Summary of “The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph” by Ryan Holiday: Steeped in Stoic philosophy, the author demonstrates how perception, action, and willpower can help us overcome difficulties and turn any problem into an opportunity.
By Ryan Holiday, 2018 for the French edition, 256 pages.
Note: This is a guest review written by Antonin from the blog Learning to Invest.
Review and Summary of “The Obstacle is the Way”
What if for any problem there hid within in it some embedded or inherent advantage and/or benefit that you could make good use of? What would you say?
We are often paralyzed by the obstacles that appear before us. We either blame society or consider ourselves to be inadequate in some way or another.
Obstacles are like invisible enemies that inhibit and frustrate us, provoking fear and anger. So, what if we could change our approach to such obstacles?
There are countless examples of how to succeed, but no one really has ever taught us how to overcome failure, how to deal with issues, and how to triumph.
Yet some people seemingly have an uncanny ability to overcome all obstacles: how do they do it? How did previous generations cope with problems far worse than ours?
The great figures of history learned to turn the negative into positive, and to use obstacles as fuel for their ambitions.
[The Stoics] had the ability to see obstacles for what they really were, the ingenuity to deal with them, and the willingness to confront a world beyond their understanding and control.
This book “The Obstacle is the Way” compiles the teachings of ancient philosophy and the principles of Stoicism in attempt to help one overcome obstacles and turn them into benefits.
The idea is not to deny reality or to say “it’s not that bad”, but to see how to “make something good out of it”.
Obstacles in our path
We all face obstacles, whether physical, psychological, financial, relational, legal, etc.
However, the obstacle in the path becomes the path.
“Those things that hurt, instruct.”
– Benjamin Franklin
The obstacles of today (various frustration, information overload, chaos) are different from those of yesterday and previous generations, who experienced wars and epidemics far more deadly. Our more prosperous times have made us a little soft.
The way through them
There are three essential steps to overcoming obstacles:
- Perception: the way we approach our problems.
- Action: the energy and creativity to turn problems into opportunities.
- Willingness to deal with failure and difficulty.
This simple (but not always easy) process starts with accepting problems. It has been applied many times in history and will be described through several examples.
These obstacles are actually opportunities to test ourselves, to innovate, and ultimately to triumph. The obstacle is the way.
PART ONE: PERCEPTION
Perception consists of seeing things as they are, without giving in to emotions, fears, and preconceived notions, which leaves only the truth.
The discipline of perception
John D. Rockefeller began working in the midst of an economic crisis in 1857. He then experienced several crises until the one in 1929. Rather than panic like everyone else, he observed what was going on and tried to learn from it.
Instead of lamenting the situation, he sought to see where the opportunities lay. This is how he came to control 90% of the oil market.
The greater the chaos, the more calm the billionaire remained, especially when those around him panicked and got greedy.
The most important thing is not the obstacle itself, but the way we perceive it, and whether we can keep our emotions under control.
Our brain is wired to recognize threats. However, we can learn to stop being slaves to our primal feelings, to remain objective, to calmly put things into perspective, and to focus on what we can do.
When perceived correctly, every event, foreseen or unforeseen, presents an opportunity to move forward.
Recognize your power
Boxer Rubin Carter, Nelson Mandela, and Malcolm X all experienced unjust imprisonment in their lives.
They were robbed of their freedom, but they made the choice not to let it affect them. The made the choice to keep their thoughts, their convictions, their power.
They used prison as a training ground to strengthen their minds and managed to take advantage of a situation that would plunge most of us into despair.
Our perception is the factor we have complete control over.
You alone have the power to label things as “good” or “bad”. That is your decision.
Steady your nerves
Certain events that occur in our daily activities can put us on edge.
Knowing how to keep our cool will allow us to not give in to stress, to be able to act calmly, and to continue on our path, without being affected.
Keeping your cool has two components:
- It is a challenge, that of refusing to give in to panic, of not being intimidated.
- But also of accepting reality and the fact that we are being put to the test.
We are ready. We are calm, serious, and we will not be afraid.
Control your emotions
You will never find astronauts panicking, because panic, for them, equates to death.
Obstacles make us emotional, but the only way to survive or overcome them is to keep our emotions in check.
Strong emotions don’t solve problems. In fact, they may even prevent us from identifying the source of a problem and therefore solving it.
However, there is a difference between cutting ourselves off from our emotions and accepting them while refusing to let them take control.
Is what just happened really catastrophic? Are you sure you will never recover from it?
Ask yourself: do I need to freak out about this? Develop self-control.
We are often not observant enough. We believe we are perceiving something quite different from objective reality.
And we can easily be objective when giving advice to someone, but when it comes to ourselves, subjectivity takes over.
It is possible to train ourselves to see things as they are:
- By imagining the problem happening to someone else.
- By describing an object or situation by what it is, not by what it represents.
Objectivity is like a muscle; it requires training for development.
Objectivity means taking the “me”, the subjective part, out of the equation.
Alter your perspective
We always tend to imagine the worst of a situation: the most debilitating perspective.
However, we can choose how we perceive: instead of adopting a point of view that fleshes out the problem, we can adopt a point of view that offers new perspective, which is focused on action.
How we interpret events determines both our reactions and actions.
George Clooney was passed on for many auditions early in his career. He didn’t understand why his talent wasn’t being recognized. By shifting his perspective from “me” to the producers, he transitioned from a selfish perspective to a broader one.
By putting himself in their shoes, understanding their wishes, he began to embody the actor they were looking for, and his career eventually took off.
The way we interpret events in our lives – our perspective – frames our responses.
Is it up to you?
‘’Grant me the serenity to accept the things I cannot change, courage to change the things I can and wisdom to know the difference.’’
This is the Serenity Prayer. It helps us to focus only on what is in our power.
Our parents, the economic situation, other people, circumstances are not in our control.
However, our emotions, views, behaviors, decisions, desires are in our control.
Focusing only on what you control increases your power. On the other hand, spending energy on things you cannot control is a waste.
Live in the present moment
Walt Disney, General Motors, Linkedin and Microsoft are all companies that emerged during a major crisis.
Rather than worry about the crisis, their leaders stayed grounded, content to sell their products and services as best they could.
Those who start from a disadvantage fare better than others because they take their survival day by day.
Train yourself to stay in the moment, through sports, disconnecting, or adopting a pet (animals always live in the present).
Focus on what is in front of you in the present moment. Ignore what it “represents” or “means” or “why it’s happening to me”.
Steve Jobs was known for ”distorting” reality and trying to make possible what was presented to him as impossible. He constantly pushed his teams to excel, asking them to meet “impossible” deadlines.
Reality is not fixed: it is our perception that will determine whether we are capable or not.
When we believe more in the obstacle than in the goal, which one will inevitably triumph?
And yet we are asked to be realistic, to listen to others, and to compromise. Is this really the best approach? Steve Jobs demonstrated that it is possible to succeed by taking the opposite path.
An entrepreneur is someone who has confidence in his ability to create something where there is nothing.
Finding the opportunity
At the beginning of World War II, the Germans achieved quick and easy victories through their method of Blitzkrieg: concentrating maximum forces to crush and demoralize the enemy.
After the landings, they launched numerous counter-attacks using the same method. However, Eisenhower and the allies then found the flaw in this strategy: letting the Germans advance to better encircle them.
Every obstacle conceals an opportunity. Grumbling about the way things are going prevents us from seeing it.
‘’There is good in everything, if only we look for it.’’
– Laura Ingalls Wilder
We can see obstacles as a chance to try different tactics, to grow and add to our skills.
Whether our obstacle is a bad boss, a competitor, or an injury, it has the power to strengthen us, if we bother to see the gift within.
Prepare to act
The worst is never an isolated event: the worst is losing your cool in addition to the event. Hence the importance of an objective perception of the situation.
Once you see the world as it is, for what it is, you must take action.
Action is the step that follows perception: the boldness to take on the obstacle.
PART TWO: ACTION
Action allows us to break down obstacles. However, action is not enough; we must take the appropriate action, that which requires courage and perseverance.
The discipline of action
Demosthenes grew up with a speech impediment. To make matters worse, he was robbed of his inheritance by his guardians.
In the hope of asserting his rights, he exercised his voice until it became loud and powerful. This is how he was able to sue his guardians, which he won: he never got his inheritance back, but his reputation as a talented orator was built.
There are many examples of people who have turned handicap, discrimination, poverty, or a disastrous situation into gold.
They didn’t have time to feel sorry for themselves. They took action because they had no other choice.
If we want to get where we want to go, to achieve our goal, there is only one way: address the problem with the right course of action.
Amelia Earhart, despite being mocked and discriminated against on the basis of gender, never gave up on becoming the first woman to fly across the Atlantic.
She took offense and ridicule, seizing every opportunity to fly, until she finally achieved her goal. She simply played the cards she had been dealt.
If you wait for the right conditions to take action, you will never start, and opportunities to solve problems will not present themselves.
It was by always moving forward, despite the sand and heat, that Rommel first crushed the British in North Africa.
Those who approach problems and life with the most initiative and energy usually emerge victorious.
Momentum doesn’t come from being passive; it comes from creating it.
During the American Civil War, Grant tried to take Vicksburg for a year without success. All his attempts had failed.
He then took a huge risk: he sent his troops down the Mississippi River, without supplies, to take all the towns around Vicksburg, until the enemy had no choice but to surrender. His relentlessness had finally paid off.
For his part, Edison tested six thousand different filaments before he found the right one and invented the light bulb.
Genius is often a matter of perseverance in disguise.
It is sometimes by exhausting all possible options that we finally find the solution.
Often, we don’t lack knowledge or skills. We just give up too easily. Feeling discouraged at times is normal, but it is tolerance for difficulty and persistence that separates those who persevere from those who give up.
The road may be long and difficult. You will fail many times. However, if you put all your energy into it and keep moving forward, you will succeed.
Start-ups operate by launching a minimum viable product. This allows them to easily and quickly change course if their product doesn’t find a customer base.
We can learn from start-ups by making failure part of the plan, seeing it as part of the learning process, and a path towards better opportunities.
There is no shame in failing, and no reason to take it personally.
The problem is not the failure, but not learning from it, not trying to understand what went wrong. The problem comes from our ego, which sees failure as something negative.
Failure paves the way – by showing us the wrong way.
Follow the process
Instead of focusing on the obstacle as a whole, or on an end result, think of it as a series of steps.
We then follow the process of taking each small step, one at a time. The process brings order to our disparate actions, or when we become distracted.
By following a step-by-step process, nothing is too big or too ambitious. Just finish that small task, and get to the next step.
The process is doing the right things right away, not worrying about what might happen next, the results, the whole picture.
Do your job and do it right
President Andrew Johnson was not ashamed to admit that before his political career he was a tailor. He was even proud to repeatedly say how he had always done a good job.
Not everything we have to do is glamorous, and sometimes we wish we didn’t have to do it. However, it may be necessary.
The goal is not to do well to get noticed, but simply to work hard, honestly, and by helping others as much as possible.
A job well done, down to the details (Steve Jobs made sure that even the interior of his products was appealing), makes us proud and gives meaning to our actions and our lives.
Conversely, considering what we have to do as a burden will not get us very far.
The way you do things is the way you can do everything.
What’s right is what works
We often wait for the ideal conditions to come along, and for everything to be perfect. However, that time spent sizing up the situation could have been used to act with what we already have.
Some rules may constrain you. How are you going to use your wit and make sure they don’t get in the way of your mission?
Sometimes, when the stakes are high, it’s better to ask for forgiveness than permission. We can’t always get from point A to point B in a perfect straight line.
Be pragmatic, like the black writer Richard Wright who, as a young man growing up in a segregated United States, managed to borrow books from the library by presenting a permission slip he had written himself, pretending to be someone else.
Think progress, not perfection.
In praise of the flank attack
During the Revolutionary War, George Washington’s army was outnumbered and less well equipped than the British army.
Rather than attacking the enemy head-on, which would have been suicide, he led frequent and rapid skirmishes and then disappeared.
In history, only 2% of wars have been won head-on. Most were won by outwitting the enemy, psychologically exhausting them, and attacking them from the flank.
If your resources and possibilities are limited, turn it into an advantage: be creative, forget the showdown, and find workarounds.
Martial arts teaches us not to resist the enemy, but to draw him in to throw him off balance.
Above all, do not feel guilty. Acting in a roundabout way does not make you a cheater, but a strategist.
Use obstacles against themselves
Sometimes the opposite action or non-action is the best way to overcome the obstacle. For example, responding to hatred with love, or letting the enemy get bogged down on its own (like Napoleon in Russia or the English in India).
When adversity seems invincible, it is always possible to use its energy to your advantage.
Pushing hard doesn’t necessarily get you a raise or a new client (which you may even attract by ignoring).
Sometimes treading water, circumventing, or backing off is the best method to eliminate what is blocking the path.
Develop the humility to accept doing things differently than you had planned, especially if the traditional approach doesn’t work. After all, the important thing is to achieve your goal.
The more we struggle, the less we will succeed (other than burning out). The same goes for our problems.
Channel your energy
Arthur Ashe was a black tennis player during the segregation years. He withstood the insults and had to restrain himself from any victory celebration.
To endure this, he channeled his emotions by pouring all the energy into his game, which became extremely versatile.
Holding back and not being able to express his emotions publicly had taught him to resist pressure, making him a better player.
When we are frustrated by the rules and constraints imposed on us, we can use that frustration to our advantage by channeling it: adversity can make us better, if we so decide.
While others struggle to follow the rules, we subtly break them and turn them to our advantage.
Seize the offensive
Most people give up when faced with discouragement or seeming disaster.
However, these are the times when we need to keep moving forward and go on the offensive.
When a scandal hit his pastor during his presidential campaign, Barack Obama did not go into hiding. On the contrary, he took initiative and delivered his famous speech on race issues that put him back in the race for the White House.
He took advantage of a negative situation to connect with his constituents.
Any negative event can be used as a platform to launch something new, something unprecedented and audacious.
For example, we can make the concerted effort to cease seeing our difficulties as exclusively negative, and rather see a problem that presents a solution.
The average person runs away from a negative situation, just as they run away from failure. They do everything to avoid trouble. Great men do the opposite. In fact, it is in such situations they thrive. They turn a personal tragedy or setback to their advantage.
Prepare for none of it to work
While we can control our perception and actions, we cannot control the world around us and how it may affect our goals.
Some things won’t work out, and there’s nothing we can do about it. However, failure always creates a new path, whether it is towards a new goal, or to train ourselves to forgive, accept, help others, etc.
We can perceive things correctly, act wisely and still fail.
THIRD PART: WILL
Willpower allows us to accept with humility what happens to us, to know when to withdraw and when to persist and learn from our difficulties. It is a power we can all control.
The discipline of the will
In addition to losing his mother as a child and experiencing several election defeats, Lincoln suffered from depression. Having endured much suffering in his life made him resilient, compassionate, and strong-willed.
These qualities were perfect for leading the country in the coming Civil War.
His resilience and ability to stand up as a leader in the darkest of times, when there was no apparent solution, was invaluable.
It is willpower that gives us the ultimate strength: the strength to endure, to contextualize, to make sense of the obstacles we cannot overcome.
Through sheer force of will, Lincoln was willing to endure anything, a long war and setbacks, to accomplish his mission.
Willpower is what enables us to adapt and resist when we are tossed about in a hostile world.
Build your inner citadel
We often assume that our weaknesses will be with us for life. Theodore Roosevelt was a very fragile child, diminished by asthma and diseased lungs. However, with proper physical training, he essentially overcame his asthma by the time he was an adult.
We can prepare ourselves to face life’s difficulties by building our indestructible inner mental citadel.
We create our mental strength through physical exercise and our physical strength through mental training.
By strengthening your willpower, working on your weaknesses, preparing for the worst and facing your fears, you will be ready when luck runs out (because eventually it will).
Anticipation (thinking negatively)
The premortem technique is to consider everything that could go wrong, before taking steps to prevent it from happening.
Since things rarely go as planned, Stoics, such as Seneca, developed the habit of comtemplating potential misfortunes.
As a result, much of what happened fell within their predictions: they had prepared for it.
By anticipating, we can reflect on the weaknesses of our project and correct them, or simply prepare ourselves for adversity and failure
Unexpected failures are discouraging and hurt. (…) The one who expects to be disappointed will not be. He will have the strength to bear it.
The art of acquiescence
Thomas Jefferson was a poor speaker, but that didn’t stop him from writing the Declaration of Independence. Edison was practically deaf, and yet that didn’t stop him from creating the light bulb.
Although we sometimes think otherwise, life’s constraints are a good thing, especially when we can accept them and use them as beacons. They force us to develop skills that we would otherwise have neglected.
Our human condition means that we have to accept and come to grips with a certain reality, which we can do nothing about.
Acceptance doesn’t mean giving up, it just means taking things as they are. Acceptance of people and things opens us to humility and learning.
Love everything that happens
To do great things, we must be able to endure tragedy and failure.
When Edison’s factory caught fire, he smiled at the thought of the junk he would be rid of and at the plan he was already devising to rebuild everything.
Lamenting the disasters that occur in our lives is not helpful. Bad things always happen, so we might as well learn to accept and appreciate them, so we can focus our energy on what is best.
Obstacles are not within our control because we did not choose them. How we deal with them, however, is entirely within our control.
Are we going to waste time feeling bad, or are we going to decide to move forward right now?
Opportunities and benefits reside in misfortune. We know that by overcoming such misfortune, we become stronger, more experienced, and more powerful.
Persistence is an action, perseverance is a matter of will. One is energy, the other is endurance.
Perseverance is when we are determined to achieve our goal, no matter how long it takes, no matter what the obstacles.
Obstacles may slow us down or lead us astray, but we can use our willpower to try again or to try differently.
While our plans may fail in spite of ourselves, it is up to us to choose between despair and determination.
Something bigger than yourself
Circumstances can sometimes get out of hand, and the situation becomes hopeless.
When we focus on others, helping them or simply leading by example, our personal fears and troubles subside.
When we can’t get anything out of a situation, instead of staying focused on our problem, we can always make sure that others benefit.
It is by helping others that we find meaning and strength as well as forget our own suffering.
We are only human beings among many others, experiencing similar difficulties at different times. All we can do is to contribute to the universe and make others stronger in order to become stronger ourselves.
Meditate on your mortality
Although we are all mortal, we often behave as if we are never going to die. We focus on trivial things.
It was after Montaigne’s near-death fall from a horse that he produced his finest work and began to travel and explore the world and its different cultures.
Reflecting and being aware of our mortality creates a perspective and a sense of urgency. It does not have to be depressing. Rather, it should invigorate us.
When we are aware every day that we are going to die, we stop grumbling, we make the best of it, we become more caring, we develop a greater appreciation for life.
Prepare to start again
Obstacles are part of life. They make it worthwhile by providing us with learning experiences, which contribute to our personal self-development.
Life is a never-ending series of obstacles. The world challenges us again and again.
Behind the mountains are other mountains.
When we overcome one obstacle, another one appears. However, as we go along, we get better and we get wiser.
We go from being afraid to being joyful at the thought of facing the next one that comes along.
Conclusion to “The obstacle becomes the way”
When one of his generals rebelled against him to remove him, Marcus Aurelius could have claimed revenge. However, he didn’t take it personally.
This obstacle showed him another way, the way of forgiveness, of goodness, of wisdom. This obstacle enabled him to showcase the qualities of a great leader.
The obstacle becomes the way, is the way.
Some do not despair in the face of obstacles. They face them light-heartedly, seeing each one as a solution, an opportunity. And they emerge stronger.
They have understood the latent power of perception, action, and will.
Practice mastering these three disciplines (perception, action, will) by applying them to each new obstacle:
See things as they are. Do what you can. Endure and bear that which you must endure and bear.
Postscript: Congratulations, you’re now a philosopher!
Throughout history, great men of action have embodied Stoic philosophy. They were not theorists, but men of action: George Washington, Eugène Delacroix, Toussaint Louverture, Wen Jiabao and many others…
Henry David Thoreau said that philosophy consisted in solving the problems of life, in theory as well as in practice. Life is its field of application.
So you too are a philosopher, now armed with the principles of the Stoics to govern your life and face its obstacles.
(The) true use of philosophy: a modus operandi in the face of life’s hazards.
Conclusion of “The Obstacle is the Way” by Ryan Holiday
Stoic thought, like philosophy as a whole, can sometimes appear boring and too theoretical.
Moreover, it was developed in a very distant era, that of ancient Greece.
Ryan Holiday shows us in “The Obstacle is the Way” that this philosophy is not at all old-fashioned and that many famous personalities have been inspired by it throughout history.
Better yet, Holiday demonstrates how we can easily integrate its fundamental principles into our daily lives, starting with our own difficulties.
We have all found ourselves faced with an obstacle that seemed insurmountable. However, did we perceive it fully and objectively, or did our emotions cloud our judgement?
Did we then really try everything to overcome it, or did we give up too quickly, forgetting to simply move forward step by step, and look for opportunity within the problem?
Finally, in the face of failure and a problem without a solution, did we sit back in despair, or did we expect to fail and immediately start again, learning from it? Are we willing to accept what is beyond us, and to see that we can always take something beneficial from it, for ourselves and for others?
Perception, action, and will are three facets of Stoic thinking that we can apply to every obstacle, no matter how big or small, that comes our way.
The book “The Obstacle is the Way” should not be left to collect dust on a shelf: it is a manual that we can refer to every time we feel we are stuck somewhere.
Antonin from the blog Learning to Invest
Strong points of The Obstacle is the Way:
- Stoic thought summarized in three main principles.
- A practical book, with many examples.
- Short chapters allow for a quick and dynamic reading experience.
Weak points of The Obstacle is the Way:
- Some chapters have a disjointed structure.
- A bit too many examples related to battlefields and war.
My rating :
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