Publisher: Portfolio

ISBN-13 : 978-1591846352

Buy: The Obstacle is the Way at  Amazon

Rating: ⭐⭐⭐⭐⭐

 

The Obstacle is the Way by Ryan Holiday

My mission in life is not merely to survive, but to thrive; and to do so with some passion, some compassion, some humor, and some style. ― Maya Angelou

Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better. (27) ― Nassim Nicholas Taleb, Antifragile

Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?” (9) —Ryan Holiday

Introduction

An obstacle is anything that gets in the way of progress or achieving a goal. It can be a physical object, a difficult situation, a personal limitation, or even another person. Obstacles can be big or small, expected or unexpected, but they all have the potential to slow us down or prevent us from reaching our destination. 

Obstacles could be physical (natural disasters, illness, disability, mental health challenges, etc), economic (poverty, financial instability); cultural and geographical (age, race, gender, language, etc), political (laws, regulations, instability), technological (lack of access, etc); personal (fear, self-doubt, procrastination, lack of skills, etc), interpersonal (conflicts with others, relationships), etc

The central message in Ryan Holiday’s The Obstacle Is the Way is that problems or challenges aren’t obstacles; they are fuel. Adversity isn’t your enemy; it’s your opportunity. Drawing from principles rooted in Stoicism, Holiday’s message is: lean in to your problems, face them head on, and use them as a route to your advantage. 

Originating in ancient Greece, Stoicism is a philosophy that centers on using reason and logic to navigate the world and our role within it. It prioritizes clear thinking and the avoidance of emotional extremes, aiming to develop an attitude of inner calm and resilience in the face of life’s challenges.

Holiday is a self-proclaimed Stoic, so the book is also a crash course in Stoicism, especially the writings of Marcus Aurelius, Epictetus, and Seneca. The title, The Obstacle Is the Way, derives from a famous line in Marcus Aurelius’s Meditations:

“The impediment to action advances action. What stands in the way becomes the way.” (7)

The book’s core message is that a formula for turning obstacles into opportunities can be learned from the examples of great (and sometimes morally complex) figures. Holiday uses historical figures such as Rubin “Hurricane” Carter, Ulysses S. Grant, Thomas Edison, Amelia Earhart, Martin Luther King, Jr., Margaret Thatcher, Steve Jobs, Barack Obama,  etc as Stoic case studies in turning adversity into opportunity. Holiday shows that they didn’t just endure their struggles;  they thrived because of them.

There are some parts that edge close to hustle-bro energy, but the book mostly stays grounded. Holiday doesn’t sugarcoat pain or ask you to smile through it; he treats difficulty as the starting point for transformation. Pain, failure, and frustration are the raw materials for creating something meaningful. Stoicism emphasizes the importance of accepting what we cannot control, while positioning virtues such as wisdom, courage, justice, and temperance as the supreme aim of our actions.

To me, the most powerful takeaway is this: You don’t get to choose the obstacle. But you do get to choose your response. That statement resonates with me, as I wrote about earlier in my summary of Viktor Frankl’s “Man’s Search for Meaning”.

“Everything can be taken from a man but one thing: the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.”
—Viktor E. Frankl, “Man’s Search for Meaning

More than a guide for navigating difficult times, this book offers a framework for living a meaningful, resilient, and effective life; showing how Stoic principles can turn our hardest challenges into catalysts for growth. It offers “a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us” (11).

Life is unfair. Plans implode. People disappoint you. Systems fail. But if you can learn to respond with clarity, creativity, and strength? That’s the way.

The Obstacle Is the Way in 3 Sentences

• Ryan Holiday’s The Obstacle Is the Way argues that obstacles aren’t roadblocks to avoid but opportunities that reveal the path forward—”what blocked the path now is a path. (145)”  
• Drawing from ancient Stoic philosophy, the book teaches three disciplines: seeing obstacles clearly and objectively (perception), taking persistent and creative action despite difficulty (action), and developing unshakeable inner strength when external circumstances can’t be changed (will). 
• By mastering these interconnected practices and focusing only on what we can control, we transform every setback into fuel for growth and improvement, turning adversity itself into our advantage.

5 Key Takeaways

1. Learn to welcome challenges and obstacles:

We should welcome obstacles as opportunities. The obstacle itself is the way forward. While challenges are an inevitable  part of life, a crisis can also be an opportunity. 

Rather than avoiding challenges, we should embrace them as opportunities for growth and advancement. Adopt a mindset that views adversity as a chance to cultivate virtue, strength, and resilience so that the very thing that stands in our way can become the path forward.

2. Perception determines reality: 

Our reaction to obstacles, especially our perception, remains within our control. How we perceive obstacles, as threats or as opportunities, fundamentally shapes our responses. 

By controlling our perception, we can turn seeming disasters into advantages. So, it’s important to get the right perspective and practice the ability to see things for what they truly are.

3. Take disciplined action: 

Take action. The philosophy emphasizes practical application and consistent effort over passive thinking. After perceiving obstacles correctly, we must act with persistence, creativity, and pragmatism. Small, consistent actions compound into significant progress, even against formidable challenges.

4. Cultivate inner strength: 

True strength comes from within. By developing willpower (our “inner citadel”), acceptance of what we cannot control, and emotional detachment from outcomes, we can endure any hardship. 

5. Practice present-moment focus and process over outcomes:

We should concentrate on what we can do right now, in this moment, rather than being overwhelmed by the magnitude of the entire obstacle or fixated on distant outcomes. This means breaking down seemingly insurmountable challenges into immediate, actionable steps and focusing intensely on executing each one well.

The Stoics taught that we can only control our efforts and decisions in the present moment, not the final results. By committing fully to the process and doing our best work right now, we often find that the obstacle naturally begins to dissolve or transform. This present-moment discipline prevents us from being paralyzed by the size of the challenge or distracted by anxiety about future consequences.

As Holiday references, this mirrors the Stoic concept of focusing on what’s “up to us” versus what’s “not up to us”; and what’s always up to us is our response in this very moment.

This fifth takeaway bridges beautifully with the other points: it’s how we practically implement right perception (#2), it’s the mechanism for taking disciplined action (#3), and it strengthens our inner citadel (#4) while helping us see each present moment as the opportunity that obstacles provide (#1).

Top Quotes

• 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)  (7)
• 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. (16)
• 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. (25)
• In every situation, life is asking us a question, and our actions are the answer. (82)
• 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. (140)

Historical Context: Stoicism and Marcus Aurelius

The core principles from The Obstacle is the Way are largely derived from Stoic philosophy, and largely from Marcus Aurelius’ Meditations. 

Meditations is a series of private notes and reflections on Stoic philosophy by Roman Emperor Marcus Aurelius (161–180 AD). Marcus Aurelius faced immense challenges during his reign, including “nearly constant war, a horrific plague, possible infidelity, an attempt at the throne by one of his closest allies, repeated and arduous travel across the empire… a rapidly depleting treasury, an incompetent and greedy stepbrother as co-emperor, and on and on and on.” (7)

Despite these burdens, Marcus Aurelius “truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity”. (8) He remained calm, rarely showed excess or anger, and “never to hatred or bitterness.” (8)

The universal verdict on Marcus Aurelius was that he proved himself worthy of the highest and most powerful station in the world.

Notable figures throughout history, including Thomas Jefferson, George Washington, Frederick the Great, and Toussaint Louverture, were influenced by Stoicism and the works of figures like Seneca, Epictetus, and Marcus Aurelius. ( 146)

The Obstacle as Opportunity

Obstacles are not merely hindrances but inherent opportunities for growth, learning, and ultimately, success. Holiday breaks down this concept into three interconnected disciplines: Perception, Action, and Will. 

Holiday presents key figures throughout history who exemplified these principles in the face of significant challenges as case studies. The ultimate aim is to equip people with a “formula for thriving (7)” and to see themselves as practical philosophers, capable of turning “bad” things into “real benefit.” (143). This approach offers “one of history’s most effective formulas for overcoming every negative situation we may encounter in life.” (7) It provides a methodology for “thriving not just in spite of whatever happens but because of it.” (7)

• Reframing Adversity: The fundamental idea is to perceive seemingly negative situations as beneficial. “Within every obstacle is an opportunity to improve our condition.” (14) Great companies and individuals are not merely destroyed or surviving crises, but “are improved by them.” This is a call to be “ceaselessly creative and opportunistic.” (13) Challenges are “opportunities to test ourselves, to try new things, and, ultimately, to triumph.” (16)
• Universal Principle: Obstacles are a constant in life, regardless of status or era. The question is not if we will face them, but “Will we be blocked by obstacles, or will we advance through and over them?” (9) Those who thrive “rally at every such challenge. That the challenge makes them better than if they’d never faced the adversity at all.” (9)
• Internal vs. External Obstacles: While historically obstacles might have been external (wars, diseases), modern challenges often stem from “internal tension… professional frustration… unmet expectations… learned helplessness,” and the “overwhelming emotions humans have always had: grief, pain, loss.” (15) Abundance itself can be an obstacle, leading to complacency.

The Three Disciplines of Overcoming Obstacles

The philosophy is structured around three interdependent disciplines—Perception, Action, and Will—that work together to transform obstacles into opportunities

“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”(16).

Perception involves how we see and understand events and the meaning we assign to them, emphasizing objectivity and limiting emotional responses. Action is about relentless persistence, ingenuity, and pragmatism in tackling challenges. Will represents our inner strength, resilience, and ability to find meaning and endure even when we cannot overcome external circumstances.

1. Perception (Seeing Clearly)

Perception is about looking at the events that happen to us, and then deciding what they mean. It is “how we see and understand what occurs around us—and what we decide those events will mean.” (17). 

Perception is important because it shapes our entire response to challenges, and determines how we interpret the events around us. 

“The phrase ‘This happened and it is bad’ is actually two impressions. The first—‘This happened’—is objective. The second—‘it is bad’—is subjective.” (34)

“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”(25).

“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 the goal, which will inevitably triumph?” (47)

“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 (such as, that a situation is absolutely hopeless or impossible to improve). Our perceptions are the thing that we’re in complete control of.” (24)

By learning to control our emotions and see things simply and straightforwardly, as they are and not as “good” or “bad,” we can prevent ourselves from being overwhelmed. 

“Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree.” (25-26)

This allows us to recognize our power to choose our response and avoid being paralyzed by fear.  By practicing objectivity in perception, we gain clarity, and learn to see the opportunity inside every obstacle.

“We decide what story to tell ourselves. Or whether we will tell one at all.” (26)

Key Principles of Perception:

Recognize Your Power: 

You’re never completely powerless. You always have a choice about how you react to any situation. You have the power to choose whether to resist or succumb. Your perspective is the only thing you have complete control over, and how you choose to see things helps create or destroy the obstacles in your life.

• “Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.” —Marcus Aurelius (23)

Steady Your Nerves: 

• Panic leads to mistakes. Stress, no matter the actual danger, can make us act out of fear. But there is always a way through a problem, so there’s little reason to get worked up. The path won’t be easy, and the stakes may be high, but solutions exist for those willing to find it.
• “What such a man needs is not courage but nerve control, cool headedness. This he can get only by practice.” —Theodore Roosevelt (27)

Control Your Emotions: 

• “Would you have a great empire? Rule over yourself,” —Publius Syrus. (30)
• Life has problems. When they happen, our emotions might get out of control. We get through these challenges by controlling our feelings. The goal is to stay calm, no matter what is going on. The ancient Greeks called this “apatheia.” 
• The idea isn’t to pretend you don’t have feelings. Real strength is learning to manage your emotions. 
• “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?”—Gavin de Becker in The Gift of Fear (31)
• 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. (31-32)
• Subconsciously, we should be constantly asking ourselves this question: Do I need to freak out about this? (32)

Practice Objectivity: 

We often don’t see reality for what it is. Instead, our brains create mental shortcuts and stories to make sense of the world quickly, but these can lead to errors. We are constantly trying to match the present reality with our expectations, beliefs, and emotions. When they don’t align, we create a story to explain the difference. This can cause significant problems because the story we create often focuses on what we think should be happening rather than what is actually happening.

Distress and unhappiness don’t come from external events themselves, but from our judgments about those events. For example, losing a job is an external event. The judgment that “this is a terrible catastrophe and I am a failure” is what causes the intense emotional pain. We can’t control the job loss, but we can control our judgment about it.

• “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) (34)
• Separate facts (“This happened”) from interpretations (“It is bad”). (34) 
• The phrase “This happened and it is bad” is actually two impressions. The first—“This happened”—is objective. The second—“it is bad”—is subjective. (34)
• In The Book of Five Rings, the sixteenth-century Samurai swordsman Miyamoto Musashi “notes the difference between observing and perceiving. The perceiving eye is weak, he wrote; the observing eye is strong” .(34)
• “Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there.” (34)
• The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or  “major setbacks” or even just “issues.” It brings its own issues to the fight. The former is helpful, the latter is not. (34)
• Perceptions are the problem. They give us the “information” that we don’t need, exactly at the moment when it would be far better to focus on what is immediately in front of us. (34)
• The goal is to “ to see these things as they really are, without any of the ornamentation.” (35)
• Objectivity means removing “you”—the subjective part—from the equation. (35)
• 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? (35)

Alter Your Perspective: 

Breaking a problem into smaller parts or seeing it from a different perspective takes away its power. You choose how you see things. You can’t change the problems you face, but a change in perspective can change how those problems feel.

• “Perspective is everything…. when you can break apart something, or look at it from some new angle, it loses its power over you.” (37)
• Remember: We choose how we’ll look at things…..We can’t change the obstacles themselves… but the power of perspective can change how the obstacles appear. (37)
• It’s your choice whether you want to put ‘I’ in front of something. (I hate public speaking.  I screwed up. I am harmed by this) These add an extra element: you in relation to the obstacle, rather than just the obstacle itself. (37-38)
• It’s your choice to put an “I” in front of a problem. When you say, “I am stuck in traffic,” you add yourself and your feelings to the situation. If you just say, “The traffic is bad,” you see the problem as something separate from you. This simple change can make the situation feel less personal and less stressful.
• With the wrong perspective, we become consumed and overwhelmed with something actually quite small. Why subject ourselves to that? The right perspective has a strange way of cutting obstacles — and adversity — down to size. (38)
• “Perspective has two 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” (38)
• 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. (39)
• “Perception precedes action. Right action follows the right perspective.” (39)

Is It Up To You?

Ta eph’ hemin, ta ouk eph’ hemin is a 2,000-year-old Stoic phrase (41) that means, “What is up to us, what is not up to us.” It’s a simple way to remember the difference between things you can control and things you can’t. 

For instance, when facing a difficult coworker, focus on what you can control: your own professional behavior and seeking help from your manager. Don’t waste your time and energy on things you can’t control, like your coworker’s personality or actions. This helps you find a real solution instead of just getting frustrated. 

• “In life, our first job is this: to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices. —Epictetus (40)
• What’s up to us includes “our emotions, our  judgments, our creativity, our attitude, our perspective, our desires, our decisions, our determination.” (42)
• What is not up to us includes: “ The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.”(42)
• When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t. (42)
• …the most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.(42)
• Focusing exclusively on what is in our power magnifies and enhances our power. (42)
• …every ounce of energy directed at things we can’t actually influence is wasted—self-indulgent and self-destructive. (42)
• To see an obstacle as a challenge, to make the best of it anyway, that is also a choice—a choice that is up to us. (42)

Live In The Present Moment

Take things day by day, and don’t borrow trouble or dwell on potential disaster.

• “Focus on the moment, not the monster that may or may not be up ahead.” (45)
• The implications of our obstacle 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.  (45)
• To live in the present, you need to find a method that works for you. Try exercising, unplugging from technology, taking a walk, or meditating. The goal is to get rid of distracting thoughts and learn to leave things alone, even when you feel the urge to dwell or ruminate.
• 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 it “means” or “why it happened to you.” (46)

Think Differently

Reality is hemmed in by rules and compromises that are human-made. You don’t need to see those as immutable or unchangeable. 

Like Steve Jobs, you can challenge what’s considered possible by creating a “reality distortion field.” Jobs believed that with enough vision and hard work, most things in life could be changed or shaped to his will, a belief so strong it influenced those around him.

• “Jobs had a much more aggressive idea of what was or wasn’t possible. To him, when you factored in vision and work ethic, much of life was malleable.” (47)
• Jobs knew that “ to aim low meant to accept mediocre accomplishment. But a high aim could, if things went right, create something extraordinary.” (47)
• Napoleon shouting to his soldiers: “There shall be no Alps!” (47)
• “Don’t be afraid…You can do it. Get your mind around it. You can do it.” —Steve Jobs. (48-49)
• Our perceptions determine, to an incredibly large degree, what we are and not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than the goal, which will inevitably triumph? (47)

Find The Opportunity

During the Battle of the Bulge, the German Blitzkrieg strategy aimed to exploit the enemy’s fear, relying on their collapse at the sight of overwhelming force. 

However, General Dwight D. Eisenhower refused to see the German thrust as a disaster.  Instead, he recognized it as a critical opportunity: the deep forward wedge of the German army had dangerously exposed their flanks. 

This mental flip allowed the Allies to turn a seemingly invincible attack into a tactical advantage, encircling the enemy and transforming what was feared to be a major reversal into one of the Allied opposition’s greatest triumphs.

• A good person dyes events with his own color…and turns whatever happens to his own benefit. —Seneca (50)
• “The present situation is to be regarded as opportunity for us and not disaster.” — General Dwight D. Eisenhower (50)
• 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. (51)
• Blessings and burdens are not mutually exclusive. It’s a lot more complicated. (52)
• Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliché but fact. (52)
• The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.  (52)
• Everything can be flipped, seen with this kind of gaze: a piercing look that ignores the package and sees only the gift. Or we can fight it the entire way. The result is the same. The obstacle still exists. One just hurts less. (53)

2. Action (Moving Forward)

Once you have a clear, objective view of a problem, it’s time to act. Action is the practical application of a clear perception. The key is to take directed action; not just any random action, but steps that serve a bigger goal. 

By being persistent, flexible, and bold, you can dismantle the obstacles in your way and move forward despite difficulty.

• Then imitate the action of the tiger; stiffen the sinews, summon up the blood. —Shakespeare (55)
•  the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary and post hoc). (55)
• 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. (55)
• … 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. With persistence and flexibility, we’ll act in the best interest of our goals (56)
• “… act with deliberation, boldness, and persistence. Those are the attributes of right and effective action.” (56)
• Action is the solution and the cure to our predicaments. (56)

Key Principles of Action:

The Discipline of Action

• We have real strength—more strength than we know. (58)
• “We’ve all done it. Said: “I am so [overwhelmed, tired, stressed, busy, blocked, outmatched].” And then what do we do about it? Go out and party. Or treat ourselves. Or sleep in. Or wait. It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.” (59)
• In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage. (59)
• People turn shit into sugar all the time (59)
• No one is coming to save you. And if we’d like to go where we claim we want to go—to accomplish what we claim are our goals—there is only one way. And that’s to meet our problems with the right action.(60)
• Therefore, we can always (and only) greet our obstacles with…with energy, with persistence, with a coherent and deliberate process, with iteration and resilience, with pragmatism, with strategic vision, with craftiness and savvy, and an eye for opportunity and pivotal moments. (60)

Get Moving

• “We must all either wear out or rust out, every one of us. My choice is to wear out.” —Theodore Roosevelt (62)
• That’s what people who defy the odds do…They start. Anywhere. Anyhow. They don’t care if the conditions are perfect or if they’re being slighted. Because they know that once they get started, if they can just get some momentum, they can make it work. (62)
• Life can be frustrating. Oftentimes we know what our problems are. We may even know what to do about them. But we fear that taking action is too risky, that we don’t have the experience or that it’s not how we pictured it or because it’s too expensive, because it’s too soon, because we think something better might come along, because it might not work.And you know what happens as a result? Nothing. We do nothing. (62)
• Tell yourself: The time for that has passed. The wind is rising. The bell’s been rung. Get started, get moving. (63)
• We often assume that the world moves at our leisure. We delay when we should initiate. We jog when we should be running or, better yet, sprinting. And then we’re shocked—shocked!—when nothing big ever happens, when opportunities never show up, when new obstacles begin to pile up, or the enemies finally get their act together. (63)

The Three Steps to Get Moving: Step 1:  Take the bat off your shoulder and give it a swing. You’ve got to start, to go anywhere. (63) Just get started. Step 2:  Go all in. Don’t let yourself get complacent or soft. Stay aggressive, stay hungry, and press ahead relentlessly. Look for that extra edge and give every action everything you’ve got. Ram your feet into the stirrups and really go for it.  (63) Could you be doing more? You probably could—there’s always more. At minimum, you could be trying harder. You might have gotten started, but your full effort isn’t in it—and that shows.   (63) …these days we tend to downplay the importance of aggression, of taking risks, of barreling forward. (64) Step 3:  Stay moving, always (64). those who attack problems and life with the most initiative and energy usually win (64) on the side of her plane [Amelia Earhart] painted the words, “Always think with your stick forward.” That is: You can’t ever let up your flying speed—if you do, you crash. Be deliberate, of course, but you always need to be moving forward. (64)

• We talk a lot about courage as a society, but we forget that at its most basic level it’s really just taking action (64)
• 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. (64)

Practice Persistence

• “The best way out is always through.” —Robert Frost (66)
• If we’re to overcome our obstacles, this is the message to broadcast — internally and externally: 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. (66)
• In 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he was the only man willing to test six thousand different filaments… (67)
• “You turn if you want to. The lady’s not for turning.” —Margaret Thatcher (67)
• Persist and resist.  —Epictetus (68)
• Persist in your efforts. Resist giving in to distraction, discouragement, or disorder. (68)
• Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with persistence and time can we cut away debris and remove impediments. Only in struggling with the impediments that made others quit can we find ourselves on untrodden territory—only by persisting and resisting can we learn what others were too impatient to be taught. (68)
• “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.” (68)
• When setbacks come, we respond by working twice as hard. (69)

Iterate

• What is defeat? Nothing but education; nothing but the first steps to something better. —Wendell Phillips (71)
•  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’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities. (71)
• On the path to successful action, we will fail—possibly many times. And that’s okay. It can be a good thing, even. Action and failure are two sides of the same coin.  (71)
•  Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail. (71)
•  anticipated, temporary failure certainly hurts less than catastrophic, permanent failure? Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over.  (72)
• Failure “shows us the way—by showing us what isn’t the way.” (74)

Follow the Process

•  …process provides us a way. It says: Okay, 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. (75)
•  Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that.  (75)
•  … 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.(76)
•  Do that now, 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. (76)
• 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. (76)
• Being trapped is just a position, not a fate. You get out of it by addressing and eliminating each part of that position through small, deliberate actions—not by trying (and failing) to push it away with superhuman strength. (77)
•  We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y. (77)
• The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture. (78)

Do Your Job, Do It Right

• Whatever is rightly done, however humble, is noble. (Sir Henry Royce)
• 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. Often when we are just starting out, our first jobs “introduce us to the broom,” as Andrew Carnegie famously put it. There’s nothing shameful about sweeping. It’s just another opportunity to excel—and to learn. (80)
• But you, you’re so busy thinking about the future you don’t take any pride in the tasks you’re given right now. You just phone it all in, cash your paycheck, and dream of some higher station in life. Or you think, This is just a job, it isn’t who I am, it doesn’t matter. Foolishness. Everything we do matters—whether it’s making smoothies while you save up money or studying for the bar—even after you have already achieved the success you sought. 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. (80-81))
• 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. That’s our primary duty. And our obligation. When action is our priority, vanity falls away. (81)
•  We will be and do many things in our lives. Some are prestigious, some are onerous, none are beneath us. (81)
•  To whatever we face, our job is to respond with:hard work, honesty, helping others as best we can. (81)
• … if we do our best we can be proud of our choices and confident they’re the right ones. Because we did our job—whatever it is. (81)
• In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well. (82)
• 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. (82)
• How you do anything is how you can do everything.We can always act right. (82)

What’s right is what works

Be pragmatic and flexible. We often get caught up in following the “rules” or waiting for the perfect moment to start. Instead, it’s better to be flexible, keep your eye on the prize, and focus on getting results, even if the method isn’t perfect. There are many ways to reach a goal, and it’s okay if your path isn’t a straight line.

• The cucumber is bitter? Then throw it out. There are brambles in the path? Then go around. That’s all you need to know. —Marcus Aurelius (84)
• In 1915, Sam Zemurray’s company, Cuyamel Fruit, purchased the same piece of land from two different owners in South America to avoid a protracted dispute. By paying both owners, he eliminated the problem and secured the land for his company’s operations without legal delay, outwitting United Fruit, his larger, more powerful competitor. 
•  He paid twice, sure, but it was over. The land was his. Forget the rule book, settle the issue. (84)
• Sometimes you do it this way. Sometimes that way. Not deploying the tactics you learned in school but adapting them to fit each and every situation. Any way that works—that’s the motto. (85)
• We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods. (85)
• Scratch the complaining. No waffling. No submitting to powerlessness or fear. You can’t just run home to Mommy. How are you going to solve this problem? How are you going to get around the rules that hold you back? Maybe you’ll need to be a little more cunning or conniving than feels comfortable. Sometimes that requires ignoring some outdated regulations or asking for forgiveness from management later rather than for permission (which would be denied) right now. But if you’ve got an important mission, all that matters is that you accomplish it. (85)
• There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. (86)
• Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. (87)
• Under this kind of force, obstacles break apart. They have no choice. Since you’re going around them or making them irrelevant, there is nothing for them to resist. (87)

In Praise Of The Flank Attack

Think about using indirect approaches. It’s not particularly effective to meet your opponent head on, especially if you are outnumbered or outmatched.  History is full of examples where generals avoided direct battles with the enemy and used guerrilla tactics instead.

• Never attack where it is obvious, (George) Washington told his men. Don’t attack as the enemy would expect, he explained, instead, “Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success.” (88)
• In a study of some 30 conflicts comprising more than 280 campaigns from ancient to modern history, the brilliant strategist and historian B. H. Liddell Hart came to a stunning conclusion: In only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main army.Only six. That’s 2 percent. (89)
• If not from pitched battles, where do we find victory? From everywhere else. From the flanks. From the unexpected. From the psychological. From drawing opponents out from their defenses. From the untraditional. From anything but (89)
• When you’re at your wit’s end . . .Take a step back, then go around the problem. Find some leverage. Approach from what is called the “line of least expectation.” (89)
• What’s your first instinct when faced with a challenge? Is it to outspend the competition? Argue with people in an attempt to change long-held opinions? Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open  (89)
• Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages…These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle (90)
• 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 alterative with so much support from other people that the opposition voluntarily abandons its views and joins your camp. (90)
• “Sometimes the longest way around is the shortest way home.” (91)

Use Obstacles Against Themselves

Instead of always fighting obstacles head-on, you can sometimes overcome them by letting them come to you. This is a strategy of indirect action where you use the energy of your opponents or the problem itself against them.

This approach is not about doing nothing; it’s about being incredibly disciplined and strategic. By allowing an obstacle to advance, you might be able to find a way to make it defeat itself. Think of a castle: it can be a fortress, but if you surround it, it becomes a prison.

Both Gandhi and Martin Luther King Jr. used this principle with great power. They met aggression and hate with non-action and love, turning their opponents’ actions into a disadvantage for them. This allowed them to absorb the energy of the opposition and use it to their own benefit, proving that sometimes, moving backward or standing still can be the most powerful way to advance.

• “Wise men are able to make a fitting use even of their enmities.” —Plutarch (92)
• Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you. You can use the actions of others against themselves instead of acting yourself. (92)
• Opposites work. Nonaction 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. (92)
• Martin Luther King Jr., taking Gandhi’s lead, told his followers that they would meet “physical force with soul force.” In other words, they would use the power of opposites. In the face of violence they would be peaceful, to hate they would answer with love—and in the process, they would expose those attributes as indefensible and evil. (93)
• Just ask the Russians, who defeated Napoléon and the Nazis not by rigidly protecting their borders but by retreating into the interior and leaving the winter to do their work on the enemy, bogged down in battles far from home. (93)
• some adversity might be impossible for you to defeat—no matter how hard you try. Instead, you must find some way to use the adversity, its energy, to help yourself. (93)
• …instead of fighting obstacles, find a means of making them defeat themselves (93)
• It doesn’t naturally occur to us that standing still—or in some cases, even going backward—might be the best way to advance. Don’t just do something, stand there (94)
• We wrongly assume that moving forward is the only way to progress, the only way we can win. Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path. (94)
• Let’s be clear, using obstacles against themselves is very different from doing nothing. Passive resistance is, in fact, incredibly active. But those actions come in the form of discipline, self-control, fearlessness, determination, and grand strategy.(94)
• The great strategist Saul Alinsky believed that if you “push a negative hard  enough and deep enough it will break through into its counterside.” Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive. (94)
• Remember, a castle can be an intimidating, impenetrable fortress, or it can be turned into a prison when surrounded. The difference is simply a shift in action and approach. (95)

Channel Your Energy

You can transform adversity into productive power. Instead of letting hardship harden you or lead to frustration, you can use that energy to fuel your actions.

The key is to be physically relaxed while maintaining mental discipline. This combination of a loose body and a restrained mind is powerful. It allows you to be bold and effective without becoming reckless or anxious.

When things go wrong, immediately return to yourself. Don’t let yourself get thrown off rhythm more than you have to. If you are constantly returning to a state of calm, it will become easier each time.

• 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)
• Transform adversity’s force into productive power. (96)
• Adversity can harden you. Or it can loosen you up and make you better—if you let it. (96)
• Instead of giving in to frustration, we can put it to good use. It can power our actions, which, unlike our disposition, become stronger and better when loose and bold. (97)
• To be physically and mentally loose takes no talent. That’s just recklessness. (We want right action, not action period.) To be physically and mentally tight? That’s called anxiety. It doesn’t work, either. Eventually we snap. But physical looseness combined with mental restraint? That is powerful (98)

Seize The Offensive

Instead of seeing a disaster, see a chance to act while others are discouraged. Be bold in a crisis and turn the obstacle into your advantage, using it to achieve what was previously impossible.

• 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. (99)
• It’s at the seemingly bad moments, when people least expect it, that we can act swiftly and unexpectedly to pull off a big victory. While others are arrested by discouragement, we are not. We see the moment differently, and act accordingly. (99)
• “You never want a serious crisis to go to waste….[A] crisis provides the opportunity for us to do things that you could not do before.”  (Advice from Rahm Emanuel to Barack Obama) (100)
• Life speeds on the bold and favors the brave. (100)
• At certain moments in our brief existences we are faced with great trials. Often those trials are frustrating, unfortunate, or unfair. They seem to come exactly when we think we need them the least. The question is: Do we accept this as an exclusively negative event, or can we get past whatever negativity or adversity it represents and mount an offensive? Or more precisely, can we see that this “problem” presents an opportunity for a solution that we have long been waiting for? (101)
• Great commanders look for decision points. For it is bursts of energy directed at decisive points that break things wide open. They press and press and press and then, exactly when the situation seems hopeless—or, more likely, hopelessly deadlocked—they press once more.  (101)
• In many battles, as in life, the two opposing forces will often reach a point of mutual exhaustion. It’s the one who rises the next morning after a long day of fighting and rallies, instead of retreating—the one who says, I intend to attack and whip them right here and now—who will carry victory home . . . intelligently. (101)
• The obstacle is not only turned upside down but used as a catapult (102)

Prepare For None of It To Work

• In the meantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases.—Seneca (103)
• What we can’t do is control the world around us—not as much as we’d like to, anyway. We might perceive things well, then act rightly, and fail anyway. (103)
• some obstacles may turn out to be impossible to overcome.  (103)
• 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 it is just learning to accept that bad things happen, or practicing humility. (103)
• If there is nothing else you can do for yourself, at least you can try to help others. (103)
• We must be willing to roll the dice and lose (103)

3. Will (Inner Strength)

Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some semblance of control, will is what we depend on when control has slipped through our fingers.(105) 

The Will is our inner power. It’s not about how badly we want something, but rather about the strength to surrender and persevere;  “quiet humility, resilience, and flexibility.” (105)  The Will allows us to endure, contextualize, and find meaning in obstacles that we cannot directly overcome. 

Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power. 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. (105)

Key Principles of Will:

The Discipline of The Will

• Clearheadedness and action are not always enough… Some obstacles are beyond a snap of the fingers or novel solution. (107)
•  we need to be able to find a greater purpose in this suffering and handle it with firmness and forbearance. (107)
• 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. (108)
• If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always. (108)
• Will is fortitude and wisdom — not just about specific obstacles but about life itself and where the obstacles we are facing fit within it. (108)
•  It gives us ultimate strength. As in: the strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome (which, as it happens, is the way of flipping the unflippable). (108)
• Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit? (110)
• The will is the critical third discipline. 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. (110)
• It is also the most difficult of all the disciplines. It’s what allows us to stand undisturbed while others wilt and give in to disorder. Confident, calm, ready to work regardless of the conditions. Willing and able to continue, even during the unthinkable, even when our worst nightmares have come true. (110)
•  In every situation, we can always prepare ourselves for more difficult times, always accept what we’re unable to change, always manage our expectations, always persevere, always learn to love our fate and what happens to us, always protect our inner self, retreat into ourselves, always submit to a greater, larger cause, always remind ourselves of our own mortality, and, of course, prepare to start the cycle once more. (110) 

Build Your Inner Citadel

Developing inner strength is an ongoing process, not something you’re born with. You build this resilience by actively facing challenges and adversity, not shying away at the slightest whiff of difficulty. Think of how pressure strengthens a stone arch. Each challenge you overcome and every mistake you learn from acts as a training opportunity, helping to build a strong inner fortress that external adversity cannot break.

• If thy faint in the day of adversity, thy strength is small.—Proverbs  24:10
• We take weakness for granted. We assume that the way we’re born is the way we simply are, that our disadvantages are permanent. And then we atrophy from there. (112)
• Not everyone accepts their bad start in life. They remake their bodies and their lives with activities and exercise. They prepare themselves for the hard road. Do they hope they never have to walk it? Sure. But they are prepared for it in any case. (112)
• Nobody is born with a steel backbone. We have to forge that ourselves. (112)
• We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice (mens sana in corpore sano—sound mind in a strong body).  (112)
• the Inner Citadel, that fortress inside of us that no external adversity can ever break down. An important caveat is that we are not born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us. (112)
• You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is—at best—indifferent to your existence. (113)
• Whether we are born weak… or we are currently experiencing good times, we should always prepare for things to get tough. (113)
• No one is born a gladiator. No one is born with an Inner Citadel. If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built. (113)
• To be great at something takes practice. Obstacles and adversity are no different. Though it would be easier to sit back and enjoy a cushy modern life, the upside of preparation is that we’re not disposed to lose all of it—least of all our heads—when someone or something suddenly messes with our plans. (113)
• “The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted. (114)

Anticipation (Thinking Negatively) (Premeditatio Malorum)

• Prepare for inevitable setbacks through “premeditatio malorum” (premeditation of evils) (116), the Stoic practice of anticipating potential disruptions and failures to mitigate their impact.
• In a postmortem, doctors convene to examine the causes of a patient’s unexpected death so they can learn and improve for the next time a similar circumstance arises. Outside of the medical world, we call this a number of things—a debriefing, an exit interview, a wrap-up meeting, a review—but  whatever it’s called, the idea is the same: We’re examining the project in hindsight, after it happened. (115)
• A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. 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. (115)
• Your plan and the way things turn out rarely resemble each other. (115)
• “Nothing happens to the wise man against his expectation. . . nor do all things turn out for him as he wished but as he reckoned—and above all he reckoned that something could block his plans.” —Seneca (116)
• Always prepared for disruption, always working that disruption into our plans. Fitted, as they say, for defeat or victory (116)
• Your world is ruled by external factors. Promises aren’t kept. You don’t always get what is rightfully yours, even if you earned it. Not everything is as clean and straightforward as the games they play in business school.  Be prepared for this. (116)
• The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves. (116)
• It’s better to meditate on what could happen, to probe for weaknesses in our plans, so those inevitable failures can be correctly perceived, appropriately addressed, or simply endured. (117)
•  About the worst thing that can happen is not something going wrong, but something going wrong and catching you by surprise. Why? Because unexpected failure is discouraging and being beaten back hurts.  (117)

The Art of Acquiescence

You should embrace life’s constraints, not fight against them. They often push you to develop new skills and find opportunities you would have otherwise missed.

Some obstacles are completely outside your control. When you’ve done everything you can, there is only one option left: acceptance. Toughness, humility, and willpower are needed to accept things for what they are, not what you wish them to be. Any external event can be beneficial if you allow it to teach you a lesson. To succeed, you must play the cards you are dealt.

• The Fates guide the person who accepts them and hinder the person who resists them.—Cleanthes (119)
• It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued. Would we rather have everything? Sure, but that isn’t up to us. (119)
•  We have to allow some accidents to happen to us. (119)
• Clearheadedness and action are not always enough. Some obstacles are beyond a snap of the fingers or a novel solution.
• After you’ve distinguished between the things that are up to you and the things that aren’t (ta eph’hemin, ta ouk eph’hemin), and the break comes down to something you don’t control . . . you’ve got only one option: acceptance.(120)
•  When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence. Let’s be clear, that is not the same thing as giving up. This has nothing to do with action—this is for the things that are immune to action.  It is far easier to talk of the way things should be. It takes toughness, humility, and will to accept them for what they actually are. It takes a real man or woman to face necessity. (120)
• All external events can be equally beneficial to us because we can turn them all upside down and make use of them. They can teach us a lesson we were reluctant to otherwise learn. (120)
• Rarely do we consider how much worse things could have been. (121)
•  The ancients (and the not so ancients) used the word fate far more frequently than us because they were better acquainted with and exposed to how capricious and random the world could be. Events were considered to be the “will of the Gods.” The Fates were forces that shaped our lives and destinies, often not with much consent. (121)
• Letters used to be signed “Deo volente”—God willing. Because who knew what would happen?  (121)
•  If we want to use the metaphor that life is a game, it means playing the dice or the chips or the cards where they fall. Play it where it lies, a golfer would say. (122)

Love Everything That Happens (Amor Fati)

“Amor Fati”, which means “love of fate,” is a mindset where you don’t just accept what happens to you; you actively love it all, the good and the bad. This means facing everything with a positive attitude. It’s about changing your perspective from “I have to do this” to “I get to do this.” By doing this, you find value and opportunity even in bad luck, and you choose to feel good no matter what is going on around you.

• 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 (123)
•  loving whatever happens to us and facing it with unfailing cheerfulness. (124)
• It is the act of turning what we must do into what we get to do. (124)
• As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones. (125)
• For every situation, 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. (125)
• 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 can choose to render a good account of ourselves. If the event must occur, Amor fati (a love of fate) is the response. (125)
• It’s a little unnatural, I know, to feel gratitude for things we never wanted to happen in the first place. But we know, at this point, the opportunities and benefits that lie within adversities. We know that in overcoming them, we  emerge stronger, sharper, empowered. There is little reason to delay these feelings. To begrudgingly acknowledge later that it was for the best, when we could have felt that in advance because it was inevitable. (125-126)

Develop Perseverance

Remember this simple phrase from Stoic philosopher Epictetus: “Persist and resist.” Persist in your efforts and keep working toward your goals. Resist the urge to give in to distractions, discouragement, or chaos. The goal is to cultivate the staying power needed to overcome obstacles and see things through.

• Gentlemen, I am hardening on this enterprise. I repeat, I am now hardening towards this enterprise. —Winston Churchill (127)
• … persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs (127)
• … perseverance is something 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. (127)
• The Germans have a word for it: Sitzfleisch. Staying power. (127)
• 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. (128)
• “Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.” (128)
• They work in conjunction with each other. That Tennyson line in full: Made weak by time and fate, but strong in will/To strive, to seek, to find, and not to yield. (128)
• Persist and persevere. (128)
• Perseverance. Force of purpose. Indomitable will. (128)
• Our actions can be constrained, but our will can’t be. Our plans—even our bodies—can be broken. But belief in ourselves? (129)
• 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. (129)
• Determination, if you think about it, is invincible. Nothing other than death can prevent us from following Churchill’s old acronym: KBO. Keep Buggering On. (129)
• Hold on and hold steady. (129)

Serve Something Bigger Than Yourself

A key to finding strength is to focus on others, not just yourself. When you are going through a difficult time, you can find a way to use that situation to help others. This shared purpose gives you strength and a moral compass.

Focusing on others can actually help diminish your own fears and troubles. If you are stuck on a problem for yourself, ask how you can make the situation better for someone else. This shifts your thinking from “I, I, I” to “We’re in this together.” During a crisis, you have a huge opportunity to be a good example for others. By being strong for those around you, you become stronger yourself. 

• 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 (131)
• It is in this moment that we must show the true strength of will within us. (132)
• People are getting a little desperate. People might not show their best elements to you. 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. This is a tremendous opportunity for you, a young person, to be heroic.  —Henry Rollins (132)
•  When we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish. With fear or heartache no longer our primary concern, we don’t have time for it. Shared purpose gives us strength. (132)
• 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? (133)
•  How can we use this situation to benefit others? How can we salvage some good out of this? 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. (133)
• Stop making it harder on yourself by thinking about I, I, I. …You’ve inflated your own role and importance. Start thinking: Unity over Self. We’re in this together. (133)
• 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. (133)
•  No harshness, no deprivation, no toil should interfere with our empathy toward others. Compassion is always an option. Camaraderie as well. That’s a power of the will that can never be taken away, only relinquished. (133)
•  We’re not special or unique simply by virtue of being. We’re all, at varying points in our lives, the subject of random and often incomprehensible events. Reminding ourselves of this is another way of being a bit more selfless. (134)
• Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive, and in the process, inch the world forward a little bit. (134)
• “Lend a hand to others. Be strong for them, and it will make you stronger.” (135)

Meditate on Mortality (Memento Mori): 

• When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully. — Dr. Johnson (135)
• Death doesn’t make life pointless, but rather purposeful. (136)
• … one can meditate on death—be well aware of our own mortality—without being morbid or a downer.  (136)
• … embracing the precariousness of our own existence can be exhilarating and empowering. (136)
• Our fear of death is a looming obstacle in our lives. It shapes our decisions, our outlook, and our actions. (136)
•  Memento mori, the Romans would remind themselves. Remember you are mortal. (137)
•  The diagnosis is terminal for all of us. A death sentence has been decreed. Each second, probability is eating away at the chances that we’ll be alive tomorrow; something is coming and you’ll never be able to stop it. Be ready for when that day comes. (137)
• Remember the serenity prayer: If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things—it is not in our control how long we will live or what will come and take us from life. (137)
• Thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating. (137)
• Instead of denying — or worse, fearing — our mortality, we can embrace it. Reminding ourselves each day that we will die helps us treat our time as a gift. (137-138)
• 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. (138)
•  Death is the most universal of our obstacles. It’s the one we can do the least about… In the shadow of death, prioritization is easier. As are graciousness and appreciation and principles. Everything falls in its proper place and perspective. 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. (138)

Prepare To Start Again  

Nature never stops, and neither do obstacles. Just when you overcome one challenge, another one appears, and the more you accomplish, the bigger the challenges get.

The goal isn’t to reach a place with no obstacles; it’s to get used to the struggle and train for it.

• 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. (140)
• As the Haitian proverb puts it: Behind mountains are more mountains. Elysium is a myth. One does not overcome an obstacle to enter the land of  no obstacles. (140)
• … 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. (140)
• 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. (140)

Become a Philosopher of Action

The philosophy of turning obstacles into advantages isn’t merely theoretical; it demands application. Historical figures who practiced Stoicism were primarily “men of action,” not just thinkers. (146, 148) The most exemplary practitioners throughout history were leaders, innovators, entrepreneurs, and pioneers who faced extraordinary challenges head-on.

Prominent figures like Marcus Aurelius, Miyamoto Musashi, Rubin, “Hurrricane” Carter, Abraham Lincoln, Thomas Edison, John D. Rockefeller, Amelia Earhart, and George Washington weren’t just thinkers but doers who applied these ideas practically in their lives and endeavors. Whether consciously studying Stoicism or naturally embodying its principles, they demonstrated the ability to overcome immense challenges and thrive because of them, and to turn seemingly impossible challenges into opportunities.

Holiday offers the example of Samuel Zemurray, the immigrant banana magnate. In a race against the powerful United Fruit Company to acquire the same strategic piece of land in Central America (a key location for expanding banana operations and transport routes), Zemurray encountered a typical obstacle: conflicting ownership claims. Two separate local parties each insisted they owned the land. 

While United Fruit got bogged down in legal reviews and bureaucratic delays, Zemurray moved fast. He simply paid both parties, resolved the dispute himself, and secured the land. By doing this, he ensured zero delays in building the railroad, no ongoing legal disputes, and complete control over a strategic asset. What appeared to be a legal quagmire was, to him, just a solvable problem. 

Zemurray, the tiny, uneducated competitor, was outmatched, right? He couldn’t play their game. So he didn’t. Flexible, fluid and defiant, he just met separately with both of the supposed owners and bought the land from each of them. He paid twice, sure, but it was over. The land was his. Forget the rule book, settle the issue. (84)

He saw clearly, acted decisively, and turned complexity into opportunity; demonstrating precisely what it means to be a philosopher of action. Holiday highlights this story to show the mindset of a philosopher of action: Zemurray wasn’t interested in being right; he was interested in getting the job done.

“This is pragmatism embodied. Don’t worry about the “right” way, worry about the right way. This is how we get things done. Sometimes you do it this way. Sometimes that way. Not deploying the tactics you learned in school but adapting them to fit each and every situation. Any way that works—that’s the motto.” (85)

Most people overvalue being “correct” or “principled” in complex situations. Zemurray shows that sometimes the fastest path through an obstacle is to sidestep the entire debate and act decisively,  even if it means doing something unconventional or seemingly redundant.

Holiday observes:

“We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods. (85)

By applying these principles, individuals become “philosophers” not in an academic sense, but in a practical one. As Henry David Thoreau observed, “To be a philosopher… is to solve some of the problems of life, not only theoretically, but practically.” (146)

The ultimate goal is to “see things philosophically and act accordingly.” (148) Holiday provides the formula: “First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.” (143)

When we follow this path, we don’t just overcome obstacles; we transform ourselves into something greater through them.

My Critiques of The Obstacle Is the Way

Holiday’s book succeeds in making Stoicism accessible and action-oriented. But we need to wield its advice with intention, context, and care. Its power lies not in denying reality, but in facing it with courage, and ensuring that our victory over obstacles does not come at the cost of our humanity.

1. The Dark Side of Relentless Action

Holiday exalts clarity and decisive action as virtues, and rightly so. But in the wrong hands, those traits can mutate into ruthlessness, or worse, exploitation.

Take Sam Zemurray. Holiday presents him as the archetypal man of action;  someone who cuts through ambiguity and seizes opportunity. His bold move to buy land from all competing claimants, while United Fruit dithered, is a brilliant example of agile thinking.  

But later in life, Zemurray engineered a coup in Honduras (and Guatamela) to protect his business empire; destabilizing a government to serve a banana empire, at the expense of labor, economic development, and democracy in Latin America. 

His actions were undeniably effective. But they also crossed a moral boundary, revealing a darker consequence of unmoored pragmatism.

Stoicism, properly understood, isn’t amoral. Holiday’s own framework, see clearly, act correctly, endure and accept, contains a built-in ethical governor: act correctly. But the book often emphasizes effectiveness over ethical reflection. The danger isn’t in Stoicism itself, but in selective Stoicism, stripped of virtue and wielded purely as a power tool.

The path of the philosopher of action must be rooted not just in results, but in right action. Obstacles can be a crucible for greatness, but that greatness must be ethical, not merely strategic.

2. The Risk of Toxic Positivity

Holiday’s core message, turn every obstacle into an advantage, can be motivating. But taken too literally or too broadly, it can become a form of toxic positivity, flirting with a kind of Stoic optimism that can become dismissive.

Not all problems are growth opportunities. Some are tragedies. Some are injustices. Grief, illness, systemic oppression: these don’t call for some superhuman Stoic transformation. They may call for mourning, resistance, or simply space to endure.

In its most rigid application, this mindset can invalidate legitimate suffering; implying that failure to “transform” hardship is a personal shortcoming, rather than a reflection of reality’s difficulty. It can unintentionally shame people for experiencing legitimate hardship, or push them toward emotional suppression in the name of “resilience.” It risks replacing depth with denial, turning Stoicism into just another performance of invulnerability.

The original Stoics were no strangers to suffering. Marcus Aurelius lost children, ruled during plague, and still wrote with compassion. Seneca, in his letters, acknowledges grief and weakness; not as failures, but as conditions to be lived with integrity.

Obstacles are not always advantages in disguise. But they can still be companions on the path, teaching patience, humility, or solidarity, rather than triumph. A more humane reading of Holiday’s philosophy allows for both struggle and strength, breakdown and breakthrough.

Actionable Advice

• Love the obstacle; not just tolerate it: Most advice tells you to “push through” hardship. Holiday, via Marcus Aurelius, says you should love the obstacle, even thank it. The shift from resistance to embrace reconditions your mindset. You’re no longer a victim or a fighter; you become an alchemist, turning obstacles into assets. When a problem arises (bad traffic, critical feedback, project failure), literally say to yourself: “Good. This is fuel. Let’s see what I can do with it.” This reframes frustration into curiosity.
• Practice voluntary hardship, before it’s needed: Most people prepare for success; Stoics prepare for failure. Holiday champions premeditatio malorum (premeditation of evils). Regularly introduce minor discomforts into your routine (cold showers, fasting, difficult exercise) and delay gratification to build your tolerance for adversity and reduce fear of future obstacles. When real hardship hits, you’ll have emotional muscle memory.
• Use inaction as power: Action bias (always doing something) is celebrated. Yet, there is power in stillness, pause, and waiting for the right moment. Overreacting or over-managing often compounds problems. Strategic restraint is a Stoic power move. For instance, when provoked,  (by an email, social media, a colleague, or a family drama, etc) do nothing for 24 hours. Let emotions cool. Decide with reason, not impulse.
• Detach from outcomes; even your goals. Goal-setting culture worships “visualizing success.” Holiday argues for indifference to the outcome. Focus on the process and let the result go. Over-attachment to a goal breeds anxiety and poor judgment. Stoic detachment lets you show up fully without ego-driven desperation. On a big project or personal ambition, write down the goal. Then cross it out and write: “What’s in my control? I’ll do only that.” Repeat this during key moments of doubt.
• Turn personal loss into public service: Holiday emphasizes using pain as fuel for others’ benefit. Transforming suffering into purpose restores agency. It keeps you from being crushed by misfortune. Take one recent setback, professional or personal, and ask: “How could this be useful to someone else?” 

Conclusion

Holiday’s The Obstacle Is the Way offers a framework for transforming adversity into advantage through the ancient Stoic disciplines of perception, action, and will. The book argues that this Stoic philosophy, practiced by figures like Marcus Aurelius, Abraham Lincoln, and Steve Jobs, offers a timeless formula for success, which boils down to: 

“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.” (145)

This philosophy teaches us to approach challenges with the fluidity that Bruce Lee described: 

Empty your mind, be formless. Shapeless, like water. If you put water into a cup, it becomes the cup. You put water into a bottle and it becomes the bottle. You put it in a teapot, it becomes the teapot. Now, water can flow or it can crash. Be water, my friend.

“Be water, my friend” — shapeless and adaptable, able to flow around obstacles or crash through them as circumstances demand. By learning to see obstacles as opportunities, taking disciplined action in the present moment, and cultivating inner strength that no external force can touch, we can turn life’s inevitable challenges into the very path of our growth.

Yet this philosophy demands careful application. Its emphasis on relentless action and transformation must be tempered with genuine compassion for legitimate suffering and grounded in ethical principles that prioritize right action over mere effectiveness. 

The book’s power lies not in promising an obstacle-free existence, but in preparing us to see things clearly, to explore every option, to develop an inner sense of strength and fortitude, and to transform what can’t be changed. When wielded with wisdom and humility, Holiday’s modern interpretation of Stoicism becomes not just a strategy for overcoming challenges, but a blueprint for living with purpose, resilience, and integrity in an unpredictable world; flowing like water through whatever container life provides.

Recommended Reading

• Meditations, by Marcus Aurelius
• Man’s Search for Meaning by Viktor E. Frankl
• Antifragile, by Nassim Nicholas Taleb
• Ego is the Enemy by Ryan Holiday

Appendix

Supporting Examples and Anecdotes

• Marcus Aurelius: His life as emperor, facing numerous crises, is the primary example of applying the philosophy.
• John D. Rockefeller: His calm demeanor during economic crises and ability to see opportunity while others panicked.
• Rubin “Hurricane” Carter: His defiance and purposeful use of time while wrongly imprisoned.
• Miyamoto Musashi: His distinction between observing and perceiving eyes in combat.
• George Clooney: His shift in perspective regarding auditions.
• Tommy John: “Bionic Man”. His focus on the possibility of a chance to succeed.
• Steve Jobs: His “reality distortion field” and aggressive view of possibilities.
• Demosthenes: His rigorous exercises to overcome a speech impediment.
• Theodore Roosevelt: His determination to overcome asthma through physical training.
• Amelia Earhart: Her willingness to take an imperfect opportunity in aviation.
• Ulysses S. Grant: His persistence in taking Vicksburg and discovering a new strategy.
• James Pollard Espy: His mastery of meteorology through process.
• James Garfield: His pride in doing simple tasks well, such as being a janitor.
• Sam Zemurray: His pragmatic approach to acquiring land for banana plantations.
• Richard Wright: His clever method for accessing banned books in the Jim Crow South.
• George Washington: His wily and evasive tactics in the Revolutionary War.
• Gandhi and Martin Luther King, Jr: His use of non-violent resistance, leveraging the opponent’s actions.
• The Russians (vs. Napoleon and Nazis): Using the harsh winter as a defense.
• Arthur Ashe: Channeling emotional energy into his tennis game.
• Abraham Lincoln: His ability to lead despite battling lifelong depression.
• Thomas Jefferson: Channeling his energy into writing due to a perceived speech impediment.
• Thomas Edison and Helen Keller: Overcoming sensory limitations.
• George Washington and Eisenhower: Acknowledging external forces while still taking action.
• Jack Johnson: His “love of fate” and cheerful demeanor during a hostile fight.
• Odysseus: His long journey home, filled with constant obstacles requiring perseverance.
• James Stockdale: His leadership and focus on others as a POW.