Is fear holding you back from the life you want to live? 

Fear of change is one of the biggest reasons people are afraid to move out of their comfort zones. It’s worth it though. It’s possible to push through the fear and overcome it, reaping the benefits along the way. 

In this article, Jay Shetty is joined by one of the world’s best-known living philosophers, multiple New York Times best-selling author, husband, father, bookstore owner, and host of the podcast, The Daily Stoic, Ryan Holiday. 

Holiday recently released his twelfth book, Courage is Calling. In it, he breaks down fear and explains courage and the elements of heroism. He shares how you can conquer your fears and apply courage to your life. Here’s our breakdown of what happened when Jay Shetty and Ryan Holiday sat down to dissect each of these topics.

The Painted Porch

Launching a new bookstore while on the cusp of a pandemic is an exciting and scary endeavor, but Holiday and his wife did just that. The Painted Porch hired their first employee in February 2020, just before the world shut down. 

“It got very terrifying and very real and very overwhelming quickly,” Holiday explains to Jay Shetty. “We thought it would be a project that would take a year, and it took two years. It was more expensive than intended and scarier than intended. But it also was an opportunity to take it slow to do it right.”

When the pandemic shut everything down, it gave people time to reflect on the things that were no longer possible and what those things mean to us. It became a great lesson in not taking things for granted. 

“I’ve been thinking more lately that not everything has to be about how I reach as many people as possible,” Holiday tells Jay Shetty. “It can be about how you reach the peak, that smaller amount of people.”


In The War of Art, author Steven Pressfield calls fear “the resistance between what you can be and where you are.”1 There is a common misconception that fear is a bad thing, and that to have a great life, you just need to have courage and be brave. Ryan Holiday believes something different.

“Courage is not just running into battle, or a burning building, or jumping out of an airplane,” Holiday tells Jay Shetty. “It’s not just physical danger, and it’s not always dramatic.”

What else is there when it comes to courage? Moral courage. Moral courage is when you have the strength to stand up for what is right even if it is unpopular. It’s the ability to be a whistleblower or the truth-teller in the face of opposition. It is the bravery to talk to a stranger or start a new venture. You march to the beat of your drum and do not care what other people think about it. 

“There’s also this really small day-to-day courage,” Holiday explains to Jay Shetty. “It’s not always this dramatic, glorious thing. I think a lot of really basic things in our lives come down to a failure of courage.”

A failure of courage equals fear. Fear is the thing that stops you from getting where you want to go. You stress over the changes you need to make and come up with a million different reasons you shouldn’t make them. Fear stops you before you begin … but it doesn’t have to. 

Having courage doesn’t mean you’re not afraid. Courageous people are not without fear. They just know how to push past those fears, and you can too. Holiday says the first step is to break down your fear to the specific thing you’re afraid of, then think about the worst-case scenario. 

“You can use the power of reason to remind yourself that sometimes things are a bad idea, and you can’t afford to lose this,” Holiday explains to Jay Shetty. “Most of the time, you break those fears down and you are able to manage that fear because you have a rational understanding of it, not the irrational, emotional understanding of it.”

Oftentimes, once you break through a fear, you question why you had the fear in the first place. 

“The things we want in life are on the other side of that fear,” Holiday explains. “All good things in life require courage. I would imagine there’s very little you’ve accomplished in life without having to conquer some level of fear.”

Building Courage

So how do you build the courage to push past the fear? Too often, we think of all the reasons we shouldn’t do something. We want to wait until we are financially stable, better known or more well-established before deciding to make a change or take a risk.

Don’t wait! The fact is, giving in to fear wastes your opportunities. In a few more years, you’ll realize how you just wasted years not doing what you want to do. 

“You lie to yourself when you tell yourself you will do it later,” Holiday tells Jay Shetty. “You’re not going to do it, because then you’re going to be too comfortable. You need to see comfort as the enemy, because comfort is what makes you afraid to make a move. You don’t want to lose that comfort level.”

Jay Shetty agrees and tells Holiday that he is more blessed than he ever imagined, but with blessing comes a responsibility to take a risk to serve others. 

“That’s really what courage is about,” Holiday says. “It is the courage to say, ‘I’m not going to think about the consequences. I’m going to do it because it is the right thing to do, come whatever may.’”


What do you think of when you think of a hero? What is it they do that makes them qualify as heroic? 

We live in a society where heroism is displayed by characters in movies, but most heroes don’t wear capes or leap buildings in a single bound. Most heroes are everyday people doing everyday things. 

“We think of courage as the triumph over fear,” Holiday tells Jay Shetty. “Maybe what we’re saying is heroic is something beyond even that.” 

In his book, Courage is Calling, Holiday tells the story of Michael Jordan making the decision to leave basketball to play baseball. Jordan took a significant risk to go from being at the top in basketball to the bottom of the game of baseball. It required courage,  but he didn’t lose much by making the change. 

On the other hand, Maya Moore, who is equally dominant in the WNBA, walked away from her successful career to free a wrongly convicted man from prison. Not only is Moore courageous, but she is also heroic because her actions benefited another person.

“Heroism, to me, is when you do something courageous that’s well beyond your self-interest, or perhaps very much at odds with your self-interest,” explains Holiday to Jay Shetty. 

The pandemic triggered many to be heroic in daily doses. People in so many professions showed up for others even when it was scary and, in some cases, unsafe for them to do so. They knew others depended on them being there, so they pushed through their fears to serve the people who needed them. That is heroic. 

If you think about heroics in terms of a business, an example might be leaving one business to start another. That is courageous. When you leave a business to create a non-profit and put aside your needs to focus on the needs of others, now that’s heroic. 

“The journey from courage to being heroic includes purpose, service, and the extension of oneself for others,” Jay Shetty shares.

The Opinion of Others

Being able to serve others means you need to let go of others’ opinions. There is never a time when you should value the opinion of others over your own judgment, yet we live in a time where opinions are given without a second thought. Just because an opinion is freely given doesn’t mean it’s more important than your own. 

“You have to be able to cultivate this sense of what you are doing and why you are doing it,” Holiday tells Jay Shetty. “Why is it valuable and important? What does it mean to you? You have to get to a place where you’re a little bit indifferent, which is a stoic term meaning that if people love it, great, if they hate it, that’s okay, too.”

Letting go of others’ opinions is about knowing your intention, deciding how you will act on it, and then doing it with confidence no matter what someone else’s opinion is. 

Each time you push through the fears standing in your way, you gain knowledge and understanding. The next time you face a fear and push through it, your confidence will grow. You will realize you can conquer the fears that stand in the way of living your life of purpose.

“The stoics would say that everything terrible has something wonderful inside of it,” Holiday tells Jay Shetty. Create the courage to push through the fear to find your wonderful!

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode with Ryan Holiday on “Eliminating Fear From Your Life and How to Push Past It Now” in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at

1 Pressfield, Steven. The War of Art. London: Orion, 2003. 

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