The Obstacle Is The Way: Notes

The timeless art of turning trials into triumphs

This was my first real introduction to the philosophy of Stoicism. Having heard a lot about it from the Tim Ferriss Podcast, I was eager to dive deeper into it. This book was a great place to start, as it delivers clear and actionable principles.

Ryan Holiday
Ryan Holiday

A media strategist and prominent writer on strategy and business.

Notes & takeaways

I think Stoicism is a deeply fascinating and critically important philosophy. But I also understand that you live in the real world, and you don’t have time for a history lecture. What you want are real strategies to help you with your problems, so that’s what this book is going to be. – Ryan Holiday

This thing in front of you. This issue. This obstacle – this frustrating, unfortunate, problematic, unexpected problem preventing you from doing what you want to do. That thing you dread or secretly hope will never happen. What if it wasn’t so bad?

What if embedded inside it or inherent in it were certain benefits – benefits only for you? What would you do? What do you think most people would do?

Probably what they’ve always done, and what you are doing right now: nothing.

The discipline of perception
There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try:

  • To be objective
  • To control emotions
  • To choose to see the good in the situation
  • To steady our nerves
  • To ignore what disturbs or limits others
  • To place things in perspective
  • To revert to the present moment
  • To focus on what can be controlled

See things for what they are.
Do what we can.
Endure and bear what we must.

What blocked the path is now the path.
What once impeded action advances action.
The obstacle is the way.

Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.

Andy Grove, former CEO of Intel

Recognize your power

Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves. Or whether we will tell one at all.

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.

Choose not to be harmed – and you won’t feel harmed. Don’t feel harmed – and you haven’t been.

Marcus Aurelius

Live in the present moment

It doesn’t matter whether this is the worst time to be alive or the best, whether you’re in a good job market or a bad one, or that the obstacle you face is intimidating or burdensome. What matters is that right now is right now.

Think differently

Having learned early in life that reality was falsely hemmed in by rules and compromises that people had been thaught 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.

For more inspiration on thinking differently, read my notes on The Everything Store

This is radically different from how we’ve been taught to act. Be realistic, we’re told. Listen to feedback. Play well with others. Compromise. Well, what if the “other” party is wrong? What if conventional wisdom is too conservative? It’s this all-too-common impulse to complain, defer, and then give up that holds us back.

Finding the opportunity

A good person dyes events with his own color, and turns whatever happens to his own benefit.


The Blitzkrieg strategy was designed to exploit the flinch of the enemy – he must collapse at the sight of what appears to be overwhelming force. Its success depends completely on this response. This military strategy works because the set-upon troops see the offensive force as an enormous obstacle bearing down on them.
This is how the allied opposition regarded the Blitzkrieg for most of the war. They could see only its power, and their own vulnerability to it.

Take that longtime rival at work (or that rival company), the one who causes endless headaches? Note the fact that they also:

  • Keep you alert
  • Raises the stakes
  • motivate you to prove them wrong
  • harden you
  • help you to appreciate true friends
  • provide an instructive antilog – an example of whom you don’t want to become

Or that computer glitch that erased all your work? You will now be twice as good at it since you will do it again.

When people are:
Rude or disrespectful:
They underestimate us. A huge advantage.

We won’t have to apologize when we make an example out of them.

Critical or question our abilities:
Lower expectations are easier to exceed.

Makes whatever we accomplish seem all the more admirable.

Build your inner citadel

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. Nobody is born with a steel backbone. We have to forge that ourselves.


If only more people had been thinking worst-case scenario at critical points in our lifetimes: the tech bubble, Enron, 9/11, the invasion of Iraq, and the real estate bubble might ave been avoidable. No one wanted to consider what could happen, and the result? Catastrophe.

Book notes: Zero To One

Today, the premortem is increasingly popular in business circles, from start-ups to Fortune 500 companies and the Harvard Business Review. But like all great ideas, it is actually nothing new. The credit goes to the Stoics. They even had a better name: premeditatio malorum (premeditation of evils).

A writer like Seneca would begin by reviewing or rehearsing his plans, say, to take a trip. And then he would go over in his head (or in writing), the things that could go wrong or prevent it from happening: a storm could arise, the captain could fall ill, the ship could be attacked by pirates.

Nothing happens to the wise man against his expectation, nor do all the things turn out for him as he wished but as he reckoned – and above all he reckoned that something could block his plans.


Always prepare for disruption:
What if…
Then I will…
What if…
Instead I’ll just…
What if…
No problem, we can always…

And in the case where nothing could be done, the stoics would use it as an important practice to do something the rest of us too often fail to do: manage expectations. Because sometimes the only answer to “What if…” is It will suck but we’ll be okay.

We are dependent on other people. Not everyone can be counted on like you can (though, lets be honest, we’re all our worst enemy sometimes). And that means people are going to make mistakes and screw up your plans. Not always, but a lot of the time.
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 only guarantee ever, is that things will go wrong.

Beware the calm before the storm.
Hope for the best, prepare for the worst.
The worst is yet to come.
It gets worse before it gets better.

The world might call you a pessimist. Who cares? It’s far better to seem like a downer than to be blindsided or caught off guard. 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.

The art of acquiescence

The fates guide the person who accepts them and hinder the person who resists them


When a doctor gives you orders or a diagnosis – even if it’s the opposite of what you wanted – what do you do? You accept it. You don’t have to like or enjoy the treatment but you know denying it only delays the cure.

If someone we knew took traffic signals personally we would judge them insane.

Things could always be worse. The next time you:
Lose money?
Remember, you could have lost a friend.
Lost that job?
What if you’d lost a limb?
Lost your house?
You could have lost everything.

Yet we squirm and complain about what was taken from us. We still can’t appreciate what we have.

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.


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 is that and the fight after that, until the end.

Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.

Made weak by time and fate, but strong in will
To strive, to seek, to find, and not to yield

Alfred Tennyson

When Antonio Pigafetta, the assistant to Magellan on his trip around the world, reflected on his boss’s greatest and most admirable skill, what do you think he said? It had nothing to do with sailing. The secret to his success, Pigafetta said, was Magellan’s ability to endure hunger better than other men.

There are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events.

Something bigger than yourself

Hoping to stain the McCain family’s prestigious military legacy and the United States, the Vietcong repeatedly offered McCain the opportunity to be released and return home. He wouldn’t take it. He would not undermine the cause, despite self-interest. He stayed and was tortured – by choice.

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

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? Take it for granted, for a second, that there is nothing else in it for us, nothing we can do for ourselves. 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. What doesn’t help anyone is making this all about you, all the time. Why did this happen to me? What am I going to do about this? You’ll be shocked by how much of the hopelessness lifts when we reach that conclusion.

Stop making it harder on yourself by thinking about I, I, I. Stop putting that dangerous “I” in front of events. I did this. I was so smart. I had that. I had that. I deserve better than this. No wonder you take losses personally, no wonder you feel so alone. You’ve inflated your own role and importance. Start thinking: Unity over self. We’re in this together.

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.

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 mortality

Death doesn’t make life pointless, but rather purposeful. And, fortunately, we don’t have to nearly die to tap into this energy.

It’s a cliché question to ask, What would I change about my life if the doctor told me I had cancer? After our answer, we inevitable comfort ourselves with the same insidious lie: Well, thank God I don’t have cancer.

But we do. 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.

Prepare to start again

The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges. But that’s what keeps life interesting. And as you’re starting to see, what’s what creates opportunities.

Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles. On the contrary, the more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.

Related book: The Compound Effect

Knowing that life is a marathon and not a sprint is important. Conserve your energy. Understand that each battle is only one of many and that you can use it to make the next one easier. More important, you must keep them all in real perspective.

Not everyone looks at obstacles – often the same ones you and I face – and sees reason to despair. In fact, they see the opposite. They see a problem with a ready solution. They see a chance to test and improve themselves. Nothing stands in their way. Rather, everything guides them on the way.

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 trial we get better – become better people, leaders, and thinkers. Because those trials and pressures will inevitably come. And they won’t ever stop coming.

On Stoicism
Today, Bill Clinton rereads Marcus Aurelius every single year. Wen Jiabao, the former prime minister of China, claims that Meditations is one of two books he travels with and has read it more than one hundred times.

If Meditations by Marcus Aurelius is antiquity, it is we who are the ruins.

Joseph Brodsky

As I tried to show in this book, countless others have embodied the best practises of Stoicism and philosophy without even knowing it. These individuals weren’t writers or lecturers, they were doers – like you.

Over the centuries though, this kind of wisdom has been taken from us, co-opted and deliberately obscured by selfish, sheltered academics. They deprived us of philosophy’s true use: as an operating system for the difficulties and hardships of life.

Philosophy was never what happened in the classroom. It was a set of lessons from the battlefield of life.

Now you are a philosopher and a person of action. And that is not a contradiction.

You now join the ranks of Marcus Aurelius, Cato, Seneca, Thomas Jefferson, James Stockdale, Epictetus, Theodore Roosevelt, George Washington, and many others. All these men explicitly practiced and studied stoicism. They were not academics, but men of action.

To be a philosopher is not merely to have subtle thoughts, nor even to found a school. It is to solve some of the problems of life, not only theoretically, but practically.

Henry David Thoreau

Personal review

The book is divided into three big sections: Perception, action, and will. Each section has about 10 chapters, exploring different aspects of that theme. Each chapter starts with a story, and the rest of the chapter expands upon the principle found in that story.


  • Interesting book, and a lot of great value
  • Motivating
  • Easy to read. Small chapters, short stories
  • Great book to read in small segments over a longer period of time
  • Inspiring stories from people who have put the stoic principles to use throughout history


  • Somewhat repetitive. Better to read in small doses
  • Some of the principles are overemphasized and the text length could be reduced

Conclusion: Worth to read in small bites, perfect as a 10-20 pager before bedtime.

Av Eirik Nereng

Markedsføring, konverteringsoptimalisering, netthandel, tech og sånne greier