46 inspiring quotes from The Obstacle Is The Way by Ryan Holiday

46 Quotes from Obstacle Is The Way for entrepreneurs


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.

46 Quotes from The Obstacle Is The Way

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

46 Quotes from The Obstacle Is The Way

Whatever we
face, we have a choice: Will we be blocked by obstacles, or will we advance
through and over them?

46 Quotes from The Obstacle Is The Way

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.
We wish it weren’t true, but it is.

46 Quotes from The Obstacle Is The Way

How skilled we are at cataloguing what holds us back!

46 Quotes from The Obstacle Is The Way

Every obstacle is unique to each of us. But the responses they elicit are the
same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.


“Bad companies are destroyed by crisis. Good companies survive them. Great
companies are improved by them.”


Great individuals, like great companies, find a way to transform weakness
into strength. It’s a rather amazing and even touching feat. They took what
should have held them back—what in fact might be holding you back right
this very second—and used it to move forward.

No philosophic writing is more accessible. It
feels like it was written last year, not last millennium.


Ancient philosophy never cared much for authorship or
originality—all writers did their best to translate and explain the wisdom of
the greats as it has been passed down in books, diaries, songs, poems, and


All great victories, be they in politics, business, art, or seduction, involved
resolving vexing problems with a potent cocktail of creativity, focus, and


“The Things which hurt,”
Benjamin Franklin wrote, “instruct.”

Abundance can be its own obstacle, as many people can attest.

We can see disaster rationally. Or rather, like Rockefeller, we can see
opportunity in every disaster, and transform that negative situation into an
education, a skill set, or a fortune. Seen properly, everything that happens—be
it an economic crash or a personal tragedy—is a chance to move forward.
Even if it is on a bearing that we did not anticipate.


We decide what we will make of each and every situation. We decide
whether we’ll break or whether we’ll resist. We decide whether we’ll assent
or reject. No one can force us to give up or to believe something that is untrue.


To one person a situation may be negative. To another, that same situation
may be positive.

Through our perception of events, we are complicit in the
creation—as well as the destruction—of every one of our obstacles.


A mistake becomes training.


Just because your mind tells you that something is awful or evil or
unplanned or otherwise negative doesn’t mean you have to agree.


We decide what story to tell ourselves.


When we aim high, pressure and stress obligingly come along for the ride


When America raced to send the first men into space, they trained the
astronauts in one skill more than in any other: the art of not panicking.


Uncertainty and fear are relieved by authority. Training is authority.


“When you worry, ask
yourself, ‘What am I choosing to not see right now?’ What important things
are you missing because you chose worry over introspection, alertness or


To paraphrase Nietzsche, sometimes being superficial—taking things only
at first glance—is the most profound approach.


Perceptions are the problem. They give us the “information” that we don’t
need, exactly at the moment when it would be far better to focus on what is
immediately in front of us: the thrust of a sword, a crucial business
negotiation, an opportunity, a flash of insight or anything else, for that matter.

Epictetus told his students, when they’d quote some great thinker, to
picture themselves observing the person having sex. It’s funny, you should try
it the next time someone intimidates you or makes you feel insecure. See
them in your mind, grunting, groaning, and awkward in their private life—
just like the rest of us.


Roasted meat is a
dead animal and vintage wine is old, fermented grapes.


Objectivity means removing “you”—the subjective part—from the
equation. Just think, what happens when we give others advice? Their
problems are crystal clear to us, the solutions obvious. Something that’s
present when we deal with our own obstacles is always missing when we hear
other people’s problems: the baggage. With other people we can be objective.


Selfishly—and stupidly—we save the pity and the sense of
persecution and the complaints for our own lives.



It’s your choice whether you want to put I in front of something (I hate
public speaking. I screwed up. I am harmed by this). These add an extra
element: you in relation to that obstacle, rather than just the obstacle itself.


For whatever reason, we tend to look at things in isolation. We kick
ourselves for blowing a deal or having to miss a meeting. Individually, that
does suck—we just missed 100 percent of that opportunity.
What we’re forgetting in that instance, as billionaire serial entrepreneur
Richard Branson likes to say, is that “business opportunities are like buses;
there’s always another coming around.” One meeting is nothing in a lifetime
of meetings, one deal is just one deal. In fact, we may have actually dodged a
bullet. The next opportunity might be better.


The way we look out at the world changes how we see these things. Is our
perspective truly giving us perspective or is it what’s actually causing the
problem? That’s the question.


If what’s up to us is the playing field, then what is not up to us are the rules
and conditions of the game.



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. That someone
decided not to fund your company, this isn’t up to you. But the decision to
refine and improve your pitch? That is. That someone stole your idea or got to
it first? No. To pivot, improve it, or fight for what’s yours? Yes.


Half the companies in the Fortune 500 were
started during a bear market or recession.


Those people with an
entrepreneurial spirit are like animals, blessed to have no time and no ability
to think about the ways things should be, or how they’d prefer them to be.

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


Remember that this moment is not your life, it’s just a moment in
your life. Focus on what is in front of you, right now. Ignore what it
“represents” or it “means” or “why it happened to you.”



An entrepreneur is someone with faith in their ability to make something
where there was nothing before. To them, the idea that no one has ever done
this or that is a good thing. When given an unfair task, some rightly see it as a
chance to test what they’re made of—to give it all they’ve got, knowing full
well how difficult it will be to win. They see it as an opportunity because it is
often in that desperate nothing-to-lose state that we are our most creative.


Obstacles illuminate new options.


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.


A clearer head makes for steadier hands.


Genius often really is
just persistence in disguise.


Persist in your efforts. Resist giving in to distraction,
discouragement, or disorder.


It’s okay to be discouraged. It’s not okay to quit.


It’s supposed to be hard. Your first attempts aren’t going to
work. It’s goings 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.


What is defeat? Nothing but education; nothing but the first steps to something better.


Failure really can be an asset if what you’re trying to do is
improve, learn, or do something new.


There’s nothing shameful about being wrong, about changing
course. Each time it happens we have new options. Problems become


Action and failure are two sides of
the same coin.


Failure puts you in corners you have to think your way out of. It is a
source of breakthroughs.

The one way to guarantee we don’t benefit from failure—to ensure it is a
bad thing—is to not learn from it.



Lessons come hard only if you’re deaf to them.



Failure shows us the
way—by showing us what isn’t the way.



Follow the process
and not the prize.


Excellence is a matter of steps. Excelling at this one,
then that one, and then the one after that.



The unordered mind loses track of what’s in front of it—what matters—and gets
distracted by thoughts of the future.


Being trapped is just a position, not a fate.


Sometimes, on the road to where we are going or where we want to be, we
have to do things that we’d rather not do. Often when we are just starting out,
our first jobs “introduce us to the broom,” as Andrew Carnegie famously put
it. There’s nothing shameful about sweeping. It’s just another opportunity to
excel—and to learn.

Wherever we are, whatever we’re doing and wherever we are going, we
owe it to ourselves, to our art, to the world to do it well.


When action is our priority, vanity falls away.


You should never have to ask yourself, But what am I supposed to do now?
Because you know the answer: your job.


Duty is beautiful, and inspiring and empowering.

In every situation, life is asking us a question, and our actions are the
answer. Our job is simply to answer well.


Think progress, not perfection.


You don’t convince people by challenging their longest and most firmly
held opinions. You find common ground and work from there. Or you look
for leverage to make them listen. Or you create an alterative with so much
support from other people that the opposition voluntarily abandons its views
and joins your camp.

Sometimes you overcome obstacles not by attacking them but by
withdrawing and letting them attack you.


When we want things too badly we can be our own worst enemy.


We get so consumed with moving forward that we forget that there are
other ways to get where we are heading. It doesn’t naturally occur to us that
standing still—or in some cases, even going backward—might be the best
way to advance. Don’t just do something, stand there!


Adversity can harden you. Or it can loosen you up and make you better—if
you let it.


[A] crisis provides the opportunity for
us to do things that you could not do before.”


Life speeds on the bold and favors
the brave.


Problems, as Duke Ellington once said, are a chance for us to do our best.
Just our best, that’s it. Not the impossible.


Will is fortitude and wisdom—not just about specific obstacles but about
life itself and where the obstacles we are facing fit within it.


Certain things in life will cut you open like a knife. When that happens—at
that exposing moment—the world gets a glimpse of what’s truly inside you.
So what will be revealed when you’re sliced open by tension and pressure?
Iron? Or air? Or bullshit?


Nobody is born with a steel backbone. We have to forge that ourselves.

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.


What you
think you deserve is also rarely what you’ll get.



The only
guarantee, ever, is that things will go wrong. The only thing we can use to
mitigate this is anticipation.



You know what’s better than building things up in your imagination?
Building things up in real life.


Indifference and acceptance are certainly better than disappointment or


There is always some good—even if only
barely perceptible at first—contained within the bad.

If persistence is attempting to solve some difficult problem with dogged
determination and hammering until the break occurs, then plenty of people
can be said to be persistent. But perseverance is something larger. It’s the long
game. It’s about what happens not just in round one but in round two and
every round after—and then the fight after that and the fight after that, until
the end.


Life is not about one obstacle, but many. What’s required of us is not some
shortsighted focus on a single facet of a problem, but simply a determination
that we will get to where we need to go, somehow, someway, and nothing will
stop us.

Persistence is an action. Perseverance is a matter of will. One is
energy. The other, endurance.


There are far more failures in the world due to a collapse of will than there
will ever be from objectively conclusive external events.


We whine and complain and mope when things won’t go our way. We’re
crushed when what we were “promised” is revoked—as if that’s not allowed
to happen.


The good thing about true perseverance is
that it can’t be stopped by anything besides death.


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.


Pride can be broken. Toughness has its limits. But a desire to help? No
harshness, no deprivation, no toil should interfere with our empathy toward



We’re all just humans, doing the best
we can.



Help your fellow humans thrive and survive, contribute your little bit to the
universe before it swallows you up, and be happy with that.



Death doesn’t make life pointless, but rather purposeful.


The paths of glory, Thomas Gray wrote, lead but to
the grave.


There’s no question about it: Death is the most universal of our obstacles.


In the
shadow of death, prioritization is easier.


As the Haitian proverb puts it: Behind mountains are more mountains.


The essence of philosophy is action.


Philosophy was never what happened in the classroom. It was a set of
lessons from the battlefield of life.


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