Copy of The Obstacle is the Way - Book Summary & Highlights

Cliff N O T E S 📝 👇 🧠 (for building your Second Brain)

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00:00 Intro

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  • Title*: The Obstacle is the Way : Reframe obstacles as Opportunities to move forward
  • Author*: Ryan Holiday *Book idea in 1 sentence*

On reframing obstacles as opportunities to move forward using Stoicism using historical stories.

01:00 Perception

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How we see and understand the events around us.

How we decide to judge and interpret those events.

Our perceptions = double edged sword

Can act as both Strengths and Weaknesses.


  • Emotional
  • Subjective
  • Short-sighted

How to solve/cure them?

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  • Learning to control emotions
  • Learning how to put things in perspective
  • Learning how to detach and examine things objectively


  • Daily Reminder*

We are in control on how we interpret events.

_Nothing is Good or Bad, but thinking makes it so_

  • Albus Dumbledore

Facing an uncontrollable, bad situation? You have 2 options:

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1. Let the negative feelings control your response

2. Filter them out and detach

Objectively, your problems might not be that bad.

_The PERCEIVING eye sees more than what is there. The OBSERVING eye sees only what is there._

How can you learn to cultivate the skill of controlling your emotions?

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  • defeat emotions with logic
  • study/learn critical thinking & rationality

Personal suggestion --> read Derek Sivers' _Getting out of a Bad State of Mind_ article.

Do that continuously, like building a new habit. It will get into your default state of being, and you will do it automatically.


“The Greeks had a word for this: apatheia. It's the kind of calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind. Don't let the negativity in, don't let those emotions even get started. Just say: No, thank you. I can't afford to panic.”

03:00 Action

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1. People who take action & act decisively are going to triumph.

2. Focus on the process, not the end goal.

3. Think about what you need to do in the present moment.

4. Do the best you can, with what you have, wherever you are.

5. Journey before the Destination.

Ryan's reference:

Thomas Edison with his many many failed 6000+ experiments to discover the missing element of his filament's bulb.

_personal favorite quote/reference injection_

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Historical reference: Theodore Roosevelt

At Harvard he was a boxer, a wrestler and a runner, but he never took any championships; he has shot big game, but has never been a first-class shot. He says himself in one of his Western books:

_I myself am not and never will be more than an ordinary shot, for my eyes are bad and my hand not over steady; yet I have killed every kind of game to be found on the Plains, partly because I have hunted very perseveringly, and partly because by practice I have learned to shoot about as well at a wild animal as at a target_

In other words, he has succeeded by his extraordinary capacity for energizing—for using every ounce of every capacity he possesses: by strenuous self-discipline, control and development. It is “the strenuous life” he glorifies, for it has made him what he is.


To access the notes to hundreds of books and get 25% off the annual premium subscription of Blinkist, visit

06:10 Will

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Will = gives you strength to contextualize events, endure hardship and derive meaning = Our Inner Citadel

The discipline of the heart and the soul.

Practical applications:

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Strengthen your Inner Citadel to be more well-equipped to approach life's obstacles in a way that let's you get the benefit out of them.

Premeditate/Visualize your Adversity aka Practice Negative Visualization

Learn to accept the things you cannot control and reframe each obstacle.

Ryan's say:

_Will is fortitude and wisdom — not just about specific obstacles but about life itself and where the obstacles we are facing fit within it_

Things that are not in your control:

  • natural calamities
  • random life-changing events
  • people.people.people: what people think of you (or in general), if they do or don't listen, their success, habits, perceptions, thoughts etc.

Things that are in your control:

  • your emotions
  • your actions
  • your judgements

_My formula for greatness in a human being, is amor fati_

~ Friedrich Nietzsche

Amor fati = The Love of Faith

“one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it … but love it.”


  • do not worry about the past
  • do not be fixated on the future
  • whatever happens, accept it firstly, and then learn to love it

Other relevant quote:

"Objective judgement, now, at this very moment. Unselfish action, now, at this very moment. Willing acceptance - now, at this very moment - of all external events. That's all you need. "

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_END _

Thank you for reading!

  • Please note that these are some quick notes I took out of Ali's video essay. You should watch the full video for additional golden nuggets and the extended version of each idea!

Ali, if you are reading this, thank you for helping me upgrade my world views. I really appreciate what you do.

You inspired me to take a more systemic approach while working on my YouTube channel and on my personal research as well.

Link to my work:

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or (newsletter)

Currently trying to combine and produce more videos on mental models, productivity, less confusion and futuristic scenarios.

Thank you and have a great day ahead!

  • Robert