Ryan Holiday is one of the world’s bestselling living philosophers. His books like The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, and the #1 New York Times bestseller Stillness Is the Key appear in more than 40 languages and have sold more than 5 million copies. His latest book (a #1 NY Times Best-Seller) is called Right Thing, Right Now. This conversation was recorded in person at Ryan’s bookstore, The Painted Porch, which sits on historic Main St in Bastrop, Texas.

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The Learning Leader Show

  • June 16, 2024 – Birthday and Father’s Day. How does stoicism impact you as a dad? “What’s at stake today is how they remember you 20 years from now.”
  • Choose a North Star — Choosing a North Star can function as a compass professionally, personally, and morally.
    • Most people don’t do the work to figure out what their North Star is… Most people default to what others do, and then they end up comparing themselves to others.
    • Ryan Holiday’s North Star? Writing…
  • Pay the taxes of life gladly: Not just from the government. Annoying people are a tax on being outside your house. Delays are a tax on travel. Haters are a tax on having a YouTube channel. There’s a tax on everything in life. You can whine. Or you can pay them gladly.
  • Oscar Wilde wrote in The Portrait of Dorian Grey “The aim of life is self-development. To realize one’s nature perfectly. That is what each of us is here for.” —- What are you here for?
  • Stoicism – “A stoic doesn’t control what happens but they focus on how to respond to what happened. The virtues of stoicism are courage, discipline, justice, and wisdom.”
  • Build a coaching tree — Popovich reference – and his coaching tree – how do we get better at making a goal to build a forest of leaders? What’s interesting about Pop’s coaching tree is there is a huge diversity of what he’s created. What’s interesting is the coaches who have learned from him are all different – they’re not replicas of Coach Popovich.
    • RC Buford (GM of the San Antonio Spurs) said, “We have a good coaching tree. That’s what we do here. In all roles.”
    • A shocking number of players have decided to stay in San Antonio, so much so that they have an alumni locker room in their practice facility because they choose to stick around afterward.
    • “I love the idea of “hey we’re an organization, and we want to win, but our ultimate job is to bring good people in, and bring them better, and learn from them along the way.”
    • “We don’t talk enough about the bad coaching trees… ultimately you measure greatness about how replicable their system is and others can take it and use it as well. Don’t just judge people on their wins, but on their coaching tree… or lack thereof.
    • When you’re hiring someone, can you both be on the same page – and there’s clarity. When I get invited to something, who am I bringing? Or when it’s a specific project, who on my team will crush it with me or on their own? Understanding that this will be a tour of duty.
  • Robert Greene “Robert knew I wanted to be a writer and he knew what I wanted to do, and it allowed me to realize that he was letting me do this to understand how the whole writing process works. If somebody wants to work with someone else, what’s the best way to reach out to that person, to try and get your foot in the door.”
  • Mentors: (Advice to mentees) “Don’t say ‘I’ll do whatever, or I’ll do anything,’ I don’t need anything done, I have very specific things that need to be done. Don’t present them with the problem of you…. Present them with the problem they have and several ideas that you have to potentially help. Be specific and present a solution to a potential problem that maybe they haven’t thought about yet.”
  • Keep your hands clean – the difference between Patrick Reed and Rory McIlroy.
  • Be kind — JM Barrie, the creator of Peter Pan said in 1902, “Shall we make a new rule of life from tonight? Always try to be a little kinder than is necessary.”
  • Discipline is a “me” virtue. Justice is a “we” virtue.
  • Make “Good” Trouble“If you got into this to gain a lot of fans, you’ll never do anything to lose fans….. you don’t have the fans, the fans have you… it’s the other way around. There’s a balance, I don’t want to speak up on every divisive issue, but at the same time if you’re not speaking up on things that you think are important, and you keep silent, then you’re creating a form of death, and you’re hurting other people that could potentially learn from your words and thoughts… You have to think about how you want to use your platform and the authority you have. It’s easy to say politicians live this way, but when’s the last time you spoke up on something you didn’t agree on?”
  • President Truman“An incredible example of an ordinary person doing extraordinary things… the last president to not have a college degree. He educated himself and had core values and a sense that he was obligated by the constitution, human decency, and trying to do what was right. He had a strong moral code that guided him in difficult stances, and he had confidence and security. When we think of Presidents and Generals who have outward accomplishments, what I love about Truman is that he watched everyone else steal millions of dollars and he continued to pay off his bankruptcy debts. It doesn’t matter that everyone else is doing it… I’m not going to do it.”
  • Goal Setting – “I don’t set any goals…” I just do the work every day, our goals are usually outcome specific and they’re rooted in what are other people going to think about the outcome of this. If I have a goal, they’re not geared towards a win or an outcome… the goal is to wake up and do… and I do it daily.”
  • The desk where we recorded: Was owned by Joan Didion… “Objects of history get me excited. My vice is I collect historically significant things, at some point, I’m going to re-sell the table… now other people have sat at it, and so I’ll probably re-sell it and donate the money… ”significant objects”.. a guy buys a random piece of junk on eBay, and then he’d have a writer write a story about the item and then they’d resell it and people would pay more money for it.”
  • Why is his publisher having him re-do the entire audio for the 10th anniversary of The Obstacle is The Way (instead of Ryan just reading the updated parts): “My voice is ten years older. A lot has happened in those ten years.”
  • Apply to be in my Learning Leader Circle

Time Stamps

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