Courage Is Calling by Ryan Holiday

Name: Courage Is Calling
Author(s): Holiday, Ryan
Published: 2021
The Core Problem: In a world where fear, pragmatism, and the desire for comfort often paralyse us into inaction, how can we overcome our innate fears and answer the call to act with courage in our daily lives?
The Bottom Line
- What it is: Courage Is Calling is a philosophical and practical guide that uses Stoic wisdom and historical examples to explore the nature of courage and provide a framework for cultivating it.
- Why it matters: It matters because fear is a choice, and choosing to cower leads to a life of regret and unfulfilled potential.
- What you’ll get: From this Note, you will get a framework for dissecting and defeating fear, a set of principles for taking courageous action, and an exploration of heroism as the highest form of courage.
Time Commitment:
Disclaimer: This content is intended for educational, commentary, and review purposes only. All opinions expressed are my own and are not affiliated with the author or publisher of the book. Any copyrighted material, including quoted excerpts, is used under the principles of fair use for criticism and analysis. For further information or to support the author, please refer to the links mentioned at the beginning of this page.
The Strategist’s Briefing
I expect this book to be mostly about lessons on courage, one of the four Stoic virtues (others being justice, temperance and wisdom).
Without even opening the book I can tell that this is going to meet the “Bring” and “Remember” value groups, let’s see what else it got.
The author, Ryan Holiday, is someone whom I have been listening and have also read a few of his books.
Indeed, his life serves as an inspiration to me as I can see that it is possible for a person to dedicate their life to learning and also get paid for the effort.
I wish to visit Holiday’s Painted Porch book shop one day, and indeed, I would not be shy in admitting that I too dream of a Sunchaser book store if I ever get a chance to build one in the future.
I cannot think of a better job than this.
Holiday focuses this book on courage, one of the four Stoic virtues. It serves as a call to action against the paralysis of fear. This Note applies the Strategist’s Lens to Holiday’s work, treating courage not as a rare, heroic trait, but as a practical, trainable skill. The goal is to deconstruct fear and provide an actionable playbook for making brave decisions, both big and small. On to the book.

Core Frameworks Deconstructed
Citation: All text highlighted in yellow in this section is cited from – Holiday, Ryan. Courage Is Calling: Fortune Favours the Brave. Kindle Edition.

People think that courage is of two kinds – physical (running into a burning building to save a stranger) and moral (speaking the truth, blowing the whistle etc.) – but Holiday says that these are just two names for the same thing – when you put your ass on the line, literally or figuratively.
But this is not a book about technicalities, no, this is a book about action and rallying readers, some of whom who may have been paralysed into inaction because of perceived limits.
The book is divided into three parts – the first one tells is about fear and how we can overcome it, the second one is about how we can be brave and third is about heroism. Each part contains principles and practices we can apply.
Fear – Rising above it
Heed the call
All of us are called to a mission at least at one point of time in our life, it may not be a “great” mission in the eyes of the world but for us it is something that is worth doing, where the work itself is the reward.
Most of the time the call is ignored in the name of pragmatism, practicality, common sense, custom and other names of fear.
And then the call sits in the recesses of our mind, tugging at us from time to time until it is too late and what is left is only regret at a life not fully realised.
Holiday asks us that when we are called to our own personal mission, to do work that we consider good in itself – will we heed the call or ignore it?
He gives the example of Florence Nightingale who grew up in luxury and for a long time ignored her call to serve humanity, but eventually she heeded the call and her work laid the foundation for professional nursing and had a lasting impact on healthcare practices.
It’s okay to be scared, not okay to cower
Feeling scared is a reaction in the present moment – when your instincts take over in the face of clear and immediate danger (real or perceived).
But what you do when the emotional reaction wears off is what actually counts – if you continue to remain scared, that is not good. Chronic fear paralyses you (can personally attest) and so you forego whatever slim chance you might have had at recovery It is important to realise that fear is a choice – we choose to cower.
Others can try to get us out of fear or get us deeper in it – but what finally happens is up to us.
Remember, fear is a choice – and if it is a choice, why wouldn’t you choose better? Attack fear logically, clearly and with empathy.
The primitive parts of out brain like to imagine a tiger behind a rustling bush than a rabbit, and for good reason, but this also means that it can be easily scared and constantly triggered in the increasingly uncertain world we live in today.
Another thing about the kind of fear that really paralyses us that it is amorphous – that is to say it is not clearly defined and so appears much more menacing than it actually is.
The way out of this is by logic (and if I may add, probability) – test those assumptions clearly and with data.
The brain appeals to us from ignorance, but that does not mean that we have to accept what it says at face value.
The weapon of choice of the scared, untrained, untamed brain is the question “what if?” – Learn to answer this question decisively and bravely.
When confronted with this question get into the details and ask the brain to spell out exactly what it is afraid of and where, how, when and why would the thing actually happen.
Analyse your fear
Get into the nitty-gritty (the “five whys“), don’t take magical or fantastical explanations for an answer – nothing happens magically, it’s just our understanding that may be lacking in explaining it, but ever since the Big Bang everything has had a cause.
Be scientific in everything, including questions your own assumptions. Soon you will find the brain runs out of answers and just starts repeating the same original “what if” fear – indicating to you that it does not know. That is it just afraid because it is afraid. I can speak from personal experience this happens.
Bookmark this moment in memory, and the next time your brain asks “what if” take it through the same scrutinising exercise until the time you learn to naturally ignore anything it says unless the risk is clear and present (i.e. the smell of something burning or loud noises) and/or presented with compelling logical evidence.
Naval Ravikant has said “Ignore those trying to scare you with a danger that isn’t clear and present.“, and this includes your own brain.
For instance, the ache in your abdomen can be from a food that does not agree with your digestive system or it can be from pancreatic cancer. The brain may want you to assume the worst but it is you who is responsible for calculating the probabilities of each, logically diving into the possible causes and acting accordingly (you can also call this S2 taking over control from S1).
Holiday talks about Ferriss’ “fear setting” exercise that helps us over come these intrusive and negative thoughts.
Focus on what you feel
Do not let the worry about what others will think of you derail you from doing what you think is the right thing to do.
Remember that you are likely to imagine more numerous and graver risks than what actually exist.
Like Seneca has said “We suffer more often in imagination than in reality.”.
Challenges are gifts in disguise, don’t fear them
When you travel the path that you believe in, you can be sure that challenges will come.
But instead of bemoaning your luck you need to understand the challenges make you better.
“Our bruises and scars become armor. Our struggles become experience. They make us better. They prepared us for this moment, just as this moment will prepare us for one that lies ahead.”.
Focus on what you can control, take it one day at a time
Imagining all sorts of possibilities and branches of how time could play out only bogs down the brain and prevents it from doing the only thing that will make a difference – taking action. This is especially true if you’re considering something complicated with various moving parts and that spans a longer time like a year or more.
The way is to make a decent plan with the information you have at the moment and get to work. Solutions will present themselves to you over time.
There is always something you can do: Apathy, thinking that nothing can be done or worse even if you did anything it would not matter is a sign that you’re allowing your fear to rule you. Know that there is always something you can do, it may not be the silver bullet but it’ll be better than nothing.
Believe in yourself: There’ll be no dearth of doubters and cynics, but you, at least you have to believe that you can succeed and that your cause is worth fighting for. Nihilism may be part of the zeitgeist today but it is a deadening approach to life.
Take the shot, all of it is chance: “All growth is a leap in the dark. If you’re afraid of that, you’ll never do anything worthwhile. If you take counsel of your fears, you’ll never take that step, make that leap.”.
Playing it safe is no guarantee
One may think by sticking to the tried and true, the safe and narrow will guarantee safety against the vagaries of the future. But no one is safe indefinitely and by not exposing yourself to challenges you just make it harder to cope during times of crisis and chaos.
“Our fears point us, like a self-indicting arrow, in the direction of the right thing to do … Fear alerts us to danger, but also to opportunity.”
Be yourself: Authentically and unapologetically. It is tempting to blend in the crowd especially during times when speaking up is most important, but that is not a sign of courage. You know you’re being yourself when you can face yourself in the mirror.
Do not let shame or embarrassment derail you: Failing in public is the risk you take for succeeding in public. Even those you think of as masters of their craft and seasoned feel the same trepidation and anxiety before any public venture whether that be a musical performance, a speech, an investor call or a sports match. But they still go out and do this thing that needs to be done.
Do the thing that needs to be done. Nothing ventured, nothing gained.
Choose the fighter tradition: In your family there would have been those who were cowards, and there would have been those who were brave. Today, in the people you consider your own, there are going to be those you consider brave. Choose that tradition, the tradition of bravery, of courage, of fighters.
Do not be afraid to ask: It’s okay to ask for help, it’s okay to admit you don’t know – doing so is not an indictment, you are asking for help so that you may proceed further. “You’re looking for a hand, not a handout. You’re looking for advice. You’re not looking to be exempted. You’re getting your wounds treated so you can get back into the fight.“.
Concept 1: Rising Above Fear
Principle: Fear is the primary obstacle to a courageous life. While feeling scared is a natural, instantaneous reaction, choosing to remain in a state of chronic, amorphous fear is a decision that paralyzes us.
Application: The antidote to fear is logic and action. You must analyze your fear by getting specific, asking the “five whys,” and challenging the “what if” scenarios your brain presents. Separate the emotional reaction from a rational assessment of risk.
Strategist’s Note: Fear is a compass. “Our fears point us, like a self-indicting arrow, in the direction of the right thing to do… Fear alerts us to danger, but also to opportunity.” The very thing you are afraid of is often the thing you most need to do.
Heeding the call to courage
Courage is contagious: Just like fear, when you act with courage you soon find others joining you, buoyed by your resolve.
The call is an opportunity: It is a chance for you to find out, for you to prove to yourself and the world, if you are cowardly or brave. Life sends you difficult times so that you can may test yourself against them and, hopefully, know beyond doubt that you can act with courage when the call comes. In doing so you rise in the eyes of the one that matters: yourself.
No one will do it but you: Remember that you can fall prey to the bystander effect. And remember that no one is going to do it but you.
Take action: All previous statements about virtue can help to counter fear, but what would be better would be to prepare, to train, to act.
The best antidote to anxiety, even fear I can say, is action.
Take action, start doing what courage demands to be done in face of the fear.
Running away is not a courageous action.
Take the first step, even if small, even if private. Just start. Just go.
Speak the truth to power
This is as true as it was in ancient times when ministers used to speak before a demanding king, as it is today when employees are speaking before a demanding CEO.
Speaking the truth to those who are meek and timid is easy, but often we want to appease the powers that be and in doing so cover up the truth so that the full picture is never revealed.
Holiday wants us to develop the habit of speaking the truth even to those who hold power over us, it may not be considered the expedient thing to do in the world that we live in today, but it is definitely courageous.
Stand your ground, demand your rights.
Follow through on your decisions
It is incumbent upon all of us to take a call, to take the shot. We may do this after, to the best of our ability, understanding, interpreting and predicting the situation, but sooner or later we have to take the shot. That is what differentiates those who act with courage and those who sit on the sidelines.
Once you have taken the decision, it is even more important to own it and follow through.
Trust that you have taken the call intelligently, wisely, and therefore the decision is worthy of being stuck to.
Do not make U-turns on your decision very easily. And if you have to pivot, make sure that you are as meticulous as you were when you took the original decision.
The first step is the hardest
After you have found the courage to take that first step, everything else after that may be challenging but it is not morally difficult.
Holiday says: “Courage is defined in the moment. In less than a moment. When we decide to step out or step up. To leap or to step back. A person isn’t brave, generally. We are brave, specifically. For a few seconds. For a few seconds of embarrassing bravery we can be great. And that is enough.“.
Practice it every day
Courage is like a muscle you have to exercise it every day.
It does not need to be grand displays of courage but smaller things where you choose the right thing to do, instead of the cop out that you may have done earlier. It does not even need to involve other people.
Simple things – like choosing to put back the cookie in the jar because you know it is the right thing to do for your health – like not clicking on the “Buy” button because you know you can do without the thing in your life – like choosing to travel coach despite being used to travelling executive – all of these and countless more are acts of courage that we can do every day.
No one can force you to do anything, you force yourself
You rationalise, explain, justify to yourself how bowing down is the expedient thing to do.
They can try and convince you, scare you, blackmail you, confuse you – but you lose only when you decide to give in to their efforts.
The ultimate form of fearlessness is when you are willing to die rather than submit to a power and its plans.
Better to take action, than wait on the sidelines
And even better to take incremental calculated actions than revolutionary and risky ones.
It is true that Fortune favours the bold, but it is also true that the longer you wait to act the more decisive and sweeping actions you will have to take.
Therefore, it is much better to take incremental decisions every day, incrementally practice every day, incrementally train every day, incrementally write every day, incrementally record every day, incrementally invest every day – so that even if something goes wrong, you have the support and safety of the familiar.
Holiday hits the nail on the head: “… it’s complacency that puts you in a position to have to take huge risks … Courage is about risk, but only necessary risk. Only carefully considered risk.“.
In a hundred years you will be a memory, a legacy – Make sure what you leave behind is something that your descendants can be proud of.
Concept 2: Heeding the Call to Courage
Principle: Courage is not the absence of fear, but the decision to act despite it. It is a muscle that must be practiced daily in small ways to be available for big moments.
Application:
- Take the first step: Courage is defined in the moment of decision. Taking the first small step is often the hardest part.
- Speak truth to power: One of the key applications of courage is to be honest, even when it is inconvenient or risky.
- Follow through: Once a courageous decision is made, it is crucial to own it and see it through.
Strategist’s Note: Don’t confuse courage with recklessness. As Holiday says, “… it’s complacency that puts you in a position to have to take huge risks … Courage is about risk, but only necessary risk. Only carefully considered risk”. Prudent, incremental action is often the most courageous path.
Becoming a hero – The highest form of courage – Risking yourself for someone else
Courage is not an absolute good: It is not a good thing to have/do no matter what – the end towards which courage is directed, matters. For example, it takes courage to face a charging bull but the end, cheap entertainment, cannot be compared with the end goal of courage to face a charging enemy on the battleground.
“There is zero glory in winning a battle—whether physical or verbal—to further immoral aims.“.
Heroism is not only about action, it is also about avoiding unnecessary conflict: Holiday suggests that courage isn’t about reckless bravado but about the deliberate choice to act rightly, even when it’s hard, and invokes Shakespeare’s counsel that aligns with this notion: avoid unnecessary conflicts, but if you must engage, do so with conviction and resolve.
Heroism is selfless: To sacrifice your resources, time, even your life so that others may be better. Selflessness is a form of love.The hero has to spend a long time being misunderstood, doubted, laughed at, seen impractical – know what you’re getting into.
Heroes lift others up: Heroism is not about self enrichment or self aggrandisement – It is about what you do for others. “life is meaningless except for its impact on other lives.“.
Heroes don’t dally
Acta, non verba: We can talk all day about courage, but it is only served through our actions. You have to take action, otherwise, for all your talk, you are no different than the next sell out.
Heroes don’t waste precious time assessing reputation risk, the reality of the situation etc. They do their duty.
Afterwards they may be called martyrs or be decorated with medals, that is not their concern any way.
With only seconds to react, they made the split-second decision to stand their ground and open fire.
Their only concern is whether they stand true to their cause when time demands it.
Holiday gives the example of Corporals Jonathan Yale and Jordan Haerter who were stationed at a checkpoint in Ramadi (Iraq) when a truck laden with explosives sped toward their position.
Their actions saved the lives of the fifty Marines and Iraqi policemen inside the base, as their resistance forced the detonation outside the compound.
“A hero is a person who does what needs to be done, not just for themselves but for others. That is, a hero makes their own luck—events don’t just happen to them.“.
The hero leads by example
They are not in their ivory tower looking down at others who sweat it out. No, the hero is in the trenches, inspiring through their actions more than their words.
This line from Holiday resonates deeply: “The parent doesn’t just tell their kid to face their fears, they have to show them what it means to do that in their own life.“.
You need to have a cause that is bigger than yourself
If you hold yourself in the highest regard, above any person or ideal, you will never be capable of true acts of heroism, which by definition require one to be selfless in the service of what they believe in.

Hope is heroic
It may seem pointless and childish in the world we live in today, people may tell us to “get real” but the reality is that all of us need hope to carry on.
And while you may be pragmatic and calculate the odds all the same, somewhere down there you need to have a glimmer of hope that despite all the odds believes, beyond logic and probabilities, that change is possible.
“The only way to lose is to abandon your courage.“.
Concept 3: Highest Form of Courage
Principle: Heroism is courage in the service of others. It is the selfless act of risking yourself for a cause greater than yourself.
Application: Heroism is not just about grand actions; it’s about leading by example, lifting others up, and taking responsibility when others stand by. It requires having a cause bigger than your own ego. The parent who shows their child how to face fear is a hero. The soldier who stands their ground to protect their unit is a hero.
Strategist’s Note: Hope is heroic. In a world prone to cynicism and despair, maintaining the belief that change is possible, despite the odds, is itself an act of supreme courage. “The only way to lose is to abandon your courage.”
High-Signal Quotations
Citation: All text in the following section is cited from – Holiday, Ryan. Courage Is Calling: Fortune Favours the Brave. Kindle Edition.
- When you do the thing others cannot or will not do. When you do the thing that people think you shouldn’t or can’t do. Otherwise it’s not courage. You have to be braving something or someone.
- When fear is defined, it can be defeated … Vague fear is sufficient to deter us; the more it is explored, the less power it has over us. Which is why we must attack these faulty premises and root them out like the cancers they are.
- Such is life. It doesn’t care about our rathers.
- No one can guarantee safe passage in life.
- The well-behaved rarely make history.
- No one is more miserable than the person who has made cop-outs and cowardice their go-to decision.
The Takeaways
Love me a good fearless book, fans the fire in me.
It is a book about action, not preaching.
A very straightforward book to be honest, and you don’t really need to read my interpretation of it – just read the book.
Throughout the book, Holiday brings to life the stories of many individuals whose acts of courage are both awe-inspiring and humbling.
One such story is that of Thích Quảng Đức, a Buddhist monk who, in 1963, made the ultimate sacrifice to protest the persecution of Buddhists in South Vietnam – I was shocked beyond words, beyond thought when I read about him – if this is not courage I do not know what is.
I found that the lessons had started to repeat in the middle of the book, it was like a mild sense of déjà vu as I started seeing the same concepts repeated in different words.
Overall, I think this is a book that you can read a chapter from every once in a while to make sure you do not get complacent.
Your 3-Point Action Plan
- Analyze One Fear. Take one vague fear that is holding you back (e.g., “fear of public speaking”). Spend 15 minutes defining it with precision using the “Fear Setting” exercise. What is the exact worst-case scenario? What is its actual probability? What specific steps could you take to mitigate it?
- Practice One Small Act of Courage. Identify one small, daily action where you typically choose the easy way out. Today, choose the courageous path. This could be making the difficult phone call you’ve been avoiding or speaking up with a contrary opinion in a low-stakes meeting.
- Heed One Call. Think of one small, positive action you know you should take—for your family, your community, or your work—but have been putting off. Don’t fall prey to the bystander effect. Take the first step yourself, today.
This book explores the Stoic virtue of courage. To understand the broader Stoic framework for living a good life, particularly regarding the preciousness of time, see the Field Note on On the Shortness of Life by Seneca.




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