Have you ever heard people talk about “ancient wisdom” but then wondered how it applies to you today?
My guest today started his journey to embody ancient wisdom as a blog nearly ten years ago to help him along his journey of self-education. Ryan Holiday wanted to write what he wished other blogs would talk about more often: life, how to be self-critical and self-aware, humility, philosophy, reading, learning, research, and strategy.
Ryan’s now written a new book called Courage Is Calling: Fortune Favors the Brave, and in this episode, we discuss how fear is actually a good thing for us, why people struggle to have courage and how to overcome that in your life, how thinking about your own mortality can help us rather than hurting us, the biggest lessons we can learn from stoicism when it comes to finding peace, wealth, and developing discipline, and so much more.
Who Is Ryan Holiday?
Ryan Holiday is one of the world’s foremost writers on ancient philosophy and its place in everyday life. As a best-selling American author, Ryan’s incredible books include The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, and Stillness Is the Key. Together, they have sold two million copies and been translated into 30 languages.
When Ryan was 19 years old, he dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power. Ryan had a successful marketing career at American Apparel before finding a creative agency called Brass Check, which has advised clients like Google, ONNIT, and Complex, and many prominent bestselling authors, including Neil Strauss, Tony Robbins, and Tim Ferriss.
Ryan’s books have a prominent following, including some NFL coaches, world-class athletes, TV personalities, political leaders, and others worldwide. Despite having grown up in Sacramento, Ryan now spends much of his time on a ranch outside Austin, Texas, where he writes and works between raising cattle, donkeys, and goats.
Ryan also owns a bookstore called The Painted Porch and hosts the podcast The Daily Stoic.
I’m very excited to talk to my good friend Ryan, so let’s jump straight in!
Courage in Today’s World in Today’s World
We often think of courage physically but seldom contemplate moral courage — something Ryan believes is even more challenging and rare these days. I asked Ryan where he thought people lack courage the most — is it just being honest with themself? Is it lying to other people? Is it not standing up for what’s right?
“I think it’s all of the above. No one is fully brave or fully a coward. It’s more like a day-in-and-day-out ‘What do you do?’ One of the places we struggle with the most is: If courage is rare, courage in pursuit of the right thing is [even] rarer, [and] the virtues are interrelated. One of the stories in the book is about the decision for Michael Jordan to walk away from basketball [for] baseball — immense courage, right? Think of the amount of people that told him he couldn’t make it. [That’s] real courage, but I contrast that with Maya Moore leaving equally dominant in the WNBA at the height of her career. [She left] not to go play a different sport, not to go on some spiritual pursuit, not to spend time with her family — but to free a man wrongly convicted spending his life in jail.” – Ryan Holiday
Ryan makes an interesting distinction about how we think about courage and underlines that the person who quits a job to dedicate themselves to a meaningful cause embodies courage in pursuit of what is right. Ryan is doing his best to integrate courage and catch himself when he criticizes others.
“I’m trying to get to a place where [being courageous] is consistently who I am and what I do, but it’s scary because, first off, what if the opportunities dry up because of it? As I’ve gotten older and have more responsibilities, you realize that it doesn’t just affect you. It affects the people who work for you and your family. I have a chapter in the book about never questioning another man’s courage, meaning [that you should catch yourself when you think] ‘Why is the mayor doing this?’ or, ‘Why isn’t LeBron James speaking up about what’s going on in China?’ It’s very easy to get in this trap where you’re criticizing other people’s courage or lack thereof instead of doing what we should be doing.” – Ryan Holiday
Ryan makes an interesting point about commentating from the sidelines when we have no consequences attached to the outcomes. A good question to ask ourselves is, “When have you gambled your career?” What stands have you taken that, though they may have made you unpopular, you felt morally obligated and willing to accept the consequences? That changes the way we view others’ decisions entirely.
Ryan points out that the older we get and the longer we’ve been in a particular industry or role, the more challenging it is for us to demonstrate this kind of courage, so he shares three ways to start.
