The Obstacle is the Way

Priyadarshini Prakash
4 min readJul 8, 2023

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Ryan Holiday, the modern Stoic, is an amazing person. I have listened to his podcast and read some of his works like Ego is the Enemy and Discipline is the Destiny. The obstacle is the way was his debut. I have huge respect for people who spread reliable philosophical content on the internet.

But I wasn’t a fan of this book. The substantial content was lurking here and there. I’m happy the book wasn’t 400 pages long like the other so-called self-help books. The content of the book is divided into three sections.

Ryan basically explains how Stoic practitioners view obstacles as a ladder than a barricade. He narrates different examples of people who turned adversity into an advantage.

The three parts of the book were:

  1. Perception

2. Will

3. Action

It begins with how we look at our specific problems, our attitude, and 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 self that allows us to handle defeat and difficulty.

A good philosophical approach is the driving force for self-made men. The question is: Are you worthy? Can you get past the things that inevitably fall 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, Desperation, Anger.

“Oh, how blessed young men are who have to struggle for a foundation and beginning in life”

- John D. Rockefeller (considered the wealthiest American at one point, business Magnate)

PERCEPTION

Our perception, how we look at things, matters the most. Ryan writes on why it is necessary to:

  1. Be objective
  2. Control emotions and keep an even keel
  3. To choose to see the good in a situation
  4. Steady our nerves
  5. Ignore what disturbs or limits others
  6. Place things in perspective
  7. Revert to the present moment
  8. Focus on what can be controlled.

The “I might not have wanted it to happen but I decide how it will affect me” attitude is what is considered a good perception. We’re never completely powerless, we decide what story to tell ourselves.

When one aims high, pressure, and stress obligingly come along for the ride, and the risk of being overwhelmed is always there. We must learn to say, No thank you, I cannot afford to panic.

How often do we see what we think is there or should be there, instead of what actually is there?

In the latter few pages of this section, he talks about how we are always trying to figure out what things mean — why things are the way they’re. We should not choose the ominous explanation over the simple one and how conventional wisdom might be too conservative.

ACTION

The section, The Action, starts with an inspiring story of Demosthenes.

At seven years old, he lost his father. The large inheritance left to him — intended to pay for tutors and the best schools — was stolen by the guardians entrusted to protect him. They refused to pay his tutors, depriving him of the education he is entitled to.

He was a fatherless, effeminate, awkward child who no one understood, who everyone laughed at. Not exactly the boy you’d expect would soon hold the power to mobilize Athens to war by his voice alone.

But stuck in his young mind was the image of a great orator, a man he’d once witnessed speaking at the court in Athens. This inspired Demosthenes to conquer his speech impediments. He devised speech exercises and practiced on his own.

He would lock himself away underground and to ensure he wouldn’t indulge in outside distractions, he shaved half his head so he’d be too embarrassed to go outside.

This is the devotion needed if you crave to achieve something. Driven by his own toil, Demosthenes. Eventually won. He became the best orator the world has ever seen and sued his twisted relatives.

The section then discusses more of why it is important to not delude ourselves with fantasies about easy solutions and how we have to stop believing that there is a chance of obstacles unobstacling themselves.

We simply do not have the luxury of running away.

WILL

In the section, The Will, Ryan discusses how we must be willing to roll the dice and lose. Prepare at the end of the day, for none of it to work.

During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We can protect our inner fortress so it may protect us. A sound mind is a sound body.

The path of least resistance is a bad teacher.

In this day and age, where technology has made anything possible, it is very easy to internalize the assumption that nature has been domesticated and submits to our whim.

Of course, it hasn’t.

Nature, in order to be commanded, must be obeyed.

As a way of wrapping it up, the book basically revolves around how we should:

First, see clearly.

Second, act correctly.

Finally, endure and accept the world as it is.

I would give this book a 7 out of 10. The obstacle is the way is an easy read and a small book that you can take with you while traveling!

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