Imagine this: School’s about to start, and you’ve got one shot at the first staff meeting.

The district sent you a slide deck that has too much text and information.

You know by the third slide, you’ll lose the room before the year even begins. But you want this year to be different. You want the meeting to be meaningful, to encourage and inspire staff to be the best versions of themselves for the students?

You don’t have to work it out alone.

Let’s say you start a conversation with Digital Danny—an AI Selfmentorship tool trained on years of coaching conversations with school leaders—and tell him straight:

“I’m worried this meeting will be all logistics and no soul. How can I make it set the right tone for the year?”

He doesn’t hand you an agenda, but he does suggest a specific structure. The first half can be about culture and vision: why you’re here, what you see in your staff, and what you believe is possible for them this year. Make it possible and personal. The second half is about logistics, framed as service to something bigger, not just a list of rules to get through.

Then, he says something you already knew but needed to hear again:

Your staff won’t remember logistics. They’ll remember how you made them feel.

They’ll remember if you treated them like partners, or just handed them a manual.

To help you do that, he points you to the Positive Spotlight tool and tells you to open with a story or a moment instead of a slide. So, you decide to ask your staff questions instead of handing them answers. You make a note to save the heavy logistics for a follow-up memo. When you’re ready to build the agenda, Digital Danny gives you one, timestamped for ninety minutes, and recommends you start with a check-in question instead of the throwaway “how was your summer?” Something like: What’s one thing you’re proud of from last year? Or what do you want to protect about school this year?

If you’ve run staff meetings for ten years, you’d still walk away with something new.

Digital Danny is someone in your corner who’s trained on 10+ years of coaching conversations with school leaders. That means when you bring him a problem, you feel like someone is sitting across from you, helping you work through it.

I Asked AI to Fix My First Staff Meeting—I Wasn’t Ready for the Answer

There are roughly 91,900 principals in this country. As one of them, you’re doing a job that used to take five people.

You’re an instructional leader, a culture keeper, a crisis manager, a politician, and the one person your staff looks to on the hardest day of the year. You don’t have a massive admin team backing you up—you’re the leadership.

That responsibility is a heavy weight.

It also prevents you from getting help with personal development.

One principal I respect, Bill Renner, once told me he waited years to get leadership support because he didn’t want to bother people. He knew everyone else was busy too. So he kept going through the motions alone, hoping he’d figure it out eventually.

That reminded me how isolated and underdeveloped I was as a new administrator, and how hard the job was for me back then. Mastermind and one-on-one coaching have helped me and so many other principals. I’ve watched it change careers, including my own. But not everyone can put $3,500 toward a mastermind or find room in their schedule for a weekly coaching call.

That gap has bothered me for years.

I wanted the same kind of thinking partner I got to build with my coaches, minus the price tag and the waitlist. That’s part of why I built Digital Danny. He’s an always-on AI tool, designed to help you think through situations that previously required a coach, mentor, or peer.

Here’s a small sample of what’s possible with Digital Danny:

• Bill Renner used it to prepare for his return to elementary school, working through the questions to ask a new team of teachers.

• Kati Cahill used it to turn a year of scattered wins into a repeatable template she now pulls from for staff meetings, newsletters, and parent tours.

• Fred Holmes used it to get honest about the story he was telling himself before a hard conversation with a direct report, so he could walk into the meeting with a clear head.

This mini-book will show you how you can do the same.

Digital Danny: The AI Thought Partner for Principals

Digital Danny is designed to guide you through the everyday thinking, deciding, and communicating that comes with leading a school.

Think of it as a peer and mentor, trained on thousands of leadership calls.

It lets you talk through any leadership challenge, at any time of day. On the drive to work, you could ask how to handle an unexpected call from the superintendent’s office. At nine at night, you can use it to write a message to a parent who’s escalating a complaint about a teacher. During lunch, you can chat with it about a staff member who pushed back hard on a decision you made.

Most principals have an a-ha moment when they think through a problem out loud.

Digital Danny gives you a way to hear yourself think when no one else is around.

It also forces you to look at how you’ve been doing your own development. Are you a Play-it-Safe Principal who waits for the district to send you somewhere, hoping a conference covers what you’re struggling with? Or do you practice the art of Selfmentorship and drive it yourself, on your own schedule, with someone in your corner who’s never too busy to talk?

Either way, I’m not here to judge.

I just know what worked for me.

When I was a principal, it took me years to drive my own leadership development. I went to conference after conference, trying to meet the right people and grow my skills. I put together peer circles and monthly meetups. I started a podcast to interview school leaders and collect knowledge. I created a community and designed a mastermind.

But honestly, I could have benefited from having more Selfmentorship tools.

So, I built Digital Danny not only to help me, but also thousands of other school leaders. I trained Digital Danny on the Better Leaders Better Schools podcast, the Ruckus Maker Club Mastermind content, one-on-one coaching calls, and all six books I’ve written on school leadership. It made the tool knowledgeable. But if you’ve ever gotten advice from someone trying to cover every angle at once, you know how that goes. It was verbose, but not particularly useful.

Eddie Yoon, a co-founder of Category Pirates and someone I’ve learned a lot from, gave me the fix: Stop trying to make him excellent at everything, and give him specific jobs to do instead. So, I thought through the daily problems principals need help with.

Four jobs kept showing up:

1. Think It Through. You’re facing a problem or a project, and before anything else, you need help sorting out what you’re dealing with.

2. Apply a Tool. Sometimes, you need someone to point you to the right framework and walk you through it. So, I added more than 30 frameworks to Digital Danny.

3. Reframe the Story. It’s easy to get stuck in a version of events that’s a little too biased toward how you see it. You need help zooming out to see it from someone else’s side.

4. Communicate It. This came from watching how principal power users used Digital Danny to refine messages that needed to land right, especially high-stakes ones.

This is also where Digital Danny splits from other AI engines.

What Makes Digital Danny Different

Ask ChatGPT, Gemini, or Claude about school leadership, and it’ll answer confidently, whether it should or not. Generic AI tools are designed to make you feel like the smartest person in the room.

Digital Danny is trained only on school leadership. Ask him something outside that lane, and he won’t guess. He’ll tell you he doesn’t know.

He also doesn’t train on your conversations. What you tell him stays between you and him. Every other AI model learns from what you feed it, which means your words become part of how it responds to everyone else using it. Digital Danny doesn’t work that way. And the tool is built into the Ruckus Maker Club—a private community and live events full of other school leaders working through similar challenges. No other AI tool can hand you that.

Digital Danny works if you’re willing to sit in the discomfort of being asked a question instead of being handed an answer.

It won’t work if you want instant answers with zero friction, need data analysis, or want a tool that flatters you into confidence instead of giving you clarity. It’s perfect if you want a thinking partner, not a task-doer. And if you’ve already bought into Selfmentorship as a practice, or are ready to.

If that sounds like you, here’s how to apply those four jobs.

Digital Danny Four Jobs Framework

Each job below includes an example from a school principal who frequently uses Digital Danny, plus a prompt you can copy straight into your own conversation.

Job 1: Think It Through

You have a problem and need to think deeply before acting.

When Bill Renner took a job as principal at an elementary school after years in middle school, he knew enough not to walk in with answers. He slowed down, started meeting with grade-level teams, and asked Digital Danny what questions he should bring to a first-grade team he didn’t yet know. The response: What are you most proud of? Where do you feel stuck? What’s something we should never change here?

To think it through, try this prompt:

“Here’s a situation I’m walking into: [describe it]. Before I decide anything, help me figure out what I need to understand first.”

Job 2: Apply a Tool

Digital Danny has more than 30 built-in frameworks, designed over a decade of teaching, coaching, and school leadership. You don’t have to know all of them or which one fits your situation—you just have to bring the problem.

This is where Kory Kliebert leans on Digital Danny for professional development. He’ll tell Digital Danny he’s working on culture with his team and needs a ten-minute personal development exercise. The reply includes frameworks and language relevant to his staff, not a generic answer he could get anywhere else.

To apply a tool, try this prompt:

“I’m working on [culture/PD/communication goal]. Is there a tool or framework that fits this? Walk me through it.”

Job 3: Reframe the Story

Sometimes you’re stuck in a version of events that’s a little too biased toward how you see it, and you need to see it from someone else’s perspective.

One principal, Fred Holmes, had a direct report who consistently showed up late, was unmotivated, and seemed checked out. Before he talked with his report, he brought the situation to Digital Danny. He wanted to understand what might be going on from the direct report’s side, not just stew in his own frustration. By the time he sat down to talk to his report, he had thought through their perspective from enough angles to have an open-minded conversation.

To reframe the story, try this prompt:

“Here’s how I’m seeing this situation: [describe]. Help me see it from the other person’s perspective. Where might I be wrong? Where might I be right?”

Job 4: Communicate It

You’ve got a message that needs to land, and you don’t have time to get it wrong.

Kory Kliebert uses Digital Danny to polish nearly every memo he sends. He’ll paste in his draft, and because the tool knows how to structure memos, he doesn’t have to re-explain himself every time. Fred Holmes does something similar before high-stakes moments. He rehearses interview answers with Digital Danny and gets direct feedback on how he sounds, not just what he says.

To communicate, try this prompt:

“Here’s a message I need to send: [paste it]. Help me tighten it, and give me a version that’s more direct and a version that’s more empathetic.”

Stack the Four Jobs

The Four Jobs work as one-off conversations. But once you’re comfortable with them, you can use more than one at a time. Here’s how Digital Danny users connect two or three jobs together across a bigger project.

Make a playbook from your brain dump (Think It Through and Apply a Tool).

Kati Cahill runs a small school without an admissions director, which means the admissions process lived entirely in her head. She’d always done it herself. But she talked it out with Digital Danny, and instead of a pile of paper checklists on her desk, she walked away with a mapped-out flow her team could run without her. She did the same thing with scheduling, something she’d kept doing herself even after she became principal. Both are now handoffs, not bottlenecks.

Turn your wins into a template (Think It Through, Apply a Tool, and Communicate It).

At the end of the school year, Kati dumped every win she could remember into Digital Danny—some from her own memory and some her staff had mentioned in checkout meetings.

Digital Danny suggested structuring it as a three-column template: what the win was, why it mattered, and when to use it. Now, she has a running reference she pulls from for staff meetings (”tell this story when you need to boost morale”), parent tours (”use this so they understand what small class sizes mean”), and newsletters. The writing still comes from her—Digital Danny doesn’t draft the newsletter—but it reminds her what’s worth sharing.

When a parent recently sent a thank-you email praising the staff, she added it straight to the template as a new entry she can pull up before a staff meeting to reset morale.

Run a framework (Think It Through, Apply a Tool, and Communicate It).

Kati had done a 90-Day Entry Plan as part of the Ruckus Maker Club Mastermind.

Previously, she had mapped it out freeform in a Google Doc, going wherever her thinking took her. This year, she went through it step by step with Digital Danny. She used the same backward-planning method, starting with her 90-day vision, but Digital Danny prompted her at every stage.

By the end, she had specific team members assigned to her Communication, Academics, and Culture columns, based on what the conversation with Digital Danny surfaced.

Get a second opinion on another tool’s answer (Reframe the Story).

Gene Park, one of our Ruckus Maker Mastermind coaches and a current elementary principal, runs his questions through ChatGPT and Digital Danny. He then asks Digital Danny, “What’s the good stuff here, and what do I need to cut?” He calls it his own mini mastermind with AI.

Every principal using Digital Danny opened the tool again and again, until it became part of how they think. One principal, Jess, had 808 conversations with Digital Danny in three months. Another had over a thousand. Most show up several times a day during the week, or run a sprint session when working through a particularly tough challenge.

Here are the basic steps to create your own Digital Danny Selfmentorship habit.

How to Start Using Digital Danny

Step 1: Choose your door.

Start by going to myprincipalcoach.com. You’ll see two ways to use Digital Danny: $100 for 90 days or $350 for the year—both include the Ruckus Maker Club and monthly Event Space jam sessions.

(If you’re already in the Ruckus Maker Club or working with me one-on-one, Digital Danny is included. Ask your coach or me how to get access.)

Here’s what it’ll look like once you’re logged in:

Step 2: Start with a real problem, not a hypothetical.

Digital Danny works because it’s specific.

“Help me think through hiring” gets a generic answer. “I have three teaching positions to fill at a school I don’t know yet, and I start in six weeks” gets you a specific way to think through the problem.

Bring a detailed problem that’s actually on your desk this week.

Step 3: Expect a question back, not an answer.

This is the biggest mindset shift.

Digital Danny gives you the answer in a roundabout way so you do the slow, deep thinking that helps you find an answer. In the hiring example above, Digital Danny didn’t hand over a checklist. He gave a timeline: start a 2-4-8 pipeline immediately, get specific about what makes the school different before writing a single job posting, and build a staff scorecard that helps attract, interview, and develop candidates once hired. He then asked a question back: What’s your clearest sense right now of what makes this school different?

Here’s what happens when you reply:

That’s the loop. You bring something half-formed, and Digital Danny finds the one thing buried in what you said, sharpens it, and hands it back better than you gave it to him. He then asks you to go deeper.

That back-and-forth is what it looks like to practice Selfmentorship.

Step 4: Show up regularly.

The principals who get the most out of the tool use it often.

For example, Fred Holmes talks to Digital Danny on his way into work most mornings to get clarity before the day starts, instead of walking onto campus and reacting to email and the news. Others use it before emailing a parent or having a tough meeting with a teacher.

When I looked at what principals bring to Digital Danny, five themes kept showing up:

1. Launching the school year. This was the most common topic. Principals used Digital Danny to make entry plans for a new campus, run the first staff meeting, create a personal development plan, write welcome-back letters, and hold new-teacher orientation.

2. Hard conversations, boundaries, and managing up. This included topics like setting boundaries with a supervisor, having the conversation you’ve been avoiding with a teacher, and working through a veteran staff member who’s checked out.

3. Naming the one thing. These messages were about belief statements, one-sentence visions, 90-day plans, and the Principal’s User Manual, usually built section by section instead of all at once.

4. Instructional leadership systems. This included walkthrough schedules, feedback that doesn’t feel like compliance theater, PLC structure and rollout, and coaching Tier 1 instruction.

5. Student behavior and discipline systems. These messages were about referral loops, PBIS protocols, cell phone policy, and backing up teachers who feel unsupported.

Underneath most messages is the same job: help me think through this situation and write a response, so it actually lands. Principals wrote letters, speeches, emails, meeting agendas, and surveys. Whatever the topic, most principals end up back at Job 4—Communicate It.

Treat it like a practice, not a one-time fix.

Step 5: Know the limitations.

Digital Danny works best as a thinking partner, not a data tool. If you need spreadsheets or analysis, that’s still a job for ChatGPT or Gemini.

He also doesn’t remember your conversations the way you’d remember a call with a friend. He holds onto the big picture but not the specific details. So if you want to reference something later, don’t count on him recalling it word for word.

That means you’re on your own for saving anything you want to keep. If you want to hold onto a conversation, copy and paste it into a separate note or document. Or, take a screenshot. Some principals do that after a good session, then add it to the Digital Danny chat for context when a similar situation comes around again.

Keep Making a Ruckus

Bill Renner, a principal and avid Digital Danny user, once told me something I haven’t stopped thinking about: Leaders don’t need to prove they have every answer. You just need to be willing to reflect, ask different questions, and keep growing.

Your growth trajectory will be different than every other principal. That’s not a problem to solve. That’s what Selfmentorship looks like—it’s a personal practice you build over time.

None of the principals in this mini-book started with a system. Kati didn’t set out to build a template. She just dumped a year of scattered wins into a conversation and let the structure find her. Fred didn’t plan to make Digital Danny part of his commute. He called him up once before a hard day, and it worked, so he kept doing it. Gene just got curious about what two different leadership tools would look like when combined.

The habit came after the results.

To start using Digital Danny, choose one thing you want to work through this week.

Maybe it’s a meeting you’re dreading, a message you’re not sure how to send, or the story you might be telling yourself about someone on your staff. No matter the situation, go to myprincipalcoach.com and let Digital Danny ask you a question.

Bring him that one thing, and see how he helps you think it through.

Keep Making a Ruckus,

Danny

Chapter 2. Justice

Fairness, service, fellowship, goodness, kindness, integrity

“Therefore I would have brave and high-spirited men, also good and simple, friends of truth, remote from guile—traits of character which belong to the very heart of justice” Cicero (1887, Book 1.19).

Danny

Stay Humble

“To escape imperialization—that indelible stain. It happens. Make sure you remain straightforward, upright, reverent, serious, unadorned, an ally of justice, pious, kind, affectionate, and doing your duty with a will. Fight to be the person philosophy tried to make you.” Marcus Aurelius (2003, p. 75).

Think back to all of the times when you were in the interview chair, hopeful that someone would believe in you enough to give you a shot as a teacher’s aide, teacher, coach, supervisor, assistant principal, principal, athletic director, central office administrator, and/or superintendent. You believed in the best for your students and staff, and you wanted to make a positive change in the world for the better. You felt you had to work hard to prove that you were there for the right reasons.

Then it happened—you got the job.

When you’ve been recognized for your efforts, it’s easy to start to believe that you deserve to be there, that you really must know what’s best. Your ego starts to sneak up on you from time to time, and when that happens, you forget your true purpose: to serve the people around you.

This is why justice starts with humility: Because to serve others, to advocate for the common good, you must be able to put aside your own ego.

Aurelius was crowned Imperator Caesar, meaning that he was the military leader and ruler of the Roman Empire. Later, the title Augustus, which signified a divine appointment, was added. He was in every way—spiritually, militarily, and organizationally—the leader of the largest empire on earth at the time. It would have been easy for him to think that he was always right, to always insist on his way as many other emperors before and after him did.

Yet, in his journals, Aurelius reminded himself not to let those titles go to his head. He reminded himself constantly that his job, the job he was privileged to have, was to use the short time he was given to fight for the common good.

You must not let your accolades go to your head. The only thing that a trophy or a piece of paper in a frame will do is collect dust. You’re here to serve, not collect fancy titles or trophies. You must always remain humble.

Quick test: When you introduce yourself to someone else in your school/district, is it, “I’m Dr. [insert last name here], and I am the [position] at this district,” or is it, “Hi, my name is [insert first name here].” Last time we checked, we are all human beings. Do you really need to remind everyone else of your titles? If you need to announce yourself as a leader, are you really a leader?

Practice Justice

Curriculum Director Williams is attending a national conference looking for a new math curriculum. He arrives a few minutes early and browses the vendor hall, looking at all of the exciting edtech products available. At one of the vendor booths, a tall young man tells him all about their incredible product. Williams is intrigued; this product would be a huge help to the math department, and the salesman is offering a bulk discount.

Williams is really flattered; the salesman seems like a kind, authentic young man. He’s a former teacher, like himself, and the salesman really seems to get what their struggles are. Williams feels drawn in; he could be friends with this guy. He has the authority to make the call but hesitates, wondering if he should run it past a few of the teachers first to get their buy-in.

The salesman can sense that Williams is waffling. He turns up the charm, asking more thoughtful questions and flattering him.

“Hey, you know what?” the salesman says. “You’re doing great work out there. How about I throw in something for you, too?” He pulls a few $100 gift cards from his pocket and tucks them in Williams’s suit pocket with a grin.

Williams is shocked. Is this a bribe?

Reflect

1. How common is this type of behavior in your environment?

2. How can you protect your ego from flattery and avoid unethical behavior?

3. What helps you to stay humble in your position?

Be Kind

“For man, evil consists in injustice and cruelty and indifference to a neighbor’s trouble, while virtue is brotherly love and goodness and justice and beneficence and concern for the welfare of one’s neighbor” Musonius Rufus (2015, Lecture XIV:9).

Just be nice—it’s that simple.

As the leader, we often have the power to approve or deny. We have the power to be gracious or strict. Most of us want to assume the best in others. We want to give latitude as often as we can. Yet it’s also natural to worry that if we’re too gracious, people might begin to take advantage of us.

Have you ever wondered if all the doctors in your community only have appointments available around school arrival or dismissal times? You’ve probably received an email or call to your office asking, “Can I leave 20 minutes early (or arrive 20 minutes late) because I have a doctor’s appointment?” If you haven’t received that email yet, buckle up. It’s coming your way soon.

When you’re dealing with everyone’s requests, everyone’s needs, it can be easy to think they’re all ganging up on you.

The truth is, you have no idea what people are dealing with in their lives. Being a leader in a school requires you to be a jack-of-all-trades, yet taking care of your staff needs to be at the top of the list. Sickness, cancer, death of a loved one, divorce, depression. Everyone is dealing with something.

The questions you need to be asking are: Are my people OK? Can I give the person in front of me the benefit of the doubt? How can I see the person in front of me as an individual with their own unique needs and circumstances instead of just one more person in a line asking for something?

Too often, you let your emotions get the best of you and focus only on the negatives of the request that requires extra work on your part.

Instead, take a minute to thank them for making their day more chaotic for the better of the school/district, fellow staff who would have to cover them since there are no subs, and most importantly, the students. Take a minute to show that you care, and see how you can serve them.

When you are the first to serve, you set the example for everyone else. Compassion fuels justice.

Practice Justice

It’s Friday, and Assistant Principal Henderson has been looking forward to this afternoon all week. She’s excited to join in on the 100th-day-of-school assembly and participate in some friendly competition with the staff and students. At 12:50 p.m., 10 minutes before the assembly begins and right as she is about to walk down to the gym, a teacher and student show up at her door.

“Could we chat with you, Mrs. Henderson?” the teacher asks.

She can see the student has been crying and wonders what’s going on. Probably bad behavior. Does this conversation really need to happen now? Don’t they know the assembly is about to start? Couldn’t it wait?

Reflect

1. If you were in AP Henderson’s shoes, what questions would you ask?

2. How could AP Henderson make this student and teacher feel welcomed and prioritized despite the inconvenience to her schedule?

3. How do you work to make every individual in front of you feel like they belong?

Protect Others

“Of injustice there are two kinds—one, that of those who inflict injury; the other, that of those who do not, if they can, repel injury from those on whom it is inflicted.” Cicero (1887, Book I.7)

It’s not enough to simply do good for others, to avoid inflicting injury, and hope for the best. If you do not protect others from injury as well, you’re part of the problem.

You’re probably thinking, “Of course I protect others from injury! I would never stand by!”

But ask yourself this: Do I know of all of the injuries that might be happening in my school under my watch? Who are the most vulnerable people in my school? What would they say about their school experience? Does everyone truly feel welcomed as part of the community?

In his book, No Name in the Street, writer and civil rights leader James Baldwin wrote:

If one really wishes to know how justice is administered in a country, one does not question the policemen, the lawyers, the judges, or the protected members of the middle class. One goes to the unprotected—those, precisely, who need the law’s protection most!—and listens to their testimony (p. 149).

The most vulnerable in your school and district are the ones who need your protection most. Do whatever you can to seek them out and know them. Make it your personal mission to advocate for their needs.

Practice Justice

Mr. Hughes has been a teacher at his school for 15 years. By now, he knows pretty much everyone in the school—or thinks he does. One day, he notices two of his students having a dispute during class. One is Evan. Mr. Hughes knows Evan well; he taught Evan’s brother and sister, and Evan’s mom is a regular volunteer at the school. Evan is gregarious and loud but generally a good kid.

“Mr. Hughes, David started it!” Evan whines. Mr. Hughes looks at David. He realizes he doesn’t know much about David except that his parents are immigrants from Mexico—or maybe Honduras? He can’t remember; he’s never met them. David doesn’t speak much in class and usually keeps to himself. Mr. Hughes knows he needs to resolve this issue quickly before the rest of the class starts to get bored and lose focus.

Reflect

1. What questions should Mr. Hughes ask?

2. How can Mr. Hughes foster a better relationship with David and all of his students?

3. What blind spots might need addressing? As Mr. Hughes’s leader, how would you help him address those blind spots?

Resist Vengeance

“Leave other people’s mistakes where they lie” Marcus Aurelius (2003, p. 122).

When you think of a character in a movie looking for “justice,” what is it that they’re usually actually looking for? Vengeance. Our understanding of justice has, in many ways, been degraded to the idea of tit for tat, of score-keeping, of repaying one another’s bad deeds with more bad deeds.

The Stoics challenge us to raise the bar.

As we just discussed, we all have an obligation to advocate for and take action on behalf of the marginalized, the injured, and oppressed. We have an obligation to restore dignity. You might even argue that we have an obligation to allow others to feel the consequences of their actions when they do something wrong. These consequences actually further the common good.

But to perpetrate further harm by exacting revenge? That’s where the Stoics draw the line. “To do harm is to do yourself harm. To do an injustice is to do yourself an injustice—it degrades you,” said Aurelius (2003, p. 119).

Still, it’s quite difficult to resist getting back at someone. What’s the worst name/thing you were ever called or accused of growing up? You probably felt angry, hurt, and totally justified in name-calling right back, even if you were able to stop yourself from doing so.

But that experience is probably small potatoes compared to what you’ve experienced as a school leader. This role isn’t for the weak of heart. All leaders, including school administrators, have been and always will be easy for the public to criticize.

Leadership can be compared to being in a fish bowl in the middle of a shooting range. Regardless of where you try to turn, everyone can see you, and everyone can fire remarks at you. There will be crude comments, hate, threats, slandering your name on any platform that will listen, and petitions asking for your removal because you made a decision that wasn’t to someone else’s liking. As I (Danny) shared in the Introduction, other school leaders may even conspire against you.

The world is full of Machiavellian people who work against the common good. Your duty is, as Aurelius said, to leave their bad deeds where they are and focus on preserving your own good character.

Follow the law, school policies, mission, and vision of where you work. Work together with your team to make informed decisions. Constantly communicate with your school board members, as there should never be any surprises. Always “read the room” before speaking to the room. Remember what you said in your interview chair before you were hired and who you serve each day. Be strong and kind, as what you do in response to others’ bad behavior will not be long forgotten. Your dignity and character should always prevail.

Practice Justice

Ms. Foster has been making Principal Parker’s life miserable all year long. She was a runner-up for his position, and unfortunately (for her), she didn’t get the job. Since then, she’s been a thorn in his side—bad-mouthing him to parents, contradicting him in front of the staff at meetings, and once, even taking credit for one of his ideas in front of the superintendent. To say Parker is angry would be an understatement.

And now it’s evaluation time. Principal Parker heads to Ms. Foster’s room, ready to look for any possible infraction or mistake. Wouldn’t it be great to see her face when he gives her a bad score?

He sits for 20 minutes, the usual amount of time, watching eagle-eyed for anything he can mark her down on. There’s nothing. He stays another 10 minutes, and then all the way till the end of the class. Finally, he has to admit she’s a pretty good teacher.

But that doesn’t mean he has to give her a good review. She certainly wouldn’t do the same for him. He sits in his office and contemplates his options.

Reflect

1. Have you ever felt like Principal Parker?

2. Have you ever been tempted, or given into the temptation, to exact revenge when something didn’t go your way?

3. How do you remain focused on the job in front of you and ensure that you do the right thing?

Chapter 3. Courage

Bravery, fortitude, honor, sacrifice

“Give me courage to meet hardships; make me calm in the face of the unavoidable” Seneca (1917, p. 218).

Glenn

Relinquish Fear

“There are more things, Lucilius, likely to frighten us than there are to crush us; we suffer more often in imagination than in reality” Seneca (1917, p. 67).

When we are in the thick of things, when the stakes and emotions are high, it’s easy to believe that whatever we are facing could last forever.

Years ago when I (Danny) lived in Scotland, I had a horrible toothache. This was a big deal for me because I had never had so much as a cavity before.

When I went to the dentist, who must have been a novice, she told me to take some paracetamol and see her in a few weeks if it didn’t get any better. She did no X-rays on my mouth, and I didn’t think to ask.

The next day, I boarded a flight to Cyprus to visit some friends and spend time in the mountains. The pain got worse and worse. My face began to swell. The throbbing was so intense, I even cried and could barely sleep.

Lying awake at night in Cyprus as my jaw throbbed, I thought, “Will this last forever?” For a moment, I even thought, “This is the end.”

When I returned home, I immediately saw a new dentist who did the proper X-rays. My tooth was infected; I would need a root canal. He did some quick work that relieved the pain almost immediately. And in a few months I was back to normal.

I count myself fortunate that I was born in a time with access to modern medicine. If I had been born 200, 500, or 1,000 years earlier, the infection might have indeed killed me—a middle aged man.

It might seem crazy to you that I was so afraid of my toothache (although if you had felt it yourself, you would understand!). But that’s how fear works; it grows in our minds like a weed, nearly impossible to uproot.

Other experiences in my life have also caused fear to take hold: a fight with my wife, the death of my father, and so on. Just like the toothache, these experiences often feel like they will last forever, but they do not.

The only permanent thing about experience is impermanence.

As school leaders, there are some experiences we just cannot escape from. They might be as small as a disciplinary meeting with unhappy parents or as large as a global pandemic. Either way, our position calls for us to step up and face whatever it is we fear. Our fears, both the real ones and the mountains we create in our imaginations, are useless. Fear does not make the situation go away; it only delays our facing it.

Seneca wrote often about fear in his letters to his friend, Lucilius. Seneca was no stranger to fear: He lived in the shadow of a mysterious disease and was banished multiple times by capricious emperors. Eventually, he was commanded to commit suicide.

Fear is a common theme in his writing—as is anger, which we’ll discuss more in Chapter 4. Nevertheless, Seneca was clear on his priorities, and he knew that the solution was not to escape from his trials but to become the kind of person who could face them with courage: “If you really want to escape the things that harass you,” he wrote, “what you’re needing is not to be in a different place but to be a different person” (Daily Stoic, n.d.-b., “Quotes” section).

Practice Courage

Dr. Greene gets a call during fourth period and learns that a large group of students across grade levels are walking out of their classes in silent protest of the school dress code.

“They’re in the courtyard,” the teacher on the phone tells her. “They all deserve detentions for walking out like that!”

Dr. Greene asks a couple of the student leaders to meet with her to explain their thoughts. The students tell her how the dress code discriminates against students of color. She can see immediately that they’re right, but she hesitates. There are several teachers on staff who have been vocal about the dress code, often citing violations and sending kids who “refuse to cooperate” to Dr. Greene’s office.

Honestly, it’s no surprise that things have come to a head. Dr. Greene is on the students’ side, but she’s afraid that if she tries to change the dress code, she’ll face significant backlash from many of her teachers.

Reflect

1. Have you ever been in a situation where you knew that doing the right thing would be met with backlash?

2. How can Dr. Greene advocate for her students and set the right expectations for teachers through this scenario?

3. What strategies do you have for confronting your fears?

Embrace Challenges

“The only contestant who can confidently enter the lists is the man who has seen his own blood, who has felt his teeth rattle beneath his opponent’s fist, who has been tripped and felt the full force of his adversary’s charge, who has been downed in body but not in spirit, one who, as often as he falls, rises again with greater defiance than ever” Seneca (1917, p. 66).

The Stoics often remind us that challenges are a necessary part of the journey to success. Remember what we learned in Chapter 1 on wisdom: We have to know the difference between what we control and what we don’t.

Unfortunately, most of what lands in the category of what we don’t control are obstacles we never invited into our lives and certainly don’t want to face—especially when we have so many goals that we’re trying to accomplish for the sake of our students, our staff, and our schools.

But it’ll be easier if we expect that challenges will come, and we embrace them with as much dignity and patience as we can muster.

We can also turn those challenges into opportunities to become better. Whether it’s that teacher we just can’t seem to make happy or the parents who are constantly frustrated about our policies, we cannot grow if we don’t allow friction in our lives, if we run away from conflict or try to avoid making people angry. It’s not possible anyway, so we might as well embrace it and use it to our benefit. Doing so repeatedly over time will build our confidence.

That confidence proves useful when facing the criticism that inevitably comes with being in a position of authority. In a speech perhaps inspired by Seneca’s words, President Theodore Roosevelt reminds us that we can’t allow those critics to stop us from fighting:

It is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself in a worthy cause; who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who knew neither victory nor defeat (Theodore Roosevelt Center, n.d.).

This is the spirit of strength and courage that the Stoics advocate for: a relentless refusal to be cowed, intimidated, or turned away from the pursuit of what’s right.

Practice Courage

Helen is the principal at an urban elementary school. She wakes up feeling great one morning and decides to arrive at the office 30 minutes earlier than normal, bringing with her coffee and breakfast for the staff. However, when Helen pulls into the parking lot, there is a couple waiting by the front door. Upon walking to the door with the coffee and breakfast, Helen can see the mother is red in the face.

“I hope you read the email that I sent last night,” the mother declares icily. Helen continues to walk slowly towards the couple, asks for their names, and wonders if she should even open the door to let them in. So much for thinking that this is going to be a great morning.

The couple responds with their names. Helen has heard of this family before, and what she’s heard was never good. These parents have a reputation for bulldozing their way over staff and manipulating leaders to get whatever they want. They love to mention their well-known lawyer if anyone dares to disagree with them.

Feeling that it is the right thing to do, Helen opens the doors and invites them in. She places the coffee and breakfast on one side of the conference table of the main office and then asks the couple to sit with her.

Helen asks when the email was sent; the last time she had checked her email was at 8 p.m. the night before. She had set a policy with staff and community leaders that if anything was urgent at night that couldn’t wait until morning, they were to call her directly.

The mother had sent the email at 1:25 a.m. When Helen explains her policy, the mother responds with a number of words that you wouldn’t use in a PG-rated movie. The father joins in the tirade, and it doesn’t take too long before their lawyer’s name is mentioned.

Helen takes a deep breath and considers how to respond.

Reflect

1. What other information is Helen missing?

2. Have you ever felt backed into a corner in your role? How did that situation resolve?

3. How could Helen plan ahead to set boundaries and build a more positive relationship with these parents?

Expect the Unexpected

“In this way you must understand how laughable it is to say, ‘Tell me what to do!’ What advice could I possibly give? No, a far better request is, ‘Train my mind to adapt to any circumstance’” Epictetus (Daily Stoic, n.d.-c., section 1).

To be a school leader in today’s world requires that you understand and embrace VUCA leadership: volatility, uncertainty, complexity, and ambiguity. The greatest school leaders admit that they do not have all the answers, but they help their school/district teams accept the realities of a VUCA world.

Leading a school in a VUCA world isn’t about adopting the newest technologies that promise quick solutions, though. It’s about finding the tools the school needs to be able to continue doing (and improving) its work within an ever-changing technological environment. The COVID-19 pandemic was, in many ways, a much-needed wake-up call for many districts who struggled to continue serving their students when they couldn’t be together in person.

It’s easy to get comfortable with what you know; it’s much harder to maintain the attitude of a constant learner and humble yourself to be open to new ideas. It’s difficult to imagine a world very different from the one you’ve always known. Yet the Stoics teach us: Expect the unexpected. And to the best of your ability, help your team to do the same.

Many school districts have a position you might not have heard of, but you’ve definitely noticed it. It’s called the Chief “Yeah, But” Officer (CYBO). This person’s comments go something like this:

“Yeah, but I’ve done it this way for 30 years, and it’s never been a problem before.”

“Yeah, but what if [insert idea they don’t like] fails?”

“Yeah, but that would never work in my classroom/school/district.”

As a leader, how have you prepared and trained your team and/or staff to embrace VUCA? Are they given the freedom to fail without the fear of becoming a failure? Do they have the psychological safety to know that you will support them when they present ideas that push the boundaries of traditional schooling? Can your team of diverse perspectives disagree with you and/or others in meetings without the fear of retaliation? Do you embrace the ideas of your innovators, or do you follow the beliefs of the CYBO in the district?

If you continuously follow the traditional scripts of outdated best practices—because that’s how you learned best, that’s what you learned from your mentor, or because of the CYBO—then how do you expect others to change their minds and adapt to any circumstance? Be the school leader you needed when you were a teacher instead of the one you resented.

Practice Courage

For the past several weeks, the rumor mill in the community has been spiraling faster than a tornado. Everywhere Superintendent Muñoz looks, people are asking if everything is going to be OK. On the news, in social media feeds, at the school sporting events, around town—just about anywhere people congregate—the heated topic is there.

Earlier in the month, the state government body required a controversial curriculum revision be made to all public school districts in the state for the upcoming year. The latest rumor is that people are going to be lined up for hours wanting to speak during the public portion of the next school board meeting and city/town council meeting. Superintendent Muñoz is already starting to stress out and dread going to the meeting.

Reflect

1. What options does Superintendent Muñoz have? What are the different ways she might handle this situation?

2. How can she avoid becoming the CYBO?

3. How do you prepare teachers and staff for the realities of a VUCA world while honoring their autonomy and preferences?

Fight to Be Better

“No matter what anyone says or does, my task is to be good. Like gold or emerald or purple repeating to itself, ‘No matter what anyone says or does, my task is to be an emerald, my color undiminished’” Marcus Aurelius (2003, p. 87).

We all face temptations from time to time. Temptations to take the path of least resistance or to choose what’s best for you over what’s best for your school. Temptations to give up when faced with poverty and trauma and bureaucracy and bickering and sadness.

It takes courage to stay devoted to your why.

It takes courage to stay devoted to your vision, your hope for a better future.

It takes courage to remember who you truly are and not to let the negative circumstances or obstacles that you face obscure the brilliance of your true colors. Aurelius (2003) said, “No matter what anyone says or does, my task is to be good. Like gold or emerald or purple repeating to itself, ‘No matter what anyone says or does, my task is to be emerald, my color undiminished’” (p. 87).

Sometimes, we can fool ourselves into believing that we are courageous because we dare to rebel or make a scene. We believe in being Ruckus Makers in education—but not because we love chaos or anarchy. We believe in being Ruckus Makers for a purpose: to make schools and the people within them better. What matters here is motivation: Are we doing it on behalf of our students and the common good? Or are we doing it to serve ourselves?

Daring for your own benefit may be brave—but it’s not courageous. The Stoics are firm on this point. Courage is the willingness to face danger for the sake of the common good.

Practice Courage

Mr. Ramirez is a new instructional coach at one of the best schools in the state. He’s lucky to have been hired there—all of his new colleagues have congratulated him, and his old colleagues have been envious. He’s also part of the leadership team. At one of their first meetings, the principal shares the school’s most recent test results with pride, noting their overall high performance.

The meeting moves on to other agenda items, but Mr. Ramirez glances through the report more closely. He notices that although overall scores are high, when looking at the breakdown of students, he can see that many of those from low socioeconomic backgrounds are still struggling. They haven’t been making the same gains—and even worse, when he digs further into their history, he can see that this problem has been occurring for the last few years. He brings it up to another teacher, but she shrugs it off.

“Look, we’re a blue ribbon school. What more do you want? We can’t make everyone happy.”

Mr. Ramirez is shocked. Is this the attitude here? He wonders if he should avoid the topic at the next leadership team meeting. After all, he’s still the new guy.

Reflect

1. What should Mr. Ramirez’s next steps be?

2. What might the consequences be if he brings this problem up to the leadership team?

3. How can you prepare to do the right thing, regardless of the consequences?

This audiobook is read by human Danny. If you prefer reading, you can purchase the book here.

Most principals chase being the best. The principals who actually transform their schools chase something different — and the difference is not semantic.

In this episode, Danny reads the conclusion to Mastermind: Unlocking Talent Within Every School Leader. He pulls the full arc of the book together: why traditional PD fails, what the ABCs of powerful professional development actually look like in practice, and why authenticity, belonging, and challenge are the three forces every school leader needs around them — whether they join a Mastermind or build their own.

This chapter also names the chain of consequences districts rarely admit out loud. When leaders lack access to high quality professional development, they become less confident. When leaders are less confident, they make poor decisions. When leaders make poor decisions, the community and the students pay for it. Danny closes with a direct invitation. You can join an established Mastermind, or you can take the framework from this book and build your own. What you cannot do — what no Ruckus Maker should do — is keep leading alone.

If you have followed this series chapter by chapter, this episode is the punctuation. If you are coming in cold, this is the thirty thousand foot view of the entire model.

⌚️ TIMESTAMPS

00:00 - Why best is not a permanent state

00:53 - Who the Mastermind is right for

01:54 - The full arc of the book in one minute

03:07 - Belonging and the cornerstones of connection

03:33 - How the Mastermind challenges leaders to level up

04:08 - The chain reaction of bad professional development

05:01 - The invitation to apply or start your own

05:59 - Jason Dropik on leading the Indian Community School

08:31 - Why a hesitant leader should lean in anyway

Grad school taught you how to run a school. It did not teach you how to create a campus experience worth showing up for.

That’s a big problem …

(if you’re a Ruckus Maker)

Because your #1 job is to create a campus experience worth showing up for.

Simply learning to be a better, more efficient manager of campus resources will not inspire your community. Bell schedules, graduation, teacher evaluation are all important. They are table stakes of running a school.

But to create something legendary?

That requires a Do School Different approach.

The kind that we write about here.

In our view, there are two types of school leaders:

• Play-It-Safe-Principals read what the system assigns them without question. They protect the way it’s always been done.

• Ruckus Makers read far and wide outside of education. Not because they think education is broken, but they prioritize learning from a wide variety of disciplines.

An echo chamber exists in every school system in the world. There is shared language, operating procedures, and other efficiencies that exist to make life easier in any system.

And if you have ever asked, “There must be a better way …” this post is for you.

I made a list of 10 books that will support your Do School Different vision. Books I love. Books that we’ve read in The Ruckus Maker Mastermind since 2016.

None are a book from the K12 industry. You’ve already read those.

This list are my favorites from the last 10+ years supporting bold school leaders. I share the top ten list in the video below. Then I ask Digital Danny, my AI clone, what he would suggest. I’m glad I did because he offered a few gems that I didn’t include originally.

Here’s the list, with one big idea from each text.

1. Stillness is the Key by Ryan Holiday

Sports psychologist Dr. Michael Gervais says elite performers never talk about effort. Working hard is table stakes.

According to Gervais, what elite performers discuss on the world stage is recovery because when you’re already working hard, recovery is what separates the best from the rest.

There’s a reason every framework I teach starts with taking care of the individual leader first (even before family). You can’t our from an empty cup.

2. The Inner Game of Tennis by Tim Gallwey

Yes, this book is about sports performance. So how does it relate to school leadership.

Gallwey names the two selves inside every Ruckus Maker.

• Self One is the critic. The voice that says why’d you say that, you’re not ready, this will never work.

• Self Two is the doer. The one who has to walk the halls and build a campus experience worth showing up for.

When Self One talks too much, Self Two plays small. And a principal playing small puts a ceiling on what results a campus can create.

3. Emotional Intelligence 2.0 by Travis Bradberry & Jean Greaves

Ruckus Makers love this book because it is super practical.

You take an assessment and score yourself across four domains of emotional intelligence: self-awareness, self-management, social awareness, relationship management.

Then, you choose your lowest area and get to work. The authors provide 15 activities per area of emotional intelligence. Do the work and your results will grow.

4. The Art of Gathering by Priya Parker

As school leaders, we bring people together all the time.

The problem is that we take these gatherings for granted and as a result, they are mediocre.

Staff meetings. Open house. Graduation.

Boring. Boring. Boring.

And here’s the thing …

With just a little bit of intentional effort, you can create legendary experiences on your campus.

The kind of stuff people are excited about.

After reading this book, you’ll never think of Open House the same.

5. Tiny Habits by BJ Fogg

According to Fogg, behavior is a function of motivation, ability, and a prompt.

B = MAP

This is a revolutionary framework.

Most school leaders (mistakenly) believe that people when staff doesn’t follow through they either are unmotivated or simply don’t care.

The B = MAP model shows this is likely wrong.

I believe people care deeply about their work (and want to know they are doing a good job too).

What is usually missing is ability (they need training and development) or a prompt (a cue that says it’s time to do “X” behavior).

When you understand this model, people start to do what you want. It’s like a Jedi power 🔮

6. The Infinite Game by Simon Sinek

Finite games have winners and losers. Finite leaders think, “In order for me to win, you must lose.”

Infinite games are about abundance.

You don’t have to lose for me to win. And what if the game never ends?

Schools and school systems compete a lot in the finite game zone. Students would benefit for us to figure out how to play a more generous, and infinite game.

7. A Beautiful Constraint by Adam Morgan & Mark Barden

The head of Random House bet Dr. Seuss $50 he couldn’t write a book using only 50 words.

Seuss accepted the bet and created Green Eggs and Ham—his best-selling book ever.

Constraints are beautiful.

The obstacles become the path to greatness once you use them as the starting (and not the end) point.

“We can’t” and “That’ll-never-work” thinking has never produced anything remarkable.

Only “What would need to be true” type of thinking gets the job done.

8. Thinking in Bets by Annie Duke

Everyone knows a time they made a very poor decision, but it resulted in a good outcome …

(I’m looking at your college years)

We also know there are times when we have a solid decision making process, and yet, the outcome stinks.

As Frank Sinatra says, “That’s life.”

The problem I see many school leaders make is that they over-value outcomes and under-value process.

And the problem with that kind of thinking is that it elevates what is NOT in your control (the outcomes) over what is in your control (the process).

Annie Duke challenges us to turn that around.

This book is a masterclass on decision making.

9. Radical Candor by Kim Scott

I fear that most educators practice what Scott calls Ruinous Empathy. That’s when you care a lot, but you are not direct. You tend to dance around issues.

But to be a Ruckus Maker you need to care and be direct. This is what Scott calls Radical Candor. It’s also the only kind of feedback that works and helps people be their best.

Gene Park is a sitting principal in NJ and current mastermind coach. He read this book with his staff and trained them on the four quadrants of Scott’s framework:

After conversations with staff, he brings up this grid and asks in the moment where his communication landed. Imagine that kind of feedback loop done every day with staff.

That’s what makes Gene a King of Culture.

10. Man’s Search for Meaning by Viktor Frankl

This book is my all time favorite for Ruckus Makers and sits in my personal book Hall of Fame.

My copy is earmarked and the “marginalia” is written everywhere.

Frankl survived Auschwitz, and his core idea is radical ownership:

Life is going to ask you what it means. How anyone else answers doesn’t matter. The only answer that counts is yours, because you’re the one being asked.

School leadership is tough. Frankl’s lived experience was objectively tougher. Learn how to thrive in adversity because expecting anything else is naive.

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

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

Glenn

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

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

1. What is within Principal Rosa’s control? What isn’t?

2. Where might Principal Rosa exert influence?

3. 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

1. What are Coach Carter’s options for next steps?

2. What will happen to this student if he leaves now?

3. 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

1. Have you ever been in a similar situation?

2. How might Principal Daniels address the discrepancy with this teacher? What should his next steps be?

3. 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

1. Have you ever been in a situation like this? What did you do?

2. If you were a mentor in Superintendent Beckett’s life, how would you advise her?

3. How could Superintendent Beckett get the relationship with her EA off on the right foot?

This audiobook is read by human Danny. If you prefer reading, you can purchase the book here.

Top surgeons hire coaches. Olympic athletes hire coaches. Fortune 500 CEOs hire coaches. So why are school principals expected to figure it out alone?

In this episode, Danny reads Chapter 5 of Mastermind: Unlocking Talent Within Every School Leader. The chapter unpacks the third and final leg of the ABCs of powerful professional development: Challenge. It is built on three pillars — mindset, taking action, and powerful community — and it lays out the specific practices that turn a Mastermind from a peer support group into a transformation engine.

Danny walks through the 12-mindset scorecard he uses to evaluate every applicant, the one statistic that explains why your goals slip through the cracks (people who write down goals plus share them weekly are 76% more likely to achieve them), the books from outside education that have shaped every cohort since 2016, and the Hot Seat — the single most valuable hour a sitting principal can spend in any given week. You will get both Hot Seat protocols, the three pitfalls that wreck them, and the prep questions Danny sends every leader before they take the seat.

If you have ever wondered why other professions get coaches and yours does not, this chapter tells you what to do about it.

⌚️ TIMESTAMPS

• 00:00 - The systemic blind spot in principal development

• 01:54 - The mindset scorecard and why it matters

• 07:24 - Why celebrating wins builds resilience

• 10:51 - The books that shape every cohort

• 19:43 - Why managers answer and leaders ask

• 20:37 - Ten coaching questions that unlock the path

• 27:26 - Scott Long builds his own internal mastermind

• 36:11 - The one big thing and the 76 percent rule

• 41:36 - Why surgeons get coaches and principals do not

• 43:24 - Annie Duke and the truth pod versus echo chamber

• 45:26 - Why the hot seat is the most valuable hour

• 49:09 - Hot seat protocol one and the three pitfalls

• 52:20 - Hot seat protocol two from Kyle Wagner

• 54:21 - The prep questions to maximize your hot seat

This audiobook is read by human Danny. If you prefer reading, you can purchase the book here.

Most principals lead with expectations. The principals who actually move their schools lead with something different.

In this episode, Danny reads Chapter 4 of Mastermind: Unlocking Talent Within Every School Leader. The chapter unpacks the second leg of the ABCs of powerful professional development: Belonging. It is built on three pillars — shared purpose, inclusive environments, and trust — and it opens with a leadership reframe most school leaders never get taught.

Expectations set you up for disappointment. Agreements set you up for a school that actually moves. Danny walks through why one approach builds resentment in your staff and the other builds momentum, then gives you a real-school example of what the conversation looks like when an AP and principal negotiate an agreement instead of trading expectations. He also unpacks the nine agreements that hold the Mastermind together, the murmuration metaphor that explains why a tight cohort outperforms a loose network, and the activities — chat waterfalls, brainwriting, pass the mic, the family photo — that build belonging on purpose instead of by accident.

If you have ever set a clear expectation with your staff and watched it land flat, this chapter tells you exactly what to do instead.

⌚️ TIMESTAMPS

• 00:00 - The murmuration metaphor for school leadership

• 03:13 - Why shared purpose beats purpose for

• 06:12 - Why agreements are stronger than expectations

• 10:20 - A real conversation that turns expectation into agreement

• 13:10 - The nine Mastermind agreements explained

• 22:26 - Assume positive intent and the choice map

• 28:26 - Why social media became the new faculty lounge

• 33:37 - The story behind every cohort name

• 40:34 - The demographic mismatch in school leadership

• 47:23 - The story Demetrius brought to the room

• 55:15 - Chat waterfalls and brainwriting that beat brainstorming

• 59:10 - Pass the mic and the family photo ritual

• 01:06:21 - How Nancy turned a broken school around

• 01:09:36 - The three elements of trust at work

• 01:11:02 - The braving inventory for leadership teams

• 01:13:00 - Why every Mastermind ends with love you

This audiobook is read by human Danny. If you prefer reading, you can purchase the book here.

Most school leaders cannot accurately name what they are feeling in real time — and that one gap is quietly running their schools.

In this chapter, Danny reads Chapter 3 of Mastermind: Unlocking Talent Within Every School Leader. The chapter unpacks the first leg of the ABCs of powerful professional development: Authenticity. It is built on three pillars — psychological safety, self-awareness, and values-driven leadership — and Danny walks through every one of them with the activities, frameworks, and confessional stories that make Mastermind cohorts work.

You will hear what Google’s Project Aristotle discovered about why some teams fly while others stall. You will learn the simple opening rituals — check-ins, permission slips, wins of the week, draw-a-peer — that build psychological safety in minutes. You will hear two stories Danny tells on himself: the colleague, the book room, and the key — and the AP in Texas he should have confronted but did not. You will get the four-word personal philosophy that has guided his leadership for years and the exact prompt to write your own.

If you have ever felt like the most important conversation you needed to have was the one you kept avoiding — this chapter tells you why and shows you what authenticity actually looks like in a Mastermind room.

⌚️ TIMESTAMPS

• 00:00 - Why psychological safety is the team multiplier

• 03:30 - Edmondson’s research and what builds safe teams

• 05:35 - Check-in questions that change a meeting

• 09:44 - Draw a peer and other unity activities

• 14:28 - Permission slips and wins of the week

• 17:31 - Why silence is a facilitator’s best tool

• 22:08 - The hot seat and rotating facilitators

• 28:35 - Self-awareness and the cost of avoiding hard talks

• 32:51 - The 2 out of 3 statistic on leader emotions

• 35:50 - Perfect or good enough as a leadership trap

• 40:02 - Between the frames and the stories we tell

• 45:31 - The check-in survey that surfaces a crisis

• 49:57 - Values-driven leadership and Frankl’s lesson

• 54:52 - The book room story and one of Danny’s worst moments

• 01:04:02 - How to write your personal philosophy

• 01:09:54 - The five sticky core values of the Mastermind

• 01:22:01 - Why memorable values are remarkable values

This audiobook is read by human Danny. If you prefer reading, you can purchase the book here.

School leadership is broken when principals lead alone — and the principals who break out of that pattern share a specific set of mindsets that districts almost never develop on purpose.

In this episode, Danny reads Chapter 2 of Mastermind: Unlocking Talent Within Every School Leader. After Chapter 1 named the three problems with traditional PD, this chapter delivers the solution: the framework behind the Better Leaders Better Schools Mastermind, the 12 mindsets that define a Ruckus Maker, and the ABCs of powerful professional development.

Danny walks through the actual filter he uses on every Mastermind application — generosity, hunger, openness to feedback, collaboration, anti-racism, ownership, compassion, and more. He also unpacks why he applies the Golden Circle to school leadership the same way Apple applies it to product design: lead with why, then how, then what. And he names the equation that has shaped every cohort he has built since 2016 — Authenticity plus Belonging plus Challenge equals Transformation.

If you have ever wondered what the principals who actually do school different have in common — and what mindset a sitting principal needs to build before any framework will work — this chapter is the answer.

⌚️ TIMESTAMPS

• 00:00 - Chris Jones on what the Mastermind unlocked

• 05:14 - Who the Mastermind serves and who it does not

• 07:56 - Why mindset matters more than skill

• 10:43 - Mindset 1: generous leaders add value first

• 11:37 - Mindset 2: hunger and the readers are leaders rule

• 13:17 - Mindset 3: welcoming candid feedback

• 14:56 - Mindset 4 and 5: open mind and collaboration

• 15:57 - Mindset 6: excellence and why A players need A players

• 16:55 - Mindset 7 and 8: anti-racist and emotionally intelligent

• 17:55 - Mindset 9, 10, 11: ownership, goals, and compassion

• 22:28 - The 9-minute application as a filter

• 29:09 - The Golden Circle applied to school leadership

• 31:56 - The ABCs of powerful professional development

• 33:52 - Why authenticity, belonging, and challenge equal transformation

Read more

Year Three Is Supposed to Be Different

He’s a third-year principal at a massive comprehensive high school. Over 200 employees. The kind of campus where you can spend an entire day reacting and never once touch the work that matters.

Everyone in his orbit keeps telling him the same thing: year three is the year. Systems are in place. Relationships are built. Now you execute.

He believes it. He’s ready. And clarity and focus have been his fight since the day he took the job.

The People Were Never the Problem

Here’s what makes his situation interesting.

Earlier in his career, at a smaller school, his line was give me the people and I’ll do the job. Now he has the people. More than he’s ever had. Two English coaches. Two math coaches. Program specialists for budgeting, testing, pathways, interventions. More than ten fully released teachers on assignment.

And the work still routes through him.

He ran an exercise with his admin team to find out where the hours actually go. Everyone tracked what they actually do in a day (not the job description, the reality).

The answer: reacting.

Referrals. IEPs. Supervision duty. Parents.

Next thing you know, it’s time to go home, and what did you really do that day?

So the problem was never headcount. Something else was jamming the handoff.

He’d Already Done the Hard Part

This wasn’t a leader who hadn’t done the work.

He’d just locked his admin team in an office for three days hammering out strategy. They’d fought their way past a feel-good goal and landed on one thematic priority for the year: instruction. Everything in service of quality bell-to-bell teaching.

He could even name his own lane. Instruction. Relationships. Strategy.

That’s the job.

Everything else, in his words, gets delegated or ignored.

But “gets delegated” is where it stalled.

Delegated to whom? With how much rope? Checked how often? He had the destination and a parking lot full of capable people. He was stuck at the handoff.

Delegation Isn’t a Switch

The first move was naming what delegation actually is. Not a switch you flip. A dial with five levels:

Read more

This audiobook is read by human Danny. If you prefer reading, you can purchase the book here.

Principal professional development is broken — and the reasons are not the ones districts talk about in board meetings.

In this episode, Danny reads Chapter 1 of Mastermind: Unlocking Talent Within Every School Leader. He names the three forces that quietly gut almost every PD program built for school leaders: inauthenticity, isolation, and missed opportunities. And he introduces the framework that became the spine of the Better Leaders Better Schools Mastermind — the ABCs of powerful professional development: Authenticity, Belonging, and Challenge.

Inside the chapter Danny unpacks why district-led PD turns into an echo chamber, why only 23% of principals have access to a mentor, why high performers get ignored while struggling principals get a coach, and why the principal who feels alone in a room of colleagues is the rule, not the exception. There is also a concrete story Danny tells on himself — a culture decision he reversed too quickly because he listened to one veteran teacher instead of his network. It is the kind of mistake every principal recognizes and the exact mistake a Mastermind would have prevented.

If you have ever sat through a district PD day and thought this is not what I needed, this episode tells you why and what to build instead.

⌚️ TIMESTAMPS

• 00:00 - The leadership challenges every principal recognizes

• 02:47 - The framework that almost did not exist

• 04:33 - Three lines that explain everything wrong with PD

• 06:32 - Inauthenticity: the absent or sporadic PD problem

• 08:32 - Why internal PD becomes an echo chamber

• 11:49 - The two fish and the water they cannot see

• 16:41 - How a Mastermind expands your circle of competence

• 21:06 - Isolation: the enemy of excellence

• 22:04 - The PD access numbers districts ignore

• 33:03 - The blind spot that cost Danny a culture win

• 36:26 - Missed opportunities: ice mistakes and reframing

• 43:40 - The mirror moment every leader has to face

• 50:19 - Why high performing principals get left alone

• 53:03 - The ABCs of powerful professional development®

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This audiobook is read by Digital Danny. If you prefer reading, click the link below.

The One Document Most Principals Never Write

Your staff spends 18 months guessing who you are as a principal. One document fixes it in an afternoon.

A principal user manual is the document that tells your team how you actually work — your scoreboard, your tells, your non-negotiables, and your worst characteristics — before they have to guess.

Average principal tenure is four years, and your people spend half of it running an interpretation of you and getting it wrong. The veteran teacher who stopped bringing you problems. The AP who CCs you on everything. The first-year teacher who won’t ask for help. That’s the cost of being unreadable.

This audiobook breaks down the eight sections of a principal user manual and why writing one is self-mentorship, not an HR exercise. It also names the four reasons most principals nod along and never write it — and dismantles each one. The hardest section is naming your own dysfunction on paper. Do it anyway: when you name it first, you take its power away before it becomes a whisper in the staff lounge.

⌚️ TIMESTAMPS

• 00:00 - The principal nobody can read

• 00:41 - Everybody is lying to you unintentionally

• 01:41 - The fix is a user manual

• 02:18 - The compounding cost of being unreadable

• 04:18 - The fork between ruckus maker and play it safe

• 06:01 - Why most principals never write it

• 08:26 - The eight sections of your user manual

• 10:49 - What your tells mean and don’t mean

• 11:26 - Naming your worst characteristics

• 12:05 - Your non-negotiables and the hell no line

• 13:22 - What you need from your team

• 13:42 - Block 90 minutes this weekend

This audiobook is read by Danny Bauer.

If you prefer reading, click the link below.

The Remarkable Vision Formula Every Principal Needs

School vision statements fail because they’re too vague to act on. Here’s the 5-step formula for building a compelling vision your whole community will row toward — and actually implement.

Most principals write a vision statement and call it done. That’s not a vision — that’s a plaque on the wall. The Remarkable Vision Formula is a five-step process built for school leaders who are ready to design the future of their campus on purpose: retreat, visualize the future, define expectations, seek feedback, and implement.

This guided retreat walks you through your remarkable life, your remarkable family, and your remarkable school — in that order. Because you can’t lead a school into a vision you haven’t lived yourself. Whether you’re leading a failing campus like Joe Clousy’s, building culture like Scott Long did with Sticky Core Values, or just tired of watching your team coast in silos — this is where the work starts.

⌚️ TIMESTAMPS

• 00:00 - Why vision without direction wastes everyone

• 01:47 - Sarah’s story: a retreat that built collective efficacy

• 03:32 - What happens when your team rows different directions

• 06:15 - The 5-step Remarkable Vision Formula explained

• 11:14 - The art and science of retreating

• 17:43 - Why visualization is not woo — the science behind it

• 20:37 - The Dream Manager and why leaders must dream first

• 27:50 - How to build your Dream 100 list

• 35:34 - Designing your remarkable family vision

• 45:23 - Joe Clousy’s failing school and the power of long-term vision

• 52:30 - Sticky core values: why one word is never enough

• 01:00:31 - The concentric circle method for getting buy-in

• 01:09:32 - Four pitfalls that stall every vision after launch

• 01:13:14 - The 20-mile march and bias toward action

• 01:16:55 - Three benefits of remarkable execution

• 01:24:51 - Why the Ruckus Maker Mastermind exists

Year One Revealed Something She Couldn’t Ignore

She’s a high school principal who just closed out year one. She inherited her admin team rather than building it. Relational, observant, the kind of leader whose North Star is simple: are kids happy to be in this building? Year one was for watching and learning. Year two is for the gas pedal.

But before she can floor it, she has to deal with what year one revealed.

One Innocent Question Blew It Open

Graduation went beautifully. Smooth ceremony. No angry parent emails. A win by every measure.

Except one.

The admin team had planned to go out for drinks afterward. A team thing. Then a family emergency pulled her home, so she skipped it.

The rest of the team still went. Almost all of them. They just didn’t tell one AP.

It surfaced days later, by accident. She asked her APs an innocent question — did you guys end up going out? — and watched one face fall.

You didn’t text me?

Then came the tears in her office. Not about one missed night. About what it signaled.

When she talked to the others, their defense was ready: she excludes us all the time. We get it, it’s crappy. But here’s why we felt this way first.

An admin team that isn’t unified. Members who don’t all like each other. A year of quiet resentment, finally out in the open.

And the team stays together next year, so none of it can be waved off.

She Did the Right Things. She Still Felt Like She Caused It.

Guilt, mostly. She’s the one who asked the question. In her mind, the conflict came out because of her.

And she’d already made smart moves. She met with each person privately before they talked to each other. Helped each one see the other’s side. The conversations happened. They went well-ish.

The Question That Changed the Whole Story

The first reframe was about the guilt: don’t feel bad this came out.

For a team to perform at its highest level, buried conflict has to surface.

Was the moment awkward? Sure. But she didn’t create the problem by asking a question. The problem was already there, doing damage in the dark. A portion of the team made a choice, as adults, and that choice had consequences.

She just turned the lights on.

The second beat came from something she’d uncovered in those private conversations. The two who felt excluded all year (the ones with the ready-made defense) got a simple question from her:

“Have you ever told her she makes you feel this way?”

Well... no.

So they wanted her to be a mind reader.

A whole school year of feeling excluded. Zero attempts to say so. Then one night of payback, justified by grievances the colleague had never once heard.

And the standard she set for them is the one worth stealing.

You don’t have to be friends. You don’t have to be friends at all. But you have to have a positive working relationship.

No pettiness. No score-keeping. Talk to each other.

What This Means for Your Team

Surfaced conflict beats buried conflict. The awkward moment isn’t the wound. It’s the start of the repair. If your team looks harmonious because nobody says the hard thing, you don’t have harmony. You have a delay.

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This audiobook is read by Digital Danny. If you prefer reading, click the link below.

What Your Staff Says About You When You’re Not in the Room

Leadership identity for principals is either something you define — or something your staff defines for you. And they won’t choose the version you’d pick.

Principal leadership identity is the most overlooked gap in school leadership. Three coaching conversations — an AP stepping into summer school, a Year 4 principal rebuilding after a beloved predecessor, a veteran asking how to finish strong — all surfaced the same blind spot: most principals have a vision for their school and no clear story about who they are as a leader.

If staff can’t describe your leadership identity in one sentence, they’ll write their own. The resistant faction, the informal influencers, the grade-level lead who’s already two steps ahead of you — they’re all filling a vacuum you left open. This episode is the coaching conversation that closes it.

⌚️ TIMESTAMPS

• 00:00 - The leadership vacuum no one talks about

• 00:57 - Three principals, one shared question

• 02:00 - What the AP and Year 4 principal were doing right

• 02:56 - Why your goals aren’t the entry plan that matters

• 03:53 - The insights: non-negotiables, maps, and informal power

• 04:49 - Leading from fear vs. investing in who’s ready

She’s a first-year principal who is anything but new to her building. Five years watching. Five years taking notes. When she finally got the seat, she moved fast. Bold decisions. High expectations. “Guns blazing,” in her own words. The kind of leader who would rather lose positions than people, and who refuses to spend another year waiting and praying for things to change.

The boldness worked. The building is moving. The vision is landing.

But it came with a cost she didn’t see coming.

Her two assistant principals have had a hard year. Tough conversations. Real accountability. Some disciplinary decisions.

All of it necessary.

And some of it counterproductive.

Because now both of them hesitate to make decisions. They’re worried about the repercussions of choosing wrong.

One of them spirals for days after a single mistake. Sky’s falling. Can’t rebound. Replays it over and over.

She doesn’t want her team living in that space. She wants to spend the summer rebuilding the dynamic. Supportive. Safe to take risks. A place where mistakes are okay — as long as they’re not sloppy ones.

And she wants to do it without taking her foot off the gas.

What She’d Already Tried

She’d told them mistakes are okay. “A hundred times,” she said.

And she’d modeled it. Or thought she had.

Every Monday in their admin meeting, she names her own misses. Dropped balls. Things she’d handle differently.

Her APs respond by comforting her. You have a million things going on. You had the best interest in mind. You’ll bounce back.

They give her good advice. They just don’t take it themselves. One of them spirals for days after a single mistake.

The Coaching Conversation

The question that opened the door for her:

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This audiobook is read by Danny Bauer. If you prefer reading, click the link below.

The 90-Day Entry Plan Every Principal Needs

A 90-day entry plan for principals is the difference between a school year you control and one that controls you. Most leaders walk into August hoping for the best — and spend the next 90 days playing whack-a-mole with fires they never saw coming.

This audiobook walks you through the five buckets of a perfect entry plan: yourself, communication, academics, culture, and operations. In that order — because most principals get the order exactly wrong. The principals who’ve used this plan don’t just survive the first 90 days. They build forward momentum that carries them through the entire year.

Every chapter ends with a take-action step. This isn’t theory — it’s your plan, built while you listen.

⌚️ TIMESTAMPS

• 00:01 - What the 90-day entry plan actually solves

• 05:00 - Why hope is not a strategy

• 10:53 - The five buckets of the entry plan

• 13:55 - You come first: the Ruckus Maker Mindset tool

• 21:06 - The principal who died at her desk

• 25:36 - The 85% rule every leader needs

• 26:33 - How to define your sticky core values

• 33:49 - Communication is how everything else works

• 39:53 - The Remarkable Vision Formula

• 48:07 - Why Whack-a-Mole destroys academic progress

• 57:40 - Empowering your team to lead PD

• 01:00:27 - Culture starts with the cigarette butts

• 01:05:55 - Belonging vs. othering in your school

• 01:12:05 - Operations: less is more, delegate more

• 01:19:22 - Building your actual 90-day plan