The Obstacle is the Way

We all face obstacles, that’s a fact. Now, it seems that some of us succeed in overcoming them easier than others. Why is that?

In this book, the author Ryan holiday tries to give a philosophical approach based on historical figures like Marcus Aurelius, Margaret Thatcher, Rockefeller on how to deal with obstacles. The common denominator of them certainly is the practice of stoicism.

Beforehand, here is the video summarizing the 5 lessons I've learnt from this book :

Stoicism gives another look at obstacles. Thanks to it:

We can see the “bad” things that happen in our lives with gratitude and not with regret because we turn them from disaster to real benefit—from defeat to victory

The objective is so to give us another look at the difficulties we will face in our life. Using examples from the greats of this world, the author shows us the way to transcend obstacles. What’s beautiful is that it’s very simple (simple but not easy). In the following, we will study the art of turning obstacles upside down thanks to the following triad :

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

As written at the end of the book :

See things for what they are.
Do what we can.
Endure and bear what we must.

What blocked the path now is a path
What one impeded action advances action.
The Obstacle is the Way.


This book will share with you their collective wisdom in order to help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles. Physical obstacles. Emotional obstacles. Perceived obstacles.

Obstacles are unique to everyone, but they all make us feel the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger. They are invisible enemies that we often neglige. The ones extremely common as well as very dangerous. We are our most dangerous and incidental enemy.

There are three major steps to overcome obstacles :

  • Look at our problems, our attitude or approach.
  • Break them down with energy and creativity.
  • Cultivate and maintain an inner will that allows us to handle defeat and difficulty.
These obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.

The Obstacle Is the Way.



Perception is what separates us from truth. Without perception, we see things naturally and straightforwardly, as they are.

It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear. But it’s worth it, for what’s left is truth.

Bat away the pests of bad perceptions is an incredible advantage for us in the fight against obstacles.


The success of Rockefeller would come from his ability to remain calm in the face of the storm. Discipline in perception helps us see things for what they really are, without pestilence of panic or fear.

For the rest of his life, the greater the chaos, the calmer Rockefeller would become, particularly when others around him were either panicked or mad with greed. He would make much of his fortune during these market fluctuations—because he could see while others could not.

Whether obstacles are fair or unfair, what matters most is how we see them, how we react to them. Your reactions concerning them determine how successful we will be in overcoming—or possibly thriving because of—them.

Our perception is all, the simple act to choose the direction of this one is powerful. Emotional reaction make us lose our perspective, it worsen the situation.

Unhelpful perceptions can invade our minds—that sacred place of reason, action, and will—and throw off our compass.

When you faced 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

Reality is not what our mind makes of it. These are just stories we tell to ourselves. They are all perceptions.

Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves. Or whether we will tell one at all.


John Glenn was the first American astronaut to orbit the earth, and he was able to keep his heart rate under a hundred beats per minute. He was in control of his emotions.

Keeping our emotions in check is key to overcome them and ultimately overcome obstacles—that make us emotional. Standing despite external events that fluctuate. We defeat them with logic, or at least that’s the idea.

Like John Glenn, avoid negativity by asking something like :

Don’t let the negativity in, don’t let those emotions even get started. Just say: No, thank you. I can’t afford to panic.

Be sure that you can control yourself in every situation in life, the answer to the question “Do I need to freak out about this?” is always “no”.


Objectivity means removing “you”. Act like someone giving you advice. Take the situation at face from an external point of view.

Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people, we can be objective. We take the situation at face value and immediately set about helping our friend to solve it.


Definitions of perspective :

  • 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.

Alter your perspective is viewing things from some new angles. The power of perspective is to defeat distracting, tiring, irrational.


In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices. — EPICTETUS
“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.” — Reinhold Niebuhr in Serenity Prayer


The present is all we have. We have to take every seemingly disadvantageous situation and find the real value beneath it.



Action is the movements we perform. We must be sure to act with deliberation, boldness, and persistence. Action is the solution and the cure to our predicaments.


Remind yourself that each new obstacle makes you stronger. The faster you overcome them, the faster and less painful it will become in the future.

The list of how we should 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


There are no ideal conditions. You need to create your momentum by yourself, right now, by getting up and getting started.


As Epictetus put it: “persist and resist.” It’s okay to be discouraged. Suppose that what your first attempts won’t doing to work. But fortunately, energy is a renewable resource.

Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.


To benefit from failure, we need to make sure we learn from it. Not to do the same thing over and over again without asking ourselves any questions.

People fail in small ways all the time. But they don’t learn. They don’t listen. They don’t see the problems that failure exposes. It doesn’t make them better.


We can compare the process as a machine executing each action, little by little, moving forward one step at a time. Dealing with each faced problem at the time it appears is paramount to solve it efficiently, this requires that you follow the process.

The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.


How you do anything is how you can do everything.
We can always act right.


Think like a radical pragmatist. Don’t think small but make the distinction between the critical and the extra. Think progress, not perfection.


Don’t waste your time throwing energy in battles driven by ego and pride. Even if this seems to be the most laborious way to approach life, and therefore the right one, this is not the case.

Remember, sometimes the longest way around is the shortest way home


Great people turn personal tragedy or misfortune to their advantage. They don’t shy away from negative situations.

Obama was known to transcend challenges and reframing them, triumphing as a result of it. Ugly incident into “teachable moment”. Obama turns the lowest moment in his campaign into a surprise offensive.

The ultimate goal of seizing offensive is to not only turned his obstacles upside down but used them as a catapult.



Will is an internal power that is not affected by the outside world. True will is quiet humility, resilience, and flexibility.

Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength.


Will is the ultimate strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome. Will enable us to be happy in an inherently unpredictable world. Confident, calm, ready to work regardless of the conditions, to continue whatever occurs.

As such, the will is the critical third discipline. We can think, act, and finally adjust to a world that is inherently unpredictable. The will is what prepares us for this, protects us against it, and allows us to thrive and be happy in spite of it. It is also the most difficult of all the disciplines.

It’s much easier to control our perceptions, and emotions than it is to try to control other’s one. Having will in these situations is paramount.

In every situation, here’s what the discipline of will can learn us :

  • 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.


As we train to build muscle, we should train to build our mental. The Stoics’ inner citadel is what enables us to fight against external adversity. It’s a structure we’re not born with, a structure that must be built and actively reinforced in the course of our life.

It’s your armor plating. It doesn’t make you invincible, but it helps prepare you for when fortune shifts . . . and it always does


Catastrophes happen all the time. If we are prepared for what could happen in the worst-case scenario, then we can handle future disasters better than the average person.

Also, anticipation is key to endure what could go wrong in our life.

With anticipation, we have time to raise defenses, or even avoid them entirely. We’re ready to be driven off course because we’ve plotted a way back.


We rarely consider how much worse things could have been in our lives, we prefer to think, instead, about what is missing. The ability to accept unexpected costs is a real superpower.

Acquiescence makes us humble and flexible and so thrive and continue to progress even when plans have changed.

The three reasons we will always get beyond obstacles :

  1. Our robustness,
  2. We can’t do anything about it anyway,
  3. It’s always negligible when you look at the big picture.


As stoics said, be cheerful in all situations, especially bad ones.

Always feel great and glad about what may happen to you.

Not: I’m okay with this.
Not: I think I feel good about this.
But: I feel great about it.
Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it.

We don’t always control what happens to us, but we control how we react to it. Amor fati (a love of fate) is crucial to have, it is embracing what happens to us. In the end, there is always good contained within the bad. And we can find it and be cheerful because of it.


Perseverance is larger than persistence. It’s not just about what happens in the second round, it’s about what happens in every round after that, and every round after that.

If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent.

Our will cannot be constrained. This means that our belief in ourselves is indestructible. We can always try another path or accept the reality and decide upon a new aim.


Our trouble with acceptance comes from the fact that we behave like we’re invincible. To create real perspective and urgency, we need to be aware of our mortality. If you succeed at taking benefits at your own death, you can face every other kind of obstacle.

If even our own mortality can have some benefit, how dare you say that you can’t derive value from each and every other kind of obstacle you encounter?


Life is a marathon, not a sprint. Each battle will make the next one easier.

“Conserve your energy. Understand that each battle is only one of many and that you can use it to make the next one easier. More important, you must keep them all in real perspective.”