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. – Marcus Aurelius from The Obstacle is the Way

Right in the preface of The Obstacle is the Way author Ryan Holiday sets the tone for the book. You can tell this is not going to be some fluffy book that gets you to regress to former pains and work through them. You’re going to be told to look at them head on and alter your perception of them.

In fact, this first quote in the preface made me think again of my favourite quotes from Jeff Goins and Chuck Swindoll.

Sometimes the route to our purpose is a chaotic experience, and how we respond matters more than what happens. – The Art of Work by Jeff Goins

Life is 10% what happens to you and 90% how you react to it. – Chuck Swindoll

I admit I didn’t realize it before reading The Obstacle is the Way but both Goins and Swindoll are channeling the essence of Stoic Philosophy in these quotes.

For those unfamiliar with, but interested in, The Stoics, this book is for you because the whole point of The Obstacle is the Way is to share the teaching of the Stoics in a bit more up-to-date manner.

This book will share with you their collective wisdom in order to help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles. Physical obstacles. Emotional obstacles. Perceived obstacles.

This is not a book for those who want to blame someone else for their problems. It’s not for someone who’s happy to accept handouts while not looking for work. It’s not for someone who’s content living a mediocre life with mediocre results. This is a book for those who want to face their problems head on because they know on the other side of that challenge or fear is the goal they want to achieve. This is for the pragmatic, down-to-earth among us who love to think but don’t stand around with their heads in the clouds.

So this will be a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck, unfucked, and unleashed. How to turn the many negative situations we encounter in our lives into positive ones — or at least to snatch whatever benefit we can from them. To steal good fortune from misfortune.

Holiday divides the book into three broad sections which cover, he asserts, the three critical steps you need to overcome obstacles. He calls them Perception, Action and the Will.


WHAT IS PERCEPTION? It’s how we see and understand what occurs around us — and what we decide those events will mean.

I think the key point, and a recurring theme in much of my reading, comes at the end of that sentence. It’s an acknowledgement that we choose what events in our life mean.

You can see this evidenced when you talk to two business people in the same town offering similar services. Often you’ll hear from one that business is not going great and no one really needs their services anymore. Talk to the other and you’ll hear that they’ve never been busier and they wish they could serve everyone around them.

What’s the difference? Simply the perception of the situation. Your perception reflects your reality. If everything is going against you and it’s all bad all the time, then of course the day you get a flat tire you’ll view it as another cosmic punch from some being that is laughing at your hardship. If things are going good, that flat tire will simply be something that happened and needs to be dealt with. Maybe you’ll even make a business deal with the tire repair shop.

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.

Control is another strong theme in the first section of the book (Perception) and a strong theme throughout Stoic Philosophy. When that tire situation happens to you do you fly off the handle and rage about the injustice of it all? Do you let out a sigh and then calmly pull out your phone to call someone to tow you? Which person do you think seems more in control of the situation? Which one do you think is going to make more effective decisions in their business?

The person with control.

Regardless of how much actual danger we’re in, stress puts us at the potential whim of our baser—fearful—instinctual reactions.

Don’t think for a second that grace and poise and serenity are soft attributes of some aristocrat. Ultimately, nerve is a matter of defiance and control.

This control must exist in a world where everything doesn’t go to plan. Where we have events outside our control. To the Stoics this would be the will of the gods which could be fickle and mean. While you may not believe in those beings of lore you have to admit that the world is a place of randomness.

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. Some of us almost crave sounding the alarm, because it’s easier than dealing with whatever is staring us in the face.

One of the best pieces of fiction I’ve ever read has the main character exuding this control in what would be extreme odds. Of course, I’m referring to The Martian where our protagonist, Mark, is left on Mars to fend for himself with not enough food to last until help arrives, and tools that weren’t made to last much past the 90-day mission. From having part of his structure blow off with him inside to short-circuiting his only line of communication to Earth, Mark continually lets that momentary freak-out happen then takes a deep breath and deals with the situation as it stands. Calm and in control and solving one little step at a time.

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Also similar is the admonition in The Hitchhikers Guide to the Galaxy: DON’T PANIC.

Perception is all about that control in all situations. Take that second but then move into calm control so that you can move on to the next section of the book…action.


But you, when you’re dealt a bad hand. What’s your response? Do you fold? Or do you play it for all you’ve got?

Action is the next step from Perception. It’s not enough to not freak out — you actually have to move forward towards goals with the same level of calm with which you perceived the situation.

The opposite of action is knowing what the solution is but then sitting there doing nothing because nothing is easier. If we take action we risk failure. In that failure we fear what others may say about us.

But in our lives, when our worst instincts are in control, we dally. We don’t act like Demosthenes, we act frail and are powerless to make ourselves better. We may be able to articulate a problem, even potential solutions, but then weeks, months, or sometimes years later, the problem is still there. Or it’s gotten worse. As though we expect someone else to handle it, as though we honestly believe that there is a chance of obstacles unobstacling themselves.

Reading that now we smile at the absurdity of anyone who would think an obstacle would ‘unobstacle’ itself and yet consultants put off that painful email to a client when they’re behind. They wait months to invoice someone because they’re afraid of what the client will say. At work, you simply complain about a situation because it’s easier than doing anything about it.

We so often sit quietly looking at that obstacle hoping it just goes away and when confronted by it without some place to hide we will deal with it, but not until then.

No one is saying you can’t take a minute to think, Dammit this sucks. By all means, vent. Exhale. Take stock. Just don’t take too long. Because you have to get back to work. Because each obstacle we overcome makes us stronger for the next one.


No. No excuses. No exceptions. No way around it: It’s on you.

The truly successful people you look up to go through the same challenges as you, or they went through them on the way to where they are now. When you sit down with anyone successful and really probe you’ll find fail products, bankruptcy, failed relationships. They took time to say the situation sucked but they didn’t stop. Like a large rock rolling downhill, they kept going towards their goal. They tried another path, took a road less traveled or bushwhacked their way through a path everyone said was impossible.

If you’re not willing to take that path, or forge your own, don’t expect to get the outsized results of the people you look up to.

So when you’re frustrated in pursuit of your own goals, don’t sit there and complain that you don’t have what you want or that the obstacle won’t budge. If you haven’t even tried yet, then of course you will still be in the exact same place. You haven’t actually pursued anything.

You need to risk that failure to get those rewards. If you don’t put all your proverbial chips on the table, then you can’t expect any return. Well maybe I should change how I said that. You shouldn’t expect any return. Many people today expect that simply going to school like everyone else should get them that huge paying job some guidance counsellor promised them in high school. So they took the safe path with everyone else. They took on debt and spent years trying to find themselves in the most expensive way possible.

Then when faced with their decisions in the form of loan bills they complain that the future they thought was coming is already full. All the others around them are vying for the same jobs with similar resumes in the same suit or dress and yet for some reason the mediocre effort with no risk should be rewarded with huge benefits.

Yet nothing was risked. This is their first experience of failure and many never get the chance to learn from it as family save them from dealing with any failure in the past.

But it’s no joke. Failure 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.

In your action, which problems will you turn into opportunities? Going through this process over and over is what will bring you success in your business and life. Thinking it’s going to be smooth sailing is a faulty assumption that’s simply going to put you years behind those who face adversity head on and deal with the world as it is, complete with the problems. They just keep taking action instead of complaining about how things are.

Complaining gets you nowhere — action does. But more than action is a force of will. To repeatedly try new ways to get to your goal despite setbacks. Which brings us to the third section of the book…Will


…the will is the critical third discipline. We can think, act, and finally adjust to a world that is inherently unpredictable. The will prepares us for this, protects us against it, and allows us to be happy and thrive in spit of it. 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. Willing and able to continue, even during the unthinkable, even when our worst nightmares have become true.

It could always get worse. Whatever you’re dealing with, there is always another step lower down, or many steps lower down. Is the budget tight this month and you need new shoes? You do have a house over your head and you’re sitting here on an Internet connected device reading a website in your leisure time instead of heading to your third job of the day.

It’s hard to see that though, in the midst of the very real problems we’ve all got going on. Too many of us revert to that inner five-year-old that sees the loss of a special paper plate as a cause to leave the family because nothing in the world could be worse.

This view that we can simply walk away from what troubles us if the problem gets too big is the opposite of a strong Will. Will keeps going. Like water encountering a rock will find a way around over years of relentless pounding, so the Will keeps pushing against the troubles until a solution is found.

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.

I think that this idea of a premortem is one of the key takeaways in our third section of the book. Going through this process will help make our ideas much more likely to succeed as we work through each section of failure and do our best to mitigate the effect that a point of failure can have on our overall idea.

All too often we simply assume that if we build something and tell a few people about it our ideal will be the next big thing. We tie so much of our self-worth up in that successful launch as well and when it does fail we’re personally devastated.

Assigning our personal worth to an idea and letting its failure affect us for more than a moment is a failure of will. It’s a failure of stepping back and objectively looking at the way the world is, accepting it and having a plan to deal with it. The failure of an idea is nothing more than life telling us to not pursue that idea at this time, in this way, with these people.

If someone we know took traffic signals personal, we would judge them insane.

Yet this is exactly what life is doing to us. It tells us to come to a stop here. Or that some intersection is blocked or that a particular road has been rerouted through an inconvenient detour. We can argue or yell this problem away. We simply accept it.

This is not to say we allow it to prevent us from reaching our ultimate destination. But it does change the way we travel to get there and the duration of the trip.

These three ideas of Perception, Action and Will are so tightly tied together it’s hard to separate them. Indeed the message in this book often feels repetitive, just like above. This harkens back to the ideas in the section on Perception around how we decide to let a situation affect us. We could yell, or we could just shrug and take the new direction that’s left to us.

Strength of Will is tied up in Perception so tightly they are almost indistinguishable. Perception is how we deal with round one in our fight. Action is heading into round two and round three. Will is still being around in round 90.

If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after — and then the fight after that and the fight after that, until the end.

Just because we have one success doesn’t mean we’ll roll into another one. And Will is what gets us back up and gets us to give it another try.

We idolize that strength of Will but do we actually train for it at all? Do our schools spend any time really developing Will in someone? Is there even a way? I’m not sure, but I’d hazard a guess that we can train into this by simply being held to our word from a young age and then needing to meet the expectations we set for ourselves with what we said we’d do. We need to stop giving people a pass. If you said you’d do A and then didn’t quite do A, you lied. You didn’t live up to your word. We can do more for the character development of those we love by calling them out in those times than by simply overlooking it and hoping that they learn from the experience.


Did the book accomplish its purpose of channeling the Stoics into things a bit more easily digested by those around today? I don’t know Stoic philosophy enough to say for sure, actually. Did I get a bunch out of this book to move forward and be a better person who’s growing in life?

Emphatically YES!

The collection of short essays found in The Obstacle is the Way should be required reading for anyone who wants to get an idea out in the world. If you want to be a leader or entrepreneur read this book and start girding yourself for the inevitable issues life is going to throw your way.

Get The Obstacle is the Way on Amazon.

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