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Introduction
“If, at some point in your life, you should come across anything better than justice, honesty, self-control, courage . . . it must be an extraordinary thing indeed” Marcus Aurelius (2003, p. 30).
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.
Chapter 1. Wisdom
Knowledge, education, truth, self-reflection
“Wisdom is the oneness of mind that guides and permeates all things” Heraclitus (2003, p. 10).
Danny
One day, when I was a principal, a parent came in very upset. Her daughter had been in a fight with a boy—and she wanted the boy suspended. Thankfully, we could see the incident on our school camera footage. It revealed that her daughter had actually started the fight, attacking the boy from behind. The mother didn’t care.
I tried my best to be empathetic, reflecting back to her: “This is what I heard you say . . . is this right?”
No matter how she felt, we had specific school policies and consequences that had to be enforced. I wrote out all of the policies and consequences on a white board. Patiently, I walked her through my options as the school leader and asked her to help me find the right consequence for her daughter (and for the boy, who fought back) within the limits I was working under. There was only so much in my control.
Thankfully, she recognized that truth and we were able to agree on consequences that felt fair to everyone.
Remember What You Control and What You Don’t
“Happiness and freedom begin with a clear understanding of one principle: Some things are within our control, and some things are not.” Epictetus (2013, p. 13).
Leadership often sounds like the key to greater freedom and autonomy. Surely when you get to make more decisions, you are more free!
But if you’ve been in leadership for a while, you know that’s not true.
Often, leadership means more responsibility but less control over the situations you’re meant to be leading.
The Stoics knew this as well. Epictetus, one of the most prolific Stoic philosophers, was born into slavery. His master was an advisor to the emperor Nero, so Epictetus could closely observe the lives of the most powerful men in the Roman Empire. But that didn’t mean they were free.
Later, when Epictetus was legally freed, he thought deeply about the question of control and freedom and wrote extensively about how to handle situations in which we often have little or no control.
Often, school leaders waste a considerable amount of time worrying about (and trying to solve) things that are ultimately out of their control. But Epictetus would say: We have to play the cards we’re dealt—and let everything else go.
So naturally, you might be thinking: What is and is not in my control?
What is in your control? Your actions.
What is out of your control? Everything else that does not fit inside the category of your actions.
For example, the following things are in your control:
Your opinions
Your goals
How you choose to spend your time
Your temper
Your attitude
Your character
And the following things are not in your control:
Your students’ lives
The outcomes of your school’s initiatives
Your teachers’ classrooms
Your reputation (phew, that’s a tough one!)
The policies established by the school board and central office
Parents and community members
The quickest path to being frustrated as a leader is misunderstanding what is in your control and trying to force certain outcomes from other people. Every leader who’s tried to force staff to adopt a new technology, initiative, or protocol knows how difficult this is!
Similarly, what other people say about you (reputation) or the actions they decide to take at school are not in your control. And when those things are hurtful or disappointing, it can send you into a tailspin of negativity.
But if you can understand that other people and their actions are outside of your control, then you can choose not to be harmed. Stoics believed it wasn’t the things outside our control that caused us distress and pain, but rather our view of those external events. Our opinions, which are within our control, are to blame.
You always have a choice about how you interpret others’ actions—that is always within your control. You can choose to take them personally, or you can choose not to be harmed. Learning from Epictetus’s writings, the emperor, Aurelius (2003), later wrote, “It doesn’t hurt me unless I interpret its happening as harmful to me. I can choose not to” (p. 87).
In his book, A Guide to the Good Life, William Irvine adds one more nuance to the idea of control. According to Irvine (2008), “There are things over which we have complete control, things over which we have no control at all, and things over which we have some but not complete control” (p. 89).
We’ve already talked about the things we do and do not have complete control over. But what about that third category? Although not everything is in your control, many things are within your influence. In school, your leadership exists in this middle ground, a gray area where you can influence outcomes but not control them. What are examples of things you have some control over but not complete control?
Imagine you are a superintendent sitting on the school board. You cannot decide which members are voted in by the community, but you can certainly help to guide and educate those members on policies and procedures. You may not be able to stop certain books from being banned by the district, but you can advocate within the community. You cannot force students to study or learn, but you can give them all the tools they need for success.
Since you cannot control other people’s actions or decisions, you would be wise to focus on becoming the best version of yourself.
Practice Wisdom
After another successful school week, Principal Rosa awakens on a Saturday morning to the ping of notifications on her phone. Last night, while Principal Rosa was enjoying much-needed family time, a parent posted pictures of a book that her child was being “forced” to read, a book that she disagrees with. Friends of the parent were incensed and filled the school’s contact form with angry messages. The social media post is going viral and commenters have even tagged local and national news outlets to try to bring attention to it. Now, on her day off, Principal Rosa finds herself fielding panicked texts from teachers, staff, and parents wondering what they should do.
Reflect
What is within Principal Rosa’s control? What isn’t?
Where might Principal Rosa exert influence?
If you were the school leader in this situation, what would you do?
Commit to Learning
“Don’t just say you have read books. Show that through them you have learned to think better, to be a more discriminating and reflective person. Books are the training weights of the mind.” Epictetus (2013, p. 99).
So many of us might think of ourselves as “lifelong learners.” It might even be in our profiles on social media! But can you think of a time when you rolled your eyes at a required PD day and dragged your feet to get there? How are you challenging yourself to learn more about the students within your community and their lived experiences? What education and leadership books have you not only read, but truly applied in your life and your school? When was the last time you tried learning a new skill and experienced the discomfort and cognitive dissonance of being a beginner—as your students do every single day?
Have you fallen into the trap of thinking, “I already know this”?
To attain wisdom, you must be willing to learn—and learning requires humility. Epictetus (1890) wrote, “What is the first business of one who studies philosophy? To part with self-conceit. For it is impossible for any one to begin to learn what he thinks that he already knows” (Book 2.17).
As a school leader, it is vital to be open-minded and willing to listen to different perspectives. Check your ego at the door, and listen empathetically to what people are saying.
Leaders are responsible for making decisions that affect the people they lead. If a leader is closed-minded and unable or unwilling to put themselves in the place of a learner, they may not be able to consider all of the options available to them, and they may make decisions that are not in the best interests of their people.
Your willingness and humility to learn is also one of the greatest examples you can set for your team and your students. If you aren’t willing to engage in a PD day because you “already know this,” why should your teachers? If you’re “not an art person” and don’t want to try learning how to create 3D models with the art class, why should your students try to wrap their heads around this complex skill?
Practice Wisdom
Instructional Coach Carter has 10 classrooms to visit today, and he’s running behind. He walks into Mrs. Cho’s seventh grade biology class where they are learning about cell division and analyzing samples under a microscope. Planning to just stay a few minutes, Coach Carter starts checking items off of his checklist.
He can’t help but notice one student who looks confused, glancing around at the other students to try to mimic what they’re doing with the microscopes. Mrs. Cho is busy helping a group of girls as this student hides in the corner, painfully disengaged. Coach Carter considers trying to help but glances at his watch; just a few minutes before he needs to be in another classroom. Besides, when was the last time he used a microscope? Could he even remember how?
Reflect
What are Coach Carter’s options for next steps?
What will happen to this student if he leaves now?
What would you do if you were Coach Carter?
Own Your Mistakes
“If anyone can refute me—show me I’m making a mistake or looking at things from the wrong perspective—I’ll gladly change. It’s the truth I’m after, and the truth never harmed anyone. What harms us is to persist in self-deceit and ignorance” Marcus Aurelius (2003, pp. 73–74).
As a “leader,” as someone to whom others look for guidance and stability, it can be hard to admit when we are wrong. What kind of leader am I if I make mistakes? we might think. We fear losing trust and influence if the people we’re leading know that we’re fallible humans, just like everyone else.
All of us are far from perfect. We’ve all made countless mistakes along our professional journeys, and those mistakes are part of the journey. Many of us have taught the acronym FAIL (First Attempt In Learning) to our students and helped them see mistakes as learning opportunities. We graciously coach our colleagues and give them whatever support they need to improve. We comfort others when they mess up. The only ones we don’t allow to make mistakes, though, are ourselves!
Here’s the secret.
Your staff already knows you make mistakes. They probably see your mistakes more clearly than you do.
What if you welcomed that information? What if you modeled how you want other learners to view their mistakes? What if, instead of protecting your ego, you made it clear that you want others to tell you when you’re missing something, when you messed up, or when you need to apologize so that you can correct it immediately?
When something goes wrong, be quick to point the finger at yourself before someone else. Own it!
According to author and speaker Danny Silk (2015), “being right doesn’t have to be sacrificed, but having to be the one who is right needs to go” (Foreword, para. 4).
When you prove to others that you want to learn from your mistakes, the people around you will actually respect you more than you’ll ever know. People love to follow authentic leaders who demonstrate that they, too, are human and working to be the best that they can. Shut your ego up, stop pointing fingers, own it, accept it, and work to correct it.
Practice Wisdom
On a cheerful morning, Principal Daniels heads to Mrs. Meyer’s room to conduct her spring evaluation. There were a few things they had discussed after her evaluation in the fall that he is hoping to see today. He slips into the back of the classroom as unobtrusively as possible, noting he has about 20 minutes to stay.
Everything seems to be going well—Mrs. Meyers is calm and engaging. She handles a small misbehavior graciously and keeps the rest of the class focused on their task. But he doesn’t see one of the items they’d discussed last time, so he feels he can’t check it off on the rubric.
At the end of his 20 minutes, he thanks Mrs. Meyers and heads out the door. He sends out her evaluation later that week with a good score but notes that the same issue has occurred again, and it needs to be corrected.
The next week, when Mrs. Meyers receives her evaluation, she calls him in tears.
“I did correct it!” she insists. “I did that the day before, but I didn’t know which day you’d be visiting, so I just had to move forward with my teaching plan.”
Principal Daniels’s face flushes with embarrassment. Did he make a mistake? Could he trust that she is telling the truth?
Reflect
Have you ever been in a similar situation?
How might Principal Daniels address the discrepancy with this teacher? What should his next steps be?
Have you ever made a mistake and had it pointed out to you? How did you make it right (or not)?
Find Your Heroes and Antiheroes
“For we must indeed have someone according to whom we may regulate our characters; you can never straighten that which is crooked unless you use a ruler” Seneca (1917, p. 54).
For years, education has not evolved. The most common critique is that it is a “factory system” where the main focus has been to teach students compliance and prepare them for jobs that were common during the Industrial Revolution.
In this system, leaders are no more than managers—super-doers, legislators, and enforcers whose job is to make sure that everyone else stays in line. Unfortunately, that’s still the most common model of leadership.
Excellent leadership role models are hard to find. Many school leaders want to be great leaders, to break out of the factory-system mold, but we haven’t seen what good leadership looks like, so we stumble to put it into practice. Many of us have only seen examples of what not to do.
Try as we might, when we’re surrounded by bad actors, they’re likely to influence us. Jim Rohn’s famous quote, “You’re the average of the five people you spend the most time with” (Canfield & Switzer, 2005, p. 189), is usually the kick in the pants a leader needs to investigate the other leaders they spend the most time with and look to as mentors. Those people will give you the best hint at who you are as a leader.
You have to ask yourself: Are these people I want to be like?
In Letters From a Stoic, Seneca (1969) writes to his friend Lucillius about the importance of mentorship and encourages him to find someone whom Lucillius admires, someone he wouldn’t want to disappoint. He writes about the tremendous gift it is to have an effective and encouraging mentor in your life, someone whom you can measure yourself against. The problem is, these mentors are few and far between.
But are they?
Maybe in the physical domain of your life.
If you find that you lack mentors, or the mentors you do have are not the ones you need, fear not. Countless biographies and autobiographies have been written by some of the greatest leaders history has ever known. Browse the shelves of your school library; you’ll find plenty.
Then there are all the classic Stoic texts that we cite throughout this book. Aurelius wrote Meditations while serving as the ruler of one of the largest empires that has ever existed. During his reign, he faced many leadership obstacles: attempted coups, political infighting, annoying coworkers, and even a pandemic. Sound familiar?
History is filled with great leadership heroes who have managed situations exactly like the one you’re going through. This is why the Stoics saw reading as one of the best ways to develop wisdom—because through books, you can learn from the greatest minds that have ever lived.
And what about the antiheroes, the people you want to be nothing like?
You can be thankful for them, too. Yes, avoid behaving like them and surround yourself with better mentors—but do watch the antiheroes. Watch how they act and how their actions impact the people around them. Watch how they continue to keep education stuck. Learn from their mistakes.
Then ask yourself: What kind of leader do I want to be?
Practice Wisdom
Superintendent Beckett has just been hired to her first superintendency, and she is stoked. Throughout the weeks of the interview process and getting to know various people within the school system, she’s gathered a list of over 30 changes and long-term goals she wants to start implementing right away. This district has a lot of problems, but Superintendent Beckett has a vision for how to improve things.
Her predecessor in the district was considered a bit of a lame duck—no vision, just someone checking things off the list. Not so for her! She has energy and enthusiasm and is excited to get started. This district hired her to get things done, and she is determined to start things off with a bang.
When Superintendent Beckett meets with her new executive assistant, though, she is cautioned to be careful, to go slow and get to know everyone first before making a lot of changes. Superintendent Beckett is frustrated by their conversation. Is her new EA trying to hold her back? Will she face opposition from others? Is this the start of an agonizing relationship?
Reflect
Have you ever been in a situation like this? What did you do?
If you were a mentor in Superintendent Beckett’s life, how would you advise her?
How could Superintendent Beckett get the relationship with her EA off on the right foot?
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