What I Learnt from “The Obstacle Is The Way”

Karteek
4 min readApr 11, 2022
The Obstacle Is The Way — Ryan Holiday

Most of us are paralyzed. Whether in our decisions, actions, thoughts, beliefs or even choosing what to do in the next minute. Whatever our personal goals, most of us have felt numb & frozen in front of the (imaginary) mountain of obstacles ahead of us.

Every Obstacle is unique to the person. But the emotions they evoke nonetheless are similar. Fear, Frustration. Anger. Confusion. Helplessness. Anxiety. And then, we do nothing.

The Obstacle is the Way is a book where Ryan Holiday does a great job of distilling Stoic philosophy & wisdom into an easy read.
The Ancient Art of Turning Adversity to Advantage”.

If one were to summarise this book in 85 words, it could be done in these words of Marcus Aurelius, the last of the Five Good Emperors of the Roman Empire:

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.

There are three parts to understanding the above lines from the book.

Here’s my take on the 3 Disciplines — Perception, Action, and Will.
Dive in:

Part 1: Perception

Choose not to be harmed — and you won’t feel harmed. Don’t feel harmed — and you haven’t been.
- Marcus Aurelius

Perception is the way we see & understand events around us — and what we decide those events mean in our life.

Just as developing a muscle needs exercise & breaking down, Perception requires challenging & breaking down. When faced with obstacles, our mind starts weaving a story. This narration in our mind, this story that we tell ourselves, builds Perception.

3 Ways To Shape Perception:

  • Stop ignoring what you fear, and explain it as an act.
    - E.g., Public Speaking. It is the act of delivering ideas or thoughts in front of an audience.
  • We don’t fear the act. We fear us in attachment with the act. Detach yourself from it.
    - You speaking in public may be the fear. But the act of Public Speaking itself, as broken down above, is not necessarily fearsome.
  • Identify the part of the act in your control.
    - The only thing in your control is the words you speak, not the audience’s judgment.

When we look at fear from a different perspective, we can break down the size of that mountain into what it truly is — some rocks, some soil, some minerals.

Break down obstacles. Detach self. Identify what’s in control.

Part 2: Action

He says the best way out is always through
And I agree to that, or in so far
As I can see no way out but through.
- Robert Frost

Action conquers fear. Directed action is the solution and the cure to our obstacles. You’ve identified what’s in your control. Let’s call this the big picture.

Every big picture is a sum total of small directed actions, one after the other.

3 Ways To Tackle This Period Of Action:

  • Deliberation: Reflect & understand the necessary steps needed.
    - Public Speaking — write the speech, practice in front of a camera alone, watch the recording, reflect on improvements, repeat.
  • Boldness: Cross a smaller milestone, and see your courage expand.
    - Show the recording to a few trusted people, practice in front of a small group, record the speech, observe improvements, repeat.
  • Persistence: Be prepared for iteration & feedback. Implement the same.
    - seek feedback, identify what works for you, let go of what doesn’t, iterate your speech, do another round of practice.

Small steps in the right direction are greater than inaction.

Part 3: Will

Everything can be taken from a man but one thing: the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.
- Viktor E. Frankl

Will is what lies inside us and can never be affected by the outside world. Will is what one can depend on when all sense of control has disappeared.

3 Ways To Strengthen One’s Will:

  • The Inner Citadel: Nobody is born with a steel backbone. We have to forge it ourselves.
    - Public Speaking — When you go up, how willing are you to face hecklers? How willing are you to face laughter? How willing are you to face mistakes? Forge that steel backbone.
  • The Art of Acquiescence: Live in acceptance that things may not always work out.
    - The first few speeches may not go well even after everything above. Accept it. Reflect. Evolve the preparation process.
  • Love Everything that Happens — Amor Fati. There will be bad days. Make them your fuel.
    - The days you forget your speech, go blank, say the wrong words, stutter — are all fuel for the will. Laugh at them. Love them. Then go back, and do it all again.

True will is quiet humility, resilience, and flexibility.

None of these things are easy. They’re not meant to be. If anything, expecting your biggest dreams to come true easily and the biggest fears to fade away easily would be an entitlement. That leads nowhere. What can lead you ahead, though:

  • Perception: See things for what they are.
  • Action: Do what we can.
  • Will: Endure and bear what we must.

If this added any value to you, consider following me on Medium. I write essays, lessons and stories on life, humanity, and our universe.

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Karteek

Writing on books, travel, stoicism, humanity, and our universe.