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Top of the Reads Book Recommendations: Courage is Calling: Fortune Favors the Brave by Ryan Holiday

Updated: Dec 14, 2023


The Book Courage is Calling: Fortune Favors the Brave by Ryan Holiday is sitting on a table with the front cover facing towards you

During the COVID-19 pandemic, many people discovered how to bake banana bread or sourdough, took to making jigsaw puzzles, or adapted their exercise regimes to work out at home. For me, Covid was when I discovered Philosophy (well I didn't "discover" it per se, philosophy has been around since the sixth century BCE, but you know what I mean!).


From what I have learned about philosophy so far, one of my favourite schools of thought has been the Stoics. We might be familiar with the word "stoic", when we think of someone who is quite serious or stern. In contrast, Stoic philosophy focuses on the mastery needed to achieve human flourishing, outlining how to attain wisdom to live a good, virtuous life.


I always thought that things like philosophy, (similar to classical music & wine), are acceptable interest areas for "posh", intellectual people. An everyday person like me liking them either made me pretentious i.e. "notions" as we like to say here in Ireland, or a pretender, because how could someone who likes Country Music also enjoy Philosophy? That sort of intellectual snobbery does Philosophy a disservice, as actually one of the underarching themes of philosophy is that it is a tool for everyone to help us live well. The ancients saw philosophy as training, intellectual and spiritual training (Kathryn Koromilas, 28 Days of Joyful Death Writing in the Stoic Salon, Day 25). The reality is that philosophy is for everyone, as in essence what philosophy does is give us concepts, moral compasses and thought experiments to question how we live, enabling us to lead better, more fulfilled lives. In philosophy they call this Eudaimonia, a combination of well-being, happiness and flourishing, or put simply "A life well lived". I love this concept so much, I've made it one of the values of my business.


The reality is that philosophy is for everyone, as in essence what philosophy does is give us concepts, moral compasses and thought experiments to question how we live, enabling us to lead better, more fulfilled lives.

Personally, I've found philosophy mind bending. It's stretched my mind to think in ways I never knew possible, leaving my thinking more flexible, and making me more open minded and curious than ever before. I am forever expanded having found philosophy. While challenging, it's also brought me much pleasure and joy, and this book is an excellent, accessible way into learning more about philosophy, especially if it's a new topic area for you.


As always in my Top of the Reads series, I won't give you a synopsis of the book as you can get that on Blinkist or Goodreads! If you like what you read, and want to buy the book, this is an affiliate link, meaning if you buy through this link, I will make a small commission from Amazon, at no cost to you: Buy here.


What I did want to talk about in this blog post, was my top takeaways from reading Courage is Calling: Fortune Favors the Brave by Ryan Holiday.

 

Fear is the enemy of courage


Firstly, know that to feel fear is a normal, regular human emotion and has a valid physiological purpose: to keep us alive. Feeling fear is not a sign of human weakness, it doesn't mean you're not brave and courageous enough. I understand now that my fear is there to keep me safe. Like when you know not to cross a road when a car is coming. The trick is to see and understand the benefit to your fear, to ask what is my fear telling me? Fear isn't all negative either: fear can point us in the direction of our dreams (p. 65). It's like envy - we think envy is a "bad" emotion to have, but often envy and jealously is pointing out that we want something that the other person has. Fear can do the same for us: it can tell us what we want.


Fear can have this shady vagueness to it, like a mist that pulls you in and envelops you. The trick to overcoming fear then is to go to the root of it. If we can define our fears, we can defeat them. Go to the root of the fear. Understand it. (p. 18) Figure out the way through. Challenge your fear by asking yourself, "How concrete are my fears?" This is where you often hear the term FEAR: False evidence appearing real (p. 17). How real and concrete is your fear - break it down and challenge it.


For example when I changed careers from a leader in corporate to an entrepreneur. I felt a lot of fear around making that change which kept me very stuck in inaction for months. What was more helpful, and got me to take action, was breaking down what specifically about the transition was creating fear, primarily a change in financial security. Once I knew the root of the fear, I was able to take practical actions to overcome the fear, like building an emergency fund, clearing debt and budgeting, which helped dissipate the fear, and give me the courage I needed to act on my dreams.


A woman taking the risk to leap across a cliff

Photo by Sammie Chaffin on Unsplash


Holiday talks about an essential distinction between being scared and being afraid (p. 14). He summarises being scared as a "temporary rush of feeling", versus being afraid as a "state of being". This is very interesting distinction, and one that I can definitely resonate with. I'm in the middle of recording my first podcast series, and I was terrified before recording my first guest episode! I knew though that it was just a rush of feeling, and a really normal one when you consider that I was in the midst of stretching my comfort zone. The feeling of being nervous & scared, wasn't my whole state of being , as I was super excited about the podcast. Can you find that distinction?


"A scare is a temporary rush of feeling"

"Fear is a state of being"


Holiday goes on to say that it's not that people who do great things don't have fear, it is their ability to master it.


"What we want in life, what the world needs - all of it is on the other side of fear. All of it is accessed through courage, should we choose to wield it"

Ryan Holiday, p. 82


Just because something is hard to do, doesn't mean we shouldn't do it. Fear is trying to keep us safe, keep us within our comfort zone. And often we'd rather stick with what is safe and known to us. Will that give us the life we want though? If not, we need to wield our courage and follow the age old advice - feel the fear and do it anyway.

 

All growth requires a leap

All growth is a leap in the dark according to Holiday (p. 54). You don't know if you are going to succeed - that isn't the point. Is anything safe or a sure thing anyway? You could choose not to leave a "secure" job that you don't feel fulfilled in because you feel it gives you financial security, and then be let go unexpectedly. Nothing in this life is guaranteed. We also don't have as much control over things as we would like to think - just look at what happened during the Covid-19 pandemic. How do you want to spend the time you have, knowing you are not even guaranteed time? After all, tomorrow you could die. Think of the terrifying costs of playing small.


A goldfish leaping out of a fishbowl, with the quote "Leap, and the net will appear"

"Just start somewhere, just do something"

Ryan Holiday, p. 105


I have this phrase written out on a post-it on my laptop, that is how much it resonates with me. As someone vulnerable to procrastination and overwhelm, I take a huge amount of confidence, self belief and power from starting small, and using that to momentum build. Momentum starts working for you - not against you (p.124). The idea is to start small on something big by chunking things down, focusing on completing little steps, that in the end add up. For instance, I don't sit down to write a whole blog post in one go. Instead I try write for 15 minutes every day. When you start taking actions, no matter how small, you begin to replace your fear with competence, learning, action. Repetition leads to confidence. Confidence leads to courage. (If you like this train of thought, check out another of my Top of the Reads, the book Atomic Habits by James Clear)


You must take action, as there is absolutely no chance of success is you do nothing, if you don't even try. Any attempt at action is better than inaction (Gies, p. 158). Just start.


"We get started. We do what we can, where we are, with what we have. It adds up"

Ryan Holiday, p. 107


All you need is a few seconds of courage, the bravery to simply get started. (If you had more time, you'd likely just overthink it!).


We can always find reasons not to do the hard things. Life doesn't provide us with perfect timing to do the things that matter. In fact, it's usually in the face of challenge and adversity that we are called to make the biggest leaps. Look at how many people start businesses in a recession. Maybe it will work out. Maybe it won't; that's not the point. You can't wait to do something only when you are guaranteed success. That's like only agreeing to run a race if you are guaranteed to win. The call is to start, to do it anyway, to focus on the activities and people who will help lead you on your path to success. In the worst case scenario, you'll likely just restart from where you began anyway. In the words of Holiday, "the only way to lose is to abandon your courage" (p.256).

 

Be yourself


Isn't it crazy to think that we need to be courageous to be our true selves?


I know it's cliched, but it doesn't make it any less true: Be yourself because everyone else is taken. There are common reasons why we feel the need to conform: societal norms, familial upbringing, the desire to fit in, to stay safe from judgment, to be safe and comfortable. Out of fear, we conform (p. 68). Challenging the status quo is always going to look different, and we need people in the world doing just that. What sort of world would women have if the women of our past didn't stand up and fight for our right to vote?


I appreciate that because of this innate human desire to fit in, to conform, it takes courage to be different, to think different, to look different. What is harder though - to be courageous, or to deny our true essence, to live a life that feels unaligned, small & painful because we are hiding away so many parts of ourself in the name of safety? People will always have an opinion, but the trick is to learn to care more about your opinion of yourself. After all, you know yourself best. If you can look in the mirror and learn to be proud of what you see, other people's opinions will start to hold less power over you.

A text quote on a dark red background from Marianne Williamson

Don't be afraid to carve out the unconventional path. To give into fear is to deny the talents and skills you were given in the first place. I love Holiday's assertion that "It's good to be difficult" (p.118). Being seen as "difficult" has deep meaning for me as I experienced this comment during my 15 years corporate career. Often advocating for things I saw as the lifeblood of a business, their customers and their people, was seen as "difficult". When I spoke with passion I was told it made another feel uncomfortable. I was even called "rude and disrespectful" by one manager. I knew these comments weren't truly reflective of who I am, however this is how some leaders choose to label me, because I was exercising my power, rather then being compliant.


We have to insist on being ourselves, not shy away from it just because it makes other people uncomfortable. You are not here to play small.


Try not get caught up in the comparison trap, although I appreciate this is increasingly difficult in our social media era. The trouble is when we do this we are often comparing apples to oranges: our start of a journey, to someone 5 years ahead, or we are comparing our inner thoughts, to someone's else outside glossy picture. We mostly want to be thinking about what we can be doing, not what others are, especially when we don't know exactly what we are comparing ourselves to. If you do feel the need to turn outwards, then do so with a positive focus to gain perspective and inspiration, not as a exercise in tearing yourself down. How? Ask for help, seek out inspiration from others, engage guidance & mentorship from those you respect, or those who have done what you are seeking to do, work with professionals who have relevant knowledge to help you.


 

To summarise, I am so happy that in the depths of one of the worse times humanity has had to live through in my lifetime, the Covid 19 pandemic, I managed to find one of the great tools of humanity, philosophy.


This book "Courage is calling: Fortune favours the Brave" by Ryan Holiday is an excellent introduction into philosophy for newcomers. (If you like what you read, and want to buy the book, this is an affiliate link, meaning if you buy through this link, I will make a small commission from Amazon, at no cost to you: Buy here.)


This blog post gives my main takeaways from the book, rather than a book review.

I walked away from this book understanding that:

  1. Fear is the enemy of courage

  2. All growth requires a leap

  3. Be yourself

Make courage a part of yourself, make it a habit How? How can you cultivate courage in your daily life? Do one thing everyday that scares you.


Courage forces us to ask, "If not now, when?" and "If not me, then who?".

 

You can also check out the Book on Audible!


I'm an avid audiobook listener with currently 200 book titles in my digital library. I love to listen to audiobooks to make use of "dead" time, like commuting, or when I am cooking, before bed or when exercising.


The Banner below contains an Audible affiliate link, meaning if you are an eligible customer who signs up for a free Audible trial, or purchases an Audible membership, I will make a small commission from Amazon, at no cost to you.

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