Introduction

Glenn

I showed up to the school board meeting already filled with a sense of dread. I knew it was going to be a tough night. Already a crowd was gathered to tear us apart.

I had tried to prepare the board members for what to expect. As the superintendent, I had been through this before, but for most of them, it was their first time being on the receiving end of the community’s wrath.

And why were they angry?

It was an unfortunate situation; the district had lost some state  funding, through no fault of our own, and we were forced to let some beloved staff go. Many in the community were furious.

The meeting went just about as bad as expected. It felt like we were lined up for the firing squad, and there could be no firing back. The people demanded an answer—but our hands were tied. Everything we did say was misconstrued and misinterpreted.

“Don’t you have any empathy?” someone asked.

I breathed deeply and pictured a rock being pounded by the crashing waves. I felt my fellow school board members squirming in their discomfort, their temperatures rising under the onslaught. I would have to be the rock.

Stillness in a World of Chaos

The world around us is volatile; it changes constantly. Our schools are a microcosm of that chaos; they are touched by disorder, trauma, and turmoil on a daily basis. All of us have our stories—we’ve seen Machiavellian maneuverings amongst staff, kids suffering in poverty and abuse, unfair policies that hurt the most vulnerable, great intentions foiled by lack of funding or support, and a host of other problems.

Meanwhile, many of our colleagues are jumping ship—and who could blame them? A survey from NASSP (2022) reported that school leaders’ stress levels are so high that over half of them are planning to leave the profession in the next three years.

No matter how noble your intentions, it’s hard to continue when you feel constantly at the mercy of everything around you. Like a ship being battered by the waves, you wonder how you can ever recover your balance, let alone get where you’re trying to go.

Most of us respond reactively. We can’t help it. We’re a product of the people we learn from, and most of us haven’t had great mentoring. At best, we’ve figured out how to be leaders on our own. At worst, we’ve witnessed or been subject to political infighting and backstabbing that’s made us cynical and wary of each other.

Many of us don’t know how to trust our teams and delegate. Our own ego, reinforced by dozens of bad experiences, tells us that we are the only ones who can get a job done “right.” And when we pile up responsibilities on ourselves, imposter syndrome takes over: I’m a fraud; there’s no way I can do all of this on my own. And yet, our ego and fear of humiliation keep us stuck.

We all face challenges in our daily role as leaders in education. We want to meet those challenges with poise, confidence, groundedness, and flexibility. We want to take a stand for our students when we need to, respond to aggravations with kindness and forbearance whenever possible, recognize the good in the people around us, and know what the appropriate actions are for each circumstance. Most of all, we want to feel the sense of inner peace that comes with knowing we’ve done our best and the assurance that no matter what comes next, we have the inner tools needed to navigate these waters.

Thankfully, many leaders before us have faced the same challenges. Our goal in this book is to equip you with the mindset and timeless practices that have served leaders for centuries. We want to introduce you to an ancient philosophy that has provided leaders an incredible foundation of wisdom, temperance, courage, and justice—sustaining them with an unshakeable equanimity through every storm.

This ancient wisdom is found in Stoicism.

Why Stoicism?

When most of us hear the word “stoic,” we think of a person devoid of emotions, someone who represses their natural urges and builds a wall between themselves and the chaotic world. Actually, a Stoic is a person committed to the practice of managing and appropriately regulating their emotions, so that they might respond in the best way no matter what the situation calls for. This ancient school of philosophy was pursued in ancient Rome and developed over hundreds of years by a group of unlikely philosophers, including a shipwrecked merchant (Zeno), a crippled slave (Epictetus), and one of the greatest emperors who has ever lived (Marcus Aurelius).

More recently, Stoicism has seen a resurgence in popularity thanks to a college dropout who was inspired by a little book of Meditations by Aurelius: Ryan Holiday. Since Ryan published his first book on Stoicism, The Obstacle Is the Way, in 2014, millions of people have enjoyed discovering how this ancient philosophy applies to and benefits their daily lives. Including us.

Danny

It was my first year as a principal. I was new and ambitious. I loved the students and the staff. I had bold dreams for how to improve our school. I rode my skateboard around campus. I wanted to try new methods and challenge my staff to adopt new practices. Even then, I was a Ruckus Maker. But not everyone was as excited as I was.

Pretty soon, I started getting formally written up—nearly every week—by the area superintendent who had been vocal about her disagreement with my leadership. The write-ups were usually petty, seemingly insignificant. For example, I got written up for showing up at 7:02 a.m. instead of 7 a.m. I was written up for posting on social media during the work day, even though I had scheduled those posts while I was off the clock.

Later, I found out that my assistant principal was informing the area superintendent of any perceived infraction I committed. Eventually, their plan to force me out worked. I quit.

In the aftermath, I had to rethink my identity. I was heartbroken and angry. How could these others have stolen my dream? How could they be so narrow-minded, so unsupportive of a new leader? I fantasized about getting revenge.

And then I heard podcaster Tim Ferriss talking about this ancient philosophy called Stoicism. I read The Obstacle Is the Way by Ryan Holiday. I realized that perhaps what I had viewed as a major setback in my life was actually an invitation to something better and even bolder than I had imagined.

I started asking myself, “How can I turn this obstacle into an opportunity?”

I continued podcasting about how to support and build up new leaders. I started writing. I built a community of fellow Ruckus Makers who wanted the freedom to dream big and serve in new ways. I found a life and a calling that was even more fulfilling, with an even bigger impact, than I could have achieved if I had remained in the principalship.

Ultimately, I’m thankful for my experience because it pushed me to get creative and go all in on what I am supposed to do. Without that negative experience, I wouldn’t have made my creative endeavors a full-time pursuit or had the time to mentor so many other leaders who needed support.

Stoicism has taught me to be grateful for every challenge and to see them as opportunities to grow.

Glenn

Growing up, my grandfather would constantly say, “It’s not the problem that you have, it’s how you handle it,” whenever something would upset or anger me and others. To this day, I echo his words to my own children because he meant so much to me and our family. He was a WWII veteran, but he rarely spoke to me about his time serving as part of the world’s Greatest Generation. 

As I continued into college, I was a double major: history and education. During that time, I was eager to learn so much more about the war he fought in as well as where he might have picked up that saying. In my pursuit, I found Marcus Aurelius, Epictetus, Seneca, and many others that I still study to this very day.

While I’ll never know where my grandfather learned it or whether he studied the ancients, I can’t help but smile knowing how this timeless saying still resonates with much of what I do as a husband, father, and educator.  Since that time, reading authors like Ryan Holiday and Robert Greene has continued my personal and professional journey into philosophy, which I’ve found especially helpful because school leadership calls for Stoicism daily.

We don’t claim to be experts on Stoicism. Neither of us has a philosophy degree. Rather, having seen the power of Stoicism in our lives and in our leadership at schools—not just for us, but for the people we serve—we want to share it with you. There are many misunderstandings and critiques of Stoicism, so we’re not going to try to convince you to adopt this way of thinking across the board (we’ll leave that to Ryan Holiday and the Stoics themselves).

Instead, we simply want to focus on the four main virtues that Stoicism teaches and help you practice using them at school. The benefit will be greater emotional equanimity for you and the people you serve. Whether you’re new to Stoic philosophy or have an entire bookshelf dedicated to it, you will be delighted to learn practices so useful you will see immediate results in your leadership.

About This Book

Cicero, one of the greatest documenters of Stoic philosophy—though not a Stoic himself, ironically—taught that the Stoics held four virtues above all:

But whatever is right springs from one of four sources. It consists either in the perception and skilful treatment of the truth; or in maintaining good-fellowship with men, giving to every one his due, and keeping faith in contracts and promises; or in the greatness and strength of a lofty and unconquered mind; or in the order and measure that constitute moderation and temperance (Cicero, 1887, Book I.5).

On the Daily Stoic (n.d.-a.), Ryan Holiday distills these descriptions into four words: wisdom, justice, courage, and temperance. The outcome of those four virtues is equanimity.

Wisdom: Cicero defines wisdom as “the investigation and discovery of truth.” It is about the relentless pursuit of learning and education. We’re all lifelong learners, right? But it’s about more than just knowledge and facts; wisdom is knowing the difference between what we control and what we don’t, between good and evil, between right and wrong—and then acting on that knowledge. Armed with wisdom, the other three virtues help us to live and operate with the people around us so that, as Cicero says, “the fellowship and union of society might be maintained.”

Temperance:  Like many other ancient wisdom traditions, Stoicism teaches to guard ourselves against extremes, to exhibit self-control in all situations. Temperance is the practice of order and moderation, of deliberating before acting, and of not being led by our impulses.

Courage: To be a “brave and great soul,” as Cicero described, each of us needs courage to resist the comfort of the status quo and act with bravery and honor despite the cost. Courage helps us to turn down temptations, tackle challenges with eagerness and curiosity, and fight every day to be a person of character.

Justice: For the Stoics, justice was the foundation of all virtues and demonstrates our interconnectedness as a human race. When operating with justice, we injure no one and we take action to prevent the injuring of others. We prioritize the common good and exercise generosity as often as possible.

Equanimity: Once we have cultivated these four virtues in our lives, the end result is ataraxia, or equanimity—a calmness of mind and soul. When we temper our emotions with reason for the good of ourselves and those around us, we can enjoy a state of inner tranquility and peace. Isn’t that what we all want?

This is the framework we will explore throughout the book. Each chapter will unpack one of the four Stoic virtues. You’ll notice that all four of these virtues blend together. They rely on each other. Temperance may sometimes require wisdom, justice may require courage, and so on. In each chapter, we’ll unpack the main ideas inherent in each virtue and offer three realistic (though hypothetical) school scenarios for you to practice these ideas.

We’re convinced that upon finishing this book, you will know how to apply self-control and perseverance to help you manage your emotions, become an open-minded thinker, and grow to be an effective problem-solver. But don’t just take our word for it.

We challenge you to think critically and test the ideas found in this book to see if they are worthy of your time and effort. Although we have thousands of years of examples and experience to prove these practices work, ultimately our opinion and experience does not matter. What matters most is that you validate these ideas and practices for yourself.

(I need to talk to my co-author Glenn if we can publish the entire book here … all future books will be released in their entirety via the app … until I get his approval, consider getting your own copy of CALM IN THE CHAOS below)