Learning From Literature

The Obstacle Is The Way by Ryan Holiday

Cover of The Obstacle Is The Way by Ryan Holiday

The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday is a self-help book published in 2014.

In our personal lives, all of us have big dreams. However, we tend to do nothing when something stands in our way. We blame our bosses, economy, politicians, other people – anything or anyone besides ourselves. In contrast, many great individuals throughout history found a way to transform weakness into a strength – Martin Luther King, Ulysses S. Grant, Thomas Edison, Margaret Thatcher, Amelia Earhart, Dwight D. Eisenhower, Steve Jobs, Barack Obama, and many more. In fact, earlier generations faced worse problems with fewer safety nets and fewer tools. The reality is that most of the time nowadays, we aren’t even in horrible situations, just minor disadvantages. 

The Obstacle Is The Way is a guide to the method and framework for understanding, appreciating, and acting upon obstacles. The book aims not only to make facing and dismantling stumbling blocks a little easier but to show how to turn every obstacle into an advantage. As Andy Grove, the former CEO of Intel, says, “Bad companies are destroyed by crises. Good companies survive them. Great companies are improved by them.” 

“This obstacle… What if embedded inside it or inherent in it were certain benefits — benefits only for you? What would you do? What do you think most people would do? Probably what they’ve always done… nothing”

Ryan Holiday

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Enjoy!

Table of Contents

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PART I : PERCEPTION

“Nothing is either good or bad, but thinking makes it so”

William Shakespeare
The Discipline of Perception
  • Perception is how we see what occurs around us and the meaning we give to those events
    • Can be a source of strength or weakness
  • We have a choice about how we respond
    • Situations by themselves cannot be good or bad — this judgment is what we bring with our perceptions 
  • Through our perception of events, we are complicit in the creation + destruction of every obstacle
    • We can’t change obstacles themselves but our perspective can change how the obstacles appear – our perception will determine how daunting it will be to overcome
    • Choose not to be harmed — and you won’t feel harmed. Don’t feel harmed — and you haven’t been
  • Discipline + perception lets you see the advantage in every situation without fear
Recognize Your Power
  • We are never completely powerless
    • External factors can deprive us of our position but our beliefs + reaction can never be controlled
Steady Your Nerves
  • When we aim high, pressure, stress, and surprises are guaranteed
    • In these situations, grace and poise > talent
    • These two attributes come before the opportunity to deploy any other skill
    • Stress puts us at the potential whim of our instinctive reactions and leads to mistakes, stop thinking clearly, and simply reacting
Control Your Emotions
  • The only way we’ll survive + overcome obstacles is by keeping emotions in check
    • Does getting upset provide you with more options, alertness and wisdom? No
    • Overcoming emotions allows you to solve problems rather than react
  • You still have feelings — real strength lies in the control of one’s emotions, not in pretending they don’t exist 
  • It is the loss of harmful / unhelpful thoughts, not blind optimism
 Practice Objectivity
  • Objectivity means removing you – the subjective part
    • When giving others advice, their problems are crystal clear and solutions obvious
Alter Your Perspective
  • Reduce your fears down to scale
  • Don’t ignore fear — take why you’re afraid and break it apart
Is It Up To You?
  • Focus on the things you can change
    • Circumstances like the situation you were born into, how you lost everything, etc. are in the past and there is a 0% chance that you can change it
  • Focusing exclusively on what is in our power magnifies our power
    • Energy directed at things we can’t influence is wasted
Live In The Present Moment
  • Focus on the present
  • Obstacles exist in the past and future
    • Stressing over finals comes from thinking about the future – implications about how your GPA will affect your job opportunities, etc
    • You can’t do any more than study the best you can
Think Differently
  • Our perceptions determine what we are / are not capable of
    • In many ways, they determine reality itself
    • When we believe in the obstacle more than in the goal, which will inevitably triumph?
Finding The Opportunity
  • See the opportunity inside the obstacle, rather than simply the obstacle that threatens you
  • The extent of the struggle determines the extent of the growth
Prepare To Act
  • The Method:
    • Control your emotions so you can see objectively
    • Mentally flip so you’re looking not at the obstacle, but at the opportunity within it

PART II : ACTION

The Discipline of Action
  • Directed action — not just any action
    • Dismantle the obstacle step-by-step / action-by-action
  • Action requires courage and creative application — not brashness and brute force 
Get Moving
  • You’ve got to start to get anywhere
    • We know our problems and possibly know what to do but are stopped by fears (too risky, don’t have the experience, too expensive, too soon, etc.)
    • Result → Nothing, because we did nothing
  • Courage is simply taking action
    • Just because the conditions aren’t exactly to your liking doesn’t mean you get a pass
    • If you want momentum, you have to create it yourself
  • Start → Really go for it
    • The importance of aggression is downplayed because of negative associations with violence/ masculinity
    • Those who attack problems with the most initiative + energy usually win 
Practice Persistence
  • Genius is often persistence in disguise
    • If you apply your entire physical / mental energy + don’t give up, inevitably one method will work
  • For almost all issues, we have the knowledge, skills, and capabilities → We don’t have the patience, energy, persistence, and will
  • “Persist and Resist”
    • Persist in your efforts
    • Resist giving into distraction, discouragement, or disorder
  • Doing new things means facing obstacles – a new path is by definition uncleared
Iterate

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

Michael Jordan
  • Failure is an asset if the goal is to improve, learn, or do something new
    • Failure shows us the way by showing us what isn’t the way 
    • It’s the preceding feature of nearly all successes
    • Like any good school, learning from failure isn’t free – Tuition is paid in discomfort / loss
  • Ask — “What went wrong here? What can be improved? What am I missing?”
  • The one way to guarantee we don’t benefit from failure is to not learn from it
Follow The Process
  • Break down obstacles into pieces and simply do what you need to do right now
    • Even mammoth tasks are a series of component parts 
  • Address each part through small, deliberate actions — not with brute force
  • Trust the process
    • If you are completing the component parts, then you’ll eventually succeed
Do Your Job, Do It Right
  • Do not be so busy thinking about the future that you don’t take pride in the current task
  • Everything you do is a chance to be your best 
What’s Right Is What Works
  • Focus on results instead of pretty methods
    • Adapt tactics you learned to fit each situation
  • What matters is whether an approach gets you to where you want to go
In Praise Of The Flank Attack
  • Take a step back and go around the problem
  • Things seems so effortless for masters because they are doing less than us
    • Only exert calculated force where it will be effective rather than straining
    • Focus our resources on only the specific areas that matter
  • You don’t convince people by challenging their longest and most firmly held opinions — you find common ground and look for leverage to make them listen 
Use Obstacles Against Themselves
  • Action is not necessarily moving forward – Nonaction can be action
    • Sometimes you need to have patience and wait for a temporary obstacle to fizzle out 
  • When we want things too badly, in our eagerness we can be our own worst enemy
    • There are other ways to get where we are heading
Channel Your Energy
  • Adversity can make you better if you let it
    • Rename it and claim it 
  • Act – don’t act out
    • We want right action, not any action
Seize The Offensive
  • A crisis provides the opportunity to do things you could not before 
  • Ordinary people shy away from negative situations
    • Great people do the opposite – they turn misfortune to their advantage
Prepare For None Of It To Work
  • We can’t control the world around us
    • We can perceive well, act right, and still fail
  • Some obstacles truly may turn out to be impossible to overcome, but use it to practice another virtue – even just learning to accept that bad things happen or practice humility 

PART III : WILL

The Discipline Of The Will
  • Will is an internal power
    • Will is the one thing we completely control
  • Prepare for adversity and practice cheerfulness even in dark times
  • True will is quiet, humility, resilience and flexibility
    • Will is not weakness disguised by bluster and ambition
  • Perception is the discipline of the mind – Action is the discipline of the body – Will is the discipline of the heart and soul
  • We will never get rid of the unpredictable parts of life
    • Certain things will cut you open like a knife – when that happens, the world sees what you’re truly made of
Build Your Inner Citadel
  • You will be better off toughening yourself up than you will trying to take the teeth out of the world
  • No one is born a gladiator, the strength must be built within us
Anticipation (Thinking Negatively)
  • Too many undertaking fail for preventable reasons
    • Far too many people don’t have a back-up plan because they refused to consider that something might not go exactly as they wish 
  • The only guarantee is that things will go wrong
    • Your plan and how things turn out rarely resemble each other 
  • Meditate on what could happen as a probe for weaknesses in your plans
  • The worst thing is not something going wrong, but something going wrong and catching you by surprise
The Art of Acquiescence
  • Just because you can’t do something, does it make you less of a person for acknowledging it and acting accordingly? 
  • You don’t have to like something to use it to your advantage, accept it
Love Everything That Happens: Amor Fati
  • Love whatever happens and face it with cheerfulness 
  • What we must do → What we get to do
  • Imagine being always calm, always in control, genuinely loving the opportunity to prove yourself and to perform for other people whether they want you to succeed or not 
  • Don’t waste a second looking back for your expectations – accept the challenge in front of you with cheer
Perseverance
  • Life is not about one obstacle but many
    • What’s required is determination that you will get to where you need to go somehow + someway
  • Our actions can be constrained, but our will can’t be
    • Belief in yourself cannot be broken
Something Bigger Than Yourself
  • Stop pretending that what you’re going through is somehow special, unfair, or some unique misfortune
    • There have been countless people in worse situations than yourself
Meditate On Your Own Mortality
  • Embracing the precariousness of our own existence can be exhilarating + empowering 
  • If we remembered how mortal we are, we wouldn’t spend so much time obsessing over trivialities
Prepare To Start Again
  • There is no end — just when you think you successfully navigated one obstacle, another emerges
  • Passing one obstacle simply says you’re worthy of more
    • You get better with every attempt
    • Don’t be afraid or overwhelmed

CONCLUSION

  1. See Clearly
  2. Act Correctly
  3. Endure + Accept The World As It Is

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