The Obstacle is the Way - Book Summary and Highlights

The Obstacle is the Way

By Ryan Holiday

Rating: 9/10

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What is Holding you Back

Every day, we face obstacles.  Some are big and some are small.  They could be physical, such as size, race, distance, disability or money.  They could be mental, such as fear, uncertainty, inexperience, prejudice.

These can range from being stuck in traffic to being stuck at home during a pandemic.  From being born with a speech impediment despite a desire to enter politics (Thomas Jefferson put his energy into writing and went onto write the Declaration of Independence) to dealing adversity (Amelia Earhart prior to becoming the first woman to fly solo nonstop across the Atlantic Ocean).

Every story we hear regarding someone achieving greatness has one thing in common.  Those individuals were able to identify their weakness (or perceived weakness) and turn it into strength.  They were able to take the obstacle at hand and turn it into a path forward.

How We React to Obstacles

The larger the obstacle, the quicker we are to give up on our goals.  Many people don't even get to the point to where they hit an obstacle.  Instead, the thought of potential obstacles is enough to stop them before they even get started.

And while each individual obstacle is unique, how we react to them is common; Fear, Frustration, Confusion, Helplessness, Depression, Anger.  It is easier to blame others instead of acknowledging that the fault is our own.  Our attitude and approach to the problem is where we went astray.

This does not mean we need to be positive about every situation.  A positive attitude will not magically solve all our problems.  However, we need to learn to be creative and opportunistic.

  • Not: This is not so bad.
  • But: I can make this good.

In overcoming these obstacles, there are three areas we need to stop and focus on:

  • Perception
  • Action
  • The Will

Marcus Aurelius, in his transcripts which became the book Meditations, summed up how to react when faced with obstacles and problems:

“Objective judgement, now, at this very moment. Unselfish action, now, at this very moment. Willing acceptance – now, at this very moment – of all external events. That’s all you need.”— MARCUS AURELIUS


Perception is not only how we see and understand everything that occurs around us, but also the meaning that we attach to these experiences.  These events, by themselves, are neither good nor bad.  What one person perceives as good, another perceives as bad.

Recognize Your Power

In all situations, we are never completely powerless.  We can choose how to perceive and react to each situation.  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

Control Your Emotions

Often, we react emotionally, be it fear, frustration, confusion, helplessness, depression or anger.  This emotional reaction causes us to lose our perspective.  But we can learn to perceive things differently.  We can learn to defeat these emotions with logic.  To see things as they truly are, not as we've made them out to be in our mind.

Practice Objectivity and Alter Your Perspective

We can accomplish this change by breaking the situation apart and looking at it from different angles.  Remove the "you" from the scenario.  Put yourself in someone else's shoes.

Is It Up to You?

Ask yourself: what is in your power and what is outside of your control?  Focusing on things we have no control over is destructive.  Instead, focus your energy on those things within your control.  Or more specifically, what you have control over and that is happening at the present moment.  We need to remember that any specific moment does not define our lives; it is just one of many moments in our lives.

"In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices."—EPICTETUS

Think Differently

Another way to adjust our perception is by changing our thought process.  This is difficult to accomplish, as many of our perceived realities have been ingrained since childhood by our families, our culture, our religion and our environment.  These perceptions ultimately determine what we are and are not capable of.  As Ryan Holiday asks, "When you believe in the obstacle more than in the goal, which will inevitably triumph?"

Prepare to Act

When you stand back, you realize that the problem is usually not as bad as we think it is.  However, the opposite is also true.  Not taking the time to step back and practice objective judgment makes the problem exactly as bad as we think.

"Where the head goes, the body follows.  Perception precedes action.  Right action follows the right perspective."—RYAN HOLIDAY

To summarize, when faced with an obstacle, we must try:

  • To be objective
  • To control emotions and keep an even keel
  • To choose to see the good in a 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


As we stated earlier, you can still take a moment to stop and think, "this sucks."  Go ahead and vent.  Just do it quickly, as we have work to do.

Get Moving

Like most things in life, the first step is to get going.  You need to take that first step to walk anywhere.  While being aggressive and taking risks can come with a negative overtone, they are both important in overcoming obstacles.

"We must all either wear out or rust out, every one of us. My choice is to wear out."—THEODORE ROOSEVELT

Practice Persistence

Once you attack an obstacle, quitting is not an option.  You may get discouraged, but you cannot quit.  You want to keep this mindset:

  • Never in a hurry
  • Never worries
  • Never desperate
  • Never stopping short


While attacking a problem, remember that failure is not always a bad thing.  If you are trying to improve or learn something new, failure can be an asset.  The lessons learned from some failures can often not be taught otherwise.  The process is cyclical; iterate, fail, and improve.

Follow the Process

Set yourself up for success.  Make sure you follow a process when taking action.  If you have something difficult to accomplish, don't dwell on the big picture as it may overwhelm you.  Break the problem into smaller tasks and tackle them, one at a time.  Iterate, finish, and move onto the next task.

Remember that disorder and distractions can kill an action.  The unordered mind loses focus and worries about tasks that are far into the future.  We are A-Z thinkers, worrying about A, obsessing on Z, and forgetting about B through Y.

"Under the comb the tangle and the straight path are the same."—HERACLITUS

Do Your Job, Do It Right

Not everything we do will be something we want to do.  But we need to remember that everything we do matters.  Everything is a chance for you to give your best.  The only demeaning part is giving less than you can give.

What's Right is What Works

There is no right or wrong way to attack an obstacle.  Focus on anything that works, on the hand you are dealt, and on the results rather than the process.

Remain flexible.  When we break tasks down, we notice there are many ways to get from Point A to Point B.  Distinguish between what is critical to reach our goal, and what is extra and doesn't add to our goal.

"The cucumber is bitter? Then throw it out. There are brambles in the path? Then go around. That’s all you need to know."—MARCUS AURELIUS

In Praise of The Flank Attack

Strategize your actions.  If you can't go through an obstacle, go around it.  Figure out where you can find leverage.  When pushed, instead of pushing back, pull until your opponent loses their balance.

Use Obstacles Against Themselves

Sometimes it's easier to find a way for obstacles to defeat themselves.  Nonaction can be action.  With patience, some obstacles may fizzle out.  Often, we want things too badly, which can make us our worst enemy.  We strip the screw we are trying to turn and make it impossible to get what we want.

"Wise men are able to make a fitting use even of their enmities."—PLUTARCH

Prepare for None of It to Work

Perhaps the most important advice is to prepare yourself that none of this may work.  The action taken may not tackle the obstacle.  Learn from this.  Find the alternative path that wasn't visible prior to the failure.  And remember that nothing can ever prevent us from trying.


When we think of will, willpower often comes to mind, along with the associated question, "How bad do we want something"?  However, the will has a lot more to do with surrender than with strength.

What makes the will stand out is that it is the one thing we control completely.  We can try to mitigate harmful perceptions and we can put all our energy into an action, but both can still fail.  Our will is within us and cannot be altered by outside events.

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

In every situation, we can:

  • Always prepare ourselves for more troublesome times.
  • Always accept what we’re unable to change.
  • Always manage our expectations.
  • Always persevere.
  • Always learn to love our fate and what happens to us.
  • Always protect our inner self, retreat into ourselves.
  • Always submit to a greater, larger cause.
  • Always remind ourselves of our own mortality.
  • And, of course, prepare to start the cycle once more.

Anticipation (Thinking Negatively)

Many of us are familiar with a postmortem — a process of looking back at a project or a situation to review what went wrong and what lessons we learned.  We want to incorporate a premortem where we look at what could go wrong before we even start.

The idea is to manage expectations.  Murphy's Law tells us that if something can go wrong, it will go wrong, so why not prepare for it in advance?  We want to hope for the best, but prepare for the worst.

"Offer a guarantee and disaster threatens."—ANCIENT INSCRIPTION AT THE ORACLE OF DELPHI

The Art of Acquiescence

When we can differentiate the things within your control and the things outside of your control, there is only one option for the latter; acceptance.  It is easy to talk about the way things should be.  It is a lot harder to accept them for what they are.

Love Everything That Happens

We need to have the ability to endure tragedy and setbacks; to love whatever happens to us and turn what we "must" do into what we "get to" do.


If persistence is an action, then perseverance is a matter of the will.  One is energy, while the other is endurance.  And while someone or something can restrain our actions, our will cannot be held back.

Something Bigger Than Yourself

Before giving up on a problem or an obstacle, think of how it may affect others.  If you cannot solve the problem for yourself, how can you make it better for other people?  Unity over self.

Meditate On Your Mortality

Being aware of our mortality creates real perspective and urgency.

When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.—DR. JOHNSON


Objective judgement.  Unselfish action.  Willing acceptance of all external events.  That's all you need.  Perception, Action and the Will.

No matter the obstacle, you can always turn it to your advantage.  You can always find the opportunity hidden within.  Remember to:

  1. See clearly
  2. Act correctly
  3. Endure and accept the world as it is

Or as Ryan closed the book, "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."

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