How Fortune Favors the Brave with Ryan Holiday

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,