Book Notes — Ryan Holliday — The Obstacle is the Way - Kloodle

Book Notes — Ryan Holliday — The Obstacle is the Way

By April 15, 2020 No Comments


Stoic philosophy is a fantastic “operating system” for your life. Ryan Holiday’s book “The Obstacle is the Way” is a summary of stoic learning. It contains examples from Seneca to Jackie Robinson. The wisdom within the book is required reading in the modern age. Resilience is a skill essential to success. The Obstacle is the Way is a primer on resilience and mental toughness.


“Our actions may be impeded, but there are no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.”

Marcus Aurelius

“The impediment to action advances action. What stands in the way becomes the way.”

Marcus Aurelius

  • Every difficulty is an opportunity to to practice a virtue; and opportunity to develop some aspect of your character.
  • Bad companies are destroyed by a crisis; good companies survive them; great companies are improved by them.

“Never forget, with every obstacle is an opportunity to improve our position”

Ryan Holiday

  • The things which hurt, instruct.
  • Look at things as they truly are. Do not attach perception. Be an impassive observer of everything around you. Make no judgements.
  • Attach no emotion to situations.
  • You have the choice over your feelings and reactions.
  • Only RATIONAL and DISCIPLINED minds succeed
  • Motivation is for amateurs. PROFESSIONALS are disciplined
  • Be objective
  • Control emotion
  • Derive the good from each situation
  • Steady your nerves
  • Ignore what disturbs and limits others
  • Place things in perspective
  • Revert to the present moment
  • Focus on what you can control (look after your own back yard)
  • There is ALWAYS a counter move.
  • Does getting upset provide you with more options?
  • If an emotion can’t change a situation, it’s unhelpful

“The perceiving eye is weak. The observing eye is strong”

  • Marcus Aurelius (Roman emperor and most powerful man in the world at that time) used to write down situations in terms of their raw observations?—?e.g. Vintage wine becomes “fermented grapes”. Emotion is taken away.
  • George Clooney became a more successful actor when he shifted his perspective. He was struggling with auditions. He changed his view from “I really need this role” to “The director has a problem, he needs to fill a role, and I am the solution”.
  • Always look for a glimmer of hope. Ask “Is there any chance of this happening?”
  • Bad situations are survived one day at a time, one moment at a time.
  • Make steady progress; keep up momentum
  • DO NOT succumb to overwhelm
  • Use constraints positively?—?make the lie of the land work for you
  • What makes other people flinch is where you should thrive
  • Meet problems with: –
  • Energy
  • Persistence
  • Coherent and deliberate process
  • Resilience
  • Pragmatism
  • Strategic vision
  • Savviness
  • An eye for opportunity and pivotal moments
  • People who achieve great things START
  • Just do SOMETHING
  • Could you be doing more? Are you really overworked?

“Always think with your stick forward”

Pilot’s mantra?—?Keep momentum moving forward whilst deciding how to respond to a situation. If you slow, the plane will go down

  • If you want momentum, you have to create it yourself.
  • Great entrepreneurs: –
  • Are never wedded to a position
  • Are never afraid to lose a little of their investment
  • Are never bitter or embarrassed
  • Are never out of the game for long

“Shut up. Go back to your station and try to think of what you are going to do yourself instead of worrying what’s going on “out there”. You know what your job is. Stop messing about and START WORKING”

Ryan Holiday

  • Do your job and do it well
  • Success happens when you show up and get on with your job
  • Take pride in whatever you are doing?—?even if it’s sweeping the floor
  • Everything we do matters.
  • Only self-absorbed idiots think they are too good for what they are currently doing
  • Treat every bit of work?—?even the things people can’t see?—?with pride
  • Masters exert force only where it is beneficial. They know the pressure points
  • Constraints force us to be creative
  • You won’t convince people by directly challenging beliefs. Convincing people comes from finding common ground and then gently showing your perspective.
  • Always listen; Never interrupt. By speaking you are regurgitating what you know. By listening you learn new things, hear new perspectives, challenge your own thinking.
  • Be physically relaxed but mentally strong
  • Learn to press forward when all around you see disaster
  • Ordinary people shy away from difficult situations. Great people plough head long into them
  • When disaster strikes, learn and develop your skill set. See disaster as an opportunity for growth.
  • During the good times, strengthen your mind and your body so that you can depend on them during the bad times
  • Be willing to expend energy and risk personal harm to build toughness.
  • The path of least resistance is a terrible teacher.
  • Conduct PRE-MORTEMS?—?think about the worst case scenarios before embarking on a task
  • Truly enjoy bad situations?—?not I feel OK; Not “I think I feel good” but “I FEEL GREAT”
  • Persistence is action. Perseverance is will. One is energy, the other is ENDURANCE

“Someone who tries all the professions, who teams it, farms it, peddles, keeps a school, preaches, edits a newspaper, goes to Congress, buys a township, and so forth, in successive years, and always, like a cat, falls on his feet, is worth a hundred of these city dolls. He walks abreast with his days, and feels no shame in not `studying a profession,’ for he does not postpone his life, but lives already.”

Ralph Waldo Emerson

  • If the world knows you can handle obstacles, it will keep throwing obstacles at you. You will keep getting stronger and stronger. Measure your success by the number of obstacles you’ve faced and conquered.

About Phill

Phillip is co-founder of Kloodle.

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