The Obstacle Is The Way

by Ryan Holiday

Troy Shu
Troy Shu
Updated at: February 23, 2024
The Obstacle Is The Way
The Obstacle Is The Way

What are the big ideas? 1. Adapting your mindset and actions is essential to overcome obstacles. 2. Challenges test and grow our resilience. 3. Comfort can hinder p

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What are the big ideas?

  1. Adapting your mindset and actions is essential to overcome obstacles.
  2. Challenges test and grow our resilience.
  3. Comfort can hinder personal growth.
  4. Overcoming obstacles involves a disciplined three-step approach.
  5. Our emotional reactions to challenges are choices.


Overcoming Obstacles Requires Adapting Mindset and Actions

  • “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?”

Life's Challenges Test Our Resilience and Ability to Grow

  • “The world is constantly testing us. It asks: Are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?”
  • “Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.”
  • “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”—Andy Grove
  • “Great individuals, like great companies, find a way to transform weakness into strength. It’s a rather amazing and even touching feat. They took what should have held them back—what in fact might be holding you back right this very second—and used it to move forward.”

Abundance and Comfort Can Hinder Personal Growth and Resilience

  • “We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.”

Transforming Obstacles into Opportunities Involves a Three-Step Discipline

  • “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.”

Emotional Reactions to Challenges Are Choices We Make

  • “Nothing makes us feel [desperate, afraid, powerless etc.]; we choose to give in to such feelings. Or, like Rockefeller, choose not to.”
  • “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.”
  • “Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree.”
  • “We decide what story to tell ourselves. Or whether we will tell one at all.”

Finding the Path Through Obstacles Requires a Balanced Approach of Defiance and Acceptance

  • “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.”

Worry and Anxiety Can Blind Us to Solutions and Opportunities

  • “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?”—Gavin de Becker in The Gift of Fear
  • “Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?”—Marcus Aurelius

Perceptions and Perspectives Shape Our Response to Obstacles

  • “The phrase ‘This happened and it is bad’ is actually two impressions. The first—‘This happened’—is objective. The second—‘it is bad’—is subjective.”
  • In The Book of Five Rings, Miyamoto Musashi notes the difference between observing and perceiving. The perceiving eye is weak, he wrote; the observing eye is strong.
  • “Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there.”
  • “Everything about our animalistic brains tries to compress the space between impression and perception.”

Detachment and Objectivity Aid in Overcoming Challenges

  • Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do? How much more quickly and dispassionately could you size up the scenario and its options? You could write it off, greet it calmly.
  • “Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.”

Focusing on the Present Moment Helps Navigate Uncertainty

  • “Focus on the moment, not the monsters that may or may not be up ahead.”

Beliefs in Obstacles Can Hinder Achievement of Goals

  • “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 the goal, which will inevitably triumph?”
  • “There is good in everything if only we look for it.”—Laura Ingalls Wilder
  • “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 the advantage, not adversity. The enemy is any perception that prevents us from seeing this.”

Action and Perception Are Crucial in Overcoming Life's Challenges

  • “Once you see the world as it is, for what it is, you must act.”
  • “We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given.”
  • “The only way you’ll do something spectacular is by using it all to your advantage.”
  • “Remember and remind yourself of a phrase favored by Epictetus: ‘persist and resist.’ Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.”

Persistence and Perspective Are Key to Navigating Obstacles

  • Nick Saban’s 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.”
  • “We don’t get to choose what happens to us, but we can always choose how we feel about it.”
  • “Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.”

Strategies for Overcoming Seemingly Insurmountable Obstacles

  • 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

The Role of Perspective and Context in Facing Life's Challenges

  • 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.


  1. How can changing your mindset and actions help you overcome obstacles in your life?
  2. What role does resilience play in facing and growing from life's challenges?
  3. In what ways can comfort and abundance hinder personal growth and resilience?
  4. How can you transform obstacles into opportunities through a disciplined approach?
  5. Why is it important to recognize that our emotional reactions to challenges are choices we make?
  6. How can a balance of defiance and acceptance help you find a path through obstacles?
  7. Why is focusing on the present moment important in navigating life's uncertainties?
  8. How do our beliefs and perceptions shape our ability to overcome challenges and achieve our goals?


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