Obstacle Is The Way, Ryan Holiday (7/10)

Rating: 7/10
Read More on Goodreads

🚀 The Book in 3 Sentences

1. A short self-help book inspired by Stoic philosophy
2. It's about how to turn the obstacles in your life into opportunities
3. It draws on various examples and practical parallels to teach its ideological lessons

🎨 Impressions

According to Nassim Taleb, a Stoic is someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.” After reading this book, as well as other books around Stoic philosophy, this resonates quite strongly. Once you've got the basic logic and framework of the philosophy down, however, I'm not sure how much of a benefit there is to doing deeper reading beside the sheer entertainment value of reading about the Stoics and their specific lives.

With that being said, I quite liked this book. It's a short and quite motivating read. It's a nice refresher to Stoic philosophy. Robert Greene is Ryan Holiday's mentor - and it shows - the book is packed with lots of stories, and force-fed advice. As with other books by Robert Greene, I do find this annoying at times, but Ryan Holiday, in my opinion, seems to have found a better balance than Greene.

😄 Who Should Read It?

I'd recommend this book to young adults trying to find their way in the world, perhaps battling with anxiety.

💬 My Favourite Quotes

"Don’t let the force of a first impression 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."

"To an incredibly large degree, our perceptions determine what we are and are not capable of. In many ways, they determine reality itself and life is a self-fulfilling prophecy."

"For whatever obstacles you come across: take a breath, do the immediate, composite part in front of you—and follow its thread into the next action. Everything in order, everything connected.
1. Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it.
2. Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first. Come back to the others later. You’ll get there.
3. The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture."

"Consider this mind-set: never in a hurry, never worried, never desperate, never stopping short"

"For whatever obstacles 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.
1. Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it.
2. Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first. Come back to the others later.
3. The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture."

"To whatever we face, our job is to respond with: i) hard work, ii) honesty, iii) helping others as best we can."

"In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well. Everything is a chance to do and be our best. Right action—unselfish, dedicated, masterful, creative—that is the answer to that question. That’s one way to find the meaning of life. And how to turn every obstacle into an opportunity."

"When we want things too badly we can be our own worst enemy. In our eagerness, we spin our tires and dig a deeper rut—one that we’ll never get out of. It doesn’t naturally occur to us that standing still—or even going backward—might be the best way to advance."

"Perseverance is the long game. It’s about what happens not just in round one but in round two and every round after—and then the fight after that and the fight after that, until the end."

📒 Summary + Notes

Introduction

• We need an approach to overcome obstacles and thrive amid chaos more than ever. A flexible approach fit for anyone to turn problems on their heads and create masterpieces - entrepreneur, artist, conqueror, coach, etc.
• 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

Part 1: Perception

The discipline of perception

• John D. Rockefeller: “I shall never cease to be grateful for the three and half years of apprenticeship and the difficulties to be overcome, all along the way."
• Few people react to perilous times like this. Rockefeller saw opportunity inside the obstacle - so what befell him was not unsalvageable misfortune but the gift of education—a chance to learn from a rare moment in economic history.
• When we face an insurmountable obstacle, we must try:
  To be objective
  To control emotions and keep an even keel
  To choose to see the good in a situation
  To steady our nerves
  To ignore what disturbs or limits others
  To place things in perspective
  To revert to the present moment
  To focus on what can be controlled

Control your emotions

• Obstacles make us emotional. We must keep those emotions in check - no matter what happens, no matter how much external events may fluctuate.
• The Greeks had a word for this: apatheia. It’s the calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling, just the loss of the harmful, unhelpful kind. Don’t let the negativity in.
• This skill must be cultivated so you can focus your energy on solving problems, not reacting to them.
• As Gavin de Becker writes in The Gift of Fear, “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?

Practice objectivity

• 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
• Pretend your situation is not happening to you. Pretend it is not important. 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?
• Think of how someone could solve a specific problem. Give yourself clarity, not sympathy. It’s an exercise, which means it takes repetition. The more you try it, the better you get at it. The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.

Alter your perspective

• “Business opportunities are like buses; there’s always another coming around.” — Richard Branson
• 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.
• 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
• George Clooney made himself the solution to the director's problem. Instead of being someone groveling for a shot, he was someone with something special to offer. He was the answer to their prayers, not the other way around. This was what he began projecting in his auditions. That he understood what the casting director and producers were looking for in a specific role and that he would deliver it in each and every situation, in preproduction, on camera, and during promotion.

Is it up to you?

• When it comes to perception, the crucial distinction to make is the difference between what is and is not in our power.

Live in the present moment

• Focus on what's in front of you, right now. Ignore what it “represents” or it “means” or “why it happened to you."

Think differently

• Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself.
• When we believe in the obstacle more than in the goal, which will inevitably triumph?
• It’s this all-too-common impulse to complain, defer, and give up that holds us back.
• Entrepreneurs have faith in their ability to make something where there was nothing before. To them, ideas no one has ever had are good things.
• 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.
• This nothing-to-lose state is when we are our most creative. Our best ideas come from there, where obstacles illuminate new options.

Finding the opportunity

• It’s one thing to not be overwhelmed, discouraged or upset by obstacles. But after you've controlled your emotions and see things objectively, you must perform a mental flip to look at the opportunity within the obstacle.
• Laura Ingalls Wilder: “There is good in everything, if only we look for it.”
• Growth and post-traumatic growth: "that which doesn't kill me makes me strong" is fact

Part 2: Action

• Directed action is what's required - everything must be done in service of the whole. Step by step, action by action, we'll dismantle the obstacles in front of us

The discipline of action

• We must greet obstacles with:
  energy
  persistence
  a coherent and deliberate process
  iteration and resilience
  pragmatism
  strategic vision
  craftiness and savvy
  an eye for opportunity and pivotal moments

Get moving

• You're going soft while you’re sleeping, traveling, attending meetings, or messing around online. You’re not aggressive enough. You’re not pressing ahead. This makes obstacles loom large.
• We tend to downplay the importance of aggression and risk-taking.
• 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.

Practice persistence

• Refuse to give up as you face obstacles. Turn your ideas and options over and over, and try each one with equal enthusiasm. Know that eventually one will work.
• Welcome the opportunity to test, grateful for the priceless knowledge this reveals.
• For most of what we attempt in life, we’re usually skilled and knowledgeable and capable enough. But we must find the patience to refine our idea, the energy to knock on enough doors to find investors and supporters, the persistence to slog through politics and drama in a working group.
• Once you start attacking an obstacle, quitting is not an option. It cannot enter your head.
• Abandoning one path for another more promising one is a far cry from giving up.
• Consider this mind-set:
  never in a hurry
  never worried
  never desperate
  never stopping short
• Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.
• You’re in this for the long haul. Because 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’s over—that every second available is yours to use.
• Temporary setbacks aren’t discouraging. They're just bumps along a long road that you intend to travel all the way down.
• It’s okay to be discouraged. It’s not okay to quit. To know you want to quit but to plant your feet and keep inching closer until you take the impenetrable fortress you’ve decided to lay siege to in your own life—that’s persistence.

Iterate

• What is defeat? Nothing but education; nothing but the first steps to something better. —WENDELL PHILLIPS
• In a world where we increasingly work for ourselves and are responsible for ourselves, it makes sense to view ourselves like a start-up—a start-up of one.
• You must change your relationship with failure. Iterate, fail, and improve.
• Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.
• 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

Follow the process

• Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand.
• For whatever obstacles 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.
• Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it.
• Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first. Come back to the others later. You’ll get there.
• The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.

Do your job, do it right

• Whatever is rightly done, however humble, is noble. (Quidvis recte factum quamvis humile praeclarum.) —SIR HENRY ROYCE
• We will be and do many things in our lives. Some are prestigious, some are onerous, none are beneath us.
• Everything we do matters—whether it’s making smoothies while you save up money or studying for the bar—even after you already achieved the success you sought.
• To whatever we face, our job is to respond with:
  hard work
  honesty
  helping others as best we can
• In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.
• Everything is a chance to do and be your best.
• Right action—unselfish, dedicated, masterful, creative—that is the answer to that question. That’s one way to find the meaning of life. And how to turn every obstacle into an opportunity.

What's right is what works

• Deng Xiaoping: “I don’t care if the cat is black or white, so long as it catches mice.”
• Pragmatism is not so much realism as flexibility.
• There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line - you just need to get to where you need to go. But we spend so much time looking for the perfect solution, we pass up what’s right in front of us.
• Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible.
• Don’t think small, but make the distinction between the critical and the extra.
• Think progress, not perfection

In praise of the flank attack

• Martial arts teach us that we must resist the impulse to push back when pushed. Instead, we must pull until opponents lose their balance. Then we make our move.
• Rather than convince people by challenging their opinions, find common ground and work from there. Or look for leverage to make them listen. Or 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 we need to learn from Amelia Earhart and just take action. But we must also be ready to see that restraint might be the best action for us to take.
• When we want things too badly we can be our own worst enemy. In our eagerness, we spin our tires and dig a deeper rut—one that we’ll never get out of.
• We get so consumed with moving forward, we forget there are other ways to get where we are heading.
• It doesn’t naturally occur to us that standing still—or even going backward—might be the best way to advance.
• We push and push—to get a raise, a new client, to prevent some exigency from happening. In fact, 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 might discover that in ignoring clients, we attract more—finding that they want to work with someone who does not so badly want to work with them. Or we rethink that disaster we feared (along with everyone else) and come up with a way to profit from it when and if it happens.

Channel your energy

• Be like a tennis player. Physically loose and mentally restrained.
• It's powerful. It drives our opponents and competitors nuts. It's like we're immune to external stressors and limitations on the march toward our goals.

Seize the offensive

• It's not enough to just take advantage of the opportunities that arise in your life - anyone can do that. You must instead learn how to press forward precisely when everyone around you sees disaster.
• When people least expect it, at the seemingly bad moments, we can act swiftly and unexpectedly to pull off a big victory.
• While others are arrested by discouragement, see the moment differently, and act accordingly.

Prepare for none of it to work

• We can't control the world. We might perceive things well, act rightly, but fail anyway. And while nothing can ever prevent us from trying, all creativity and destruction aside, after we've tried, some obstacles may turn out to be impossible to overcome.
• But that which blocks our path actually presents a new path with a new part of us. 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.

Part 3: Will

• If action is what we do when we have agency over our situation, will is what we depend on when agency has disappeared. Placed in unchangeable and undeniably negative situations, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That's will power.

The discipline of the will

• Schooled in suffering, Abraham Lincoln learned “to comfort those who suffer too.” This, too, is part of the will—to think of others, to make the best of a terrible situation that we tried to prevent but could not, to deal with fate with cheerfulness and compassion.
• In every situation, we can
  Always prepare ourselves for more difficult times.
  Always accept what we’re unable to change.
  Always manage our expectations.
  Always persevere.
  Always learn to love our fate and what happens to us.
  Always protect our inner self, retreat into ourselves.
  Always submit to a greater, larger cause.
  Always remind ourselves of our own mortality.

The art of acquiescence

• Life gives you plenty to work with. Taking people and events as they are is quite enough material already.
• Follow where the events take you, like water rolling down a hill—it always gets to the bottom eventually.
• Because (a) you’re robust and resilient enough to handle whatever occurs, (b) you can’t do anything about it anyway, and (c) you’re looking at a big-enough picture and long-enough time line that whatever you have to accept is still only a negligible blip on the way to your goal.
• We’re indifferent and that’s not a weakness.
• Francis Bacon: nature, in order to be commanded, must be obeyed.

Love everything that happens: amor fati

• To do great things, we must endure tragedy and setbacks. We must love what we do and all that it entails, good and bad. We must learn to find joy in every thing that happens.
• Obstacles warrant only one response: a smile. Cheerfulness in all situations, especially the bad ones.
• The goal is:
• Not: I’m okay with this. Not: 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 did when it did. I am meant to make the best of it.

Perseverance

• If persistence is attempting to solve some difficult problem with dogged determination until the break occurs, then plenty of people can be said to be persistent.
• Perseverance is larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after—and then the fight after that and the fight after that, until the end.
• The Germans have a word for it: Sitzfleisch. Staying power. Winning by sticking your ass to the seat and not leaving until after it’s over.
• 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—and there will be many in life—until we get there. Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.

Something bigger than yourself

• 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. This is a tremendous opportunity for you, a young person, to be heroic.
• 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.
• This kind of myopia is what convinces us, to our own detriment, that we’re the centre of the universe.
• Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you.

Meditate on your mortality

• Embracing the precariousness of our own existence can be exhilarating and empowering.
• Montaigne had a uniquely playful relationship with his existence and a sense of clarity and euphoria that he carried with him from that point forward.
• Our fear of death is a looming obstacle in our lives. It shapes our decisions, our outlook, and our actions.
• Life will be over soon enough; death chides us that we may as well do life right. Why would you do the wrong thing? Why feel fear? Why let yourself and others down?
• We can learn to adjust and come to terms with death and find relief in the understanding that there is nothing else nearly as hard left.

Prepare to start again

• The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges.
• Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles.
• On the contrary, 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.