The Principal I Thought I Was

During this past holiday season, I attended my wife’s holiday party. It was exactly what you would expect from a room full of educators. Easy laughter, shared frustrations, food, drinks, and that lightened emotional state that comes when the end of a quarter and a break are finally in sight.

As we sat talking, my wife and her colleagues started pointing out the “babies” who had recently joined her team. New teachers. Fresh energy. Wide-eyed optimism. At some point, we realized something that stopped us for a moment. Some of them were the same age as our own kids.

Then one of her colleagues walked in, stopped in her tracks, and stared at me.

She looked familiar, but I could not immediately place her. She eventually sat with us and said, almost casually, that I had been her principal at Thea Bowman.

I was only at Thea Bowman for one year. It was my first year as a principal. I was thirty years old and, if I am honest, there were plenty of moments when I questioned whether I should be running a high school at all. I am sure some of my peers questioned it too. After all, I was just a baby.

She went on to say that I was the best principal she had ever had.

She FaceTimed a friend on the spot, excited to show her that I was there. She talked about her senior year, the memories, and how I made sure it was something she would always remember. Every word she shared was positive.

Her version of that year could not have been more different from mine.

When I think about my first year as a building principal, my mind goes elsewhere. I think about the athletic director debacle. I think about the battle with the board that ended with me moving to another school. I think about the very public debates with parents who questioned my knowledge of school law and my readiness for the role. I think about how I was given a monumental task and struggled mightily to stay afloat.

Those are the moments that stuck with me.

That conversation, though, pulled me back to something we often say in education. Students may not remember all of the lessons or the activities, but they will remember how you made them feel.

We remembered that year very differently. What stood out to her was not the missteps, the tension, or the visible cracks in my leadership. What stayed with her was that she felt seen, supported, and cared for.

That night reminded me of a core belief I have carried with me ever since. Leadership, at its heart, is about taking care of your people.

My approach that year was far from perfect. It was not always smooth or polished. I made mistakes. I learned publicly. I carried more weight than I knew how to manage at the time. But somewhere in the middle of all that, at least one student knew that I cared.

Over time, the mistakes faded. The conflict blurred. What remained was how she felt in that space and during that season of her life.

It made me wonder how often we judge our leadership by the moments that haunt us, while others carry entirely different memories forward. And it left me sitting with a quiet question.

What will people remember about how we made them feel, long after we have moved on from the roles we are still replaying in our own minds?

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