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School & District Management Opinion

When I Left the Classroom for Administration, Did I Join the Dark Side?

The transition into school leadership is messy and imperfect. Here’s what keeps me going
By Sarah Berman — January 07, 2025 4 min read
Being able to empathize with both the dark and light sides of teaching and administrative work.
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I always wanted to be a teacher. My grandmother was a teacher, my mother was a teacher, and despite other interests, it was my calling, too. It is in my genes. I have also always felt the call of leadership. Several years ago, after 18 years in the elementary classroom, several years as union vice president of my local, two master’s degrees, a principal certificate, and a year home with my own three children during the pandemic, I decided it was time. I started applying for administrative jobs. When I ultimately got a high school assistant principal position and told my longtime teacher colleagues, the sentiment was almost universal: “Ah, you’re going to the dark side.”

“Nah, not me,” I thought. “I’ll always be a teacher first. I’ll never forget what it was like to be in the classroom.”

I was going into administration because I had leadership skills, almost two decades of teaching experience, and an intense desire to ensure that all the students in the school could have the experience I tried to create in my classroom. I was going into administration because I wanted to mentor new teachers. I wanted to be in the classrooms and help teachers be the best they can be, demand excellence and integrative, authentic learning experiences, all the while still feeling like a teacher.

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Those are the things I told my colleagues, because those things were true—they still are. But fast forward four years, and here’s what I have learned: It is really hard not to go to “the dark side.” The greatest challenge I have faced as an administrator is how to still feel like a teacher first.

My visions of what an administrator did and was and what an administrator actually does did not fully align. I want to be in classrooms every day. I want to be with students, watch what’s happening, and provide meaningful feedback to teachers. I want to be fully immersed in the learning experiences of our students and the curriculum. I want to provide meaningful professional development for teachers, model lessons, serve as a mentor, and connect on a daily basis.

However, my role as a high school assistant principal consists of supervising approximately 30 teachers and serving as house principal for a grade of more than 300 students. I handle discipline for my grade level. I serve as one of the testing coordinators in my school, which involves creating spreadsheets, assigning rooms and proctors, sending countless emails, and ensuring that we are following all state guidelines.

I spend many days in back-to-back meetings about everything from policy and procedures to disciplinary hearings for students. Days go by where I do not set foot in a classroom. I don’t know the ins and outs of the curriculum, and while I aim to provide meaningful feedback, the opportunities are too infrequent to be truly effective.

I discipline students and don’t have the time to follow up with every teacher who wrote a referral.

I have some great days and some days where I feel like I have no idea what I accomplished. I wonder: Did I, in fact, go to “the dark side”?

Priorities and balance are two of the biggest challenges of being an administrator. No matter how clear we make our priorities, the priorities go out the window when we have to put out fires.

The hardest part is I truly miss being a teacher. I miss the daily connection with the same group of students. I miss the satisfaction of watching them learn and understand something new in real time. I miss being creative with ways to teach a new concept or have my students come in and tell me how they used what they learned in real life. I miss being on the front lines of learning.

I have considered packing it all in and going back to the classroom. Believe me, some days I just want to be able to close my door and be with my students and shut out all the other nonsense.

But something keeps me in this role. I think what keeps me here is the same reason I wanted to do this in the first place. I do want to effect change on a greater scale. I do want to serve as a mentor and provide a welcoming and enriching environment and learning experience for hundreds of students, not just the 25 in my class.

As I try to remind myself, I am still learning. I am a teacher, a learner, and a work in progress. Would I be more effective in an elementary school? Maybe.

Can I work more on clerical tasks at home so I can get in more classrooms during the day? Sometimes.

How can I constantly reevaluate the priority list so I can spend my days doing what I sought out to do? I’m not always certain.

How can I juggle and not drop all the balls? On some days, I can’t.

As I continue to recommit daily to this role, I don’t ever want to be on “the dark side.” I am a teacher, first and foremost, but the further I get from the classroom, the darker it can feel.

But I don’t think we need to make that darkness our default. I think, with a tremendous amount of mental effort, we can design our days and our work to stay close to the students, teachers, and classrooms, and the reasons that this role is important. I’ll be the first to admit that trying to accomplish all that is messy and imperfect.

This job of school leadership is hard—not harder than being a teacher but a different “hard.” So, as they say, “Choose your hard.” I have never been one to shy away from a challenge. I’m too competitive and hardheaded for that. So, I choose this “hard.”

I’m still figuring it out, but I do know that I want to remain, always, in the light.

A version of this article appeared in the January 29, 2025 edition of Education Week as What I Learned When I Left the Classroom for Leadership

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