Business Book Review: Courage is Calling by Ryan Holiday

Fortune favours the brave. Safe efforts lead to safe results. Rewards are reserved for those who took the risk others weren’t brave enough to.

My Rating: ★★★★

Length: 304 pages

Publisher: Profile Trade

Released: 2023

Key Takeaways for Personal Branding

Courage is Calling is an instalment in Ryan Holiday’s series exploring Stoic virtues. Drawing on iconic examples from the ancient world and modern history, he valiantly makes the call to be brave - because, as history has shown us, fortune favours the brave.

As Holiday highlights:

"To each,” Winston Churchill would say, “there comes in their lifetime a special moment when they are figuratively tapped on the shoulder and offered the chance to do a very special thing, unique to them and fitted to their talents. What a tragedy if that moment finds them unprepared or unqualified for that which could have been their finest hour.”

More than physical bravery in the face of fear, the book is as much, if not more, about mental bravery too. Against facing potential ridicule, or worse, with fortitude.  For taking risks with ideas when others play it safe, understanding that without risk, there is no reward:

"If it were easy, everyone would do it. If everyone did it, how valuable would it be?"

Acknowledge that playing it safe means doing what the majority is doing. And doing what the majority is doing leads to safe results, not extraordinary ones. Embracing the road to your extraordinary won’t be easy - because if it was, everyone would be doing it:

"We like to think we can have an extraordinary life by making ordinary decisions, but it’s not true. It’s actually all the ordinary decisions—the safe ones, recommended by every expert, criticized by no one—that make us incredibly vulnerable in times of chaos and crisis."

“If it wasn’t scary, everyone would do it. If it was easy, there wouldn’t be any growth in it.”

Never Let Them Intimidate You

Courage is Calling draws on many different disciplines and ancient wisdom to emphasise the importance of courage, including the Bible. The most repeated phrase in the Bible is “Be not afraid” (it’s referenced over 365 times):

"Though an army besiege me,” Psalm 27 reads, “my heart will not fear; though war break out against me, even then will I be confident.”

For thousands of years, humans have known that all roads lead back to courage in the face of fear.

No matter what your own beliefs, the message rings true - Muhammad Ali understood both his beliefs and how he prioritised them. When a promoter of his first title fight tried to get Ali to disavow his Muslim faith with a threat of cancelling the match, Ali told him:

“My religion’s more important than fighting”.

The brave will not be intimidated, nor are they bystanders to their beliefs:

"We want to live in a world of brave people, we want to be brave … and we’re afraid to talk about it because we might look foolish! The brave don’t despair. They believe. They are not cynical, they care. They think there is stuff worth dying for—that good and evil exist. They know that life has problems but would rather be part of the solution than a bystander.”

Life Happens in Public - Get Used to It

A fundamental element of being brave is not caring what people think. It’s the only way to do brave work. Brave work usually draws attention:

"You just learn to stop thinking about what they think. You’ll never do original work if you can’t. You have to be willing not only to step away from the herd but also to get up in front of them and say what you truly think or feel. It’s called “public life” for a reason."

"While most of us will not make our living on the screen, we all have to face this reluctance to be seen. Our fear of what other people think, of embarrassment or awkwardness, is not the same fear that holds a man back from running into battle, but it is a limitation, a deficiency of courage that deprives us of our destiny all the same.”

"There is no change, no attempt, no reach that does not look strange to someone. There’s almost no accomplishment that is possible without calling some attention to yourself. To gamble on yourself is to risk failure. To do it in public is to risk humiliation."

Make them Proud

Henry Longfellow said:

“Lives of great men all remind us we can make our lives sublime and, departing, leave behind us footprints on the sands of time.”

Footprints matter because they leave a trail for those to come.

Holiday highlights the importance of making your ancestors and others who came before you proud.  And when you drift, their footprints are your path back to where you belong.

When Apple drifted from its innovative and rebellious roots, Holiday reminds us of a key tactic Steve Jobs used to get the brand back on track:

“One way to remember who you are,” he said, “is to remember who your heroes are."

Courage is Calling calls attention to them as your guide:

"Standing here, watching you, protecting you. Remind yourself what they would do right here and right now. You can’t let them down. So be braver. Right now. Here, in this decisive moment."

"Most of our brave ancestors and predecessors are gone now, and yet does their example not return to us? Does their memory not float above us to be reached whenever needed? We must turn to them in our darkest moments. This is readymade courage we can draw on whenever we feel ourselves wavering”

“When we are afraid, we can look up at those who came before us. We can visit the monuments they erected. We can read the documents they wrote. Because this is our tradition. They have passed us a baton. Will we accept it?"

Favourite Quotes

"The paradox of course is that almost everything new, everything impressive, everything right, was done over the loud objections of the status quo. Most of what is beloved now was looked down on at the time of its creation or adoption by people who now pretend that never happened.”

“By definition, each of us is original. Our DNA has never existed before on this planet. No one has ever had our unique set of experiences. Yet what do we do with this heritage? We push it away. We choose not to be ourselves. We choose to go along, to not raise any eyebrows."

“Because the courage to be different is the courage to think different, to see what others don’t see, to hear what others don’t hear. It’s not a coincidence that so many whistleblowers and artists were weirdos. It was precisely their weirdness that allowed them to see what everyone else was unable to see.”

“If we do, on the outside, look the same as everyone else, we better make damn sure that on the inside everything is different.”

It has been said that “one man with courage makes a majority.”

“What we are familiar with, we can manage. Danger can be mitigated by experience and by good training. Fear leads to aversion. Aversion to cowardice. Repetition leads to confidence. Confidence leads to courage.”

“Training is not just something that athletes and soldiers do. It is the key to overcoming fear in any and all situations. What we do not expect, what we have not practiced, has an advantage over us. What we have prepared for, what we have anticipated, we will be able to answer. As Epictetus says, the goal when we experience adversity is to be able to say, “This is what I’ve trained for, for this is my discipline.”

“Start small … on something big. Eliminate one problem. Move things one iota. Write one sentence. Send one letter. Make a spark."

“If you’re going to speak out: Sign your name. Sign your name on everything you do. That’s the brave—no, the basic—thing to do."

“They will laugh at you. Losers have always gotten together in little groups and talked about winners. The hopeless have always mocked the hopeful. The scared do their best to convince the brave there is no point in trying. Since the time of the Sophists, academics have, for whatever petty reason, used their considerable brains to muddy the waters rather than clear them."

Courage is Calling by Ryan Holiday:  Available on Amazon.