The Obstacle is the Way

The Obstacle is the Way: The Timeless Art of Turning Trials Into Triumph by Ryan Holiday


The impediment to action advances action.
What stands in the way becomes the way. - Marcus Aurelius

The Obstacle is the Way is a crash course on one of the main lessons of stoicism: overcoming obstacles.

We will face obstacles in life, that's unavoidable. This book can teach us to see the obstacles for what they really are, how to use them to grow, and how they push us forward in the right direction.

Stoicism and Overcoming Obstacles

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Stoicism is a branch of philosophy dealing with human behavior. It reminds us that we do not control external events, but we can control how we react to them.

Stoicism is not riddled with complicated theories of man and the universe. Rather, stoicism is a practical philosophy. It's built for action, not endless debate. 

The stoics taught that we can overcome destructive emotions by acting only on what can be acted upon.

This always reminds me of the Serenity Prayer, particularly the famous first stanza:

God, grant me the serenity to accept the things I cannot change,
The courage to change the things I can,
And the wisdom to know the difference.

I don't believe you need to be Christian or even particularly religious to understand the value of this prayer and how it relates to the book.

Whatever we face in life, we have a choice. Will we be blocked by obstacles, or will we advance through them?

Stoicism is a formula for thriving not just in spite of whatever happens but because of it.

Overcoming Obstacles

Stoicism can help overcome obstacles in three critical steps: perception, action, and will.

  • Perception: How should we look at problems?
  • Action: The energy and creativity to break them down and turn them into opportunities.
  • Will: The cultivation of inner strength that allows us to handle difficulty and defeat. 

By practicing all three of these components we will succeed in overcoming, and possibly thriving, because of obstacles.

Perception is how we interpret our surroundings.

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

Stoicism teaches us to not become overwhelmed with the world around us. We learn to filter out prejudice, expectation, and fear so all that's left is the truth. 

How we perceive obstacles will prove to be an incredible advantage in the fight to overcome them.

The Discipline of Perception

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

We will run into countless obstacles in life.. some will be fair and others will be unfair. Stoicism teaches that the obstacles themselves don't matter, what matters is how we see them, how we react to them, and if we can keep our composure.

Practice Objectivity

Nothing either good or bad, but thinking makes it so
— Shakespeare

There are no good or bad events without us. There is only our perception. There is the event itself and then there is the story we tell ourselves about what it means.

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.

An employee in your company makes a careless mistake that costs you business. This can be a chance to teach a lesson that can be learned only by experience.

Someone messed up. That hasn't changed. But you can approach with anger and fear, or can keep your cool and take advantage of the situation. A mistake becomes training.

To make situations more objective, remove yourself from the situation. When we give advice to other people their problems are crystal clear to us and the solutions seem obvious.

Imagine your close friend is in the situation. What advice would you give to them?

Steady Your Nerves and Control Your Emotions

Surprises are guaranteed. They will catch us off guard and scare us. On the path to greatness we will always be at risk of being overwhelmed. In these cases we don't need more talent, we need more grace and poise. 

If we don't have grace and poise we won't have the chance to use any of our other skills. Seeing an obstacle for what it is begins with us controlling our emotions. 

The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind.

Don’t let the negativity in, don’t let those emotions even get started.

Remember, there is always something we can do, a countermove, a way around.

No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

When you feel negative emotions, think: does getting upset provide you with more options? Sometimes it does. But if not, it's an unhelpful or even a destructive emotion.

Actions are commonplace, but the right actions are not. The right actions are focused and directed to dismantle obstacles in front of us. The right actions are backed by persistence and flexibility.

Action is the solution and the cure to our predicaments.

The Discipline of Action

There’s an explosion, metaphoric or otherwise. Are you the guy running toward it? Or running away from it? Or worse, are you paralyzed and do nothing?

This little test of character says everything about us.

It doesn’t matter what happens to you or where you came from. It only matters what you do with what you’ve been given.

Disciplined action doesn't mean you can't be frustrated. If something bad happens you're allowed to think, "Dammit. This sucks!" We're human after all.

But don't stay in that place. Take a breath and take stock of the situation, and then get to work. That's the difference between those who achieve greatness and those who don't. Everyone hits obstacles and everyone experiences anger and self-pity, but those who are successful don't stay there.

You have to get back to work. Because each obstacle we overcome makes us stronger for the next one.

Get Started and Stick With It

Accomplishing anything requires action. You have to start. Anywhere you can. Anyhow you can. Just start.

There will never be a perfect moment or perfect opportunity to begin.

If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.

Remember and remind yourself of a phrase favored by Epictetus: “persist and resist.”

Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

It’s okay to be discouraged. It’s not okay to quit.

Even when you want to quit, you plant your feet and inch closer and closer. There are always options. Settle in for the long haul and then try each and every possibility, and you’ll get there. That's persistence.

Trying Until You Succeed

If you keep trying without any success, take a step back and find a way to go around the problem. 

Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open.

We can get so caught up in moving forward that we sometimes forget that success sometimes requires we move sideways, or even backward to get around an obstacle.

This requires a certain level of humility. You have to accept that the way you wanted to go just not be possible and you might have to go a less traditional route. That's okay! And don't be afraid to fail. The one way we don’t benefit from failure is to not learn from it. 

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

For more on the upside of quitting, read Think Like a Freak by Steven Levitt and Stephen Dubner.

Perceptions can be managed. Actions can be directed.

We can think clearly, look for opportunities, and respond creatively but what we can’t do is control the world around us.

We might perceive things well, then act rightly, and fail anyway. Run it through your head like this: Nothing can ever prevent us from trying. Ever.

Will is our internal power, which can never be affected by the outside world.

Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength.

The Discipline of Will

If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.

Will is the one thing we can completely control. We can attempt to change our perceptions or give 100% of our energy to something but those attempts may be stopped or defeated. But our will is different because it's within us.

Build Your Inner Citadel

We're all dealt a certain hand in life. We'll face obstacles and roadblocks that there's nothing we can do to prevent.

If you were dealt a bad hand, don't accept it. Remake yourself. Prepare yourself for the long road ahead.

The brain is a muscle like any other active tissue. You can build and tone your brain through the right exercises. Over time you can train your brain to productively respond to any and all obstacles. You build your inner citadel.

Inner Citadel, that fortress inside of us that no external adversity can ever break down.

The Power of Negative Visualization

When facing big events or big decisions conduct a premortem, a technique created by psychologist Gary Klein.

In a postmortem, we’re examining a project in hindsight after it happened.

A premortem is different. In it, we look to envision what could go wrong, what will go wrong, before we even start.

The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation.

By conducting premortems we anticipate what could go wrong.

We’re like runners who train on hills or at altitude so they can beat the runners who expected the course would be flat.

We are prepared for failure and ready for success.

Amor Fati

In this chapter, Ryan Holiday tells a wonderful short story about Thomas Edison that I think about frequently. I've reproduced it here:

At age sixty-seven, Thomas Edison returned home early one evening from another day at the laboratory. Shortly after dinner, a man came rushing into his house with urgent news: A fire had broken out at Edison’s research and production campus a few miles away.
Fire engines from eight nearby towns rushed to the scene, but they could not contain the blaze. Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories, threatening to destroy the entire empire Edison had spent his life building.
Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees, looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.”
Don’t worry, Edison calmed him. “It’s all right. We’ve just got rid of a lot of rubbish.”
That’s a pretty amazing reaction. But when you think about it, there really was no other response.
What should Edison have done? Wept? Gotten angry? Quit and gone home? What, exactly, would that have accomplished?
You know the answer now: nothing.

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

You're Now a Philosopher

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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.

The essence of philosophy is action. Stoicism is the ability to turn the obstacle upside down. We learn to see our problems for what they really are and their greater context. We see things philosophically and we act accordingly.

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.

Where to Buy

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Buy the book on AmazonBarnes and NobleBAM, or just Google it. (I receive no kickback or commission for these links or summaries. See my disclosure for more.)


  • How John D. Rockefeller practiced stoicism to become one of the richest men on the planet
  • How Rubin "Hurricane" Carter used stoicism when he was put in prison for 20 years for a crime he didn't commit.

  • Why stoicism is the first skill they teach potential astronauts

  • How stoicism can help addicts in recovery

  • Stoic strategies used by the Allies in World War Two

  • How stoicism has evolved over the years

  • The benefits of meditating on our own mortality

  • And much, much more!

Erik Cianci