You’re Going to Want to Hear (and Read) Ryan Holiday – a Q&A with a Fanboy

In preparation for the upcoming ESHA Head’s Retreat, Liz Hofreuter interviews Joe Powers, self-proclaimed Ryan Holiday fan-boy. Joe describes how Stoicism provides him the perspective to face the complexities of our roles more effectively while maintaining our own well-being. Join us in Austin, TX to hear from Ryan Holiday himself.

Liz Hofreuter: How would you introduce Ryan’s work to other heads?

Joe Powers: I would introduce Ryan Holiday’s work as simple yet profound wisdom from ancient scholars, philosophers and theorists that has tremendous application to the work we do today. Our work as heads is immensely complex right now. By taking a radically simple approach, the kind found in the wisdom of the Stoics, we can actually apply it to the highly complicated situations we find ourselves in. For example, I think we oftentimes try to meet complications and complexity with complicated and complex problem-solving strategies. Whereas if we take a simplified approach, using this age-old wisdom, we actually have a better chance of getting better results and better performance.

Liz: So we have overcomplicated our very own lives by forgetting the simplicity?

Joe: Yes. I think when you add in social media… when you put in the 24/7 news cycle… the way we consume information, it’s not all our fault. It’s just that the world in which we live is so much noisier and rapidly louder than ever before, so taking a moment to pause and center yourself in the chaos allows you to respond. As the title says, Stillness is the Key. Right? 

Liz: In my 15 years of headship there were plenty of times that people were “coming at me hot.” How would Ryan Holiday suggest that I stay calm when there’s literally a barrage of parents or teachers or worse at the doorstep?

Joe: I’ll say two things.

One, I think we have to have the courage to say, “Let’s pause for a minute. Let’s take this problem part by part and look at each part and see how we can solve it. When chaos comes at you, your response can’t be chaos. It has to be a sense of calm, a sense of understanding. “I hear you. I understand.” Holiday talks about Seneca a lot and the fact that anger is never going to get us to the end result that we need to get to. We actually have to compartmentalize it, put it away, and move forward.  It’s a radically simple concept, however, we don’t always apply it in the work we do. Anger and frustration met by anger and frustration is only going to make the explosion bigger.  Whereas anger and frustration, met with a calming spirit and a sense of commitment, will diffuse the situation and help us move it forward.

Two, I also think that routines and structure are really important. For example,  I walk every day now.  I’ve quit more gyms than I will ever care to admit. I am an active person. I golf, but every day now, one of my ways to get myself grounded is to walk. I keep my headphones on, but I rarely listen to music when I walk. I use them to drown out some of the noise around me and it lets me really think inside myself. I think taking a walk is one of the best things that I do every day. It’s kind of like a breath. It takes off some of the anxiety and allows me to think a little bit more freely outside the context of my office… where usually most of this “stuff” happens.

Liz: In all of Ryan’s books in front of you, do you have a favorite quote? Is there a dog-eared page that you go back to more than others?

Joe: Do I have a favorite? My most recent favorite is not necessarily in a book. It’s listening to Ryan’s podcast when he’s interviewing Buzz Williams, head basketball coach at Texas A&M, talking about the influence of George Ravelling, from whom I also get a daily email called The Daily Coach – it’s all about leadership. A lot of it has to do with sports. But it transcends sports.  Ryan’s discussion with Buzz talking about his interviews on leadership with George Ravelling. I am fascinated by what’s going to be coming out of that work – how much he relies on and how that friendship with George has shaped his leadership. You take these principles of others and apply them to every day – just living life. 

But you asked about a quote. I can’t really pick out one, but in Ego is the Enemy, a great book and obviously described in the title, he’s got a chapter called “Always Stay a Student.” It actually talks about Genghis Khan quite a bit and how he learned a lot from the people that he conquered. “It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more. It’s remembering Socrates’ wisdom lay in the fact that he knew that he knew next to nothing.” I think that’s something I try and practice every day. Learn from those people around me. Learn from the kids. We can learn a lot from our kids if we’re paying attention. 

Liz: With that comment, I think you might have very well found yourself a good introduction of this work to other heads of school. If a head of school hasn’t read one of his books, which one do they go out and buy to read first and to get him to sign when they come to our ESHA retreat in Austin, Texas?

Joe: Good question. Honestly, I’d go with Ego is the Enemy. Well, let me see, maybe Obstacle is the Way is the first book to read because it teaches you that many obstacles are going to be in our way to achieve something – how do we get through them? How do we work with them? How do we learn from them? An obstacle is an opportunity. It’s not something that should defeat us. I think that would be a great first read. 

Liz:  In my quick research to prepare for our conversation, I found a list of questions from 2014 attributed to Ryan Holiday. Let’s run through them as they apply to our complex work as school leaders.

Liz: Do you think the answers you gave me were influenced by Ryan Holiday?

Joe: I absolutely do. I really appreciate Ryan’s storytelling and his ability to connect the age-old wisdom of 2000-3000 years ago to what is radically real today in a world that’s so noisy. It really just simplifies a lot of what we do. I find myself applying it on a daily basis. Our work is about coaching people, working with them, and inspiring their leadership. Whether it’s the quote on Seneca and not being angry or the wisdom from the Ego is the Enemy about always being a student – keeping those things front and center is important. So yes absolutely, Ryan has had an impact on my daily work, not only as an educator but as a husband, as a father also. 

Liz: Can you articulate how excited you are that you’re going to meet him and hear him speak? 

Joe: I’m going to control myself. I’m not going to get all weird or anything like that although I am a fan boy. I’m excited to meet him and just to say thank you for the work. 

I’m super excited to go to The Painted Porch – his bookstore – because my son and I talk about it all the time  – so I’m going to make sure I go there to get a book. 

Liz: Whether all the credit goes to Ryan Holiday or to you, I am envious of the people who work with you because you are a true leader inspiring others to be better themselves. Thank you Joe, for what you’re contributing in this space of K-8 education. 

Joe: Just always trying to be a student.

Learn more about stoicism and staying a student from Ryan Holiday himself at the ESHA Heads Retreat in Austin, Texas, from October 27-29. For more information on the retreat or to become an ESHA member, please reach out here.