The Obstacle Is The Way by Ryan Holiday: Summary and Notes

the obstacle is the way summary“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.”

Rating: 8/10

Related: The Daily Stoic, Ego is the Enemy, Stillness is the Key

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The Obstacle Is the Way Short Summary

The Obstacle Is The Way by Ryan Holiday offers great lessons on how to overcome challenges in every aspect of your life. Ryan, in the tradition of other stoics before him, argues that rather than being stumbling blocks, obstacles are opportunities. They ask you to persevere, to think creatively, persist, and even change your perspectives. A great motivational book for anyone looking to do great things in life. I highly recommend it.

The Obstacle

Obstacles are the things that stand in your way. They are the challenges you face in life, at work, in relationships, and so on.

Examples of obstacles include height, poverty, pain, unemployment, illness, emotional issues, and physical limitations.

Overcoming the obstacle is the way to success. Obstacles are opportunities in disguise.

In other words, the obstacle is the way.

Obstacles present an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, or creativity.

To find the way, you must overcome the obstacle.

There are many strategies for doing so and it depends on the obstacle that stands in your way.


Perception is how you process and see the things around you.

Perceptions can be a source of strength or weakness. Being emotional, shortsighted, and subjective can only add to your troubles.

When faced with obstacles, how you see them matters and shows in the way that you handle them.

For example: Like everybody else, Rockefeller was hit hard by the panic of 1857 but rather than give up he found the events to be great learning opportunities. He knew how to adapt and see opportunity in every calamity. In later life, he would be thankful for the troubles of his life.

“We can see opportunity in every disaster, and transform the negative situation into an education, a skill set, or a fortune.”

When faced with insurmountable obstacles you can try to:

  • Be objective
  • Control emotions and keep an even keel
  • See the good in a situation
  • Steady your nerves
  • Ignore limitations
  • Place things in perspective
  • Live by the present moment
  • Live at the present moment
  • Focus on what can be controlled

Focus Your Power

You decide what to make of every situation that you face. This is the power that each one of us has. You decide to give up or continue, to resist or submit.

“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.”

Your perception can help you destroy obstacles or see them as opportunities.

For example:

A company can see an employee’s mistake as a disaster or as an opportunity to teach them how to perform better next time. It is all a matter of perception.

Steady Your Nerves

Whenever you aim high, stress and pressure are guaranteed. You need to keep a calm head in high-stress situations.

Steadying your nerves is a matter of defiance and control. It is also a matter of responsibility or acceptance that is up to you to right the situation.

Control Your Emotions

In some situations, emotional control is a matter of life and death.

For example:

During the Apollo missions, John Glenn, the first American to orbit the earth had been drilled for many hours in emotional control.

Because overreaction in space or at critical moments could be a matter of life and death. Sometimes, the obstacle is how you react to events around you.

“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.”

Practice Objectivity

“In our own lives, how many problems seem to come from applying judgments to things we don’t control, as though there were a way they were supposed to”

You need to practice objectivity in your life. Take a step back from the problems that you are facing and assume that for a moment they are happening to someone else.

And think of all the ways that someone could solve the problem.

Alter Your Perspective

“Perspective is everything. That is, when you can break apart something, or look at it from some new angle, it loses its power over you”

With the right perspective, it is very easy to cut through obstacles and see them for what they are. Perspective has two definitions:

  1. Context. A sense of the larger picture of the world and not just what immediately lies in front of you
  2. Framing.  How you look at the world

For example:

Instead of seeing a job interview as an obstacle for you, see it as an obstacle to the hiring manager. Hiring is an opportunity for the company to solve its staffing problem, not an opportunity for you to solve your joblessness. Present yourself as the solution in this case.

A big problem can be reduced to small bits and suddenly what seemed like an impossible task becomes a series of small steps.

It Is Up To You

Look for things that you can change and focus on those. Here is a list of the things that are up to you:

  • Judgments
  • Creativity
  • Attitude
  • Perspective
  • Desires
  • Decisions
  • Determination

This is the playing field and everything here is fair game.

“When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t. That’s the difference between the people who can accomplish great things, and the people who find it impossible to stay sober—to avoid not just drugs or alcohol but all addictions.”

Focus on the moment. Not on the things that lie ahead of you.

“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.”

Finding The Opportunity

With the right perception and attitude, it is easy to find opportunities in the obstacles that you face.

Adversarial growth and post-traumatic growth: What doesn’t kill you makes you stronger.

“The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.”


After forming the right perspective. It is time to act. Persist in your efforts.

Resist giving in to distractions, discouragement, or disorder.

“Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with persistence and time can we cut away debris and remove impediments. Only in struggling with the impediments that made others quit can we find ourselves on untrodden territory—only by persisting and resisting can we learn what others were too impatient to be taught.”.


Try again and again.

“In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up—a start-up of one. And that means changing the relationship with failure. It means iterating, failing, and improving. Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.”

When faced with failure ask yourself: What went wrong here? What can be improved? What am I missing?

Follow the Process

Create a system for your success. Create a system for reacting to fear, stress, loss, and distractions.

These things will be constant in life, so it is best to know how to deal with them.

“When it comes to our actions, disorder and distraction are death. The unordered mind loses track of what’s in front of it—what matters—and gets distracted by thoughts of the future. The process is order, it keeps our perceptions in check and our actions in sync.”

Having a process demands that you take responsibility and ownership. It prompts you to act even in little ways.

Do Your Job Right

No matter what your job is, do it right. It so happens that sometimes on your road to success, you have to do things that you do not like. Right action is one way to turn obstacles into opportunities.

Everything you do matters. It is a chance for you to put in your best effort and learn in the process.

Whatever your job is, respond with hard work, honesty, and by helping others the best way you can. 

In Praise of The Flank Attack

When faced with an obstacle, it is sometimes strategic to seek soft and weak points. Throughout history, many generals have avoided facing an enemy head-on but instead relied on guerilla tactics.

“Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-to-head attack. These Things force us to be creative, to find workarounds, to sublimate the ego, and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle.”

Huge size can be a disadvantage in itself because it is harder to develop a good technique.

Use Obstacles Against themselves

One way to overcome obstacles is by letting them attack you. It is a strategy that was employed to great success by Martin Luther King and Gandhi.

Rather than face the obstacle head-on, you can use the actions of others and let them wear out. Nonaction can be action.

For example: During the civil rights marches, Martin Luther King asked his followers to meet brute force with soul force and love with hate.

“Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive.”

Seize The Offensive

Adversity can harden you. But rather than allow it to dominate your thinking, you can channel the negative emotions to push yourself forward.

“If you think it’s simply enough to take advantage of the opportunities that arise in your life, you will fall short of greatness. Anyone sentient can do that. What you must do is learn how to press forward precisely when everyone around you sees disaster. It’s at the seemingly bad moments, when people least expect it.”

Look for decision points. It is the one who is ready to push despite the opposing forces who are able to progress in life.

Prepare For None of It to Work

Even though you can manage perceptions and your own actions, things can still not go according to plan. You need to be prepared for that.

Will is that internal power within yourself that can’t be altered by external factors. You depend on your will before and after an action.

You turn around your negative or destructive situations to constructive situations by willpower.

By learning acquiescence and practicing cheerfulness, you prepare for adversity.

True will is defined as the humility, resilience, and flexibility of one to flip over the obstacle to success.

In preparation for adversity over your fears and distractions you should always:

  • Prepare yourself for more difficult times
  • Manage your expectations
  • Accept what you are unable to change
  • Persevere
  • Submit to a greater, larger cause
  • Remind yourself of your own mortality
  • Protect your inner self, retreat into yourself
  • Learn to love your fate and what happens to you