From the Superintendent’s Chair

The part of school leadership most people never see.

Firsthand reflections on what I miss, what I don’t miss, and why experienced public-school leaders must speak honestly about the work.

Casey Jaynes in conversation with fellow Kentucky education leaders
Photo: Jennifer Willhoite / Carroll County Schools

The series

Experience should inform the conversation.

Principals and superintendents are often advised to “take the high road” and avoid responding when public education is misunderstood or misrepresented. Professionalism matters—but silence can leave misinformation unchallenged.

This series offers an honest view from inside the work: the moments that make school leadership meaningful, the pressures few people witness, and the facts communities deserve. The goal is not to argue for argument’s sake. It is to advocate clearly, constructively, and confidently for public schools.

What I Miss

The people and moments that make the work matter.

Students finding their path. Educators growing into leaders. Communities rallying around their schools. The daily reminders that public education changes lives.

Browse What I Miss stories →
What I Don’t Miss

The weight behind decisions that look simple from the outside.

Middle-of-the-night calls, incomplete information, competing risks, and the responsibility of making decisions that affect thousands of people.

Browse What I Don’t Miss stories →

Latest What I Miss reflection

Sometimes the best thing I could do was go see kids

Today’s Something I MISS about being superintendent…

There were days as superintendent when the phone wouldn't stop ringing. A personnel issue needed attention. A parent was upset. A budget decision had to be made. Something happened on a bus. Someone was mad about something on Facebook. And there were probably three meetings waiting for you.

On those days, sometimes the best thing I could do was simply get out of the office and go see kids. And if you REALLY needed to remember your “why,” you went to preschool!

They didn't care that I was the superintendent. They didn't care about the budget, the board meeting or whatever problem seemed so important an hour earlier. On this particular day, what WAS important was hair! So there I sat, in my suit, on the preschool floor with a star hair band on my head.

And you know what? For a few minutes, everything else could wait. Those visits had an amazing way of putting the job back into perspective.

Because beneath the budgets, board meetings, buses, buildings, test scores and everything else that comes with running a school district…eventually everything we do in public education comes back to a kid.

I definitely miss that.

What I Miss · School Leadership

The 171: leaders who understand the weight of the chair

“The 171.”

That’s what I like to call the 171 public school superintendents across Kentucky.

After an armed individual came onto Trimble County school property after dismissal, the systems worked: staff responded, students were moved to safety, doors were secured and law enforcement responded quickly.

But there is another side to this story that most people will never see.

The superintendent side.

Every morning, something far more important than budgets, buildings, transportation, personnel or technology walks through your doors.

Other people's children.

Regardless of district size, geography, politics, athletics or anything else…when something happens in one of our school districts, every superintendent in Kentucky understands exactly what the person sitting in that chair is feeling.

I may not sit in that chair anymore…but I will always understand the weight carried by those who do.

Latest What I Don’t Miss reflection

When rising fuel costs put school services under pressure

Today’s something I DON'T miss about the superintendency……

Rising diesel fuel prices and what that does to already stretched school district budgets.

Kentucky school transportation is funded at only about 70% by the General Assembly. That means local districts must make up the difference from their General Fund. When fuel prices rise, that gap becomes even larger.

Those additional costs have to come from somewhere. They can mean fewer dollars available for employee salary increases, instructional materials, technology, school safety or other services for students.

No superintendent wants to reduce services, change bus routes or ask local taxpayers for more money.

When state funding does not keep pace with actual costs, districts have to make difficult decisions to balance the budget and keep buses on the road.

What I Miss · School Leadership

The camaraderie and idea generation of Kentucky superintendents

Something I miss about the superintendency.

Today and tomorrow KASS has their fall meeting in Lexington.

The invite goes out to all 171 superintendents in KY, many cannot attend due to conflicts and other issues in their home district, but usually over half attend.

I will miss the camaraderie and idea generation of this group of individuals. The idea generation and collaboration of this group is one of the highlights of the fall for me. It was a time to reflect on the first few weeks of school, talk to others about what issues they were facing and return to the district with new ideas on how to address our individual community needs.

It is also a time where we would generate our legislative agenda, which almost always focused on funding public schools at 2008 levels, the accountability model (which I am sure will be a huge topic today and tomorrow) and ironically how social media impacts each of our districts (more about that later in my series of talks around various topics).

I miss this group of amazing leaders who give 10-18 hours of their lives each day in service of their students, faculty and staff, community and for many state and national leadership advocacy.

The first What I Miss reflection

What I miss most: the kids

Something I miss…

The kids.

A memory from 2015—the ALS Ice Bucket Challenge—captures exactly why. The cold water may have been the challenge, but the laughter, energy, and connection with students are what stayed with me.

The students are always at the center of the work.

School leadership involves budgets, accountability, schedules, facilities, and difficult decisions. But those responsibilities only matter because of the young people schools serve.

I miss their humor, their honesty, their curiosity, and the everyday moments that could turn an ordinary school day into a memory that lasts for years.

That is what I miss most.

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