6 min read

Welcome to another edition of PEN Mondays! This week, we’re kicking it off with another series set on walking you straight to the Principals office.

Who’s the Principal?

You! (Well…maybe)

This four-part series explores how teachers and administrators aren’t perpetually against each-other, but are standing side-by-side, moving forward toward the same goal: The betterment of your students.

Our last Monday series focused on AI in education. If you want to check it out, you can catch up with those posts (and many others) on our website! Check it out here:

Part 1 - Part 2 - Part 3

Ah, administration.

That mystical realm where the coffee is slightly fancier, the stress is exponentially higher, and every email begins with “URGENT.” For teachers, it can feel like a completely different world—one where your colleagues suddenly start speaking in acronyms and disappear into meetings that seem to last longer than the school year.

But here’s the thing: most administrators didn’t wake up one day and say, “You know what? I want to stop teaching and start sending strongly worded memos about lunchroom protocol.” 

Most of them started as teachers, just like you. So, how do you know if you’re ready to make that leap into leadership? Let’s unpack what it means to be “administration material.”

WHY WOULD ANYONE EVEN WANT THIS JOB?

Let’s start with the obvious question: Why would you willingly trade your classroom for an office where the biggest perk is your own stapler? It’s not about the stapler (although, let’s be honest, it’s a nice touch).

It’s about the chance to make a bigger impact.

As a teacher, you change lives one classroom at a time. As an administrator, you influence an entire school. You shape the culture, solve problems on a grander scale, and create an environment where both students and staff can thrive.

It’s the difference between being the actor in a play and directing the entire production—stressful, yes, but incredibly rewarding if done well.

And sure, the paycheck doesn’t hurt either. Let’s not pretend that a bump in salary to fund your caffeine habit and that endless supply of Expo markers isn’t a factor.

ARE ADMINISTRATORS REALLY “THE ENEMY”? 

If you’ve ever caught yourself muttering, “What were they thinking?” after an administrative decision, you’re not alone.

Teachers often see administrators as out of touch, perched in their offices making policies that feel completely disconnected from reality. But here’s a secret: the good ones know better. 

Most administrators haven’t forgotten what it’s like to be in the classroom. They’ve done the late-night grading marathons, handled the chaos of field trips, and explained—probably more than once—that glitter is banned from the art supply list. They’ve been there.

The question is, if you step into their shoes, can you stay grounded? Can you make decisions with the classroom in mind and lead with empathy instead of ego?

The best administrators don’t forget where they came from, and they use their experience to guide their leadership.

ARE YOU ADMINISTRATOR MATERIAL?

Not everyone is cut out for administration, and that’s okay. Schools need great teachers just as much as they need great administrators. But if you’re curious, here are a few traits to reflect on:

•  Do you love problem-solving? Administrators deal with everything from budget crises to playground politics. If you’re energized by challenges and can think on your feet, this might be your jam.

• Can you handle chaos? Teachers juggle a lot, but administrators are the Olympic-level multitaskers of the school world. One minute you’re calming an angry parent; the next, you’re negotiating with the district about funding. If this sounds exciting instead of exhausting, you might be on to something.

• Do you care about people? Sure, spreadsheets and policies are part of the job, but at its heart, administration is about relationships. If you’re good at building trust and supporting others, you’ve already got a key ingredient.

WHAT’S NEXT?

If you think you might be administration material, start by talking to the leaders in your school. Ask them what they love about their roles, what challenges they face, and how they balance the workload.

You might be surprised to learn how much of their day is spent advocating for teachers and students, not just enforcing policies.

Consider taking on leadership roles in your current position, like department head or organizing professional development. These experiences will give you a taste of what it’s like to lead—and help you decide if you want to take it further.

Most importantly, don’t rush. Leadership isn’t for everyone, and that’s okay. Being a great teacher is just as impactful as being a great administrator.

But if you’re ready for a new challenge, one that stretches your skills and makes a broader impact, administration might just be your next step.

So, are you ready to trade your lesson plans for school-wide strategy sessions? Stick with this series as we explore what it takes to transition into leadership, thrive in the role, and stay true to the values that brought you to education in the first place.

Because whether you’re running a classroom or an entire school, the goal remains the same: to make a difference. 

WHAT DO YOU THINK?

We would LOVE to hear from you!

Reply to this email, or send us a message on Instagram (link below)! We’re here to walk with you in these crazy times!

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