The Obstacle is the Way by Ryan Holiday

The Obstacle is the Way

27 min read

5/14/19

  • Thrive not just in spite of whatever happens but because of it

  • Our actions may 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

  • Turn the obstacle upside down

  • There is always a way out or another route to get to where you need to go

  • Setbacks and problems are expected and never permanent

  • We have a choice: will we be blocked by obstacles or will we advance through and over them?

  • The world is constantly testing us. It asks: are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?

  • The challenge makes us better than if we’d never faced the adversity at all

  • Most of us are paralyzed

  • Only one thing is at fault: our attitude and approach

  • Earlier generations faced worse problems with fewer safety nets and fewer tools. They dealt with the same obstacles we have today plus the ones they worked so hard to try to eliminate for their children and others

  • We lack a method and a framework for understanding, appreciating and acting upon the obstacles life throws at us

  • 'Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them' - Andy Grove

  • Great individuals, like great companies, find a way to transform weakness into strength

  • The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition

  • When you have a goal, obstacles are actually teaching you how to get where you want to go—carving you a path

  • 'The things which hurt, instruct' - Benjamin Franklin

  • Today, most of our obstacles are internal, not external

  • Instead of opposing enemies, we have internal tension

  • Many of our problems come from having too much. We're soft, entitled and scared of conflict

  • Great times are great softeners

  • 'Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance—now at this very moment—of all external events. That's all you need' - Marcus Aurelius

  • 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 actually opportunities to test ourselves, to try new things, and, ultimately, to triumph

  • The Obstacle Is The Way

  • Perception is how we see and understand what occurs around us—and what we decide those events will mean

  • To prevent becoming overwhelmed by the world around us, we must learn how to limit our passions and their control over our lives

  • Filter our prejudice, expectation, and fear. What's left is truth

  • “Be fearful when others are greedy and greedy when others are fearful” - Warren Buffet

  • Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions. You muse realize: nothing makes us feel this way; we choose to give in to such feelings. Or choose not to

  • We have a choice of how we respond to this situation

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

  • Anger is not constructive

  • 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

  • “Nothing either good or bad, but thinking makes it so” - William Shakespeare

  • There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means

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

  • There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and of course the stakes are high, but the path is there for those ready to take it

  • Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check. This is the skill that must be cultivated—freedom from disturbance and perturbation—so you can focus your energy exclusively on solving problems, rather than reacting to them

  • When you worry, ask yourself, “what am I choosing to not see right now?” What important things are you missing because you chose worry over introspection, alertness or wisdom?

  • If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion

  • Real strength lies in the control, or the domestication of one’s emotions, not in pretending they don’t exist

  • I am in control, not my emotions. I see what’s really going on here. I’m not going to get excited or upset

  • You’re probably not going to die from any of this

  • Does what happened keep you from acting with justice, generosity, self control, sanity, prudence, honesty, humility, straightforwardness?

  • “Don’t let the force of an impression when it first hit you knock you off your feet; just say to it; hold on a moment; let me see who you are and what you represent. Let me put you to the test” - Epictetus

  • The observing eye sees simply what is there. The perceiving eye sees more than what is there. The former is helpful, the latter is not

  • Sometimes being superficial—taking things only at first glance—is the most profound approach

  • It’s so much better to see things as they truly, actually are, not as we’ve made them in our minds

  • Objectivity means removing “you”—the subjective part—from the equation

  • Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do? How much more quickly and dispassionately could you size up the scenario and it’s options? You could write it off, freer it calmly

  • “Man does not simply exist but always decides what his existence will be, what he will become the next moment. By the same token, every human being has the freedom to change at any instant” - Viktor Frankl

  • Perspective is everything

  • When you can break apart something, or look at it from some new angle, it loses its power over you

  • Fear is debilitating, distracting, tiring, and often irrational

  • The task is not to ignore fear but to explain it away. Take what you’re afraid of and break it apart

  • We choose how we’ll look at things

  • “Business opportunities are like buses; there’s always another coming around” - Richard Branson

  • What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand

  • Perspective has two definitions: 1. Context: a sense of the larger picture of the world, not just what is immediately in front of us. 2. Framing: an individual’s unique way of looking at the world, a way that interprets its events

  • Be someone with something special to offer. Be the answer to their prayers, not the other way around. Be the person for the job

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

  • “In life our first job is this, to divide and distinguish things into two categories: externals I can not control, but the choice I make with regard to them I do control. Where will I find good and bad? In me, in my choices” - Epictetus

  • Is there a chance? Do I have a shot? Is there something I can do?

  • Look for a a chance, no matter how slight or tentative or provisional. If there is a chance, be ready to take it and make good use of it. Be ready to give every ounce of effort and energy to make it happen

  • 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

  • Focusing on the things you can change is where you can make a difference

  • What is up to us? Our emotions, judgements, creativity, attitude, perspective, desires, decisions, determination

  • What is not up to us? Everything else. The weather, economy, circumstances, other people’s emotions or judgements, trends, disasters, et cetera

  • If what’s up to us is the playing field, then what is not up to us are the rules and conditions of the game. Factors that winning athletes make the best of and don’t spent time arguing against

  • Focusing exclusively on what is in our power magnifies and enhances our power

  • Taking things day by day is the real secret. Focus on the moment, not the monsters that may or may not be ahead

  • Ignore the totality of your situation and learn to be content with what happens, as it happens

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

  • When you factor in vision and work ethic, much of life is malleable

  • Our perceptions determine what we are and are not capable of

  • Don’t be afraid. You can do it. Get your mind around it. You can do it

  • An entrepreneur is someone with faith in their ability to make something where there was nothing before

  • 'A good person dyes events with his own color... and turns whatever happens to his own benefit' - Seneca

  • It's one thing to not be overwhelmed by obstacles, or discouraged or upset by them. But after you have controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you're looking not at the obstacle but at the opportunity within it

  • 'There is good in everything, if only we look for it' - Laura Ingalls Wilder

  • It's our preconceptions that are the problem. They tell us that things should or need to be a certain way, so when they're not, we naturally assume that we are at a disadvantage or that we'd be wasting our time to pursue an alternate course. When really, it's all fair game, and every situation is an opportunity for us to act

  • That which doesn't kill me makes me stronger

  • The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity

  • 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

  • Once you see the world as it is, for what it is, you must act

  • A clearer head makes for steadier hands. And then those hands must be put to work. Good use

  • Everything must be done in the service of the whole. Step by step, action by action, we’ll dismantle the obstacles in front of us. With persistence and flexibility, we’ll act in the best interest of our goals

  • Action requires courage. Our movements and decisions define us: we must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action

  • You’ve got to act. And you’ve got to start now

  • In life, it doesn’t matter what happens to you or where you come from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage

  • Each obstacle we overcome makes us stronger for the next one

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

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

  • Start. Anywhere. Anyhow. Don’t care if the conditions are perfect or if you’re being slighted. Know that once you get started, you can get some momentum and can make it work

  • You’re going soft. You’re not aggressive enough. You’re not pressing ahead. You’ve got a million reasons why you can’t move at a faster pace. This all makes the obstacles in your life look very large

  • Always think with your stick forward

  • Be deliberate but you always need to be moving forward

  • Stay moving, always

  • Those who attack problems and life with the most initiative and energy usually win

  • Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started

  • “He says the best way out is always through and I agree to that, or in so far as I can see no way out but through” - Robert Frost

  • 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

  • Genius often is just persistence in disguise

  • For most of what we attempt in life, chips are not the issue. We’re usually skilled and knowledgeable and capable enough. But do we have the patience to refine our idea? The energy to beat on enough doors until we find investors or supporters? The persistence to slog through the politics and drama of working with a group?

  • Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure,'it that’s a far cry from giving up. Once you can envision yourself quitting altogether, you might as well right the bell. It’s done

  • Never in a hurry, never worried, never desperate, never stopping short

  • Persist in your efforts. Resist giving in to distractions, discouragement, or disorder

  • There’s no need to sweat this or feel rushed. No need to get upset or despair. You’re not going anywhere-you’re not going to be counted out. You’re in this for the long haul

  • When you play all the way to the whistle, there’s no reason to worry about the clock. You know you won’t stop until it is over—ever second available is yours to use. Temporary setbacks aren’t discouraging

  • It’s okay to be discouraged. It’s not okay to quit

  • It’s supposed to be hard. Your first attempts aren’t going to work. It’s going to take a lot out of you—but energy is an asset we can always find more of. It’s a renewable resource. Stop looking for an epiphany, and start looking for week points. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there

  • When people ask where we are, what we’re doing, how that situation is coming along, the answer should be clear: we’re working on it. We’re getting closer. When setbacks come, we respond by working twice as hard

  • “What’s defeat? Nothing but education; nothing but the first steps to something better” - Wendell Phillips

  • Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes. There nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities

  • When failure does come, ask: what went wrong here? What can be improved? What am I missing? This helps birth alternative ways of doing what needs to be done, ways that are often much better than what we started with. Failure puts you in corners you have to think your way out of. It is a source of breakthroughs

  • Great entrepreneurs are never wedded to a position, never afraid to lose a little of their investment, never bitter or embarrassed, never out of the game for long

  • It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback—giving you precise instructions on how to improve, its trying to wake you up from your cluelessness. It’s trying to teach you something. Listen

  • “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” - Nick Saban

  • You’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize

  • Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that

  • Exist in the present, take it one step at a time, don’t get distracted by anything else

  • The process is about finishing. Finishing the smallest task you have right in front of you and finishing it well

  • Don’t think about the end—think about surviving. Making it from meal to meal, break to break, checkpoint to checkpoint, one day at a time

  • When you really get it right, even the hardest things become manageable. Because the process is relaxing. Under its influence, we needn’t panic. Even mammoth tasks become just a series of component parts

  • For whatever obstacle you come across, we can take a breath, do the immediate, composite part in front of us—and follow its thread into the next action. Everything in order, everything connected

  • When it comes to our actions, disorder and distraction are death. The unordered mind loses track of what’s in front of it—what matters—and gets distracted by thoughts of the future. The process is order, it keeps our perceptions in check and our actions in sync

  • Replace fear with the process. Depend on it. Lean on it. Trust in it

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

  • Sometimes, on the road to where we are going or where we want to be, we have todo things that we’d rather not do

  • 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

  • Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well

  • We will be and do many things in our lives. Some are prestigious, some are onerous, none are beneath us

  • Our job is to respond with hard work, honesty, and helping others the best we can

  • Respect the craft and make something beautiful

  • How you do anything is how you can do everything

  • We can always act right

  • It’s better to focus on making due with what we’ve got. Focus on results instead of pretty methods

  • Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection

  • Take a step back, then go around the problem. Find some leverage. Approach from what is called the 'line of least expectation'

  • Part of the reason why a certain skill often seems so effortless for great masters is not just because they've mastered the process—they really are doing less than the rest of us who don't know any better. They choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics

  • 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 in your life you need to have patience—wait for temporary obstacles to fizzle out. Let two jousting egos sort themselves out instead of jumping immediately into the fray. Sometimes a problem needs less of you and not more

  • When we want things too badly we can 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 get so consumed with moving forward that we forget that there are other ways to get where we are heading

  • The best way to get what we want might be to reexamine those desires in the first place. Or it might be to aim for something else entirely and use the impediment as an opportunity to explore a new direction. In doing so, we might end up creating a new venture that replaces our insufficient income entirely. Or we rethink that disaster we feared and come up with a way to profit from it when and if it happens

  • 'When jarred, unavoidably, by circumstance revert at once to yourself and don't lose the rhythm more than you can help. You'll have a better grasp of harmony if you keep going back to it' - Marcus Aurelius

  • Be physically loose and mentally tight

  • '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

  • If you think it's simply enough to take advantage of the opportunities that arise in your life, you will fall short of greatness. Anyone sentient can do that. What you must do is learn how to press forward precisely when everyone around you sees disaster

  • 'You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are not immediate and must be dealt with. A crisis provides the opportunity for us to do things that you could not do before' - Rahm Emanuel

  • Ordinary people shy away 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. They turn personal tragedy or misfortune to their advantage

  • This crisis in front of you? You're wasting it feeling sorry for yourself, feeling tired or disappointed. You forget: Life speeds on the bold and favors the brave

  • Nothing can ever prevent us from trying

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

  • Problems are a chance for us to do our best

  • We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work

  • We have it within us to be the type of people who try to get things done, try with everything we've got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next

  • Will is our internal power, which can never be affected by the outside world

  • Leadership requires determination and energy. And certain situations, at times, call on leaders to marshal that determined energy simply to endure. To provide strength in terrible times

  • Will is the one thing we control completely, always

  • Always prepare ourselves for more difficult times, accept what we're unable to change, manage our expectations, persevere, learn to love our fate and what happens to us, protect our inner self, retreat into ourselves, submit to a greater cause, and remind oursevles of our own mortality

  • Far too many ambitious undertakings fail for preventable reasons. Far too many people don't have a backup plan because they refuse to consider that something might not go exactly as they wish

  • The only guarantee is that things will go wrong

  • 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

  • Be prepared for failure and ready for success

  • When the cause of our problem lies outside of us, we are better for accepting it and moving on

  • Things can always be worse

  • 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 and find joy in every single thing that happens

  • Love whatever happens to us and face it with unfailing cheerfulness

  • Turn what we must do into what we get to do

  • We're in our own fight with our own obstacles, and we can wear them down with our relentless smile

  • Learning not to kick and scream about matters we can't control is one thing. Indifference and acceptance are certainly better than disappointment or rage. Very few understand or practice that art. But it is only a first step. Better than all of that is love for all that happens to us, for every situatioon

  • 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 get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good?

  • We know the opportunities and benefits that lie within adversities. We know that in overcoming them, we emerge stronger, sharper, empowered

  • Life is not about one obstacle, but many. What's required of us is not some shortsighted focus on a single facet of a problem, but simply a determination that we will get to where we need to go, somehow, someway, and nothing will stop us

  • We will overcome every obstacle until we get there. Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance

  • No matter how many times we are thrown back, we alone retain the power to decide to go once more. Or to try another route. Or, at the very least, to accept this reality and decide upon a new aim

  • We control ourselves

  • The true threat to determination is not what happens to us, but us ourselves. Why would you be your own worst enemy? Hold on and hold steady

  • '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

  • 'You must never lower yourself to being a person you don't like. There is no better time than now to have a moral and civic backbone. To have a moral and civic true north. There is a tremendous opportunity for you, a young person, to be heroic' - Henry Rollins

  • When we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish. A shared purpose gives us strength

  • The desire to quit or compromise on principles suddenly feels rather selfish when we consider the people who would be affected by that decision

  • 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?

  • If not for me, then for my family or the others I'm leading or those who might later find themselves in a similar situation

  • Start thinking: unity over self. We're in this together

  • Whatever you're going through, whatever is holding you down or standing in your way, can be turned into a source of strength—by thinking of people other than yourself. You won't have time to think of your own suffering because there are other people suffering and you're too focused on them

  • Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger

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

  • Remember you are a mortal

  • We may not say it, but deep down we act and behave like we're invincible

  • We forget how light our grip on life really is. Otherwise, we wouldn't spend so much time obsessing over trivialities or trying to become famous, make more money than we could ever spend in our lifetime, or make plans far off in the future

  • What would I change about my life if the doctor told me I had cancer? We all do. We will all die eventually

  • Reminding ourselves each day that we will die helps us treat our time as a gift. Someone on a deadline doesn't indulge himself with attempts at the impossible, he doesn't waste time complaining about how he'd like things to be. They figure out what they need to do and do it, fitting in as much as possible before the clock expires

  • In the shadow of death, prioritization is easier. Why would you do the wrong thing? Why feel fear? Why let yourself and others down? Life will be over soon enough; death chides us that we may as well do life right

  • We can learn to adjust and come to terms with death—this final and most humbling fact of life—and find relief in the understanding that there is nothing else nearly as hard left

  • Each time, you'll learn something. Each time, you'll develop strength, wisdom, and perspective. Each time, a little more of the competition falls aways. Until all that is left is you: the best version of you

  • The more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You're always fighting uphill. Get used to it and train accordingly

  • Knowing that life is a marathon and not a sprint is important. Conserve your energy. Understand that each battle is only one of many and that you can use it to make the next one easier

  • Passing one obstacle simply says you're worthy of more. The world seems to keep throwing them at you once it knows you can take it

  • Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Never attempting to do the impossible

  • Simply flipping the obstacles that life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round

  • Something stands in someone's way. They stare it down, they aren't intimidated. Leaning into their problem or weakness or issue, they give everything they have, mentally and physically. Even though they did not always overcome it in the way they intended or expected, each individual emerged better, stronger

  • What stood in the way became the way. What impeded action in some way advanced it

  • Nothing stands in their way. Rather, everything guides them on the way

  • 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

  • Fate doesn't have to be fatalistic. It can be destiny and freedom just as easily

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

  • Perceive things as they are, leave no option unexplored, then stand strong and transform whatever can't be changed

  • It will not be easy, but you are prepared to give it everything you have regardless, ready to endure, persevere, and inspire others

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

  • What blocked the path now is a path. What once impeded action advances action. The obstacle is the way

  • 'To be a philosopher is not merely to have subtle thoughts, nor even to found a school... it is to solve some of the problems of life, not only theoretically, but practically' - Henry David Thoreau

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