The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

by Ryan Holiday

When facing a problem too often we become stuck, depressed, or frustrated. But it needn’t be this way. There is a formula for success. Step by step, we can learn how to turn our adversities into advantages. We can decide if obstacles limit us or if they are opportunities.

Summary Notes

Preface & Introduction

The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

People often see an obstacle as a problem, but everything depends on our perception. We can decide if an obstacle limits us or if it is an opportunity. Obstacles force us to act with or practice some virtue like patience, courage, or creativity.

In fact, many obstacles can be seen as only some disadvantages. We do not suffer hunger or war but exaggerate our less-than-favorable conditions into big things. We complain that we are too short, too old, too poor, but what we are really missing is the proper attitude and approach.

When an obstacle appears many people, instead of acting, do nothing and only complain about it. They blame others for the situation but do not see that they could change it if they acted. Whenever we are faced with an obstacle we have a choice - we can let it block us, or we can overcome it and learn something from it in the process. Like oxygen to a fire, obstacles can be the fuel to our blaze.

We have to remember that the solution to our obstacles is not only to be positive and think that others are in a worse situation. The way is to see the obstacle reasonably, to not be afraid of confronting it, and to act.

Overcoming obstacles requires three steps: Perception, Action, and Will. This is a simple process but not easy. We can, however, learn how to do it.

Actions to take

Part I: Perception

Perception is how we see and understand what occurs around us. We observe and then decide what meaning to apply to those events in our lives.

The Discipline of Perception

Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things.

All of us come across obstacles in life - both fair and unfair. What matters is how we see and react to them. If we feel desperate, powerless, or despair - that is our choice. We cannot forget that it is only our perception, and we can discipline it. To do that we have to:

  • Be objective
  • Control our emotions
  • See the good in the situation
  • Steady our nerves
  • Belittle what disturbs and limits others
  • Put things in perspective
  • Be focused on the present
  • Concentrate on what can be controlled

Actions to take

Recognize Your Power

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

There is no good or bad without our mind. There is the situation itself and the story we create in our brains about what it means.

We are never completely powerless. Our thoughts, our beliefs, and our reactions can be controlled. The same event, which for one person is negative, for another may be positive. Just because a situation, for many people, is horrible and hopeless, does not mean that we have to agree with it. We decide what kind of story we tell ourselves. This is the power of perception.

Of course, it is not about seeing the world through delusional, rose-colored glasses. The goal is to see it objectively.

Actions to take

Steady Your Nerves

What such a man needs is not courage but nerve control, cool-headedness. This he can get only by practice.” — Theodore Roosevelt

When our goals are high, pressure and stress come along. Unpleasant situations are almost guaranteed. In such a case, talent is not the attitude that could help. Grace and poise are more desirable because they give the opportunity to deploy other skills.

Two opposite reactions can help you calm your nerves. First, defiance like: “It is not about me. I do not want to be involved in that situation”. The second - acceptance - “OK, it is my problem and I have to go step by step to resolve the problem”. What we have to remember is that there is always a countermove, an escape, or a way through.

Stress leads us to baser-fearful-instinctual reactions. By holding our nerve, we can do our best. We can prepare ourselves for the reality.

Actions to take

Control Your Emotions

When people panic, they make mistakes.

When the first astronauts were sent to space, they were trained in the “art” of not panicking. When people panic they ignore procedures, they deviate from the plan. They just react, without thinking clearly, and usually in an irresponsible way. Fears mostly come from unfamiliarity, but with enough exposure to similar situations, we can raise our tolerance for stress and uncertainty.

When we get free of disturbances and perturbations, we can focus our energy on solving problems, rather than reacting to them. Our emotional reactions can’t change the conditions of the situation; they are unhelpful and destructive.

Many can say “But it’s what I feel.”. Of course, we can show our emotions and cry, but we cannot lie to ourselves and say that it will help solve the problem. These are two different issues.

Actions to take

Practice Objectivity

The phrase ‘This happened and it is bad’ is actually two impressions. The first—‘This happened’—is objective. The second— ‘it is bad’—is subjective.

The perceiving eye is weak, the observing is strong. This is because the observing eye sees what actually is there without distractions, judgments, and exaggerations. The perceiving one adds all the fears, uncertainty, bad experiences, setbacks, and unmet expectations, transforming events to insurmountable obstacles. The additional “information” that perception gives, disturbs us and doesn’t let us think clearly.

A good strategy in helping us to see our problems objectively is to imagine that our friend is in this situation and we can give them a piece of advice. Then the solutions seem to be obvious because we can get rid of all the baggage of our emotions. Objectivity means removing “you” - the subjective part.

Actions to take

Alter Your Perspective

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

We decide how we will look at situations that appear in life. We can not change the obstacle in itself, but the perspective can change how we perceive it (easy, difficult to overcome).

By introducing "I" before an obstacle (for example, I don’t like public speeches, I am afraid of it) we unnecessarily add an extra element, which may result in exaggerating the problem. Of course, we do not want to ignore the fear, but we can explain it away.

Perspective has two definitions:

Context: a sense of the larger picture, not just what is in front of us.

Framing: a particular way of viewing things that depends on one’s experience and personality.

Both can be used to change a situation that we previously saw as difficult or impossible to overcome.

A good example of changing the perspective is George Clooney. He applied for roles for a long time and yet he continued to be rejected. Finally, he tried a new perspective. He understood that casting was an obstacle for producers too. They needed an actor for a role and he was the solution. He started presenting not only his acting skills but also the idea that he was the right man for the job. His new approach won.

The difference between the right and wrong perspective is everything.

Actions to take

Is It Up To You?

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

When we face a problem, the crucial thing is to recognize what parts we can control and what parts we can't control.

What parts are up to us:

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

What parts are not up to us:

  • the economy
  • the weather
  • circumstances
  • other people’s emotions or judgments
  • trends
  • disasters, etc.

Choosing to complain, argue, or give up leads to nowhere. It is important to focus on what we can change; on where we can make improvements. If, for example, your startup didn’t receive an investment - that isn’t up to you. What is, is trying again or completing a pivot.

Actions to take

Live In the Present Moment

Focus on the moment, not the monsters that may or may not be up ahead.

Our minds do not take things or situations as they are. We always add some additional meaning to them. We consider if something is fair or not, what is behind it, what others would say. We waste so much energy on mulling over the situation that we could be used to overcome it.

For all species, except humans, things are what they are. Animals do not add meaning to things or situations. Because of that, they can enjoy the present.

The implications of our problems are theoretical. They are in the past or in the future. The more we live in the present the easier it will be to face our problems.

It is good to remember that a moment is not our life, but just a moment in our life.

Actions to take

Think Differently

Genius is the ability to put into effect what is in your mind. There’s no other definition of it.” — F. Scott Fitzgerald

One of the best examples of thinking out of the box is Steve Jobs. He didn’t want to hear excuses like “It is impossible” or “We need more time”. For him aiming low meant to accept a mediocre accomplishment. Instead, he wanted to accomplish great things. In contrast to him, most people believe in obstacles more than in goals. The reason for this can be that most of us were taught to be realistic and listen to feedback. But sometimes that limits us. Only high goals can lead to the creation of something extraordinary. Steve Jobs rejected the first judgments and the objections because those objections mostly rise from fear.

The best ideas and inventions come out of obstacles that force people to see a new way of doing things. These entrepreneurs and inventors had faith in their ability to make something out of nothing. For them, the statement “no one has ever done this” was a positive thing.

Actions to take

Finding the Opportunity

There is good in everything, if only we look for it.” — Laura Ingalls Wilder

Besides controlling our emotions connected to an obstacle (like being overwhelmed, discouraged, or upset) we can go further and look for an opportunity within it. We have to remember that everything depends on our perception. Thanks to obstacles, we have a unique opportunity to experiment with different solutions, tactics, or to achieve new skills.

Here are a few examples of how to find a positive opportunity in situations that seem to be bad.

It is hard to see good things in having a boss, or longtime rival at work, that makes each day a horrifying experience, but if we look closer, they also:

  • keep us alert

  • motivate us to prove them wrong

  • harden us

  • help us to appreciate true friends

  • provide an instructive antilog - an example of whom we don’t want to become.

In a situation where we didn’t save the changes in the document we worked on, and all our work was erased, we normally curse and are angry. But there is also, at this moment, something positive - by doing the work once again, we will be twice as good at that topic.

When people are:

  • Rude or disrespectful: They underestimate you. This can be a huge advantage.

  • Critical or question your abilities: Lower expectations are easier to meet and every accomplishment is more admirable.

Of course, we want to avoid unpleasant situations, but we have to remember that in most cases it is only because of our perception. Our perception is the enemy that prevents us from seeing the advantages.

We can compare an obstacle to a gift that does not have nice packaging. It is not about seeing the glass-half-full, but rather, about converting something negative into something positive.

Actions to take

Prepare to Act

Problems are rarely as bad as we think - or rather, they are precisely as bad as we think.

Behind a successful action stands a proper perception - objective, rational, ambitious, and clean. The worst thing is never the event itself but all the emotions and additional meanings we add to the event. Then we have two problems, where one is completely unnecessary.

When we learn the right perception and how to manage our emotions we are ready to act.

Part II: Action

Action is commonplace, right action is not.

Our problems should be solved step by step, action by action. Effective actions need courage, but not brashness; creativity - not brute force. Attributes of a right action are deliberation and persistence. By thinking, talking about, or avoiding action, it is unlikely that problems will be solved by themselves. We need to decide to act.

The Discipline of Action

No excuses. No exceptions. No way around it: It’s on you.

Demosthenes was born with a debilitating speech impediment, but despite this, he became one of the most famous orators in history. When asked about the three most important traits of speechmaking, he replied: “Action, Action, Action!”.

To get to know better ourselves we should think about how we respond to problems that appear. These three questions tell a lot about our character. Do we run toward them? Do we run away from them? Or, are we paralyzed and do nothing? It is at this moment when so many of us fail - we choose to run away instead of taking action.

In life-threatening situations, like an accident, even though we are in shock, we know what to do. For example, we get our arms up around our face. In such moments we don’t think, complain, or argue. We act. We have more strength than we expect. We can act in this way in everyday life too.

We can observe a similar way of acting in people who struggle with poverty, discrimination, physical disabilities, etc.. Most of them don’t feel sorry for themselves, they don’t give up. They don’t have a choice, so they do the best they can for themselves.

Unfortunately, in everyday life we postpone action. We act frail, powerless. We expect that others will do something instead of us, or that the obstacle will disappear. Instead of hiding, we should greet obstacles with:

  • energy

  • persistence

  • a coherent and deliberate process

  • iteration and resilience

  • pragmatism

  • strategic vision

  • craftiness and savvy

  • an eye for opportunity and pivotal moments

Actions to take

Get Moving

If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.

People who achieve incredible things, do the most important thing - they start - no matter what. Even if conditions are not good, or it’s not the “right” moment (typical excuses), they complete the first step.

In contrast, we very often wait too long for the perfect time, better opportunities, and as result we do nothing. A solution to this can be to think how quickly time is passing. We don’t have a better option, we have to start now.

Nowadays we downplay the importance of attributes like aggression, taking risks, barreling forward. We negatively associate them with aggression, violence, or masculinity, but we don’t see the positive aspects of them that move us forward.

Actions to take

Practice Persistence

We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.

The story of Thomas Edison shows that by persistence and pertinacity we can achieve great things. Many think that he was a genius but what really distinguished him from others was that he didn’t give up. Before discovering the bulb, he tested six thousand different filaments! His story is not the exception to the rule, but it is the rule.

Like Edison in his laboratory, we in our lives should try option after option with the same enthusiasm. Each try eliminates a wrong track, gives us knowledge, and brings us closer to the solution.

When we try new things obviously we will meet obstacles. Only with persistence and time will what was unknown and difficult become familiar and clear.

Actions to take


What is defeat? Nothing but education; nothing but the first steps to something better.” — Wendell Phillips

In the old business model, companies, based on some research, were preparing finished, polished products and on launch day was when they received their first feedback. If the product didn’t meet expectations, the companies lost all the time and resources they invested.

Nowadays the Minimum Viable Product (MVP) business model dominates. The MVP is the most basic version of the core product idea, that many startups release. They then wait for the customers’ feedback. If the feedback is poor, in this stage, it is much cheaper to fail and do a pivot. This strategy is close to the idea of taking failure as a good thing.

A failure can be an advantage if you use it to try to improve, to look for different ways to do something, or to learn something. There is nothing shameful about being wrong, by failure you become stronger. Action and failure are two sides of the same coin.

In business, we take failures less personally than in private life. We understand that they are part of the business. It is good to start thinking in this way in your personal life.

The only case in which we don’t benefit from failure is when we don’t draw conclusions from it.

Actions to take

Follow the Process

We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y.

Very often big tasks terrify us. We think that they are too ambitious or outside our grasp, but when we divide them into small actions, they seem to be more feasible. We should see overcoming an obstacle as a process. Be focused on the part that we do at the moment, and do it well, and then later move to the next step.

Panic, disorder, and distraction are the enemies of the process. When we act in an unordered way, we lose track of what’s in front of us. We think too much about the future, about the final result, all the while missing the possible opportunities of the moment.

Of course, we want to have goals, because our actions need to have a purpose. By just dividing them into manageable proportions, we replace fear with the process. We feel the strength and we know what to do.

Actions to take

Do Your Job, Do It Right

Whatever is rightly done, however humble, is noble. (Quidvis recte factum quamvis humile praeclarum.)” — Sir Henry Royce

Sometimes, before we reach our goal, we need to go through paths we would rather like to avoid. But, wherever we are, whatever we do, we have to be dedicated to it and do it well. There is no shameful work. Each work deserves our best. That includes hard work, honesty, and helping others. If we do our best we can be proud and confident in our choices.

The psychologist Viktor Frankl claims that in every situation, life is asking us a question: “What is the meaning of life?” and our actions are the answer. By right actions (unselfishness, dedication, masterfulness, creativity, etc.) we can turn all obstacles into opportunities.

Actions to take

What’s Right Is What Works

Don’t worry about the “right” way, worry about the right way. This is how we get things done.

Very often we try to do everything too perfectly. We focus on how things are supposed to be, what methods we ought to use, we wait for the best conditions. In this way we limit ourselves. It is much better to think outside of the box, to use available methods, to ask for forgiveness rather than permission, or even ignore some outdated rules or law.

We don’t have to go from point A to point B in a straight line like we were taught at school. There are many ways. We have to adapt to the current situation, compromise to the conditions. Act and progress.

Actions to take

In Praise of the Flank Attack

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

The study of 30 conflicts, including more than 280 campaigns from ancient to modern history, shows that only 6 big victories were a result of a direct attack on the enemy’s main army. That is less than 2%. 98% were the result of creativity, unexpectedness, and nontraditional methods, that drew opponents out from their defenses allowing an attack from the flanks.

We are used to “attacking” our problems head-on, which doesn’t always works. Instead, we should follow the successful strategists and look for other ways. Even if it is not an impressive way. Shortcuts are welcomed.

Sometimes having the advantage of size, power or strength is an illusion. Such people or companies lose their flexibility, they are not prepared for the not-front encounter. We can use a side-door strategy, which is a vast and creative space.

Actions to take

Use Obstacles Against Themselves

Wise men are able to make a fitting use even of their enmities.” — Plutarch

In history, we can find many examples of how not taking action led to victory. The best of these are the Russians, who defeated Napoléon and the Nazis by letting them march into the Russian interior to be trapped by winter. Sometimes not taking an action is an action - if we use the power of others and absorb it into our own.

If we see that the problem is enormous, that persistence and iterate don’t work, instead of fighting against the obstacle and wasting energy, we can find a way of making the obstacle defeat itself. Just like a castle can be an unconquerable fortress, or a prison when surrounded. Simply by shifting the action and the approach.

Of course, there is a difference between doing nothing and using obstacles against themselves. Passive resistance is an action because it includes discipline, self-control, fearlessness, determination, and strategy.

Actions to take

Channel Your Energy

External factors influence the path, but not the direction: forward.

In our lives, we waste a lot of energy on small, unimportant things. When something disturbs us, we redirect all our resources to it, forgetting about our aim. This leads to nowhere. Adversities can give us a lot of power, we just have to channel them in the right direction, to use them properly. What is not easy can motivate us even more.

Actions to take

Seize the Offensive

The best men are not those who have waited for chances but who have taken them; besieged chance conquered the chance, and made chance the servitor.” — E. H. Chapin

It is in our nature to avoid obstacles and difficult situations, but they can afford us great opportunities. Politics very often use crisis, catastrophes, and problematic moments to make big moves or pass reforms that normally would be postponed indefinitely. We can apply this to our lives too. For example, instead of being depressed after breaking off a relationship, you can travel unencumbered, or go dancing classes, or go to any class to learn something new. A negative moment can become a catalyst. Use it to deploy what you had planned for a long time.

Actions to take

Prepare For None of It to Work

In every situation, that which blocks our path actually presents a new path with a new part of us.

Even if we follow all these steps - if we see obstacles from the right perspective, think clearly and act right, and are prepared for a failure, we are not able to control everything. Sometimes problems may be impossible to overcome. In such cases, we can take advantage of practicing new skills like acceptance, forgiveness, or humility.

Part III: Will

Will is our internal power, which can never be affected by the outside world. It is our final trump card.

The will is often understood as how bad we want something. It actually has more in common with surrender than with strength. True will is connected to humility, patience, and flexibility.

The Discipline of the Will

If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.

Of the 3 disciplines, Perception, Action, and Will, it is only the last one that we can control 100%. It is inside us, it lets us endure, contextualize, and derive meaning from the obstacles that we cannot overcome. It also prepares us for when our perception and action may fail, it protects us against that and allows us to thrive and be happy in spite of it.

Actions to take

Build Your Inner Citadel

If thou faint in the day of adversity, thy strength is small.” — Proverbs 24:10

Too often we assume that how we were born is something permanent. We take disadvantages for granted, but we have a choice, we don’t have to accept a bad start in life. We can work on it.

Inner Citadel by Stoics is described as fortress inside of us, where no external adversity can enter. What is important is that we are not born with it. We have to build and reinforce it during our good times to protect us in the bad ones.

Actions to take

Anticipation (Thinking Negatively)

Hope for the best, prepare for the worst.

We all know the term postmortem, which means that doctors examine the cause of an unexpected death. In a wider context, outside of the medical world, we can examine something in hindsight, after it happened. In contrast, there is a new technique called premortem. In it, we try to envision, in advance, before something starts, what can go wrong.

We should always be prepared for disruptions and include them in our plans. This doesn’t mean that nothing bad will happen, but with collected resources, and by being mentally prepared, we can be in control of the situation if it does. If nothing bad happens - great. It is much better to be pleasantly surprised than unpleasantly disappointed.

Too often we imagine and expect that everything will go well. As a result of our anticipation of bad things happening, we can accustom ourselves to reality. The aim is not to ruin dreams, but to raise defenses, to have the strength to bear what the future brings, and to avoid mistakes.

Actions to take

The Art of Acquiescence

The Fates guide the person who accepts them and hinder the person who resists them.” — Cleanthes

Acceptance of situations that we can’t control and change (like incapacity, accidents, weather catastrophes, and other external events) gives us the strength to cope with them and allows us to develop different skills. When we resist, instead of adjusting to reality, we get stuck in the same place and we lose energy fighting with something that we don’t have any influence over. That energy we could channel in the right direction.

Acceptance is not the same thing as giving up. This is an action that is the start of moving on. We don’t have to like something to cope with it, or even to take advantage of it.

Unfortunately, we prefer to spend time imagining perfect situations. We don’t appreciate what we have and we focus on what we don’t. This doesn’t lead to success.

Actions to take

Love Everything That Happens: Amor Fati

Cheerfulness in all situations, especially the bad ones.

The next step, after discarding expectations and accepting undesirable situations, is to love them. This sounds unnatural, but it is the only way to enjoy every single moment in our life. And we are talking about real acceptance and love, not just tolerating the situations.

We don’t have control over everything that happens to us, but we can always choose how we feel about it. Good moods help us cope with problems. When we are depressed, we are passive and don’t make progress.

Actions to take


The good thing about true perseverance is that it can’t be stopped by anything besides death.

First, we have to differentiate between the terms persistence and perseverance. Persistence refers to an action and energy, perseverance is a matter of will and endurance. Perseverance, determination, is not only about solving some difficult problem. By persevering, we can understand something larger and long-term.

When we learn perseverance, we learn the best tool to cope, not only with one problem but with many. Actions can be limited, plans or resources destroyed, but the strong will doesn’t have barriers and cannot be exhausted. It is impossible to control all situations, but we can control ourselves, which is sufficient.

Actions to take

Something Bigger Than Yourself

A man’s job is to make the world a better place to live in, so far as he is able - always remembering the results will be infinitesimal - and to attend to his own soul.” — Leroy Percy

Sometimes a situation occurs that is so hopeless it seems that nothing can be done. In such cases, we can find something to be grateful about and look for ways to help others. If there is nothing we can do for ourselves, we can use the situation to benefit others. It gives us a mission. We can feel that we still have something to do. Also, when we focus on others, we don’t think about suffering and complaining. When we are strong for others, we also get real strength for ourselves.

Even in horrible situations, we mustn’t lower ourselves to become a person we wouldn’t like to be.

Actions to take

Meditate On Your Mortality

When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.” — Dr. Johnson

Most people who were close to death, say that it changed their life. If they were given a second chance at life, they treated that time as a gift and wanted to enjoy it much more than before. Death doesn’t mean that life is pointless, but rather that it has a purpose.

When we are close to death, we don’t spend time on complaining or obsessing over trivialities. Instead, we think clearly, urgently, and with a right perspective and priorities. We don’t have to be at that point in our life to start acting in this way. We just need to remember we are mortal: Memento more.

Actions to take

Prepare to Start Again

Behind mountains are more mountains.” — Haitian proverb

When we finally overcome one obstacle, a new one will probably appear in our way. This is normal. It may even be better to say that if we could handle one, we are worthy of handling more challenges. We should remember that behind each problem, stands new opportunities, new skills to develop, and new wisdom to obtain.

Actions to take

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