3 Steps To Overcoming Any Obstacles: My Key Takeaways From "The Obstacle Is The Way" by Ryan Holiday



Obstacles are a part of life. 

Without them there would be no growth, no sense of achievements and frankly speaking, it would make our lives so boring! Obstacles of life will come at you in varying shapes and sizes. They can be:

  • fair and/or unfair,
  • big and/or small, and
  • challenging and/or paralysing. 

Most of us don't get to choose our obstacles but we can choose how we respond. We can either be paralysed by an obstacle and blame our bosses, the economy and the external circumstances that are out of our control or, we can decide to transform our weaknesses and obstacles into strengths and opportunities. 

Like oxygen to a fire, obstacles can be used to fuel our ambitions. Transforming the obstacle in the path to become a path itself. As Benjamin Franklin writes: "The things that hurt... instruct." Read below for my key takeaways from the book The Obstacle Is The Way by Ryan Holiday: the three steps of overcoming any obstacles in life. 



1. Don't be Fooled By Your Primitive Brain. Have the right Perception.

Would you have a great empire? Rule over yourself
— Publius Syrus

The first step of overcoming obstacles is by having the "right perception". Our perceptions are always subjective and they can be deceiving. 

The sixteenth-century Samurai Miyamoto Musashi is renowned for his countless victories in sword-fights (even without being armed) and his ability to discern between a real threat and opportunity was his life-dependent skill. In the Book of Five Rings he writes: "The perceiving eye is weak, the observing eye is strong." Musashi is teaching us that the observing eye simply sees with is there while the perceiving eye sees more than what is there. 


Problems that we face are rarely as bad as we think or rather, they are precisely as bad as we think

Here's an example. 

The human body is wired to activate the fight-or-flight response in reaction to danger or pain. This is an uncontrolled response (deeply embedded in our primitive/survival instincts) that forces your body to shift into self-protection mode. In face of perceived or real danger, this automatic response elicits the following changes within seconds: 

  • The primitive brain (amygdala) sounds a general alarm.
  • Adrenaline and stress hormones are released.
  • Non-essential physiological processes switch off.
  • Digestion stops, skin chills,
  • and blood is redirected to muscles in preparation of burst of emergency action.
  • Blood pressure skyrockets to infuse the body with more oxygen,
  • Liver releases glucose for immediate source of energy. 

This primitive or survival instincts were life saving for our ancestors. When they came across a wild lion, this gave them a chance of survival. The flaw is that we still hold this primitive design. You're life is not threatened when: 

  • You are late for a meeting
  • You receive a fine ticket for parking
  • You stress about your finances
  • When you are about to give a public speech

and yet, the fight-or-flight mode becomes activated. This is how perceived setbacks become true obstacles. Through our own eyes of perception, we become an accomplice. We become responsible for creating our own obstacles and barriers. Instead of falling victim of our primitive design, we should discern and try to perceive objectively if it is a true obstacle or an hidden opportunity.

Ryan Holiday suggests that we try:

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



2. Thinking will not overcome obstacles but action will.

We must all either wear out or rust out, every one of us. My choice is to wear out
— Theodore Roosevelt

The second step of overcoming your obstacles is to take action. Obstacles become bigger and more intimidating when you stop to look at them. We’ve heard so many times that taking massive action is the key to positively changing our lives. But it’s easier said than done. 

Unlike such cliché advice, Ryan gives the following tips about taking action:


Ryan further puts emphasis on painting a realistic picture. He comments: 

“It’s supposed to be hard."

"Your first attempts aren’t going to work. It’s going to take a lot out of you – but energy is an asset we can always find more of. It’s a renewable resource. Stop looking for an epiphany, and start looking for weak points."

"Stop looking for angels, and start looking for angles."

"There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.”


It’s important to acknowledge that obstacles are meant to be difficult! Without the difficulty there would be no sense of achievement and everybody would be doing it! When you are faced with an obstacle, rather than to focus on the end goal, break it down into smaller actionable steps.  

Simplify what needs to be done right now and do it well.

It’s all about doing the right things, in the right way and following the process not the prize


3. Know that you're problems are not special. stop being a victim.

You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is – at best – indifferent to your existence
— Ryan Holiday, The Obstacle Is The Way

Stop being a victim, the world owes you nothing! 

You have to stop pretending or lying to yourself that you're a victim.

That you're problems are unique.

That it's unfair. 

The reality is that you're problems have been faced a thousand times before you and there are people who overcome them. 


Here’s a great excerpt from the book:

Perhaps you’re stuck in bed recovering.

Well, now you have time to write. Perhaps your emotions are overwhelming and painful, turn it into material.

You lost your job or a relationship? That’s awful, but now you can travel unencumbered.

You’re having a problem? Now you know exactly what to approach that mentor about.

Seize this moment to deploy the plan that has long sat dormant in your head.

Every chemical reaction requires a catalyst. Let this be yours.

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 are their best in these situations. They turn personal tragedy or misfortune—really anything, everything—to their advantage.

But this crisis in front of you? You’re wasting it feeling sorry for yourself, feeling tired or disappointed. You forget: Life speeds on the bold and favors the brave.

We sit here and complain that we’re not being given opportunities or chances. But we are.

At certain moments in our brief existences we are faced with great trials. Often those trials are frustrating, unfortunate, or unfair. They seem to come exactly when we think we need them the least.

The question is: Do we accept this as an exclusively negative event, or can we get past whatever negativity or adversity it represents and mount an offensive? Or more precisely, can we see that this “problem” presents an opportunity for a solution that we have long been waiting for?
— The Obstacle Is The Way, Ryan Holiday

It’s also important to have your emotions in check during times of difficulty.

A good example is John Glenn, the first American astronaut to orbit the Earth. 

“John Glenn… spent nearly a day in space still keeping his heart rate under a hundred beats per minute. That’s a man not simply sitting at the controls but in control of his emotions. Life is really no different. Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check—if we can keep steady no matter what happens, no matter how much external events may fluctuate.”

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. Having your emotions in check is vital because:

1)      If an emotion can’t change the condition or the situation you’re dealing with, that emotion is likely to be unhelpful or quite possibly, destructive.

2)      Emotion leads to either helpful or devastating outcomes because it is the very fuel that drives you to take specific actions. 


See things for what they are, do what you can immediately, set realistic expectations and have your emotions in check! 

If you internalise and act on the above principles, you are well on your way to forging a bulletproof mindset of success. One that will tear down all of your obstacles. What blocked your path previously will now become a path itself. 

P.S. Always remember that there is no end to your obstacles! As long as you have worthy goals in life, new obstacles will always emerge. But this is what makes life interesting. This makes the effort and the hustle all worth it. With each trials turned into triumph, you will develop strength, wisdom and perspective. Soon, you will be left with the best version of yourself and all the great feats you’ve accomplished in life.