Ryan Holiday: The Stoic Rules to Stop Overthinking, Stay Calm & Live a Better Life

**Sarah Grynberg** (0:00)
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Ryan Holiday is the bestselling author of The Daily Stoic and The Obstacle Is The Way, two books that have introduced millions of people to the timeless wisdom of stoicism. What I love most about Ryan's work is his ability to take ancient philosophy and make it incredibly practical for the challenges we face today.
In this conversation, we explore how stoicism can help us navigate uncertainty, overcome ego, let go of what we can't control, and turn life's biggest obstacles into opportunities for growth. We also talk about discipline, raising children, living with purpose, and why reflecting on our own mortality can actually help us live a fuller, more meaningful life.

**Ryan Holiday** (1:25)
What I really like is doing the thing. So if I woke up tomorrow and it all fell by 90 percent, if it all fell by 95 percent, I mean, I'd have to have a smaller team and that would change maybe where I send my kids to school or something, but my life wouldn't change that much because what I like doing is the thing. I think it's really powerful when you find that thing and then you can let the external results be the sort of cherry on top. That's, I think, the ideal place you want.

**Sarah Grynberg** (2:07)
Through my years of studying and researching the connection between human behaviour, personal growth and transformation, I have discovered the keys to unlocking greatness within others. In this podcast, I share stories and experiences from my own teachings along with conversations with inspiring guests to help you learn the simple tips, habits, practices and strategies to cultivate an extraordinary existence.
Ryan will be returning to Australia and New Zealand this October for his live tour. My hope is that this conversation helps you discover the beauty of Stoicism, not as an ancient philosophy but as a practical way of living. If it leaves you feeling a little calmer, a little more grounded and better equipped to navigate whatever life throws your way, then we've done our job. Ryan, welcome to A Life Of Greatness.

**Ryan Holiday** (3:04)
Thanks for having me.

**Sarah Grynberg** (3:05)
I've had many guests on this podcast over the last seven and a half years, but you are someone that I've actually wanted for a very long time. So this is really special and I'm excited that you're here today.
You are actually coming back to Australia. We were just talking about it in not very long. You're coming here in a couple of months.

**Ryan Holiday** (3:24)
Yeah. October. So very soon.

**Sarah Grynberg** (3:26)
And what are you talking about when you're here?

**Ryan Holiday** (3:28)
Well, I haven't written it yet. I don't know if I should be admitting that or not. Now, I like to talk about how we apply philosophy to our actual lives. So I sort of try to think about where I'm talking, what I'm going through, what's happening in the world. I try to take what I think are some of the greatest hits from this philosophy that I write about, which is Stoke philosophy. And I try to tell stories. I think that's how we learn best. And I think that's how we demonstrate ideas best. So I'll probably pick my favorite stories from Stoke philosophy that I think connect to what's happening in the world and hopefully talk about it to some people who I think are of the different nationalities. I do feel that this is a naturally lowercase stoic part of the world. It's not the British stiff upper lip, but there's a little bit more happiness and sun and outdoorsy-ness to your part of the world, which I like. But there is that expression, no worries to me is quintessential stoicism.
It's all good, man. I love that. So anyways, that's a long answer to your question, but I'm excited to be there.
Two years ago, we had a great time. We spent a month with my two kids. So they were very excited to have any excuse to come back as a mom.

**Sarah Grynberg** (4:48)
Amazing, amazing. We can't wait to see you here. I'd love to start at the beginning.
Ryan, what was life like for you before stoicism? Everyone knows you as the guy that is able to explain stoicism in such a beautiful way. But why did stoicism become a prominent part of your life? What were you doing before?