The Obstacle Is The Way

 · 11 mins read

:memo: Please Note
  • The following book summary is the result of a collection of personal notes, highlights and thoughts extracted from the book.
  • Most of the content is a direct quotation from the book and original authors work.

In “The Obstacle is the way (The Timeless Art of Turning Trials into Triumph)” Ryan Holiday offers a guide on how stoicism has been used throughout time in order to approach obstacles and overcome them to reach new heights so that to be ready to solve more complex problems.

Takeaway Points


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.

  • First, see clearly.
  • Next, act correctly.
  • Finally, endure and accept the world as it is.

Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.

Philosophy was never what happened in the classroom. It was a set of lessons from the battlefield of life (something we need to keep close to us and implement in our daily life).


Perception it’s how we see and understand what occurs around us—and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective and shortsighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives. While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are — neither good nor bad. 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.

There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try:

  1. To be objective
  2. To control emotions and keep an even keel To choose to see the good in a situation
  3. To steady our nerves
  4. To ignore what disturbs or limits others
  5. To place things in perspective
  6. To revert to the present moment
  7. To focus on what can be controlled
  8. This is how you see the opportunity within the obstacle.

They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions. Which is to say, we are never completely powerless.

Through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles. 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.

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.

We defeat emotions with logic, or at least that’s the idea. Logic is questions and statements. With enough of them, we get to root causes (which are always easier to deal with).

To paraphrase Nietzsche, sometimes being superficial — taking things only at first glance — is the most profound approach. In our own lives, how many problems seem to come from applying judgments to things we don’t control, as though there were a way they were supposed to be? How often do we see what we think is there or should be there, instead of what actually is there? Having steadied ourselves and held back our emotions, we can see things as they really are.

The Stoics use contempt as an agent to lay things bare and “to strip away the legend that encrusts them.” Marcus Aurelius had a version of this exercise where he’d describe glamorous or expensive things without their euphemisms — roasted meat is a dead animal and vintage wine is old, fermented grapes. The aim was to see these things as they really are, without any of the ornamentation.

Objectivity means removing “you”—the subjective part—from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious.

Perspective is everything: That is, when you can break apart something, or look at it from some new angle, it loses its power over you.

George Clooney spent his first years in Hollywood getting rejected at auditions. He wanted the producers and directors to like him, but they didn’t and it hurt and he blamed the system for not seeing how good he was. This perspective should sound familiar. It’s the dominant viewpoint for the rest of us on job interviews, when we pitch clients, or try to connect with an attractive stranger in a coffee shop. Everything changed for Clooney when he tried a new perspective. He realized that casting is an obstacle for producers, too — they need to find somebody, and they’re all hoping that the next person to walk in the room is the right somebody. Auditions were a chance to solve their problem, not his.

Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.

It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary and post hoc).

What is up to us?

  • Our emotions
  • Our judgments Our creativity
  • Our attitude
  • Our perspective Our desires
  • Our decisions Our determination


Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action. Everything must be done in the service of the whole. Step by step, action by action, we’ll dismantle the obstacles in front of us. With persistence and flexibility, we’ll act in the best interest of our goals. We must be sure to act with deliberation, boldness, and persistence.

Therefore, we can always (and only) greet our obstacles

  • with energy
  • with persistence
  • with a coherent and deliberate process
  • with iteration and resilience
  • with pragmatism
  • with strategic vision
  • with craftiness and savvy
  • and an eye for opportunity and pivotal moments

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.

Failure shows us the way—by showing us what isn’t the way.

When it comes to our actions, disorder and distraction are death.

The process is the voice that demands we take responsibility and ownership. That prompts us to act even if only in a small way. Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it.

We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods.

Pragmatism is not so much realism as flexibility. Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection. Under this kind of force, obstacles break apart. Since you’re going around them or making them irrelevant, there is nothing for them to resist.

The way that works isn’t always the most impressive. Sometimes it even feels like you’re taking a shortcut or fighting unfairly. There’s a lot of pressure to try to match people move for move, as if sticking with what works for you is somehow cheating. Let me save you the guilt and self-flagellation: It’s not.

Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you. You can use the actions of others against themselves instead of acting yourself. Just ask the Russians, who defeated Napoléon and the Nazis not by rigidly protecting their borders but by retreating into the interior and leaving the winter to do their work on the enemy, bogged down in battles far from home.

When we want things too badly we can be our own worst enemy.


Will is our internal power, which can never be affected by the outside world. Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power. In actuality, the will has a lot more to do with surrender than with strength.

If 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.

The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted. Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel? Because these things will happen to you. No one knows when or how, but their appearance is certain. And life will demand an answer.

Knowing that life is a marathon and not a sprint is important. Passing one obstacle simply says you’re worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt.


“Our actions may be impeded . . . but there can be no impeding our intentions or dispositions. The impediment to action advances action. What stands in the way becomes the way. Never forget, within every obstacle is an opportunity to improve our condition.” - Marcus Aurelius

“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” - Andy Grove, former CEO of Intel

“Objective judgment, 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.” - Marcus Aurelius

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

“Would you have a great empire? Rule over yourself.” — Publius Syrus

“God, grant me the serenity to accept the things I cannot change The courage to change the things I can, And the wisdom to know the difference.” - The Serenity Prayer

“This too shall pass” - Abraham Lincoln

“Man proposes but God disposes.”

“My formula for greatness in a human being is amor fati: that 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.” - Friedrich Nietzsche

Book Authors: Ryan Holiday


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