The Obstacle Is The Way Book Summary

The Obstacle Is The Way | Free Book Summary

The Obstacle Is The Way

Ryan Holiday

Media strategist Ryan Holiday explains how modern individuals can utilize some revered Stoic principles to turn obstacles into advantages.

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Stoicism: Overcoming Obstacles

Through the ages, people have relied on the philosophy of Stoicism to conquer their difficulties.

Stoicism – an operating manual for life – is a pragmatic philosophy that helps people overcome their difficulties.

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The Key Takeaways

  • Stoicism rests on three primary disciplines: “perception, action and the will.”
  • Perception is the way you see the world. Viewing it realistically or with a bias can help or hinder you.
  • The right action is always directed, deliberate, bold and persistent.
  • The world can break your body, but thanks to willpower, it can never break your spirit and mind. You control your will.

The Positive Side Of Obstacles

  • Obstacles that stand in the way of progress can actually promote progress.
  • People improve by facing and meeting challenges head-on.
  • The obstacles you overcome provide benefits you could not otherwise realize.



Wisdom Through The Ages

Stoicism and Marcus Aurelius’s wisdom motivated men and women throughout history, helping to spark the Renaissance, the Enlightenment, the Industrial Revolution, the US civil rights movement, and Silicon Valley’s amazing high-technology advances.

Stoicism addresses real-life issues that confront everyone: “Are you worthy?” “Can you get past the things that inevitably fall in your way?” “Will you stand up and show… what you’re made of?”

The Discipline Of Perception

  • How you see the world provides meaning to the events of your life. Don’t assign “good or bad” labels to events.
  • Put aside your fears and prejudices. See things for what they are. See the truth, not a biased interpretation of it.
  • How you think about and react to obstacles while maintaining your composure defines you.

Lessons Learned

Stay objective. When necessary, change the way you interpret what you see. Don’t agonize over the past or worry about the future. Focus your thoughts and actions on the present. Find the good in the bad. Stay bold.

The Discipline Of Will

The world can knock you down and break your heart. But if you harness your willpower, no knockdown blow can deter you. Your will—not anyone else’s—puts you firmly in charge of your life and accomplishments. Proper willpower is steady, not blustery.

You connect to your internal power without boasting; the best strength of will springs from “humility, resilience, and flexibility.”

Stoicism: The Operating Manual Of Life

Across the centuries, academics in their ivory towers tried to assume ownership of philosophies such as Stoicism and tried to guard it as part of their exclusive domain. As developed by Seneca, Zeno, and others, the philosophy of Stoicism was never intended to be isolated as a remote, sterile intellectualization.

Those sages first promulgated Stoicism as “an operating system for the difficulties and hardships of life,” and that is how it should remain.

A Stoic Story: Recognizing Your Power

During the 1960s, Rubin “Hurricane” Carter was a leading middleweight title contender. Carter was unjustly convicted in a triple-homicide case. In jail, he never ceded power to the warden or guards. He maintained his independence and his identity. Carter—and not the authorities—held control over his mind and spirit. He spent his time in prison working on his legal case.

After 19 years, Carter got his verdict overturned. Once released from prison, he never looked back.

A Stoic Story: Altering Your Perspective

The American industrialist John D. Rockefeller once worked for just 50 cents a day as a bookkeeper in Cleveland, Ohio. As an investor, he rode out major national financial crises in 1857, 1873, 1907, and 1920. Where others saw catastrophe and chaos, the objective, unemotional Rockefeller saw valuable lessons and opportunities.

So much so, that by 1877, his perception and his nerves helped him corner “90% of the oil market.”

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