New book from NYT bestselling author Lewis Howes is now available!

New book from NYT bestselling author Lewis Howes is now available!


Ryan Holiday

How Fortune Favors the Brave


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.

“Fear could be a sign that you’re on the cusp of something. Fear indicates growth.” @ryanholiday  

Three Lessons for Adversity

The Stoics’ teachings can be daunting. Thankfully, Ryan guides us on where everyone can start learning how to help develop more courage and live a more extraordinary life now. Ryan shares three things that everyone can take away from the Stoics to improve the quality of their life.

“One of the questions we ask ourselves when we’re afraid of something is, ‘What would I do if [something bad happens]?’ and Marcus Aurelius goes, ‘You’ll meet that [challenge] with the same weapons you’ve met all your other problems.’ Remember that you’ve been scared before, and you’re still here. Our fear is underestimating or undercounting how good we are at what we do.” – Ryan Holiday

What a powerful reminder that we’ve overcome other challenges and we’re still here! You’ll figure it out! Imagine if you quit your job — while it feels daunting, the truth is, you found the job you just quit, and you will find a better job armed with new experience and greater personal awareness. Remembering what you’re capable of is the first important step. 

“Number two, the Stoics say that we should always be training, [which is] one of the reasons I think it’s important to have a physical practice [and] seek out adversity. Difficulty means when stuff happens, you’re [ready for it]. Epictetus, one of the early Stoics, was a slave, and he says you want to get to a point where, when stuff happens, you’re able to say, ‘This is what I trained for.’” – Ryan Holiday

I know the Navy SEALs say, “They use the body to test the mind,” and here, the second important thing we can do is seek out adversity so we can train our minds for future events.  

“The third one would be the Stoic exercise of Memento Mori, which means, ‘Remember you will die.’ … If I’m spending my time cowering in fear or worrying, I’m acting as if I have power over things that I don’t. There’s this famous Stoic story where the emperor sees a philosopher he hates and he says, ‘I’m sentencing you to death.’ [The philosopher replies,] ‘I was already sentenced to death — you have no more power over me [more] than life itself.’” – Ryan Holiday

Ryan believes people misunderstand Memento Mori — it doesn’t mean don’t wear a motorcycle helmet or pretend the pandemic is not real. What people should understand from Memento Mori is that we need to focus on the parts of safety and concern that are in our control. What are you going to spend your time on? If you’re spending that time worrying and stressing over things you can’t control, what you’re doing is rejecting the life that you have in front of you.

These three Stoic principles are easy to understand but take daily practice to master. Part of embracing the Stoic lifestyle is to embrace the journey of life instead of chasing outcomes — they help us become more present.

Stoicism and Being Present

Having struggled in my life, specifically when my dream ended after my football injury, I battled with figuring out my identity and what value I could add to the world. 

Reflecting on my career’s journey, I’ve learned that no matter how magical I imagine the next level is, it’s never what I thought it would be. I understand why moving the goalposts creates ultra-successful people, but as Ryan highlights, they rarely are happy.

“The journey I’m on, what I’m trying to do, is [to] be proof it is possible to be world-class at what you do and come from a place of contentment and fullness.” – Ryan Holiday

I can relate to Ryan’s observations by thinking about my own early experiences living moment to moment and day by day, which taught me firsthand how to deal with struggle, pain, and adversity. I now constantly try to recreate that struggle in other ways, like leveling up my business. 

“You never feel like you’ve made it. New York Times bestseller, Olympic gold medal, All-American whatever the thing is, there’s an anticlimactic miss to it. The problem is, people can go two ways: You feel the “Now what?” and go find something really meaningful or realize it was never about accomplishments it was always about being present and meaning and connection. It’s about the friends you made along the way.” – Ryan Holiday 

What a true statement — we have to decide what success is to us and not base it on what other people think. Ryan is determined not to feel like he ever needs his success, or that his success will always make him feel good. He understands that his goalposts will keep moving, and he’ll end up never feeling fulfilled if he doesn’t choose to find fulfillment within himself.

Feeling good can be as simple as choosing to be a good person, which helps attract more good people and events into your life. I’ve had loads of discussions with guests about the Law of Attraction, and Ryan shares his unique perspective on a Stoic comparison. 

Three Stoic Disciplines vs. The Law of Attraction

We cover manifestation extensively on the podcast — I recommend listening to this episode with Bob Proctor — so I’m curious to know what Ryan thinks the Stoics would think regarding the law of attraction and manifesting abundance? 

“Marcus Aurelius says, ‘Our life has been dyed by the color of our thoughts.’ If you have positive thoughts, you will see positive things in the world. If you see everything that’s nasty and bitter and unfair and crappy, that’s what you will see in the world, so our perceptions do color our reality for sure.” – Ryan Holiday

Ryan says that the Stoics thought seeing everything positively was step one, but it’s the positivity that sets up the action that makes the positivity real. 

“When the Stoics see an opportunity inside of a disaster, they’re not just sitting around going, ‘Oh, this will solve itself.’ They get to work on that thing.” – Ryan Holiday

As we have learned, the Stoics understood that perception plays a pivotal role in how our lives are, and it’s the first of three disciplines: 

The Discipline of Perception — understanding what you tell yourself you wish for matters.  

The Discipline of Action — understanding that to make positivity real, you need to take action.  

The Discipline of Will — what you endure or put up with in pursuit of your aspirations.

So much of life is outside your control. That’s why the Stoics believed in learning to deal with life’s suffering — after all, the most challenging parts of life are inevitable. What the Stoics’ understanding of life means for us is that we should not feel disheartened by the certainty of challenges but instead, we are empowered to take ownership and prepare ourselves on how to handle challenges that cross our path. 

Why You Should Listen to This Ryan Holiday Podcast Episode Right Now…

Did you find this episode as interesting as I did? This conversation was jam-packed with practical tips on integrating ancient wisdom and teachings from the Stoics into everyday life. I highly recommend listening to the entire podcast because I just couldn’t fit everything in here! Make sure you check out Ryan’s latest book, too — Courage Is Calling: Fortune Favors the Brave.

At the end of the episode, Ryan shared his definition of greatness:

“If you touched, however briefly, the full you, tapped into the full measure of your powers — that’s greatness. Maybe you get it for a whole career. Maybe you get it for one thing, one moment. Maybe nobody sees it — but [you experience it].” – Ryan Holiday

You can check out Ryan’s website and sign up for his free email about Stoicism every day and learn more about him. Ryan also has a fantastic YouTube channel you can check out to learn more about how you can incorporate ancient wisdom into your daily life. If you loved this episode, please do me a favor and tag @dailystoic and me, @lewishowes, on Instagram with a screenshot of your greatest takeaways. 

If no one’s told you lately, I want to remind you that you are loved, you are worthy, and you matter. Now it’s time to go out there and do something great!


To Greatness,

Lewis Howes - Signature

“All accomplishments are ephemeral. All that matters is what you do for the people you care about.” @ryanholiday  

Some Questions I Ask:

  • Why do you think it is so hard for people to face their insecurities, their shame, their fears, and their doubts?
  • What is something from the Stoics that everyone should learn right now to help them have more courage and live a greater life?
  • What is your thought process on reaching financial goals in the context of a philosophical point of view?
  • What would the Stoics be investing in?
  • What process did the Stoics use to heal anger and anxiety?
  • Where would you like to be a year from now internally?

In this episode, you will learn:

  • How fear is actually a good thing.
  • Why people struggle to have courage and how to overcome that.
  • Why thinking about our own mortality can help us rather than hurt us.
  • The biggest lessons we can learn from stoicism when it comes to finding peace, wealth, and developing discipline.
  • And much more…
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Ryan Holiday

Transcript of this Episode

Music Credits:


Kaibu by Killercats

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