As I’m sitting down to write this right now, it is 11:39 PM on Sunday night. My summer vacation has just a few short hours remaining. Tomorrow is the first day of school for my students, and as far as I can recall, I believe this will be year 16 of teaching for me.
I’ve always said that the first day of school is not unlike opening day in baseball. A lot of players will tell you that if you aren’t getting at least a few butterflies on opening day, you probably need to retire. I’d say the same thing for teachers. If there isn’t at least some sort of buzz, some anticipation about day one, you probably need to find another line of work.
It’s funny the way the clock turns. Today we’re squeezing out the last drops of summer vacation, and tomorrow we’re right back to the nine-month grind. Granted, the days have actually been getting shorter since the summer solstice back in June—a lot of people don’t even realize that—but the mental shift still hits like a truck.
I went out to Sierra‘s house this evening. It was a rainy, lazy Sunday, so we just hung out and watched a few Star Trek episodes. She actually liked Strange New Worlds. And here’s the crazier part: it was her suggestion. She had mentioned a couple of days ago about just hanging out and watching movies, and even offered to watch a Star Trek show, so I figured Strange New Worlds would be a great entry point for her. I texted her as I was driving back tonight, and she said she might even go ahead and watch an episode on her own. Massive green flag. To be quite honest, I couldn’t imagine a better way to end my summer.
But back to the business at hand.
Tomorrow is the start of a new school year, and we have a new principal. I’ve only met with him twice—Thursday and Friday of this past week—and so far, he seems to be saying all the right things. He definitely wants to do things a lot differently than our previous administration did, which I am completely on board with.
Our saving grace on day one—maybe even for the whole first week—is that the students usually return in something of a honeymoon phase. These are the days when kids will literally raise their hand and ask if they can pick up a pencil they dropped. Those polite niceties usually go out the window after the first full week, however. What I’m really curious to see tomorrow morning is how the returning students respond when they see we have a full-time security officer on staff again, finally. It’s going to be a completely different ballgame for them, and the expectations are going to be much higher than they’re used to.
Just like any classroom or school behavior management, you’re guaranteed to see a few kids tomorrow who will try to test the boundaries, just to see what they can and cannot get away with.
Walking into year 16, I can honestly say the teacher armor feels lighter. But that’s only because I’m battle-tested and I’ve been through this before. I’ve been through leadership changes at other schools, though in those past instances, the new administrator was already an assistant principal in the building, so the transition wasn’t quite as jarring for the kids. This time? I have no idea how tough or how fair this new administrator is going to be, so it’s going to be pretty entertaining to watch it all shake out over the next few days.
The season’s about to change—if not calendar-wise, at least in my head. The summer reset actually stuck, and none of it was just a typical “summer fling.” I’m stepping into the new routine with eyes wide open, curious to see what the coming months hold, both professionally and personally.
Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.
Today’s post is inspired by the WordPress Daily Prompt. While I’ve taken the topic in my own direction for the Road beyond 1,000 Days, you can find more responses to today’s prompt HERE.
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The article “the first day pivot“ first appeared on Rebuilding Rob


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