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The Obstacle Is The Way book summary

The Obstacle Is The Way book cover

Practical Stoic philosophy, divided into three main sections: Perception, Action and Will. Each section is further split into short chapters. Each chapter is centered around a theme, frequently filled with real-life examples of individuals who have displayed a particular Stoic quality, with a lot of motivating philosophical prose in between.

The pattern of each example individual's story is as follows:

  • There will be an obstacle in their way
  • Instead of feeling scared / intimidated / fearful / embarassed, they confront the obstacle with everything they have, mentally and physically
  • They emerge on the other side, stronger


  • Our actions may be impeded… but there can be 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.
  • The impediment to action advances action. What stands in the way becomes the way.
  • Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?
  • Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.
  • Andy Grove, former CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”
  • Overcoming obstacles is a discipline of three critical steps. It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty. It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

Part 1: Perception

  • He had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.
  • Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings. Or, like Rockefeller, choose not to.
  • There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try:
    • To be objective
    • To control emotions and keep an even keel
    • To choose to see the good in a situation
    • To steady our nerves
    • To ignore what disturbs or limits others
    • To place things in perspective
    • To revert to the present moment
    • To focus on what can be controlled
    • This is how you see the opportunity within the obstacle.
  • There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.
  • Defiance and acceptance come together well in the following principle: There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.
  • If your nerve holds, then nothing really did “happen”—our perception made sure it was nothing of consequence.
    [ Note: Steady your nerves like Ulysses Grant. If you perceive it not to have happened, it will be nothing of consequence. ]
  • No, because I practiced for this situation and I can control myself. Or, No, because I caught myself and I’m able to realize that that doesn’t add anything constructive.
    [ Note: constantly ask yourself "do i need to freak out about this"? ]
  • Perceptions are the problem. They give us the “information” that we don’t need, exactly at the moment when it would be far better to focus on what is immediately in front of us.
    [ Note: We observe objectively, then perceive subjectively...and jump to emotional conclusions. We need to practice limiting the perception stage by training ourselves to stand back and just observe. ]
  • What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand.
    [ Note: Depending on whether perspective is what is actually causing the problem ]
  • Perspective has two definitions.
    • Context: a sense of the larger picture of the world, not just what is immediately in front of us
    • Framing: an individual’s unique way of looking at the world, a way that interprets its events
  • Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.
  • And what is up to us?
    • Our emotions
    • Our judgments
    • Our creativity
    • Our attitude
    • Our perspective
    • Our desires
    • Our decisions
    • Our determination
    • [ Note: Accept what we cannot change, but have the strength to change what you can. ]
  • Focus on the moment, not the monsters that may or may not be up ahead.
    [ Note: 50% of Fortune 500 companies were started in a recession. ]
  • Remember that this moment is not your life, it’s just a moment in your life. Focus on what is in front of you, right now. Ignore what it “represents” or it “means” or “why it happened to you.”
  • Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph?
  • The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.
    [ Note: The enemy is not the obstacle! ]

Part 2: Action

  • “Always think with your stick forward.” That is: You can’t ever let up your flying speed—if you do, you crash. Be deliberate, of course, but you always need to be moving forward.
    [ Note: That's what Amelia Earhart painted on the side of her plane. ]
  • ...genius often really is just persistence in disguise.
    [ Note: Edison tested 6000 specimens to discover the lightbulb. ]
  • Even though we know that there are great lessons from failure—lessons we’ve seen with our own two eyes—we repeatedly shrink from it. We do everything we can to avoid it, thinking it’s embarrassing or shameful. We fail, kicking and screaming. Well why would I want to fail? It hurts. I would never claim it doesn’t. But can we acknowledge that anticipated, temporary failure certainly hurts less than catastrophic, permanent failure?
  • The process is about finishing. Finishing games. Finishing workouts. Finishing film sessions. Finishing drives. Finishing reps. Finishing plays. Finishing blocks. Finishing the smallest task you have right in front of you and finishing it well.
  • Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires.
  • How you do anything is how you can do everything. We can always act right.
  • In fact, having the advantage of size or strength or power is often the birthing ground for true and fatal weakness. The inertia of success makes it much harder to truly develop good technique.
  • The way that works isn’t always the most impressive. Sometimes it even feels like you’re taking a shortcut or fighting unfairly.
  • We wrongly assume that moving forward is the only way to progress, the only way we can win. Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path.
  • Ordinary people shy away from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They are their best in these situations. They turn personal tragedy or misfortune—really anything, everything—to their advantage.
  • Some actions are rendered impossible, some paths impassable. Some things are bigger than us. This is not necessarily a bad thing. Because we can turn that obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill—even if it is just learning to accept that bad things happen, or practicing humility.

Part 3: Will

  • Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always.
  • In every situation, we can
    • Always prepare ourselves for more difficult times.
    • Always accept what we’re unable to change.
    • Always manage our expectations. Always persevere.
    • Always learn to love our fate and what happens to us.
    • Always protect our inner self, retreat into ourselves.
    • Always submit to a greater, larger cause.
    • Always remind ourselves of our own mortality.
    • And, of course, prepare to start the cycle once more.
  • Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down. An important caveat is that we are not born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us.
  • ...the person who has rehearsed in their mind what could go wrong will not be caught by surprise. The person ready to be disappointed won’t be. They will have the strength to bear it.
    [ Note: Do premortems and anticipate what can go wrong and figure out the response so you can be better prepared. ]
  • You don’t have to like something to master it—or to use it to some advantage. When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence. Let’s be clear, that is not the same thing as giving up. This has nothing to do with action—this is for the things that are immune to action.
  • We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good?
    [ Note: No matter what misfortunes may happen, just keep smiling and keeping a positive outlook. ]
  • Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.
    [ Note: Persistence is getting through the next round. Perseverance is staying on for the entire journey. ]
  • Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that.
    [ Note: It shouldn't only be about you. Will is much more powerful when there are others that you are thinking about. ]
  • In the shadow of death, prioritization is easier. As are graciousness and appreciation and principles. Everything falls in its proper place and perspective.
    [ Note: memento mori ]
  • The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.” It’s a loop that becomes easier over time.
  • See things for what they are. Do what we can. Endure and bear what we must.

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