Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More

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Ryan Holiday, Author of:

  • Let his personal connection to the ex-CEO and desire to be challenged lead him to accepting a terrible role consulting for American Apparel
  • We need to be careful what work we say yes to, as it will take us away from other more important things such as family, more interesting/rewarding work

Lessons from American Apparel:

  • When bad things happen, our ego is what makes it worse. It prevents us from stepping away.
  • When you sign a contract, you need to have an “out”, so you can walk away.
  • It is not healthy if you choose chaos and stress over the things that are important to you.
  • Choice of a life or accomplishment, one tends to take away from the other – choose wisely
  • Are you working to live or living to work?


  • Human BEING not human DOING.
  • Life can become unmanageable because you can’t prioritize.
  • Work is a drug for some.
  • Don’t necessarily work a lot, but they can’t stop. Always need to do something.
  • Type A personalities tend to live where the action is.
  • You should be able to create opportunities from anywhere.
  • Don’t live where you might succumb to too many distractions.
  • Workaholics Anonymous might help if you need it

The Obstacle is the Way:

  • Because of Tim Ferris and Shane Parrish, it got popular in the sport world.
  • Michael Lombardi recommended it.
  • John Snider, the manager of the Sea Hawks.
  • Managing emotions, keeping a clear head and making the best with what you have are all things professional athletes need to learn.
  • Eric Weinstein: ”generalized fame is overrated, but selective fame is useful.”
  • 1000 true fans and Small Giants are all about selective fame.

Internal versus External:

  • Why Ego? It’s interesting to see people act against their own interest because of ego.
  • Ego is the biggest internal obstacle.
  • Pride, vanity, delusions, greed, wanting all the attention prevent us from accomplishing what we want.
  • Ego sucks us down like the law of gravity.
  • Prevents the connection to reality.

Sherman VS Grant

  • H. Liddell Hart: “there’s a difference between someone who is utterly confident and people whose image is a slow accumulation of success.”
  • William Tecumseh Sherman and Ulysses S. Grant were two civil war heroes.

Sherman knew his own limits, Refused presidency to do things he was good at.

  • Grant tried to pursue and make money in things he had no skills.
    • Endless need to impress people who were already impressed.
  • Billions: “When people call you superman long enough, you start to believe it.”
  • Tim was given advice when The 4-Hour Workweek hit the best seller list: “You’re never as good as they say you are and you’re never as bad as they say you are”

Howard Hughes versus Elon Musk

  • Just because someone seems successful to you doesn’t mean they’ve accomplished what they wanted. (Kayne West)
  • Ego is the most dangerous when you’re already successful and trying to move on to your next goal.
  • Howard Hughes lost millions of dollar trying to accomplish insane projects.
  • Elon Musk did a thinking exercise by Aristotle called Going to first principles.


  • Fahrenheit 451:the people don’t want to be offended, so they burned the books.”
    • It’s not a government who dictates book burning, it’s a society afraid to be offended
    • #socialjustwarriors
  • Protect everyone’s feeling.
  • Take’s away form the actually alarming things happening.
  • Nowadays, anyone who disturbs or offends are badly viewed.
  • This trend tends to choke freedom of speech.
    • Nice things don’t need to be protected, it is the awful speech that needs protection
  • Scott Adams (Dilbert): ”being creative is like drilling for oil, sometimes you miss and sometimes it catches on fire.”
    • Meaning sometimes, smart people say dumb things.
  • I f you get accused of being racist or sexist, react by saying: How do you define that word? Make them fight themselves.
  • By being offended your wasting your own resources

How do someone improve themselves?

Previous Podcast with Ryan Holiday: The Canvas Strategy – What Ben Franklin and Bill Belichick Have in Common

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