The Obstacle Is The Way

Introduction

Ryan Holiday's The Obstacle Is the Way draws its inspiration from Stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience.

  • Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger and tougher.
  • As the Roman Emperor Marcus Aurelius wrote nearly 2000 years ago:
    "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".
  • Marcus Aurelius's words reveal the secret to an art known as turning obstacles upside down. This means acting with a "reverse clause" so that there is always a way out or an alternative route to your goal. By always expecting setbacks or problems and viewing them as temporary, we ensure that what impedes us can also empower us.
  • Despite the stress and burden, he truly saw each of these obstacles as an opportunity to practice virtue: patience, courage, humility, resourcefulness, reason, justice and creativity.
The Obstacle Is The Way



The Obstacle Is The Way

When facing frustrating, unfortunate, problematic or unexpected challenges (the obstacles), most people are paralyzed and simply wish the situation were not true.

  • Every obstacle (whether mental, physical, emotional or perceived) is unique, yet the responses it elicits are almost universally the same: fear, frustration, anxiety, confusion, resentment, depression, anger and despair.
  • Driven by this dissatisfaction, we do nothing but blame our boss, the economy, politicians or other people, and writing ourselves off as failures. When, in reality, only one thing is at fault: our attitude and approach.
  • Only great individuals find a way to transform a weakness into a strength or a negative situation into a positive one, using it as an opportunity to move forward or steer in a better direction.

Overcoming obstacles is a discipline of three critical steps: Perception, Action and Will.

  • It begins with how we look at our specific problems - our attitude or approach; continues with the energy and creativity we use to actively break them down and transform them into opportunities; and concludes with the cultivation and maintenance of the inner will that allows us to handle defeat and difficulty.
  • While the process is simple, it's never easy.

Obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.



Perception

Perception is how we see and understand what occurs around us, and the meaning we assign to those events.

  • What matters most is not what these obstacles are, but how we perceive them, how we react to them, and whether we maintain our composure.
  • If we are emotional, subjective, and short-sighted, we only compound our troubles.
To prevent becoming overwhelmed by the world, we must learn to limit our passions and their control over our lives, just as the ancients practiced.
  • It takes skill and discipline to bat away the pests of poor perception, to separate reliable signals from deceptive ones, and to filter out prejudice, expectation, and fear.
But it is worth the effort, because what is left is truth.
  • While others are excited or afraid, we will remain calm and imperturbable.
  • We will see things simply and straightforwardly, as they truly are - neither good nor bad.
  • This calm clarity will give us an incredible advantage in the fight against obstacles: it allows us to train ourselves to spot opportunity within the chaos when everyone else is paralyzed by fear or consumed by paranoia, or to see reality with ruthless objectivity while others are blinded by success.

Hence, when faced with a seemingly insurmountable obstacle, we must try

  • To steady our nerves
    • When we aim high, pressure and stress inevitably follow. Events will catch us off guard, threaten or frighten us. Unpleasant surprises are virtually guaranteed. The risk of being overwhelmed is constant.
    • In these situations, talent is not the most sought-after characteristic. Grace, poise and serenity are because they must be present before any other skill can be deployed.
    • Ultimately, nerve is a matter of defiance and control. 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.
  • To control emotions and keep an even keel
    • Panicking out of an emotional freak-out often causes people to make mistakes and to disregard procedures, ignore rules and deviate from the plan.
    • They become unresponsive and stop thinking clearly, reacting purely by survival instinct, rather than according to what they need to do (e.g. they choose worry over introspection, alertness or wisdom).
    • Hence, there is a need to master the art of not panicking - freedom from disturbance and perturbation - so you can focus your energy exclusively on solving problems, rather than reacting to them.
    • With enough exposure from training, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity.
    • Understand that anger or despair is not constructive; they do not provide you with more options. However, real strength lies in controlling your emotions with logic, not in pretending they do not exist. Feel them, and cry if you want to.
    • It might help to say this over and over whenever you feel the anxiety begin to come on: I am not going to die from this. I am not going to die from this. I am not going to die from this.
    • Alternatively, try Marcus Aurelius’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility or straightforwardness.
    • We should be constantly asking ourselves this question: Do I need to freak out about this?
  • To be objective
    • Situations are not inherently good or bad; that is a quality we assign to them through our perceptions.
    • Through our perception of events, we are complicit in the creation and the destruction of every one of our obstacles.
    • There is the event itself and the story we tell ourselves about what it means.
    • The Stoic knew that it was not events or things that upset us, but our opinion about those things that caused the problem.
    • We can use observing eyes to see things as they really are and, in turn, question our impulsive impressions.
    • Objectivity means removing “you” - the subjective part - from the equation. To achieve it, ask what advice you would give someone else in your situation, pretending it is not happening to you or is not important, and then act upon that advice.
  • To place things in perspective
    • Perspective has two essential definitions:
      • Context: A sense of the larger picture of the world, not just what is immediately in front of us.
      • Framing: An individual’s unique way of looking at the world - a way that interprets its events.
    • How we interpret the events in our lives - our perspective - is the framework for our response. It determines whether we will even respond at all, or whether we will simply lie there and take it.
    • We cannot change the obstacle themselves - that part of the equation is set - but the power of perspective can change how the obstacles appear. How we approach, view and contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.
    • For whatever reason, we tend to look at things in isolation. We kick ourselves for blowing a deal or having to miss a meeting. Individually, that does suck - we just missed 100% of that specific opportunity. However, one meeting is nothing in a lifetime of meetings; one deal is just one deal. In fact, we may have actually dodged a bullet. The next opportunity might be better.
    • What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand. Think of it as selective editing - not to deceive others, but to properly orient ourselves.
  • To focus on what can be controlled
    • If a chance arises, no matter how slight or tentative, we must be ready to take it and make good use of it with effort.
    • Focusing on what you can change is where you can truly make a difference.
    • What is up to us? Our emotions, judgments, creativity, attitude, perspective, desires, decisions, and determination. We decide whether we will break or whether we will resist. No one can force us to give up or to believe something that is untrue. Our perceptions are the things we are in complete control of. We are never completely powerless because others can never control our thoughts, our beliefs or our reactions.
    • Everything else is not up to us: the weather, the economy, circumstances, other people's emotions or judgments, trends, disasters, etc.
    • In its own way, the most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.
  • To revert to the present moment
    • Our problem is that we are always trying to figure out what things mean - why things are the way they are - as though the "why" matters. In the end, we get ourselves so worked up that we have no energy left to actually deal with our problems.
    • The real secret of business success is to focus on the moment, not on the monsters that may or may not be up ahead, or whether the market is good or bad.
    • The implications of our obstacle are theoretical - they exist in the past and the future. We live in the moment. The more we embrace that, the easier the obstacle will be to face and move past.
    • Focus on what is in front of you, right now. Ignore what it "represents", what it "means" or "why it happened to you". There is plenty else going on right here to care about any of that.
  • To ignore what disturbs or limits others
    • Reality was falsely hemmed in by rules and compromises that people had been taught as children. Assumptions are not law; they need to be questioned. Limits can be pushed, and the "impossible" achieved.
    • Aiming low means accepting mediocre accomplishment, but a high aim could, if things go right, create something extraordinary. This is because although our doubts (and self-doubts) feel real, they have very little bearing on what is and is not possible. Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself.
    • We should not listen too closely to what other people say (or to what the voice in our head says, either).
    • Could the conventional wisdom of "be realistic", "listen to feedback," "play well with others," and "compromise" be too conservative for an entrepreneur, especially one building a truly novel or disruptive product where nothing existed before?
  • To choose to see the good in a situation
    • It is our preconceptions that are so often at the root of the problem. They tell us that things should or need to be a certain way, so when they are not, we naturally assume that we are at a disadvantage or that we would be wasting our time to pursue an alternate course. When, in reality, it is all fair game, and every situation is an opportunity for us to act.
    • There is good in everything, if only we look for it.
      • A long-time rival at work (or that rival company), the one who causes endless headaches, also keeps you alert and motivated to become better.
      • When people are rude or disrespectful, they underestimate us.
      • When people are critical or question our abilities, lower expectations are easier to exceed.
      • The struggle against an obstacle propels the fighter to a new level of functioning. "What doesn't kill me makes me stronger."

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

  • The worst thing to happen is never the event itself, but the event plus losing your head, which results in two problems instead of one.
  • Once you see the world as it is, for what it is, you must act.
  • Boldness is acting anyway, even though you fully understand the negative aspects and the reality of your obstacle.

NOTE: The concept of perception is in concord with the idea of truth presented in The Fifth Agreement. According to that work, the human mind creates the stories of our dream - whether that dream becomes heaven or hell - which exists only because of our belief. The ultimate truth remains as it is, neither inherently good nor bad.



Action

Action is commonplace, right action is not.

  • As a discipline, it is 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 will dismantle the obstacles in front of us.
  • With persistence and flexibility, we will act in the best interest of our goals.
  • 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.

In life, it does not matter what happens or where you came from.

  • What matters is what you do with what happens and what you have been given. The only way you will do something spectacular is by using it all to your advantage.
  • Yet, many of us fail by opting away from action - we think, complain, distract, argue, act powerless, sleep in, and wait as though we expect someone else to handle it or as if there is a chance of obstacles un-obstacling themselves.
  • Even if it feels better to ignore or pretend, deep down you know you have to act to truly make it better. Only then can people truly turn "mess" into success.
  • We do not have the luxury of running away or hiding. We have an obstacle we have to lean into and transform, so that we can accomplish our goals. There is only one way: meet our problems with the right action.

Therefore, we can always (and only) greet our obstacles with

  • Energy
    • "I will do it tomorrow" is one of the most insidious, seductive lies in the world.
    • To become great at things, people start anywhere and anyhow. They do not care if the conditions are perfect or if they are being slighted, because they know that once they get started, if they can just get some momentum, they can make it work.
    • When we fear that taking action is too risky, that we do not have the experience or resources, or that it isn't how we pictured it, we end up doing nothing. Hence, get started, get moving.
      • Do not sit there and complain that you do not have what you want when you have not tried anything yet - instead you have been bypassing opportunities or waiting for the obstacle to resolve itself.
    • Then, ask an honest question: could you be doing more? You probably could; at a minimum, you could be trying harder.
  • Persistence
    • If we are to overcome our obstacles, this is the message to broadcast internally and externally: We will not be stopped by failure, nor will we be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.
    • Thomas Edison tested six thousand different filaments for incandescent lights and eventually found one - proving that genius often really is just persistence in disguise. He knows clearly that option after option, eventually - inevitably - one will work.
    • Remember, once you start attacking an obstacle, quitting is not an option. Abandoning one path for another that might be more promising is a far cry from giving up. Persist in your efforts; resist distraction, discouragement, and disorder.
    • There is no need to sweat this or feel rushed. No need to get upset or despair. You are not going anywhere - you are not going to be counted out. You are in this for the long haul.
    • When people ask where we are, what we are doing, or how that "situation" is coming along, the answer should be clear: We are working on it. We are getting closer. When setbacks come, we respond by working twice as hard.
    • External factors influence the path, but not the direction: forward.
  • Iteration and resilience
    • In Silicon Valley, startups do not launch with polished, finished businesses. Instead, they release their "minimum viable product" (MVP) - the most basic version of their core idea with only one or two essential features.
      • The point is to immediately see how customers respond, enabling the company to fail cheaply and quickly if that response is poor, instead of investing time and effort in a product customers do not want.
    • Failure can truly be an asset if what you are trying to do is improve, learn, or do something new. It is the precursor to nearly all successes. There is nothing shameful about being wrong or about changing course.
      • In fact, the MVP model embraces failure and feedback; it gets stronger by failing, dropping the features that do not work or that customers do not find interesting, and then focusing the developers' limited resources on improving the features that do.
    • In a world where we increasingly work for ourselves and are responsible for ourselves, it makes sense to view ourselves like a startup. We should change our relationship with failure to one of iterating, failing, and improving.
      • Our capacity to try is inextricably linked with our ability and tolerance for failure.
      • On the path to successful action, we will fail, possibly many times.
      • Failure puts you in corners you have to think your way out of (i.e., breakthroughs).
    • Stories of great success are often preceded by epic failure - the people involved were not afraid to lose a little of their investment, never bitter or ashamed to fail, but got back to the game with improvements.
      • They expected failures and turn them into a learning curve for the greater victory down the road.
      • The wrong way of facing failure is to choose to quit or continue trying the same thing over and over without recognizing the problems that failure exposes.
    • Failure shows us the way - by showing us what is not the way.
  • A coherent and deliberate process
    • Often, we shy away from writing a book or making a film, even though it is our dream, because it seems like so much work - we cannot imagine how we get from here to there.
      • We compromise or settle, feeling the real solution is too ambitious or outside our grasp.
      • The truth is we have simply and wrongly assumed that it has to happen all at once.
    • Instead of thinking about a single, very difficult task, break it down into pieces.
      • Simply do what you need to do right now, and do it well, 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.
      • Take it one step at a time and finish each one well, undistracted by anything else (e.g., thoughts of the future or discouragements).
    • Sometimes, on the road to where we are going or where we want to be, we have to do things that we would rather not do.
      • However, it matters if you do it with pride and try to do it better than anyone else (dedication).
      • Only self-absorbed people think they are too good for whatever their current station requires.
      • Every project matters, and the only degrading part is giving less than one is capable of giving.
    • In every situation, life is asking us a question, and our actions are the answer. When we approach our tasks seriously, conscientiously, and perform them well, we are essentially declaring: "This matters. I matter. Life is meaningful".
  • Pragmatism
    • Don't worry about the "right" way (e.g., rigid adherence to rules); worry about the right way (any way that works). This is how we get things done.
    • We often spend too much time thinking about how things are supposed to be, or what the rules say we should do, trying to get it all perfect.
      • It is better to focus on making do with what we have got.
      • All that matters is that we accomplish the results instead of continually searching for the perfect solution.
    • As Deng Xiaoping once said, "I do not care if the cat is black or white, so long as it catches mice".
    • Think progress, not perfection. Be willing to compromise at some point so that you get it done and make it work.
  • Strategic vision
    • The first instinct when faced with a challenge is to outspend the competition, argue with people to change long-held opinions, or try to barge through the front door. This is going to be harder.
    • Rather, when you are at your wit's end and straining with all your might, take a step back, then go around the problem to find some leverage. Approach the challenge from what is called the "line of least expectation" to achieve victory.
    • We should exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics, which are often driven by ego and pride.
  • Craftiness and savvy
    • There are some adversities it might be impossible for you to defeat, no matter how hard you try. Instead, you must find ways to use the adversity (the obstacle), and its energy, to help yourself.
    • To illustrate, in the business, here are some things you may have gained for free: the tough market has eliminated a lot of competition; competitor companies underestimate you and ignore you entirely.
    • We get so consumed with moving forward that we forget there are other ways to get where we are heading. It does not naturally occur to us that standing still - or in some cases, even going backward - might be the best way to advance.
  • An eye for opportunity and pivotal moments
    • At those seemingly bad moments, when people least expect it, we can act swiftly and unexpectedly to pull off a big victory.
    • Throughout history, crisis provides the opportunity to do things that could not be done before (e.g., the much-needed reforms that otherwise would have little chance of passing).
    • Ordinary people shy away from negative situations (e.g., failure). Great people turn personal tragedy or misfortune - really anything, everything - to their advantage.

Perceptions can be managed. Actions can be directed.

  • Even though nothing can ever prevent us from trying, some obstacles may turn out to be impossible to overcome.
  • In every situation, the obstacle that blocks our path actually presents an opportunity to practice some other virtue or skill.
    • If someone you love hurts you, there is a chance to practice forgiveness.
    • If your business fails, now you can practice acceptance.
    • If there is nothing else you can do for yourself, at least you can try to help others.
  • Everything is a chance to do our best and to be our best, not to achieve the impossible.
  • We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work.



Will

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

  • We orient our mind and we take action, but all this is dependent on will.
  • Placed in some situation that seems unchangeable and undeniably negative, we determine what we will be able to do and how we will do it, whether we can turn it into a breakthrough, a learning experience, a humbling experience, or a chance to provide comfort to others.
  • That is willpower. But that 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.

Too often, people think that will is how badly we want something.

  • There is also surrender in our strength. We should embrace “God willing” over “the will to win” or “willing it into existence”, for even those attributes can be broken.
  • 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.

In every situation, we can

  • Always prepare ourselves for more difficult times
    • The Inner Citadel is what the Stoics called the fortress inside us, which no external adversity can break down.
    • An important caveat is that we are not born with this fortress; it must be built and actively reinforced.
    • In good times, we strengthen our minds and bodies so that we can depend on this resilience during difficult times. We protect our inner fortress so that it may protect us.
    • We build our mental fortitude through physical exercise and our physical resilience through mental discipline.
    • The path of least resistance is a terrible teacher. Strength of will must be developed so that we can succeed in achieving our goals, despite any obstacles that may arise.
  • Always manage our expectations
    • A premortem is an exercise where we envision what could go wrong with a plan before we even start. Far too many ambitious undertakings fail for preventable reasons, often because people refuse to consider that things might not go exactly as wished and therefore fail to create a backup plan.
    • The initial plan and the final outcome rarely resemble each other. What you feel you deserve is also rarely what you will get. Yet, we often deny this reality and are repeatedly shocked by how events unfold.
    • Consider how differently major events might have unfolded if more people had rigorously planned for worst-case scenarios: the dot-com bust, the Enron collapse, the 9/11 attacks, the 2008 financial crisis, or the withdrawal from Afghanistan. Their negative impacts might have been avoided or at least significantly mitigated.
    • Every project must make concessions to reality. We all depend on other people, and not everyone is perfectly reliable. Others will make mistakes that can disrupt even the best-laid plans. Therefore, we must always be prepared for disruption and work that possibility into our plans, fitting ourselves for either defeat or victory. After all, a pleasant surprise is far better than an unpleasant one.
    • 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.
      • It always takes longer than you expect…even when you take this into account.
    • Anticipation does not magically make things easier, of course. Through this foresight, we understand the range of potential outcomes and know that they are not all good. We can then accommodate any of them by preparing our defenses or even avoiding certain risks entirely. By acknowledging that things could go wrong, we can confidently get back to the task at hand.
    • In short, we are prepared for failure and ready for success.
  • Always accept what we are unable to change
    • It is a common paradox that many of the things we despair over and resist ultimately turn out to be good for us, forcing us to change and adapt. Still, that does not change the initial heartbreak or the difficulty of the moment.
      • To respond, move on, and eventually see the "good" in a situation, we must begin with acceptance. This acceptance takes time and is no small feat.
      • It does not always feel that way, but life's constraints can be beneficial, especially if we accept them and let them direct us. They push us to explore new paths and develop skills we might never have pursued, or they teach us lessons we would otherwise be reluctant to learn.
    • Life deals us unavoidable, inalterable situations.
      • It might tell us to stop, that an intersection is blocked, or that a road has been rerouted through an inconvenient detour. We cannot argue or yell these problems away; we must simply accept them.
      • This does not mean we allow challenges to prevent us from reaching our ultimate destination. But it does change how we get there and the duration of the trip.
      • Think of it like a doctor's orders: you don't have to enjoy the treatment, but you accept it because denying it only delays the cure.
    • The Stoics called this attitude the Art of Acquiescence: the practice of ceasing to kick and fight against reality and, instead, coming to terms with it.
      • To be clear, this is not the same as giving up.
      • Acquiescence is about your internal state of acceptance; it is separate from the external actions you still need to take.
    • We rarely consider how much worse things could have been, yet things can always be worse. For example, instead of losing a job, you could have lost a limb.
      • We often complain about what was taken from us instead of appreciating what we still have, like the ability to travel by airplane or connect with loved ones through video chat.
    • The ancients used the word "fate" far more frequently than we do because they were more acquainted with how capricious and random the world could be.
      • Events were often considered the "will of the gods".
      • The Fates were seen as powerful forces that shaped our lives and destinies, often without our consent.
      • This is a reminder to be humble and flexible enough to acknowledge that many events are out of our control - that there is always something that can alter our life's plan. And that something is not us. As the saying goes, "Man proposes, but God disposes".
  • Always learn to love our fate and what happens to us
    • After we discard our expectations and accept what happens (particularly the bad things), the next step is to love whatever happens and face it with unfailing cheerfulness.
    • We should focus our energy, emotions, and efforts where they will have a real impact. This means learning to find joy in every single thing that happens, even in tragedy and setbacks, rather than wasting energy on resistance.
    • We do not get to choose what happens to us, but we can always choose how we feel about it. If a negative event must occur, amor fati - a love of fate - is the ideal response, as there is no value in any other reaction.
    • Face what comes, and if you can, do it with a smile.
  • Always preserve
    • If persistence is the dogged determination to hammer away at a difficult problem until it breaks, then plenty of people are persistent. But perseverance is something larger. It is the long game. It is about what happens not just in round one, but in round two and every round after - and then the fight after that, and the one after that, until the very end.
    • Life is not about a single obstacle, but many. What's required is not a shortsighted focus on one problem, but a larger determination to get where we need to go - somehow, someway - and let nothing stop us. We must be resolved to overcome every obstacle, knowing there will be many.
    • Persistence is an action, while perseverance is a matter of will. Of course, the two work in conjunction with each other.
    • The power of true perseverance is that it can only be stopped by death.
      • Our actions can be constrained, but our will cannot.
      • Our plans - even our bodies - can be broken, but our belief in ourselves is untouchable.
      • No matter how many times we are thrown back, we alone retain the power to go on once more, to try another route, or, at the very least, to accept a new reality and choose a new aim.
  • Always protect our inner self, retreat into ourselves.
  • Always submit to a greater, larger cause.
    • When we focus on others - by helping them or setting a good example - our own fears and troubles diminish.
      • When our primary concern is no longer our own fear, heartache or suffering, we have less time to indulge it.
      • The desire to quit or compromise your principles suddenly feels selfish when you consider the people who would be affected by that decision.
      • Shared purpose gives us strength.
    • When you are stuck on an intractable or impossible problem, one of the best ways to find a new path forward is to ask: "If I cannot solve this for myself, how can I at least make this better for other people?"
      • You can always remember that a decade, a century, or a millennium earlier, someone just like you stood right where you are, struggling with the very same thoughts.
      • They had no idea you would exist, but you know they did.
      • And a century from now, someone will be in your exact position once more.
    • Stop making it harder on yourself by focusing on "I, I, I". Start thinking: "Unity over Self. We’re in this together."
      • Be strong for others, and it will make you stronger.
  • Always remind ourselves of own mortality
    • We struggle with acceptance because our relationship with our own existence is deeply flawed.
      • We may not say it, but we act as if we are invincible - impervious to the trials and tribulations of mortality.
      • We think, "That stuff happens to other people, not to me. I have plenty of time left."
      • We forget how tenuous our grip on life really is.
      • Otherwise, we would not spend so much time obsessing over trivialities, trying to become famous, making more money than we could ever spend, or crafting plans far off in the future. All of these pursuits are negated by death. They all presume that death will not affect us, or at least, not when we do not want it to.
    • Death is not one of the things we control, but we will all succumb eventually.
      • Your days were numbered the moment you were born. With each passing day, the probability that we will be alive tomorrow shrinks.
      • Beyond taking reasonable precautions like watching what we eat and avoiding needless risks, we cannot control how long we will live or what will ultimately end our life.
    • This awareness of mortality can create powerful perspective and urgency.
      • Reminding ourselves each day that we will die helps us treat our time as a gift. Someone on a deadline doesn't indulge in impossible fantasies or waste time complaining about how they'd like things to be. They don't take people for granted; they are grateful for everything. They figure out what they need to do and do it, fitting in as much as possible before the clock expires.
    • This awareness of mortality can create real perspective and urgency.
      • Reminding ourselves each day that we will die helps us treat our time as a gift.
      • Someone on a deadline does not indulge themselves with attempts at the impossible, they do not waste time complaining about how they would like things to be.
      • They do not take people for granted, they are grateful for everything.
      • They figure out what they need to do and do it, fitting in as much as possible before the clock expires
    • Death is our most universal obstacle and the one we can do the least about. Even so, in the shadow of death, prioritization is easier. Since life will be over soon enough, we may as well live rightly with grace, fearlessness, appreciation and principle.
  • Always prepare to start cycle once more
    • The great law of nature is that it never stops; there is no end. Just when you think you have successfully navigated one obstacle, another emerges. But that is what keeps life interesting and, as you are starting to see, that is what creates opportunities.
    • Life is a process of breaking through impediments - a series of fortified lines that we must overcome. With each one, you will learn something and develop the strength, wisdom and perspective to become the best version of yourself.
    • As the Haitian proverb puts it: "Behind mountains are more mountains."
      • There are always more obstacles and bigger challenges.
      • You are always fighting uphill and against the wind, so get used to it and train accordingly.
    • Passing one obstacle simply says you are worthy of more.
      • The world seems to keep throwing challenges at you once it knows you can take them.
      • Therefore, be no longer afraid. Instead, be excited, be cheerful, and eagerly anticipate the next round.



Summary

Throughout The Obstacle Is the Way, the principles of Stoicism are interwoven with a series of historical and contemporary stories, illustrating their application in matters ranging from personal financial setbacks and tragedies to grand strategic challenges.

  • The book's core goal is to teach us how to get unstuck and unleashed from the harsh realities of modern life, such as rising unemployment, skyrocketing costs of education and living, the challenge of navigating a devastating global pandemic (COVID-19), and pervasive technological disruption.
  • In every story, the subjects stare down their obstacles and approach them with everything they have, mentally and physically. They see each challenge not as a barrier, but as an opportunity to test and improve themselves. The obstacle does not just stand in their way - it becomes the way forward.
See things for what they are.
Do what we 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.

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