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From Classroom to Leadership to Administration: A Journey Full of Lessons, Laughter, and Love for Education

  • Writer: Eileen Olmedo
    Eileen Olmedo
  • Jan 12, 2025
  • 3 min read


When I started my career as a teacher in 2007, I was like a starry-eyed protagonist in an education-themed rom-com. I loved everything about teaching—the thrill of planning units, the satisfaction of nailing a great lesson, and the nerdy joy of diving into the plan/teach/assess cycle. Seriously, who doesn’t get a little rush from color-coded rubrics and perfectly timed group activities?


There were plenty of twists and turns. From teaching AP to learning IB, and then also putting on plays and musicals with my students. In 2017, Hurricane Maria hit and for several months we had to pivot instructions because we didn't have power or internet. If I couldn't teach my unit called "Bias in the Media," I could teach Macbeth "old school:" reading out loud, discussing scene by scene, and having students perform. Then we moved to Miami and I taught middle school for the first time. Another highlight of my career! But then came 2020, a plot twist none of us saw coming. Virtual learning turned my world—and my living room—into a chaos of “mute buttons,” tech troubleshooting, and students who could vanish into cyberspace faster than I could say, “Can everyone see my screen?” When we moved to the hybrid model, I found myself teaching “roomies” in masks while trying to keep “zoomies” from playing video games during class. It was like running two marathons at once—blindfolded, with Wi-Fi that kept dropping out.


It was exhausting, but it taught me something profound: teaching is so much more than content delivery. It’s about connection—eye contact, a shared laugh, a reassuring smile. And when half your face is covered by a mask, you learn the art of expressive eyebrows.


By the time I transitioned to a leadership role as IB/MYP Coordinator, I was ready for a new challenge. What I didn’t know was just how much I’d be stretched. Coordinating two campuses meant developing Jedi-level time management skills, balancing the unique personalities of two school cultures, and learning to decipher what each teacher needed to feel supported. Some days I felt like an educational UN ambassador, navigating delicate treaties over lesson plans, assessments, and professional development.


Then, the next chapter: assistant principal. If teaching was my rom-com, administration is my action-adventure—complete with high-stakes parent meetings, teacher crises, and the occasional sprint down the hallway to cover for someone in need. My days are wonderfully unpredictable. One moment I’m observing a first-grade class that makes me want to sing “Head, Shoulders, Knees, and Toes,” and the next, I’m fielding middle school drama that could rival the plot of Mean Girls.


Being an AP is a whirlwind. Sometimes, I’m the cheerleader, encouraging teachers to try new strategies. Other times, I’m the coach, working with students to help them achieve their goals—or at least hand in their homework. And let’s not forget the moments when I’m the referee, mediating between an upset parent and a stressed-out teacher.  Being an AP is a whirlwind. I start my day with morning duty, greeting students at the door and setting the tone for the day. From there, I dive into classrooms to observe teaching and learning, juggle meetings, manage lunch duty, and collaborate with our team to strategize and problem-solve. Evenings are for family time and processing the day's events, reflecting on what went well and what I can improve tomorrow.


Yes, it’s hard work. Some days, my to-do list feels longer than a CVS receipt. But I love it. I love walking into classrooms and seeing the spark of curiosity in students’ eyes. I love collaborating with teachers who pour their hearts into their lessons. I love being part of a team that’s working together to build a school where every student feels seen, supported, and inspired.


To those of you considering a leap into leadership or administration, let me tell you this: it’s worth it. It’s challenging, yes. But it’s also rewarding in ways I never imagined. You’ll grow. You’ll be stretched. You’ll learn. And if you’re lucky, you’ll get to spend your days doing what you love—supporting teachers, students, and families as they navigate their own educational journeys.


So here’s my advice: don’t be afraid of the transition. Embrace it. Lean into the chaos, the learning curves, and the moments that make you laugh out loud. Because at the end of the day, this work isn’t just a job—it’s a calling. And I, for one, wouldn’t have it any other way.


 
 
 

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