Notes from “THE OBSTACLE IS THE WAY” by Ryan Holiday

An excellent Self-Help Book based on the Stoicism. It inspires, motivates and helps reader to take actions instead get stuck due to obstacle.

My favorite line: “Transform fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking”

My elder daughter Saanvi has made this bookmark using her origami skills and I love it 🙂

Discipline in perception let’s you clearly see the advantage and the proper course of action in every situation— without the pestilence of panic or fear

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

A mistake becomes training 

Tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head

Preparing for the realities of the situation steadying our nerves so we can throw our best at it 

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

The art of not panicking 

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. 

Unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty 

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 Greek word apatheia is the kind of calm equanimity that comes with the absence of irrational or extreme emotions 

No thank you, I can’t afford to panic

Gavin de Becker – The Gift of Fear “When you worry, ask yourself, ‘What am I choosing to not see right now? What important things are you missing because you choose worry over introspection, alertness or wisdom?

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.

Remind yourself – I am in control, not my emotions. I see what’s really going on here. I’m not going to get excited or upset.

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

Do I need to freak out about this?

No, because I practiced for this situation and I can control myself. 

No, because I caught myself and I’m able to realise that that doesn’t add anything constructive 

“Don’t let the force of an impression when it first hit you knock you off your feet; just say to it: Hold on a moment; let me see who you are what you represent. Let me put you to the test.” ~ Epictetus

The book of Five Rings Miyamoto Musashi

“The Perceiving eye is weak, the Observing eye is strong” – Miyamoto Musashi 

Objectivity means removing “you” — the subjective part from the equation

Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter.  

Man does not simply exist but always decides what his existence will be, what he will become the next moment. By the same token, every human being has the freedom to change at any instant — Viktor Frankl 

Perspective is everything 

When you can break apart something , or look at it from some new angle, it loses its power over you.

Fear is debilitating, distracting, tiring, and often irrational. Use the power of perspective to defeat it. 

Take what you’re afraid of — when fear strikes you — and break it apart.

Business opportunities are like buses, there is always another coming around 

Expand our perspective to whatever will  keep us calmest and most ready for the task at hand. 

The difference between the right and the wrong perspective is everything 

Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective. 

I live our first job is this, to divide and distinguish things into two categories: externals I can not control; but the choices I make with regard to them I do control. Where will I find good and bad? In me, my choices — Epictetus 

One Question to ask over and over again – “Is there a chance? Do I have a shot? Is there something I can do?

God, grant me the serenity to accept the things I cannot change

The courage to change the things I can,

And the wisdom to know the difference. 

“Ta eph’hemin, ta our eph’hemin” – what is up to us, what is not up to us.

What is up to us?

Our emotions

Our judgements 

Our creativity

Our attitude 

Our perspective 

Our desires 

Our decisions

Our determination

Live in the present moment

The Trick to forgetting the big picture is to look at everything close up – Chuck Palahniuk

Most people start from disadvantage and do just fine. It’s not unfair, it’s universal. Those who survive it, survive because they took things differently day by day — that’s the real secret.

Focus on the moment, not the monsters that may or may not be up ahead.

“We cannot spend the day in explanation” Emerson

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 now. Live in the moment!

Discard distracting thoughts, leave things well enough alone — no matter how much you feel like doing otherwise.

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”

Malleable – capable of being extended or shaped by beating with a hammer or by the pressure of rollers. 

Think Differently

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

Don’t be afraid, you can do it. Get your mind around it. You can do it!

Be realistic

Listen to feedback

Play well with others


conventional wisdom is too conservative…

It is often in that desperate nothing-to-lose state that we are our most creative

Our Best ideas comes from there where obstacle illuminate new options

Finding the opportunity

“A good person dyes events with his own color … and turns whatever happens to his own benefit.” — Seneca

The present situation is to be regarded as opportunity for us and not disaster Dwight D. Eisenhower

There is good in everything, if only we look for it – Laura Ingalls Wilder

It’s our preconceptions that are the problem

It’s all fair in the game, and every situation is an opportunity for us to act

Take on a long time rival at work (or rival company etc), the one who causes endless headaches? Note the fact that they also:

  • Keep you alert
  • Raise the stakes
  • Motivate you to prove them wrong
  • Harden you
  • Help you to appreciate true friends
  • Provide an instructive antilog — an example of whom you don’t want to become

Blessings and burdens are not mutually exclusive. It’s a lot more complicated. 

Adversarial growth and post-traumatic growth. “ That will doesn’t kill me makes me stronger” is not a  cliche but fact

Conniving — to cooperate secretly; conspire (often followed by with)

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

Seeing through the negative, past its underside, and into corollary: the positive.

Prepare to act

Then imitate the action of the tiger; stiffen the sinews, summon up the blood. – Shakesphere

The Discipline of action

Greet our obstacles

  • With energy
  • With persistence
  • With a coherent and deliberate process
  • With iteration and resilience
  • With pragmatism
  • With strategic vision
  • With craftiness and savvy
  • And an eye for opportunity and pivotal moments

Each obstacle we overcome makes us stronger for the next one

Get Moving

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

He says the best way out is always through And I agree to that, or inso far. As I can see no way out but through ~ Robert Frost

You’ve got a million reasons why you can’t move at a faster pace.

If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started. Don’t settle down in your comfort zone.

Practice Persistence

He says the best way out is always through And I agree to that, or in so far As I can see no way out but through

Genius often really is just persistence in disguise

Never in a hurry

Never worried

Never desperate

Never stopping short

Persist and Resist ~ Epictetus

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

Only by persistence and time can we cut away debris and remove impediments. 

The first is intuition — and comes with a burst — then difficulties arise – Edison

Stop looking for angels and start looking for angles

When setbacks come, we respond by working twice as hard


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

As engineers now like a quip: Failure is a Feature.

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

Problems become opportunities. Failure is a source of breakthroughs

Action and Failure are the two sides of the same coin.

Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail

Great entrepreneurs are:

Never wedded to a position

Never afraid to lose a little of their investment

Never bitter or embarrassed

Never out of the game for long

They don’t see the problem that failure exposes. It doesn’t make them better. 

LISTEN to feedback – giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something.

Lessons come hard only if you’re deaf to them. Please Don’t be..

We turn what would otherwise be disappointing into opportunity. Failure shows us the way — by showing us what isn’t the way. 

Follow the process

Under the comb

The tangle and the straight path

Are the same — Heraclitus

Follow the process and not the prize.

Excellence is a matter of steps. 

When it comes to our actions, disorder and distraction are death. The unordered mind loses track of what’s in front of it — what matters — and gets distracted by thoughts of the future. 

The process is order, it keeps our perceptions in check and our actions in sync.

Being trapped is just a position, not a fate. You get out of it by addressing and eliminating each part of that position through small, deliberate actions — not by trying (and failing) to push it away with superhuman strength

Goals help put the blips and bumps in proper proportion 

The process is the voice that demands we take responsibility and ownership. That prompts us to act even if only in a small way.

Replace fear with the process, Depend on it. Lean on it. Trust in it.

The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.

Do your job, do it right

Whatever is rightly done, however humble, is noble (Quidvis recte factum quamvis humile praeclarum) — Sir Henry Royce

These men went from hubble poverty to power by always doing what they were asked to do – and doing it right and with real pride. And doing it better than anyone else. In fact, doing it well because no one else wanted to do it.

We’re so busy thinking about the future, you don’t take any pride in the tasks you’re given right now. You just phone it all in, cash your paycheck, and dream of some higher station in life. Or you think, This is just a job, it isn’t who I am, it doesn’t matter. 

When action is our priority, vanity falls away.

Our job is to respond with:

Hard work


Helping others as best as we can

Respect the craft and make something beautiful ~ Steve Jobs

We are not inventing the next iPad or iPhone, but we are making something for someone — even if  it’s just our own resume.

What’s right is what works

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

It doesn’t matter how you get your opponents down after all we only have to take them down with courage and confidence

The first iPhone was revolutionary, but it still shipped without a copy and paste feature or a handful of other features Apple would have liked to have included.

Think progress not perfection. Under this kind of force, obstacles break apart. They have no choice.

In Praise of the flank attack

Whoever cannot seek the unforeseen sees nothing, for the known way is an impasse. – Heraclitus

Never attack where it is obvious. 

Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success.

Self-Flagellation –  is the disciplinary and devotional practice of flogging oneself with whips or other instruments that inflict pain.

Use obstacles against themselves

Wise men are able to make a fitting use even or their enmities – Plutarch

Physical force with soul force

When we want things too badly we can be our own worst enemy. In our eagerness, we strip the very screw we want to turn and make it impossible to ever get what we want. We spin our tyres in the snow or mud and dig a deeper rut — one that we’ll never get out of.

We get so consumed with moving forward that we forget that there are other ways to get where we are heading. 

Use the impediment as an opportunity to explore a new direction

Staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path

Passive resistance is incredibly active

Push a negative hard enough and deep enough it will break through into its counterside ~ Saul Alinsky

Channel your energy

Physically loose and  mentally tight

Stay free where it matters: INSIDE

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

Think of water. When dammed by a man-made obstacle, it does not simply sit stagnant. Instead, its energy is stored and deployed, fueling the power plants that run entire cities. 

We act out, instead of act.

External factors influence the path, but not the direction: Forward

Seize the offensive

The best men are not those who have waited for chances but who have taken them; besieged chance, conquered the chance, and made chance the servitor – E H Chapin

Imperiled – to put in peril or danger

Unencumbered – An encumbrance is a limitation on the ownership of a property

I intend to attack and whip them right here and now

The obstacle is not only turned upside down but used as a catapult

Prepare for none of it to work

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 – Seneca

Perceptions can be managed. Actions can be directed.

Nothing can ever prevent us from trying. Ever

If someone you love hurts you, there is a chance to practice forgiveness. If your business fails, now can you practice acceptance. If there is nothing else you can do for yourself, at least you can try to help others

Problems are a chance for us to do our best. 


Will is our internal power which can never be affected by the outside world

True will is quiet humility, resilience, and flexibility

Sanguine – marked by eager hopefulness : confidently optimistic. 

This too shall pass

Gird – to prepare (oneself) for action. 

Leadership requires determination and energy

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

Always prepare ourselves for more difficult 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…

Build your inner citadel

If thy faint in the day of adversity, thy strength is small

The path of the least resistance is a terrible teacher


Premortem –  Gary Klein

If you’re not humble, life will visit humbleness upon you ~ Mike Tyson

Nothing happens to the wise man against his expectation. Nor do all things turn out for him as he wished but as he reckoned – and above a he reckoned that something could block his plans

Manage Expectations

You don’t get what is rightfully yours, even if you earned it. 

Beware the calm before the storm,

Hope for the best, prepare for the worst

The worst is yet to come

It gets worse before it gets better

Its better to meditate on what could happen, to probe for weaknesses in our plans, so those inevitable failures can be correctly perceived, appropriately addressed, or simply endured

We are prepared for the failure and ready for the success

The art of Acquiescence

The fates guide the person who accepts them and hinder the person who resists them. — Cleanthes

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.

Channeling requires consent. It requires acceptance.

When a doctor gives you orders or a diagnosis — even if its the opposite of what you wanted — what do you do? You accept it. You don’t have to like or enjoy the treatment but you know that denying it only delays the cure.

When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The stoics have a beautiful name for this attitude, They call it the Art of Acquiescence.

We squirm and complain about what was taken from us. We still can’t appreciate what we have. 

The answer is in the lap of the Gods.

Be humble and flexible to acknowledge the change in our lives.

Man proposes but God disposes.

As fate would have it.

Heaven forbid.

Nature permitting.

Murphy’s law.

You are robust and resilient enough to handle whatever occurs

You can’t do anything about it anyway

You’re looking at a big-enough picture and long-enough timeline that whatever you have to accept is still only a negligible blip on the way to your goal.

Nature, in order to be commanded, must be obeyed – Francis Bacon

Love everything that happens: Amor Fati

We don’t get to choose what happens to us but we can always choose how we feel about it.


Gentlemen I am hardening on this enterprise. I repeat, I am now hardening towards this enterprise

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

Made weak by time and fate, but strong in will

To strive, to seek, to find, and not to yield

Perseverance. Force of purpose. Indomitable will. 

“With the exercise of self trust new powers shall appear” ~ Emerson 

“The barriers are not erected which can say to aspiring talents and industry, Thus far and no further” ~ Beethoven

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.

Something Bigger Than Yourself

“A man’s job is to make the world a better place to live in, so far as he is able — always remembering the results will be infinitesimal — and to attend to his own soul” ~ Leroy Percy

People are getting a little desperate. People might not show their best elements to you. You must never lower yourself to being a person you don’t like. There is no better time than now to have a moral and civic backbone. To have a moral and civic true north. This is a tremendous opportunity for you, a young person, to be heroic.

If I can’t solve this for myself, how can I at least make this better for other people?

If not for me, then for my family or the others I’m leading or those who might later find themselves in a similar situation 

Unity over self. We’re in this together.

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. 

Meditate on your mortality 

“When a man know he is to be hanged in a fortnight, it concentrates his mind wonderfully” ~ Dr Johnson

Death doesn’t make life pointless, but rather purposeful. And we don’t have to nearly die to tap into this energy

Embracing the precariousness of our own existence can be exhilarating and empowering 

Memento Mori

Be ready for when that day comes

Thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.

Prepare to start again

Live on in your blessings, your destiny’s been won. But our calls us on from one ordeal to the next. ~ Virgil

Life is a process of breaking through these impediments — a series of fortified lines that we must break through 

One does not overcome an obstacle to enter the land of no obstacles 

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

The world seems to keep throwing obstacles at you once it knows you can take it. Which is good, because we get better with every attempt.

Final Thoughts 

The obstacle becomes the way

When the fire is strong, it soon appropriates to itself the matter which is heaped on it, and consumes it, and rises higher by means of this very material

Fate doesn’t have to be fatalistic. It can be destiny and freedom just as easily.

First see clearly.

Next, act correctly.

Finally, endure and accept the world as it is.

Transform fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking

We gather strength as we go. That’s how it works, That’s our motto

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.


“To be a philosopher is not merely to have subtle thoughts, nor even to found a school… it is to solve some of the problems of life, not only theoretically, but practically.” ~ Henry David Thoreau

Please buy this awesome book @ Amazon and enjoy the anecdotes of Stoicism.

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