This is the best and by far the most useful book I’ve read in a long time. It’s roughly based on the Stoic philosophers (Marcus Aurelius, Seneca, Epictetus). (*) It is a pleasingly quick, light, and breezy read particularly for something which may contain the secret of life! Against it are the facts that the author can be a little bit bombastic, a little on the breezy side, and sometimes speak in slightly too general terms, giving it the feel of platitudes. Also, he’s occasionally guilty of violating #13 in Twain’s Rules governing literary art: “Use the right word, not its second cousin.”

But these are pretty tiny quibbles. Overall, this stuff is pure gold, for success in anything (including and particular life).
My father told me that “attitude is everything”. As I go on, I realise he was much righter than I (or perhaps even he) ever knew.
I’m leaving out (with a few tiny exceptions) all of the wonderful examples from the lives of the famous and less-famous and the rest of us, that Holiday uses to illustrate his principles and just cutting to the principles. I know this is going to make it sound more platitudinous, and ungrounded. So I’d probably encourage everyone who lives in the world to pick up a copy of this amazing book. (Excepting those of you who know all this stuff already and it seems as if nearly everyone was way ahead of me!)
PREFACE
What Marcus Aurelius wrote is undoubtedly one of history’s most effective formulas for overcoming every negative situation we may encounter in life. A formula for thriving not just in spite whatever happens but because of it.
It turns out that this wisdom is a remarkable constant down through the ages. It is the driving force of self-made men and the succor to those in positions with great responsibility and great trouble all those who have had to confront obstacles and struggle to overcome them. That struggle is the one constant in all of their lives.
We are the rightful heirs of this tradition. It’s our birthright. Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them? We might not be emperors, but the world is still constantly testing us. It asks: Are you worthy?
INTRODUCTION
This obstacle this frustrating, unfortunate, problematic, unexpected problem preventing you from doing what you want to do. What if embedded inside it or inherent in it were certain benefits benefits only for you?
We’re dissatisfied with our jobs, our relationships, our place in the world. We’re trying to get somewhere, but something stands in the way. So we do nothing. When really only one thing is at fault: our attitude and approach.
On the other hand, not everyone is paralyzed. We watch in awe as some seem to turn those very obsrtacles, which stymie us, into launching pads for themselves. What do they have that we lack? It’s simple: a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.
As it turns out, this is one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition. Every impediment only served to make the inferno within them burn with greater ferocity.
The ancient Stoics had the ability to see obstacles for what they were, the ingenuity to tackle them, and the will to endure a world mostly beyond their comprehension and control.
THE OBSTACLES THAT LIE BEFORE US
All great victories involved solving vexing problems. When you have a goal, obstacles are actually teaching you how to get where you want to go.
THE WAY THROUGH THEM
Overcoming obstacles is a discipline of three critical steps: Perception, Action, and the Will.
PERCEPTION
What is perception? It’s how we see and understand what occurs around us and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness.
THE DISCIPLINE OF PERCEPTION
You will come across obstacles in life fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure. You will learn that this reaction determines how successful we will be. (*)
Desperation, despair, fear, powerlessness these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings.
Seen properly, everything that happens be it an economic crash or a personal tragedy is a chance to move forward. We must try:
- To choose to see the good in a situation
- To steady our nerves
- To focus on what can be controlled
RECOGNIZE YOUR POWER
We decide what we will make of each and every situation. They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions. “Nothing either good or bad, but thinking makes it so,” as Shakespeare put it.
There is the event itself and the story we tell ourselves about what it means. That’s a thought that changes everything, doesn’t it? Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. We decide what story to tell ourselves.
STEADY YOUR NERVES
When we aim high, pressure and stress obligingly come along for the ride. Surprises are almost guaranteed. In these situations, talent is not the most sought-after characteristic. Grace and poise are.
CONTROL YOUR EMOTIONS
Welcome to the source of most of our problems down here on Earth. Everything is planned down to the letter, then something goes wrong and the first thing we do is trade in our plan for a good ol‘ emotional freak-out. (*)
This is the skill that must be cultivated freedom from disturbance and perturbation so you can focus your energy exclusively on solving problems.
ALTER YOUR PERSPECTIVE
The fundamental notion that girds not just Stoic philosophy but cognitive psychology: Perspective is everything. (*)
IS IT UP TO YOU?
So what if you focused on what you can change? To argue, to complain, or worse, to just give up, these are choices. Choices that more often than not, do nothing to get us across the finish line.
THINK DIFFERENTLY
Having learned early in life that reality was falsely hemmed in by rules and compromises that people had been taught as children, Steve 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. (*)
Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself.
FINDING THE OPPORTUNITY
It’s one thing not to be overwhelmed by obstacles. After you have controlled your emotions, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it.
PREPARE TO ACT
Problems are rarely as bad as we think or rather, they are precisely as bad as we think. The worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems. (*)
What is action? Action requires courage. Our movements and decisions define us. Action is the solution and the cure to our predicaments.
THE DISCIPLINE OF ACTION
We forget: 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. No excuses. No exceptions. No way around it: It’s on you.
GET MOVING
But we fear taking action that is too risky. 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.
Now let’s say you’ve gotten started. Fantastic. But let’s ask an honest question: Could you be doing more? You probably could there’s always more. At minimum, you could be trying harder. Your full effort isn’t in it. Is that going to affect your results? No question.
The next step: ramming your feet into the stirrups and really going for it. You always need to be moving forward. Stay moving, always.
PRACTICE PERSISTENCE
In persistence, Grant had not only broken through: In trying all the wrong ways, he discovered a totally new way the way that would eventually win the war. Grant’s story is not the exception to the rule. It is the rule. This is how innovation works.
Proving that genius often really is just persistence in disguise. In applying the entirety of his physical and mental energies in never growing weary or giving up Edison had outlasted impatient competitors, investors, and the press to discover the power to illuminate the world. (*)
Too many people think that great victories like Grant’s and Edison’s came from a flash of insight. That they cracked the problem with pure genius. But their genius was in unity of purpose, deafness to doubt, and the desire to stay with it. Working at it works. It’s that simple. (But again, not easy.)
Remember a phrase favored by Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.
It’s supposed to be hard. Your first attempts aren’t going to work.
ITERATE
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.
Failure puts you in corners you have to think your way out of. This is why stories of great success are often preceded by epic failure because the people in them went back to the drawing board.
It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something. Listen.
FOLLOW THE PROCESS
How often do we compromise or settle because we feel that the real solution is too ambitious or outside our grasp? How often do we assume that change is impossible because it’s too big?
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.
DO YOUR JOB, DO IT RIGHT
Sometimes, on the road to where we are going or where we want to be, we have to do things that we’d rather not do 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.
Everything we do matters. Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires. Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty.
Each project matters, and the only degrading part is giving less than one is capable of giving. To whatever we face, our job is to respond with:
- hard work
- honesty
- helping others as best we can
The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is someone else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions.
WHAT’S RIGHT IS WHAT WORKS
You’ve got your mission, whatever it is. To accomplish it, like the rest of us you’re in the pinch between the way you wish things were and the way they actually are. (*)
IN PRAISE OF THE FLANK ATTACK
In only 6 of the 280 campaigns studied was the decisive victory a result of a direct attack on the enemy’s main army. That’s 2 percent. 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.
Take a step back, then go around the problem. Find some leverage.
If we’re starting from scratch and the established players have had time to build up their defenses, there is just no way we are going to beat them on their strengths.
Part of the reason why a certain skill often seems so effortless for great masters is not just because they’ve mastered the process they really are doing less than the rest of us who don’t know any better. They choose to exert only calculated force where it will be effective. (*)
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.
Don’t waste your energy in battles driven by ego and pride rather than tactical advantage.
USE OBSTACLES AGAINST THEMSELVES
Gandhi didn’t fight for independence for India. The British Empire did all of the fighting and, as it happens, all of the losing. Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you.
Martin Luther King Jr. told his followers that in the face of violence they would be peaceful, to hate they would answer with love.
Just ask the Russians, who defeated Napoleon 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 and in battles far from home.
Sometimes in life you need to have patience wait for temporary obstacles to fizzle out. Let two jousting egos sort themselves out instead of jumping immediately into the fray.
SEIZE THE OFFENSIVE
If you think it’s simply enough to take advantage of the opportunities that arise in your life, you will fall short of greatness. What you must do is learn how to press forward precisely when everyone around you sees disaster.
Ordinary people shy away from negative situations. What great people do is the opposite. They are their best in these situations. They turn personal tragedy or misfortune really anything, everything to their advantage. But this crisis in front of you? You’re wasting it feeling sorry for yourself, feeling tired or disappointed.
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?
Great commanders look for decision points. For it is bursts of energy directed at decisive points that break things wide open.
PREPARE FOR NONE OF IT TO WORK
We can always think clearly, respond creatively. What we can’t do is control the world around us. We might perceive things well, then act rightly, and fail anyway. Some obstacles may turn out to be impossible to overcome.
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.
It’s an infinitely elastic formula: In every situation, that which blocks our path actually presents a new path.
THE DISCIPLINE OF THE WILL
If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and soul. The will is the one thing we control completely, always.
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.
BUILD YOUR INNER CITADEL
Are you prepared? Could you actually handle yourself if things suddenly got worse? (*)
Remake your bodies and your lives with activities and exercise. Prepare yourselves for the hard road.
Nobody is born with a steel backbone. We have to forge that ourselves. We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice.
It is said of the Jews, deprived of a stable homeland for so long, their temples destroyed, and their communities in the Diaspora, that they were forced to rebuild not physically but within their minds.
To Roosevelt, life was like an arena. To survive, he needed to be strong, resilient, fearless, ready for anything. (*)
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.
To be great at something takes practice. Obstacles and adversity are no different.
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.
ANTICIPATION (THINKING NEGATIVELY)
Far too many people don’t have a backup plan.
Always prepare for disruption, always work that disruption into your plans.
And in the case where nothing can be done: manage expectations. Because sometimes the only answer to “What if…” is, It will suck but we’ll be okay.
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. We are dependent on other people. If this comes as a constant surprise each and every time it occurs, you’re not only going to be miserable, you’re going to have a much harder time accepting it and moving on to attempts number two, three, and four. (*)
THE ART OF ACQUIESCENCE
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. Would we rather have everything? Sure, but that isn’t up to us.
You know you’re not the only one who has to accept things you don’t necessarily like, right? It’s part of the human condition. If someone we knew took traffic signals personally, we would judge them insane.
You don’t have to like something to master it or to use it to some advantage. 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.
LOVE EVERYTHING THAT HAPPENS (AMOR FATI)
To do great things, we need to be able to endure tragedy and setbacks. We have to learn to find joy in every single thing that happens loving whatever happens to us and facing it with unfailing cheerfulness.
We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good? (*)
We know, 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.
You love it because it’s all fuel.
PERSEVERANCE
If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then perseverance is something larger. It’s the long game the fight after the fight, and the fight after that.
What’s required of us is a determination that we will get to where we need to go, somehow, some way, and nothing will stop us.
There are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events.
The good thing about perseverance is that it can’t be stopped by anything besides death.
Our actions can be constrained, but our will can’t be. Our plans even our bodies can be broken. But belief in ourselves? No matter how many times we are thrown back, we alone retain the power to decide to go once more. Determination, if you think about it, is invincible. (*)
SOMETHING BIGGER THAN YOURSELF (*)
When we focus on others, our own personal fears and troubles will diminish. Shared purpose gives us strength. Because now we have something to do. We’re going to be of service to others.
Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.
MEDITATE ON YOUR OWN MORTALITY
Death doesn’t make life pointless, but rather purposeful. Embracing the precariousness of our own existence can be exhilarating and empowering.
We forget how light our grip on life really is. Otherwise, we wouldn’t spend so much time obsessing over trivialities, or trying to become famous, make more money than we could ever spend in our lifetime, or make plans far off in the future.
It doesn’t matter who you are or how many things you have left to be done, somewhere there is someone who would kill you for a thousand dollars or for a vile of crack or for getting in their way.
What would I change about my life if the doctor told me I have cancer? We comfort ourselves with, Well, thank God I don’t have cancer. But we do. The diagnosis is terminal for all of us. 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.
Reminding ourselves of this helps us treat our time as a gift. Someone on a deadline doesn’t waste time complaining about how he’d like things to be.
In the shadow of death, prioritization is easier. As are graciousness and appreciation and principles. Death chides us that we may as well do life right.
PREPARE TO START AGAIN
The great law of nature is that it never stops. There is no end. (*)
Life is a process of breaking through impediments. Each time, you’ll learn something. Each time, you’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you.
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. (*) There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.
Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Flipping the obstacles life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round.
FINAL THOUGHTS
Yes, it’s unlikely that anyone is going to make an armed run at our throne anytime soon. But people will make pointed remarks. They will cut us off in traffic. (*) Our rivals will steal our business. We will be hurt. Forces will try to hold us back. Bad stuff will happen. We can turn this to our advantage. Always. It is an opportunity. Always. And if our only option is simply to be a good person and practice forgiveness? Well, that’s still a pretty good option.
Not everyone looks at obstacles and sees reasons to despair. They see a chance to test and improve themselves. It is so much better to be this way, isn’t it? There is a lightness and a flexibility to this approach that seem very different from how we and most people choose to live. With our disappointments and resentments and frustrations.
- First, see clearly.
- Next, act correctly.
- Finally, endure and accept the world as it is.
Of course, it is not enough to simply read this or say it. We must practice these maxims, rolling them over and over in our minds and acting on them until they become muscle memory. So that under pressure and trials we get better become better people, leaders, and thinkers.
But don’t worry, you’re prepared for this now. You understand the process. You are schooled in the art of managing your perceptions and impressions. You’re cool under fire. You see opportunity in the darkest of places. You are able to direct your actions with energy and persistence. You assume responsibility for yourself teaching yourself, and pursuing your rightful place in the world. You are iron-spined and possess a great and powerful will. You realize that life is a trial. It will not be easy, but you are prepared to give it everything you have regardless, ready to endure, persevere, and inspire others.
Reviewing all this, I think my conclusion is that this book is profoundly wise.
And its title is actually my new mantra. It seems to encapsulate the core lesson perfectly. Now, every time something goes not quite right, I say it aloud “the obstacle is the way!” reminding myself that every obstacle contains an opportunity, and it is totally our choice whether we regard it that way or not. And with this as your mantra, when you remember to look for the advantage in every little bit of adversity… you are very nearly unstoppable. At the very least, you have a gigantic leg up on the universe.
Here, not very incidentally, is why this stuff is so interesting and important to me: Basically, I have gone through the vast majority of my time on Earth with extremely poor skills for dealing with adversity and it is adversity that turns out to be one of life’s few real universals. Generally, my historical pattern has been to collapse into a puddle of uselessness at life’s most minor hiccups. (I’d get back up again, but sometimes not for weeks. And usually not without believing for a while that I was done for good.) And what I am only now starting to realise is how very, very, very crippling a handicap in life this has been. I’ve lacked what turns out to be perhaps the greatest skill in life: dealing with adversity, the one human universal.
There are many formulations of the principle. Where I ultimately really got it from, actually, was from reading and writing obsessively about the military world’s special operators for whom RESOLVE and resilience are their unfailing guiding principles. (I’m going to write more about that tomorrow, as the topic deserves to be above the fold.)
Anyway, as I noted yesterday, most of what I’m doing right this second in life is trying to get two things right. This here is the second one. (And it is probably the work of a lifetime.) (*)

Whom I now realise that I, and I expect most people, have been misunderstanding all this time. Stoic philosophy is not, by any means, simply about enduring suffering with a stiff upper lip. It is about perceiving the world clearly; recognising what is in, and what is outside, of our control; remembering what’s important not as much as we think; mastering the self and overcoming unhelpful and destructive emotions; and finally acting, where one can act effectively and honourably and in accordance with virtue and duty and letting the rest go with grace.

Hi there!

“Attitude is everything.” - Rich Fuchs

Anyone who has known me over the years will be familiar with the emotional freak-out. See the section following the excerpts, on my personal history with (or, rather, without) these principles.

“Reality is negotiable.” - Tim Ferris

Holiday actually borrows directly from Edison himself here: “The first requisite for success is the ability to apply your physical and mental energies to one problem incessantly without growing weary.”

The source of all drama: conflict between man and the world, between man and other men, between man and himself. (See the very last section below!)

What Tim Ferris calls “minimum effective dose”.

For many years, I always said I could deal with anything as long as all the various aspects of my life were always on a general upward trajectory. Ha!

Teddy R’s famous Man In the Arena passage: “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

“Character consists of what you do on the third and fourth tries.” - James A. Michener

Pretty damned liberating thought, no?

“Nothing in the world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan Press On! has solved and always will solve the problems of the human race.” - Calvin Coolidge

“Today’s subforties have very different horrors, prominent among which are anomie and solipsism and a peculiarly American loneliness: the prospect of dying without even once having loved something more than yourself.” - David Foster Wallace

“When you get back from the gym, you must immediately pack your kitbag for the next time. Because it doesn’t end. It never ends.” - Tony Parsons

Oh, boy, is this an excellent lesson for me to learn! (I spent ten years trying to get published, thinking that would permanently fix everything in my life!)

This Is Water, anyone?

Oh and the two things are not necessarily unconnected! This is actually the really amazing bit. I’ve realised that it may be this universal principle that we must all struggle to become our best selves in order to complete our quests and get where we are going which is also the great secret and ultimate archetype at the core of all good storytelling. Talk about seeing “behind the veil”!