devoid of purpose or direction that they not only lack urgency in their own life, but they actively impede others who know where they want to go.”

  Our noteRyan explains why he feels rage toward people who move slowly and lack direction.

• Stoicism and politics

  “The idea that the Stoics were indifferent to current or political events is preposterous, not only because Cato held multiple public offices, Panaetius was a diplomat, Publius Rutilius Rufus was an anti-corruption crusader”

  Our noteRyan refutes the claim that Stoicism encourages apathy toward social and political issues.

• Artistic value barometer

  “The claim is that it is FALSE to rely on art's ability to move us as barometer of its value.”

  Our noteRyan discusses the 'Affection Fallacy' which claims emotional impact shouldn't determine a work's value.

• Purpose of creation

  “Ultimately, I think you have to ask yourself the ultimate purpose of art. Is it not to create a reaction, subtle or overt or otherwise?”

  Our noteRyan argues that the primary goal of creative work is to elicit a response from the audience.

• The purpose of journaling

  “That's how I think of journaling : it's me actively fighting to be the person that philosophy wants me to be. So each morning, usually after a long walk , I go to my office and pull out three small notebooks.”

  Our noteRyan describes his daily journaling routine as a tool for self-improvement.

• Functional illiteracy

  “"If you haven't read hundreds of books," Mattis says, "you're functionally illiterate.”

  Our noteQuoting General James Mattis on the necessity of reading for leaders and professionals.

• Learning from mistakes

  “How dare you waste your investor's money by not reading and learning from the mistakes of other entrepreneurs?”

  Our noteRyan argues that failing to learn from history is unethical for business owners.

• Learning through action

  “"We become builders by building and we become harpists by playing the harp," he writes. "Similarly, then, we become just by doing just actions, temperate by doing temperate actions, brave by doing brave actions."”

  Our noteRyan quotes Aristotle to show that character is built through repetitive practice and action.

• Effects Based Thinking

  “Life is an effects based operation. And then means looking at things not as they are but what they're intended to be.”

  Our noteRyan defines his concept of effects-based operations in daily life.

• Life decisions

  “I am now at a point where I have to make some rather serious decisions about my life. And it is with these sort of questions that I am at my very best and my very worst.”

  Our noteRyan reflects on the internal struggle of making major career and life choices.

• Discreet conflict management

  “That's when I realized that as long as you don't broadcast your beefs, you can get away cold with murder. It's even better if you don't allow the beef to take place.”

  Our noteThe importance of not broadcasting disputes or letting them escalate publicly.

• The Obstacle Is the Way

  “The mind adapts and converts to its own purposes the obstacle to our acting. And then he concluded with powerful words destined for a maxim. "The impediment to action advances action. What stands in the way becomes the way."”

  Our noteRyan explains the core Stoic principle of turning obstacles into advantages.

• Deepening foundational knowledge

  “The Classical World: An Epic History from Homer to Hadrian by Robin Lane Fox (really long but really good. solidifies a lot of what I read in primary texts but didn't understand)”

  Our noteRyan explains how a comprehensive history book helped him synthesize primary source material.

• Curiosity and discovery

  “I bought this just so I could have it (it was like $10 at Borders) and then I started flipping through it and got hooked.”

  Our noteRyan describes how he unexpectedly got hooked on a massive 1,600-page book about the JFK assassination.

• The Strategy Paradox

  “We tend to wrongly think that strategy is about coming up with a genius plan and then committing to it. In fact, this is often a recipe for disaster, particularly in business.”

  Our noteCritiquing the common misconception that rigid commitment to a single plan is good strategy.

• Audience connection strategy

  “We shouldn't be thinking about acquiring a larger audience but rather how to become better connected with the one you already have.”

  Our noteRyan discusses the strategic error of prioritizing reach over depth in online communities.

• Seeking expert guidance

  “So if someone knows the subject a little, I'd genuinely appreciate being taught or discussing it.”

  Our noteHe is reaching out to his audience to find someone who can explain entropy to him.

• Logical Fear Deconstruction

  “We must break fear down logically. Go to the root of it. Explain it. Tell yourself: It's just money. It's just a bad article. It's just a meeting with people yelling at one another.”

  Our noteRyan explains how to use logic to strip away the emotional power of intimidating situations.

• Action over procrastination

  “No, Don't Do It Later. Do It Now - The Case Against Procrastination.”

  Our noteRyan Holiday argues for immediate action instead of delaying tasks.