There’s a moment every school leader reaches sometime in May where they stop thinking about “finishing strong” and start thinking about one thing:
Let’s just land this thing safely.
As a high school principal, I used to compare the end of the school year to being the pilot of an airplane. Everyone else on board was already thinking about where they were headed next. Students were thinking about summer. Teachers were counting down the days. Families were planning vacations. Seniors were preparing for graduation parties and celebrations.
Meanwhile, I was still sitting in the cockpit trying to safely land the plane.
And that’s the part many people outside leadership never fully understand.
The final weeks of a school year are not slow. They are not relaxing. They are filled with emotion, responsibility, decisions, and pressure.
While much of the building felt the Stress of wrapping things up, I often found myself carrying something heavier. I worried about student safety as we approached prom, graduation, and end-of-year celebrations. I thought about the decisions kids might make. I carried staffing needs that still had to be addressed, finalized evaluations, and attended event after event while trying to show up with energy, encouragement, and a smile on my face.
Truthfully, I often felt like I was holding my breath, hoping we could bring the year to a close in a safe and positive way.
And then there were the events.
If you have ever served as a high school principal, you know there is no such thing as a “night off” during the last month of school. Awards nights. Honors assemblies. Banquets. Scholarship nights. Senior celebrations. Concerts. Athletic events. Graduation rehearsals.
People want to see their principal there because those moments matter.
And they should.
What many people never see, however, is the emotional and mental energy required to keep showing up fully present for all of it.
Then comes graduation itself.
From the outside, graduation looks polished and celebratory. Families see the ceremony. Students see the milestone. The community sees the tradition.
Leaders see the details.
The planning, coordination, communication, and contingency work behind the scenes.
Every graduation I led went exceptionally well, and I am incredibly proud of that. But those moments did not happen by accident. They happened because of intentional leadership and an incredible team that cared deeply about getting it right for kids and families.
That’s true of many things in leadership.
The smooth moments people experience are often built on countless unseen hours of intentional work behind the scenes.
What also makes the end of the year difficult is that no two endings feel the same.
Some years end with celebration and joy. Some end carrying Grief after the loss of a student or staff member. Some leave you reflecting on retirements and the incredible impact certain educators had on generations of kids. Some years leave you exhausted.
And some years simply leave you proud.
As leaders, we carry all of those Emotions simultaneously.
Oddly enough, I never felt lonely at the end of the year. I was too busy for that. More than anything, I looked forward to the quiet recovery that came once everyone headed off for summer break.
That’s when I finally started unpacking the backpack.
The stress, the emotions, and the things I could never fully share while school was still in session.
Typically, after the school year ended, I would take a couple weeks away with my Family and slowly begin unpacking everything I had carried throughout the year.
Eventually, though, I learned something important:
Recovery alone was not enough. Reflection mattered too.
Long before I began teaching leaders about balcony-level leadership, I was practicing it myself at the end of each school year. I would step back and reflect on the goals I had set at the beginning of the year, placing them into three categories:
Then I asked myself why—not to beat myself up or feel guilt, but to learn.
Over time, I began doing this same Exercise with my leadership team. Those conversations became incredibly valuable because they helped us celebrate Growth honestly while identifying where distraction, chaos, or shifting priorities pulled us away from what mattered most.
I think that reflection is critical for leaders right now because leaders are often terrible at acknowledging what they actually accomplished.
So let me say this leader to leader:
You have done a great job. You matter more than you know, and the people you lead likely appreciate your work more than they say out loud. Give yourself some grace.
This job is incredibly difficult. Not everyone can do it.
But you did it.
You carried the pressure.
You showed up for people.
You made hard decisions.
You navigated difficult moments.
You kept moving your school forward.
And now, hopefully, you can finally exhale a little.
Because the truth is, the end of the year for a principal is an incredible well of emotions. You feel like collapsing, crying, jumping for joy, swelling with pride, all while wanting to curl up in a ball away from everyone.
It’s a ride very few people ever get to experience.
But damn…is it worth it.
As you think about building belief and alignment within your team, it’s also worth considering how your systems support students who need more.
One of the areas where I see teams struggle is academic intervention. The desire to help is there—but the time, staffing, and structure often aren’t.
That’s where partners like HeyTutor can make a real difference.
HeyTutor provides high-dosage tutoring in Math and ELA, both in-person and online, with trained tutors who integrate directly into your school systems. Their model is built around consistency, small-group support, and real-time data tracking—so your team can see growth and adjust instruction along the way.
If you’re looking for ways to better support students without overwhelming your staff, it’s worth exploring what they offer HERE.
I partnered with HeyTutor to get this in front of you—working with brands I believe in is how I keep this content coming. #paidpartnership
If you’re ready to move your team from compliance to commitment, here are a few ways I can support you:
