Ryan Holiday is the best-selling author of more than 10 books including The Obstacle Is The Way, Ego Is The Enemy, and most recently, Courage Is Calling. He’s sold millions of copies and his work impacts leaders all over the world.

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  • A philosophy of offense. General James Mattis was once asked by a tv reporter, “what keeps you up at night?” And he said, “I keep people up at night.” Captured his philosophy of offense (a bias for action… People who make it happen)
  • Preparation makes you brave. —- the Army life handbook that was handed out to millions of soldiers in the Second World War. All about preparation. As Epictetus says the goal when we experience adversity is to be able to say, “this is what I’ve trained for, for this is my discipline.”
  • Never question another man’s courage. “It’s very easy to judge. It’s very hard to know.” Waste not a second questioning another man’s courage. Put that scrutiny solely on your own.
  • Be strong and of good courage. We hear in the book of Joshua. William Faulkner said  “be scared. You can’t help that. But don’t be afraid.”
  • You can’t spend all day in deliberation — the story of a Spartan king who was marching across Greece. As he entered each new country, he sent envoys to ask whether he should be prepared to treat them as friends or enemies. Most of the nations decided quickly and chose friendship. But one king wanted to think about his options. So he thought and thought and thought until it was chosen for him. “Let him consider it then,” the frustrated Spartan General said as he fixed his jaw. “Which we March on.” Even if you choose not to decide, you still have made a choice. You are voting to let them decide.
  • The power of poise — in the year 175, Marcus Aurelius was betrayed by his general Avidius Cassius in an attempted coup. He could have been scared. He could have been furious. He could have exploded. But this would not happen. He said, “the nearer a man is to a calm mind, the closer he is to strength.”
  • Ernest Shackleton — Arctic expedition got stuck in the ice. His motto —fortitudine vincimus By endurance we conquer
  • The courage to care — General Mattis said “cynicism is cowardice, it takes courage to care.” Only the brave believe, especially when everyone else is full of doubt. the story of Theodore Roosevelt the biographer Herman Hagedorn wrote “is the story of a small boy who read about great men and decided he wanted to be like them.”
  • Ryan shared a personal story about his experience working for American Apparel and his relationship with founder/CEO, Dov Charney. He was asked to do something immoral and he declined… But, he didn’t stop Dov from doing it. “It doesn’t age well to just be scared in the moment. All that’s left is what you didn’t do.”
  • When you earn some power or develop a platform, how will you use it? When Lyndon Johnson became President, he said, “What the hell is the presidency for if not to do big things?”
  • Consistency — How does Ryan produce so much work (publishing lots of books) on a consistent basis? You have to show up every day. Tackle the smallest component part of the project for that day. Do what’s in front of you.
  • Why does Ryan work out every day? “I like to think, ‘who’s in charge?’ I’m in charge.”
  • Excellence =
    • All leaders are readers
    • Curiosity is a must
    • Desire for knowledge
    • Self-discipline
    • An element of service – it’s not just about you
  • How does Ryan define success?
    • Autonomy. “The power of my own life, who I spend time with, and what I’m doing. I don’t want to be a slave to the system.”
  • Apply to be part of my Leadership Circle


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