The Obstacle is the Way –– Ryan Holiday

#book  #stoicism  #philosophy  

I wasn't going to read this book originally because I was afraid it might be too preachy, or tell me things I've previously read up about stoicism and the stoic philosophers. I decided to listen to the audiobook whenever I had chores around the house, in hopes that I would learn some practical philosophy. I was pleasantly surprised to find that it had some really valuable information and thought and actually enjoyed most of the book, thought it does get a little repetitive. I also realized that almost everything in the book is a well-articulated version of advice I've given a friend, or family member.

Summary:

  • The book introduces concepts of [[stoicism]] and how to apply them in real life. The principles in the book can be applied to any and all obstacles we face in our daily lives. The practicality of stoicism is what draws most people towards it.

  • The essence of [[philosophy]] is action –– in making good on the ability to turn the obstacle upside down with our minds. Understanding our problems for what's within them and their greater context. To see things philosophically and act accordingly. Now, you are a philosopher and a person of action, and that is not a contradiction.

Notes

  • Preface
    • What Marcus Aurelius wrote is one of history's most effective formulas for overcoming negative situations we may encounter.
      • "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."
    • Whatever we face, we have a choice: will we be blocked by obstacles, or will we advance through and over them?
  • Introduction
    • All great victories, in whatever field they may be, involved resolving difficult problems with creativity, focus and daring. When you have a goal, obstacles are actually teaching you how to get where you want to go.
    • Most of our obstacles are internal, and not extrernal.
    • Many of our problems come from having too much: technology, food, traditions that tell us the way we're supposed to live our lives. We're entitles and scared of conflict.
    • Overcoming obstacles is a discipline of three steps. It begins with how we look at a specific problem, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; and finally the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.
      • Three interdependent, interconnected and fluidly contingent disciplines: Perception, Action and the Will.

Perception

  • Perception is how we see and understand what occurs around us - and what we decide those events will mean. If we are emotional, subjective, or shortsighted, we only add to our troubles. Perceptions are a source of strength or weakness. [[Maya and the concept of perception]]
  • The Discipline of Perception
    • Desperation, despair, fear, powerlessness - these reactions are functions of our perceptions. Nothing makes us feel this way, we choose to give into such feelings.
    • Humans are still primed to detect threats and dangers that no longer exist. We have a choice about how we respond to a situation - we can be blindly led by primal feelings or we can understand them and learn to filter them.
    • This is how you see the opportunity within the obstacle. It does not happen on its own. It is a process—one that results from self-discipline and logic.
  • Recognize Your Power
    • Situations, by themselves, cannot be good or bad - we give valence to them. This is a judgement we as humans bring to them with our perceptions.
    • Through our perception of events, we are complicit in the creation, as well as the destruction, of every one of our obstacles.
    • 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. [[Maya and the concept of perception]]
  • Steady Your Nerves
    • When we aim high, pressure and stress are bound to come along for the ride. Things will happen that catch us off guard, threaten or scare us. Surprises are almost always guaranteed - the risk of being overwhelmed is always there.
    • Regardless of how much actual danger we’re in, stress puts us as the potential whim of our baser — fearful — instinctual reactions. There is always a countermove, an escape or a way through, so there is no reason to get worked up.
    • In these situations, talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill.
  • Control Your Emotions
    • Uncertainty and fear are relieved by authority. Training is authority. With enough exposure, one can adapt out ordinary and innate fears that rise mainly from unfamiliarity.
    • Unfamiliarity is simple to fix, though not easy, which makes it possible to increase our tolerance and capacity for stress and uncertaintly.
    • If an emotion can't change the condition or the situation you're dealing with, it is likely an unhelpful emotion, or even a destructive one.
    • No one said anything about not feeling it. Real strength lies in the control or as [[Nassim Taleb]] puts it, the domestication of one's emotions –– not in pretending they don't exist.
  • Practice Objectivity
    • The truth is, things happen, and that's about it. We add valence to it, saying the situation is "good" or "bad", when in reality, it just is.
    • Take your situation and pretend it is not happening to you. Pretend it's not important and 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 its options? You could write it off, greet it calmly.
  • Alter Your Perspective
    • When you can break apart something, or look at it from a new angle, it loses its power over you.
    • We retain the ability to inject perspective into a situation. We can't change the obstacles themselves, but we can change how the obstacles appear by perceiving them differently.
    • Small tweaks can change what seems like an impossible task. Where we feel weak, we realize we are strong. With perspective, we discover leverage we didn't know we had.
    • How we interpret the events in our lives, our perspective, is the framework for our forthcoming response - whether there will even be one or whether we'll just lie there and take it.
    • Where the head goes, the body follows. Perception precedes action, and right action follows the right perspective.
    • 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 way of looking at the world, a way that interprets its events.
  • Is It Up To You?
    • The crucial distinction to make is the difference between things that are in our power and things that aren't. That's the difference between people who can accomplish great things, and the people who find it impossible to stay sober - to avoid not just drugs or alcohol, but all addictions.
    • The most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.
  • Live in the Present Moment
    • (For me, this is the hardest tip to implement, apart from acceptance.)
    • Most people start from disadvantage, and often with no idea that they are doing so. It's not unfair, it's universal. Those who survive it, survive because they took things day by day.
    • One thing is certain - it's not simply a matter of saying "Oh I'll live in the present." You have to work at it, catch your mind when it wanders and not let it get away from you.
    • Remember that this moment is not your life, it's just a moment in your life. Focus on what is in front of you, right now. Ignore what it "represents" or "means or "why it happened to you".
    • The implications of our obstacles are theoretical — they exist in the past and the future. We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.
  • 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

    • Our perceptions determine, to an incredible extent, what we are and aren't capable of. In many ways, they determine reality itself. [[Maya and the concept of perception]]
    • This is radically different from how we’ve been taught to act. Be realistic, we’re told. Listen to feedback. Play well with others. Compromise. Well, what if the “other" party is wrong? What if conventional wisdom is too conservative? It’s this all-too-common impulse to complain, defer, and then give up that holds us back.
    • When given an unfair task, some rightly see it as a chance to test what they’re made of—to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative.
  • Prepare to Act
    • Problems are rarely as bad as we think, or rather, they are precisely as bad as we think.
    • 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 when it happens.
    • The demand on you is this: once you see the world as it is, for what it is, you must act. The proper perception - objective, rational, ambitious, clean - isolates the obstacle and exposes it for what it is.
    • A clearer head makes for steadier hands, and then those hands must be put to good use.

Action

  • Action is commonplace, right action is not. As a discipline, it's not any kind of action that will do, but directed action. 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.
  • Action requires courage, not brashness –– creative application and not brute force. 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. Nothing else, not thinking or evasion or aid from others. Action is the solution and the cure to our predicaments.
  • The Discipline of Action
    • The problem is that it feels better to ignore or pretend. But you know deep down it isn't going to make it any better. You've got to act, and you've got to start now.
  • Get Moving
    • That's what people who become great at things do - they start. Anywhere, anyhow. They don't care if the conditions are perfect or if they are being slighted. Because they know that once they get started, they can just gain some momentum, they can make it work.
    • We tend to downplay the importance of aggression, taking risks, of barreling forward nowadays. It's probably because it's been negatively associated with certain notions of violence or masculinity.
    • The final part: stay moving, always.
    • When you're frustrated in pursuit of your own goals, don't sit there and complain that you don't have what you want or that this obstacle won't budge. If you haven't even tried yet, then of-course you will be in the exact same place. You haven't actually pursued anything.
    • 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, by getting up and getting started.
  • Practice Persistence
    • Genius is often really just persistence in disguise.
    • [[Epictetus]]'s favoured phrase: "persist and resist". Persist in your efforts, resist giving into distraction, discouragement or disorder.
    • It's okay to be discouraged, it's not okay to quit. In other words, it's supposed to be hard, and first attempts aren't going to work. It's going to take a lot out of you, but energy isn't a finite asset.
    • When people ask where we are, what we're doing, how that "situation" is coming along, the answer should be straightforward and clear: we're working on it, getting closer. When setbacks come, we respond by working twice as hard.
  • Iterate
    • When failure does come, ask: What went wrong here? What can be improved? What am I missing?
    • The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not learn from it.
    • With each and every failure, you have feedback––precise instructions on how to improve and a wake up call from your cluelessness. It's trying to teach you something. Listen.
    • Lessons come hard only if you're deaf to them. Don't be.
    • Action and failure are two sides of the same coin. Anticipated, temporary failure certainly hurts less than catastrophic, permanent failure.
    • Failure shows us the way –– by showing us what isn't the way.
  • Follow the Process
    • How often do we compromise or settle because we feel that the real solution is too ambitious or outside our grasp? How many people get paralyzed by all their ideas and inspirations? They chase them all and go nowhere, distracting themselves and never making headway.
    • All these issues are solvable. Each would collapse beneath the process. We just wrongly assume that it has to happen all at once, and give up at just the thought of it.
    • Subordinate strength to the process, replace fear with the process.
    • We spend a lot of time thinking about how things are "supposed" to be, or what the rules say we should do. When really, it'd be better to focus on making due with what we've got.
  • Do Your Job, Do It Right
    • Sometimes, on the road to where we are going or where we want to be, we have to do things that we'd rather not do. But you, you're so busy thinking about the future, you don't take pride in the tasks you're given right now.
      • A simple change in mindset I've learnt helps: you don't have to do it, you get to do it.
    • Everything we do matters, even after you already achieved the success you sought. Everything is a chance to do and be your best. Only self-absorbed people think they are too good for whatever their current station requires.
    • Our job is to respond with hard work, honesty and helping others as best we can.
    • Whether anyone notices, whether we're paid for it, whether the project turns out successfully –– it doesn't matter. We can and always should act with those three traits, no matter the obstacle.
  • What's Right is What Works
    • Pragmatism is not so much realism as flexibility. But we all spend so much time looking for the perfect solution that we pass up what's right in front of us. [[Paralyzing perfectionism]]
    • The goal is to start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible.
    • Think progress, not perfection.
  • In Praise of the Flank Attack
    • Take a step back, then go around the problem. Find some leverage. Approach from what is called the "line of least expectation."
    • 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. Or you create an alternative with so much support from other people that the opposition voluntarily abandons its views and joins your camp.
  • Use Obstacles Against Themselves
    • Opposites work. Non-action can be action. It uses the power of others and allows us to absorb their power as our own. Letting them, or the obstacle, do the work for us.
    • Sometimes, you need to have patience and wait for temporary obstacles to fizzle out.
  • Channel Your Energy
    • To be physically and mentally loose takes no talent. That's just recklessness. To be physically and mentally tight is anxiety. But physical looseness combined with mental restrained? That is powerful.
  • Sieze the Offensive
    • If you think it's simply enough to take advantage of the opportunities that arrive 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.
    • 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 - really anything, and everything - to their advantage.
  • Prepare for None of It to Work
    • Run it through your head like this: nothing can ever prevent us from trying. Ever.
    • All creativity and dedication aside, after we've tried, some obstacles may turn out to be impossible to overcome.
    • We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work.
    • Some things are bigger than us. This is not necessarily a bad thing. Because we can turn that obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill — even if its just learning to accept that bad things happen, or practicing humility.

Will

  • Will is our internal power, which can never be affected by the outside world. It is out final trump card.
  • We can turn any negative experience into a learning experience. That is will power. But it needs to be cultivated. We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times.
  • People think that will is how bad we want something, but in actuality, it's more about surrender than strength.
  • True will is quiet humility, resilience and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.
  • The Discipline of the Will
    • If perception and action were the disciplines of the mind and the body, will is the discipline of the heard and soul. The will is one thing we control completely, always.
    • We can think, act and finally adjust to a world that is inherently unpredictable. The will is what prepares us for this, protects us against it, and allows us to thrive and be happy in spite of it. It is also the most difficult of all the disciplines.
    • Will is fortitude and wisdom — not just about specific obstacles but about life itself and where the obstacles we are facing fit within it.
  • Build Your Inner Citadel
    • To be great at something takes practice: obstacles and adversity are no different.
    • No one knows when or how, but the appearance of obstacles is certain, and life will demand from us. The goal is to be prepared for what it entails.
  • Anticipation (Thinking Negatively)
    • A pre-mortem is different. In it, we look to envision what could go wrong, what will go wrong, before we even start. Far too many ambitious undertakings fail for preventable reasons. For too many people don't have a backup plan because they refuse to consider that something might not go exactly as they wish.
    • With anticipation, we have time to raise defenses, or even avoid them entirely. We're ready to be driven off course because we've plotted a way back. We can resist going to pieces if things didn't go as planned. With anticipation, we can endure.
      • Where is the line between right and wrong anticipation? In one, we prepare ourselves for the worst and the other, we get sucked into thinking of the worst before letting it even happen. There's a difference between being ready, and spiraling into negative thinking.
  • The Art of Acquiescence
    • After you've distinguished between the things that are up to you and the things that aren't, and the break comes down to something you don't control - you've got only one option: acceptance.
    • You don't have to like something to master it, or use it to some advantage.
  • Love Everything That Happens: Amor Fati

    • "My formula for greatness in a human being is amor fati: that one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it - but love it." — [[Nietzsche]]

    • 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.
    • It is the act of turning what we must do into what we get to do.
    • The goal is not "I'm okay with this", nor "I think I feel good about this" but "I feel great about it". Because if it happened, then it was meant to happen and I am glad that it happened when it did, I am meant to make the best of it.
    • And then, proceed to do exactly that.
  • Perserverance
    • If persistence is attempting to solve some difficult problem with determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger - it's the long game. It's about what happens not just in round one, but every round to follow –– and then the fight after that, until the end.
    • Life isn't about just 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 and someway.
    • Persistence is an action, perseverance is a matter of will. One is energy, the other is endurance.
  • Something Bigger Than Yourself
    • 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.
    • Pride can be broken, toughness has its limits. But a desire to help - no harshness, no deprivation, no toil should interfere with our empathy towards others. Compassion is always an option. That's a power of the will that can never be taken away, only relinquished.
    • 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.
  • Meditate on Your Mortality
    • Every culture has its own way of teaching the same lesson: Memento Mori.
    • Reminding ourselves each day that we will die helps us treat our time as a gift.
  • Prepare to Start Again
    • Behind mountains are more mountains. (Haitian proverb)
    • One does not overcome an obstacle to enter the land of no obstacles. Instead, 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. Each battle is only one of many.
    • Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Never attempting to do the impossible—but everything up to that line.
    • 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.

Final Thoughts

  • What stood in the way became the way. What impeded the action in some way advanced it.
  • First, see clearly. Next, act correctly and finally, endure and accept the world as it is.
  • The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who "transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking." It’s a [[self-perpetuating loop]] that becomes easier over time.
  • We must practice these maxims, rolling them over and over in our minds and acting on them until they become muscle memory.
  • What the greats did was simple - simple, but not easy.

  • 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

  • See things for what they are. Do what we can. Endure and bear what we must What blocked the path now is the path. What once impeded action advances action. The obstacle is the Way.
  • Notes with help from Aidan Hornsby and Graham Mann

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