(Book) The obstacle is the way – Ryan Holiday

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The obstacle is the way - Ryan Holiday - kurt.nz

This is one of those books that you can read at any time of your life, and it’s still relevant. Human nature is to avoid obstacles and look for the easiest path. This directly addresses that, and highlights the benefits to be had by overcoming obstacles. Not just avoiding them, but turning them into advantages.

A challenge and a bit of a kick in the pants.

The obstacle is the way – Ryan Holiday (highlights, my thoughts in italics)

Our actions may be impeded … but there can be no impeding our intentions or dispositions . Because we can accommodate and adapt . The mind adapts and converts to its own purposes the obstacle to our acting .

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

And from what we know , he truly saw each and every one of these obstacles as an opportunity to practice some virtue : patience , courage , humility , resourcefulness , reason , justice , and creativity .

Kurt: This can be applied to customer relations for example. Every potentially bad customer experience can be a way to go above and beyond in solving the issue, blowing them away with how you fix things. Every issue is an opportunity.

Let’s be honest : Most of us are paralyzed . Whatever our individual goals , most of us sit frozen before the many obstacles that lie ahead of us .

What do these figures have that we lack ? What are we missing ? It’s simple : a method and a framework for understanding , appreciating , and acting upon the obstacles life throws at us .

Andy Grove , former CEO of Intel , outlined when he described what happens to businesses in tumultuous times : “Bad companies are destroyed by crisis . Good companies survive them . Great companies are improved by them.”

It’s not just : How can I think this is not so bad ? No , it is how to will yourself to see that this must be good — an opportunity to gain a new foothold , move forward , or go in a better direction . Not “ be positive ” but learn to be ceaselessly creative and opportunistic .

“ The obstacle in the path becomes the path . Never forget , within every obstacle is an opportunity to improve our condition . ”

Objective judgment , 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 .


This insight lives on today in Warren Buffet’s famous adage to “ be fearful when others are greedy and greedy when others are fearful . ” Rockefeller , like all great investors , could resist impulse in favor of cold , hard common sense .

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


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 .

Don’t think for a second that grace and poise and serenity are the soft attributes of some aristocrat . Ultimately, nerve is a matter of defiance and control.

Does what happened keep you from acting with justice , generosity , self – control , sanity , prudence , honesty , humility , straightforwardness ?

He wasn’t going to be someone grovelling for a shot . He was someone with something special to offer . He was the answer to their prayers , not the other way around .

In its own way , the most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change .

Or we get ourselves so worked up and intimidated because of the overthinking , that if we’d just gotten to work we’d probably be done already .

One thing is certain . It’s not simply a matter of saying : Oh , I’ll live in the present . You have to work at it . Catch your mind when it wanders — don’t let it get away from you . Discard distracting thoughts .

Genius is the ability to put into effect what is in your mind. There’s no other definition of it.


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 .

When people are : — rude or disrespectful : They underestimate us . A huge advantage . — conniving : We won’t have to apologize when we make an example out of them . — critical or question our abilities : Lower expectations are easier to exceed . — lazy : Makes whatever we accomplish seem all the more admirable .

Problems are rarely as bad as we think — or rather , they are precisely as bad as we think .

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 .

Okay , you’ve got to do something very difficult . Don’t focus on that . Instead break it down into pieces . Simply do what you need to do right now . And do it well . And then move on to the next thing . Follow the process and not the prize .

We are A – to – Z thinkers , fretting about A , obsessing over Z , yet forgetting all about B through Y .

But you , you’re so busy thinking about the future , you don’t take any pride in the tasks you’re given right now .

When action is our priority , vanity falls away .

How you do anything is how you can do everything .

Pragmatism is not so much realism as flexibility . There are a lot of ways to get from point A to point B . It doesn’t have to be a straight line . It’s just got to get you where you need to go .

Opposites work . Nonaction can be action . It uses the power of others and allows us to absorb their power as our own . Letting them — or the obstacle — do the work for us .

Sometimes a problem needs less of you — fewer people period — and not more .

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 .

Great commanders look for decision points . For it is bursts of energy directed at decisive points that break things wide open .

In the meantime , cling tooth and nail to the following rule : not to give in to adversity , not to trust prosperity , and always take full note of fortune’s habit of behaving just as she pleases .


We must prepare for adversity and turmoil , we must learn the art of acquiescence and practice cheerfulness even in dark times .

“ This too shall pass ” was Lincoln’s favorite saying , one he once said was applicable in any and every situation one could encounter .

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 .

A premortem is different . In it , we look to envision what could go wrong , what will go wrong , in advance , before we start . Far too many ambitious undertakings fail for preventable reasons . Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish .

It doesn’t always feel that way but constraints in life are a good thing . Especially if we can accept them and let them direct us . They push us to places and to develop skills that we’d otherwise never have pursued .

My formula for greatness in a human being is amor fati : that one wants nothing to be different , not forward , not backward , not in all eternity . Not merely bear what is necessary , still less conceal it … but love it .


We’d be so much better following the lead of Emerson’s counterexample . Someone who is willing to try not one thing , but “ tries all the professions , who teams it , farms it , peddles , keeps a school , preaches , edits a newspaper , goes to Congress , buys a township , and so forth , in successive years , and always , like a cat , falls on his feet . ”

Determination , if you think about it , is invincible . Nothing other than death can prevent us from following Churchill’s old acronym : KBO . Keep Buggering On .

Help your fellow humans thrive and survive , contribute your little bit to the universe before it swallows you up , and be happy with that . Lend a hand to others . Be strong for them , and it will make you stronger .

Reminding ourselves each day that we will die helps us treat our time as a gift . Someone on a deadline doesn’t indulge himself with attempts at the impossible , he doesn’t waste time complaining about how he’d like things to be .

Why would you do the wrong thing ? Why feel fear ? Why let yourself and others down ? Life will be over soon enough ; death chides us that we may as well do life right .

One does not overcome an obstacle to enter the land of no obstacles . On the contrary , the more you accomplish , the more things will stand in your way . There are always more obstacles , bigger challenges . You’re always fighting uphill . Get used to it and train accordingly .

Never rattled . Never frantic . Always hustling and acting with creativity . Never anything but deliberate . Never attempting to do the impossible — but everything up to that line . Simply flipping the obstacles that life throws at you by improving in spite of them , because of them . And therefore no longer afraid . But excited , cheerful , and eagerly anticipating the next round .

First , see clearly . Next , act correctly . Finally , endure and accept the world as it is .

The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who “ transforms fear into prudence , pain into transformation , mistakes into initiation and desire into undertaking . ”