Copyright © Ryan Holiday, 2014, 2015
Ryan Holiday is a media strategist for clients such as Tucker Max and Dov Charney, and worked on the publicity campaign for Tim Ferris’s the 4-Hour Work Week. After dropping out of college at nineteen, he went on to advise bestselling authors and multi-platinum musicians. He is the Director of Marketing at American Apparel and his strategies are used as case studies by Twitter, YouTube and google. He currently lives in New Orleans.
Estimated reading time: 25 minutes.
This book objectives:
- 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.
- This will be a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck, unfucked, and unleashed. How to turn the many negatives situations we encounter in our lives into positive ones, or at least to snatch whatever benefit we can from them.
Main ideas:
- Setbacks or problems are always expected and never permanent.
- Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?
- Let’s be honest. Most of us are paralyzed.
- Obstacles are not only to be expected but embraced. Because these obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.
- Let’s be honest. Most of the time we don’t find ourselves in horrible situations we must simply endure.
- We decide what we will make of each and every situation.
- Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. We decide what story to tell ourselves.
- In space, the difference between life and death lies in emotional regulation.
- Do I need to freak out about this?
- What if you focused on what you can change? That’s where you can make a difference.
- We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.
- Our best ideas come from there, where obstacles iluminate new options.
- Action is the solution and the cure to our predicaments.
- It’s okay to be discouraged. It’s not okay to quit.
- You’re never going to find that kind of perfection. Instead, do the best with what you’ve got.
- Nothing can ever prevents us from trying. Ever.
- Problems are a chance for us to do our best. Just our best, that’s it. Not the impossible.
- 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 path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us.
- When we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish.
- Understand that each battle is only one of many and that you can use it to make the next one easier.
Comments extracted from the book, they could be right or wrong, you decide for yourself:
- Marcus Aurelius: «Our actions can be impeded … but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting. The impediment to action advances action. What stands in the way becomes the way».
- Setbacks or problems are always expected and never permanent.
- Marcus Aurelius truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity. He rarely rose to excess or anger, and never to hatred or bitterness.
- Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?
- That thing you dread or secretly hope will never happen. What if it wasn’t so bad?
- Let’s be honest. Most of us are paralyzed. Whatever our individual goals, most of us sit frozen before the many obstacles that lie ahead of us.
- Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.
- We blame our bosses, the economy, our politicians, other people. When really only one thing is at fault: our attitude and approach.
- Andry Groove, former CEO of Intel: «Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them». Great individuals, like great companies, find a way to transform weakness into strength.
- Let’s be honest. Most of the time we don’t find ourselves in horrible situations we must simply endure. Rather, we face some minor disadvantage or get stuck with some less-than-favorable conditions. Or we’re trying to do something really hard and find ourselves outmatched, overstretched, or out of ideas. The same logic applies. Turn in around. Find some benefit. Use it as fuel.
- 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.
- This will be a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck, unfucked, and unleashed. How to turn the many negatives situations we encounter in our lives into positive ones, or at least to snatch whatever benefit we can from them.
- Old Zen story: «Never forget, within every obstacle is an opportunity to improve our condition».
- Benjamin Franklin: «The Things which hurt, instruct».
- We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can atest.
- 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.
- Perception, Action, and the Will.
- Obstacles are not only to be expected but embraced. Because these obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph. The Obstacle Is the Way.
- Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective and short-sighted 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 straightforwardly, as they truly are, neither good or bad. This will be an incredible advantage for us in the fight against obstacles.
- 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. Or, choose not to.
- Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things.
- Humans are still primed to detect threats and dangers that no longer exists.
- We have a choice about how we respond to this situation, or any situation, for that matter.
- When faced with 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.
- We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll assent or reject. No one can force us to give up or to believe something that is untrue. Our perceptions are the thing that we’re in complete control of. We are never completely powerless.
- Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. We decide what story to tell ourselves. Or whether we tell one at all.
- Theodore Roosevelt: «What such a man needs is not courage but nerve control, cool headedness. This he can get only by practice».
- We are a pile of nerves.
- if your nerve holds, then nothing really did «happen», our perception made sure it was nothing of consequence.
- When America raced to send the first men into space, they trained the astronauts in one skill more than in any other: the art of not panicking.
- When people panic, they make mistakes. They override systems. They disregard procedures, ignore rules. They deviate from the plan. They become unresponsive and stop thinking clearly. They just react.
- Panic hast to be trained out. And it does not go easily.
- Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve.
- Fortunately, unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty.
- In space, the difference between life and death lies in emotional regulation.
- Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check.
- The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind. Don’t let the negativity in, don’t let those emotions even get started. This is the skill that must be cultivated so you can focus your energy exclusively on solving problems, rather than reacting to them.
- Does getting upset provide you with more options?
- Real strength lies in the control or, as Nassim Taleb put it, the domestication of one’s emotions, not in pretending they don’t exist.
- You can always remind yourself: I am in control, not my emotions. I see what’s really going on here. I’m not going to get excited or upset.
- 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.
- It might help to say it over and over again whenever you feel the anxiety begin to come on: I am not going to die from this.
- Subconsciously, we should be constantly asking ourselves this question: Do I need to freak out about this?
- The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees «insurmountable obstacles» or «major setbacks» or even just «issues». It brings its own issues to the fight. The former is helpful, the latter is not.
- How often do we see what we think is there or should be there, instead of what actually is there?
- Perceptions are the problem. They give us the «information» that we don’t need, exactly at the moment when it would be far better to focus on what is immediately in front of us.
- The sixteenth-century Samurai swordsman Miyamoto Musashi and most martial arts practitioners focus on mental training as much as on physical training. Both are equally important, and require equally vigorous exercise and practice.
- Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious. Something that’s present when we deal with out own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.
- Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. Think of all the ways that someone could solve a specific problem.
- The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.
- Perspective is everything.
- We are scared of obstacles because our perspective is wrong, a simple shift in perspective can change our reaction entirely.
- How we approach, view, an contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.
- Is our perspective truly giving us perspective or is it what’s actually causing the problem? That’s the question.
- What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand.
- Where the had goes, the body follows. Perception precedes action. Right action follows the right perspective.
- Is there a change? Do I have a shot? Is there something I can do?
- Recovering addicts learn the Serenity Prayer:
- 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.
- What if you focused on what you can change? That’s where you can make a difference.
- What is up to us:
- Our emotions.
- Our judgments.
- Our creativity.
- Our attitude.
- Our perspective.
- Our desires.
- Our decisions.
- Our determination.
- To argue, to complain, or worse, to just give up, these are choices. Choices that more often than not, do nothing to get us across the finish line.
- The most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.
- Focusing exclusively on what is in our power magnifies and enhances our power.
- To see an obstacle as a challenge, to make the best of it anyway, that is also a choice, a choice that is up to us.
- Chuck Palahniuk: «The trick to forgetting the big picture is to look at everything close up».
- We get ourselves so worked up and intimidated because of the overthinking that if we’d just gotten to work we’d probably be done already.
- Half the companies in the Fortune 500 were started during a bear market or recession. Half.
- Focus on the moment, not the monsters that may or may not be up ahead.
- For all species other than us humans, things just are what they are. Our problem is that we’re always trying to figure out what things means, why things are the way they are. As though the why matters.
- It doesn’t matter whether this is the worst time to be alive or the best, whether you’re in a good job market or a bad one, or that the obstacle you face is intimidating or burdensome. What matters is that right now is right now.
- We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.
- Catch your mind when it wanders, don’t let it get away from you. Discard distracting thoughts.
- Focus on what is in front of you, right now. Ignore what it «represents» or it «means» or «why it happened to you».
- F. Scott Fitzgerald: «Genius is the ability to put into effect what is in your mind. There’s no other definition of it».
- Be open. Question.
- Steve Jobs refused to tolerate people who didn’t believe in their own abilities to succeed. Even if his demands were unfair, uncomfortable, or ambitious.
- Our best ideas come from there, where obstacles iluminate new options.
- The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth.
- 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.
- Action is the solution and the cure to our predicaments.
- In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given.
- 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
- That’s what people who defy the odds do. They start. Anywhere. Anyhow. They don’t care if the conditions are perfect or if they’re being slighted. Because they know that once they get started, if they can just get some momentum, they can make it work.
- 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.
- It’s okay to be discouraged. It’s not okay to quit.
- The answer should be clear: We’re working on it. We’re getting closer. When setbacks come, we respond by working twice as hard.
- Saban, head coach of the University of Alabama football team: «Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand».
- When it comes to our actions, disorder and distraction are death.
- When we know what we’re really setting out to do, the obstacles that arise tend to seem smaller, more manageable.
- Moving forward, one step at a time. Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it.
- Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first. Come back to the others later. You’ll get there.
- The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.
- Sir Henry Royce: «Whatever is rightly done, however humble, is noble».
- You’re so busy thinking about the future, you don’t take any pride in the tasks you’re given right now.
- Everything we do matters. Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires.
- In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well. Right action (unselfish, dedicated, masterful, creative) that is the answer to that question.
- All we need to do is those three little duties, to try hard, to be honest, and to help others and ourselves. That’s all that’s been asked of us. No more and no less.
- So many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.
- You’re never going to find that kind of perfection. Instead, do the best with what you’ve got. At some point, you have to compromise. What mattered was that you got it done and it worked.
- Think progress, not perfection.
- Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle. In fact, having the advantage of size or strength or power is often the birthing ground for true and fatal weakness. The inertia of success makes it much harder to truly develop good technique.
- The great philosopher Soren Kierkegaard would rarely t ell the reader «do this» or «think that». Instead he would show new ways of looking at or understanding the world.
- You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen.
- Sometimes the longest way around is the shortest way home.
- Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you.
- Sometimes in your life you need to have patience, wait for temporary obstacles to fizzle out.
- Sometimes a problem needs less of you and not more. When we want things too badly we cant be our own worst enemy. In our eagerness, we strip the very screw we want to turn and make it impossible to ever get what we want.
- We wrongly assume that moving forward is the only way to progress, the only way we can win.
- The boxer Jose Louis knew that racist white boxing fans would not tolerate an emotional black fighter, so he sublimated all displays behind a steely, blank face. Known as the Ring Robot, he greatly intimidated opponents by seeming almost inhuman.
- Ordinary people shy way from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They are their best in these situations.
- Nothing can ever prevents us from trying. Ever.
- Problems are a chance for us to do our best. Just our best, that’s it. Not the impossible.
- Will is our internal power, which ca never be affected by the outside world. It is our final trump card. If actions is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.
- True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition.
- Abraham Lincoln battled crippling depression his entire life, nearly driving him to suicide on two separate occasions.
- This was Lincoln: always ready with a new idea or innovative approach but equally prepared for the worst. And then prepared to make the best of the worst.
- If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.
- Will is also the most difficult of all the disciplines. It’s what allows us to stand undisturbed while others wilt and give in to disorder. Confident, calm, ready to work regardless of the conditions. Willing and able to continue, even during the unthinkable, even when our worst nightmares have come true.
- 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.
- And, of course, prepare to start the cycle once more.
- Could you actually handle yourself if things suddenly got worse?
- We take weakness for granted. We assume that they way we’re born is the way we simply are, that our disadvantages are permanent. And then we atrophy from there.
- What the Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down. An important caveat is that we are no born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us. If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built.
- The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us.
- Mike Tyson: «If you’re not humble, life will visit humbleness upon you».
- Seneca: «Nothing happens to the wise man against his expectations».
- In the case where nothing could be done, the Stoics would use it as an important practice to do something the rest of us too often fail to do: manage expectations. It will suck but we’ll be okay.
- Common wisdom provides us with the maxims:
- Beware the calm before the storm.
- Hope for the best, prepare for the worst.
- The worst is yet to come.
- It gets worse before it gets better.
- The world might call you a pessimist. Who cares? It’s far better to seem like a downer than to be blindsided or caught off guard.
- About the worst thing that can happen is not something going wrong, but something going wrong and catching you by surprise. But the person who has rehearsed in their mind what could go wrong will not be caught by surprise.
- We can resist going to pieces if things didn’t go as planned. With anticipation, we can endure. We are prepared for failure and ready for success.
- It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued.
- When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence.
- Rarely do we consider how much worse things could have been. And things can always be worse.
- We squirm and complain about what was taken from us. We still can’t appreciate what we have.
- The ancients (an the not so ancients) used the word fate more frequently than us because they were better acquainted with and exposed to how capricious and random the world could be. Events were considered to be the «will of the Gods». The Fates were forces that shaped our lives and destinies, often not with much consent.
- There is always someone or something that could change the plan. And that person is not us. As the saying goes: «Man proposes but God disposes».
- We’re indifferent and that’s not a weakness.
- To do great things, we need to be able to endure tragedy and setbacks. We’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens.
- There is always some good contained within the bad. And we can find it and be cheerful because of it.
- Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.
- The good thing about true perseverance is that it can’t be stopped by anything besides death.
- Our actions can be constrained, but our will can’t be.
- Determination is invincible.
- When we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish.
- Sometimes when we are personally stuck with some intractable or impossible problem, one of the best ways to create opportunities or new avenues for movement is to think: If I can’t solve this for myself, how can I at least make this better for other people?
- Stop pretending that what you’re going through is somehow special of unfair. Whatever trouble you’re having is not some unique misfortune picked out especially for you. It just is what it is.
- We may not say it, but deep down we act and behave like we’re invincible. Like we’re impervious to the trials and tribulations of morality. That stuff happens to other people, not to ME.
- There are always more obstacles, bigger challenges. Get used to it and train accordingly. Life is a marathon and not a sprint. Conserve your energy. Understand that each battle is only one of many and that you can use it to make the next one easier.
Have you read this book? Any other similar book? Do you have anything to say about what this book is saying? Do you recommend any book related to this matter? Anything at all? I’ll be glad to know what you think about it in the comments.
Some related links:
Some related books:
- Discipline is Destiny by Ryan Holiday.
- The Art of Living Consciously by Nathaniel Branden.
- Can’t hurt me by David Goggins.
- Lecciones de estoicismo de John Sellars.
- El pequeño libro de la filosofía estoica de Javier G. Recuenco y Guillermo de Haro.
- Invicto de Marcos Vázquez.
raul

















