Notes on The Obstacle is The Way

By Ryan Holiday

These are my notes on ideas and concepts I found interesting — not a comprehensive summary of the book. Buy the book →

I. Perception

The Discipline of Perception

You will come across obstacles in life — fair and unfair. What matters most is not what these obstacles are are but how we see them, react to them, and whether we keep our composure.

Too often we react emotionally, get despondent and lose our perspective. All that does it turn bad things into really bad things.

We must learn to see opportunity inside every obstacle.

A few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try to:

1. Be objective.
2. Control emotions and keep an even keel.
3. Choose to see the good in the situation.
4. Steady our nerves.
5. Ignore what disturbs or limits others.
6. Place things in perspective.
7. Revert to the present moment.
8. Focus on what can be controlled.

Recognize Your Power

We are never completely powerless: We decide what we will make of each and every situation. We decide whether to break or whether to resist.

Our perceptions are the only thing that we’re in complete control of.

Through our perception of events, we are complicit in the creation—and destruction — of every one of our obstacles.

Steady Your Nerves

Stuff is going to happen that catches us off guard, threatens or scares us. Surprises (unpleasant ones, mostly) are almost guaranteed. The risk of being overwhelmed is always there.

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

There is always a countermove, an escape or a way through, so there is no reason to get worked up.

Control Your Emotions

Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check.

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.

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.

Subconsciously, we should be constantly asking ourselves this question: Do I need to freak out about this?

Practice Objectivity

How many problems seem to come from applying judgments to things we don’t control? How often do we see what we think is there or should be there, instead of what actually is there?

A useful exercise: Take your situation and pretend it is not happening to you. Pretend it isn’t important, that it doesn’t matter.

Alter Your Perspective

When you can break apart something, or look at it from a new angle, it loses its power over you.

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.

It’s your choice whether you want to put ‘I’ in front of something. This adds an extra element: you in relation to the obstacle, rather than just the obstacle itself.

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.

Perspective has two definitions:

1. Context: a sense of the larger picture of the world, not just what is immediately in front of us.
2. Framing: an individual’s way of looking at the world, a way that interprets its events.

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.

Is It Up To You?

There’s no point focusing on the past. That stuff is done. Delivered. Zero in one hundred chances that you can change it.

What if you focused on what you can change? That’s where you can make a difference.

What is up to us?

• Our emotions.
• Our judgments.
• Our creativity.
• Our attitude.
• Our perspective and our desires.
• Our decisions.
• Our determination.

Live In The Present Moment

Focus on the moment, not the monster that may or may not be up ahead.

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.

Think Differently

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?

Finding The Opportunity

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.

The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this. Everything can be flipped.

Or, we can fight it the entire way. The result is the same. The obstacle still exists. One just hurts less.

II. Action

The Discipline of 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.

It feels better to ignore or pretend. But you know deep down that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.

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.

Each obstacle we overcome makes us stronger for the next one.

Get Moving

At minimum, you could be trying harder. You might have gotten started, but your full effort isn’t in it — and that shows. Be deliberate, of course, but you always need to be moving forward.

We talk a lot about courage as a society, but we forget that at its most basic level its really just taking action — whether thats approaching someone you’re intimidated by or deciding to finally crack a book on a subject you need to learn.

Practice Persistence

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.

As often is the result from persistence and dedication, in exhausting all the other traditional options, you will be forced to try something new.

The thing standing in your way isn’t going anywhere.

Iterate

On the path to successful action, we will fail — possibly many times. That’s okay: Action and failure are two sides of the same coin.

Anticipated, temporary failure certainly hurts less than catastrophic, permanent failure.

Failure shows us the way — by showing us what isn’t the way.

Follow The Process

So, 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. The process is about finishing.

When it comes to our actions, disorder and distraction are death.

What’s Right is What Works

Forget the rule book, settle the issue.

We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. When, really, it’d be better to focus on making due with what we’ve got.

There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line.

In Praise of the Flank Attack

When you’re at your wit’s end, take a step back, then go around the problem.

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 alternative with so much support from other people that the opposition voluntarily abandons its views and joins your camp.

Use Obstacles Against Themselves

Sometimes you overcome obstacles not by attacking them, but by withdrawing and letting them attack you.

Opposites work. Nonaction can be action. It uses the power of others and allows us to absorb their power at our own. Letting them — or the obstacle — do the work for us.

So instead of fighting obstacles, find a means of making them defeat themselves.

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.

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 to press forward precisely when everyone around you sees disaster.

When a failure or an accident or a tragedy happens, use it.

Ordinary people shy away from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They turn personal tragedy or misfortune — really anything, everything — to their advantage.

Prepare For None of It To Work

Nothing can ever prevent us from trying. Ever.

But, some things are bigger than us. 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 its just learning to accept that bad things happen, or practicing humility.

III. Will

The Discipline of The Will

Clearheadedness and action are not always enough. Some obstacles are beyond a snap of the fingers or a novel solution.

Will is fortitude and wisdom — not just about specific obstacles but about life itself and where the obstacles we are facing fit within it.

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.

Build Your Inner Citadel

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. Not everyone accepts their bad starts in life.

We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice.

Whether we are born weak or we are currently experiencing good times, we should always prepare for things to get tough.

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)

Your plan and the way things turn our rarely resemble each other.

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.

The only guarantee ever is that things will go wrong.

The Art of Acquiescence

Clearheadedness and action are not always enough. Some obstacles are beyond a snap of the fingers or a novel solution.

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.

Rarely do we consider how much worse things could have been.

Love Everything That Happens: Amor Fati

We have to learn to find joy in every single thing that happens.

There is no value in any other reaction.

We don’t get to choose what happens to us, but we can always choose how we feel about it.

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.

Perseverance

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

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.

Our actions can be constrained, but our will can’t be.

Something Bigger Than Yourself

Stop making it harder on yourself by thinking about I, I, I. Don’t inflate your own role and importance.

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.

Lend a hand to others. Be strong for them, and it will make you stronger.

Meditate on Your Mortality

Our fear of death is a looming obstacle in our lives. It shapes our decisions, our outlook, and our actions.

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.

In a Nutshell:

Perceive things as they are, leave no option unexplored, then stand strong and transform whatever can’t be changed.

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

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