My scheduling nightmare

Last night, I had a nightmare. I dreamed I was back on staff at a high school as an assistant principal. Halfway through the school year, I suddenly realized I hadn’t completed any teacher observations or evaluations. Worse yet, I didn’t even know which teachers I was responsible for evaluating, nor was I clear on which section of the student population fell under my responsibility for discipline or guidance.

In the dream, I started asking myself, “Am I really on staff here as part of the team, or am I just some kind of consultant?” I thought, “Maybe I should go ask the principal what I’m supposed to be doing. This is so embarrassing.”

Then I woke up, relieved to find it was only a dream. It’s December 2024, and my actual day ahead includes four scheduled conversations:

• One with a principal of an elementary school in Akron, Ohio.
• Another with a team of career tech educators in southern Ohio.
• A third with a fellow consultant and author friend in North Carolina.
• A fourth with an assistant superintendent in Kentucky.

Much of my schedule for the 2024-25 school year was planned over the summer, but today’s meetings reflect the varied nature of my work. The first meeting was anticipated since summer but finalized just this week. The second has been locked in for months. The third is a last-minute addition, scheduled only yesterday. The fourth has been on the books since the fall.

Why am I sharing this?

It’s a reminder to myself (and to you) that prioritizing our responsibilities happens in phases. When possible, we place critical tasks on the calendar well in advance, allocating consistent blocks of time over the week, month, or year.

For instance, I block time on Mondays and Wednesdays for writing. Tuesdays and Thursdays are reserved for developing content for the podcast or recording episodes. Fridays are set aside for podcast interviews. Trainings are added to my calendar for the entire year as soon as I secure a contract—sometimes as far as six months before signing the agreement.

In other words, I design my calendar around the outcomes I want to achieve. By doing this, I leave room for last-minute meetings or additional conversations in the remaining open spaces.

None of this is groundbreaking, but I consistently talk with leaders who have clear ideas and intentions for actions they believe would yield significant results for themselves, their staff, or their students. When I ask where on their calendars they’ve scheduled time to work on these initiatives, the answers vary. Sometimes they’ve planned ahead, and sometimes they haven’t.

My guess is that your calendar reflects two things: your priorities (those tasks you’ve scheduled in advance because they’re too important to miss) and your missed opportunities. This isn’t a guilt trip—just a reminder that we schedule what we prioritize.

Do you want to exercise more?

Do you want to spend more time with your children?

Do you want to be in classrooms more often than you’re stuck in your office?

Give yourself permission to block out time for the tasks and actions you know will lead to your desired outcomes.

Let’s Wrap This Up

Even though I’ve been practicing this approach for years, I’m far from perfect. Apparently, I still stress about these things as a school leader—otherwise, I wouldn’t be having “assistant principal nightmares.” Maybe it’s a sign of age that I’ve graduated from nightmares about being a student or teacher to nightmares about being an administrator.

As a first-year assistant principal, my nightmare was a reality. I was so busy putting out fires that I rarely made it into classrooms and constantly lagged behind on observations and evaluations. It wasn’t until I learned to block time on my calendar for my most important priorities that I began to shift my focus from the urgent to the important.

I hope this funny nightmare story serves as a helpful reminder: You can avoid real-life nightmares by taking a hard look at your calendar. Don’t see scheduling as a chore; see it as an opportunity to design the future experiences you want.

The urgent and last-minute tasks will still be there, but with a well-planned calendar, you’ll manage them while hitting the milestones you set in advance.

Will Parker is the Founder and CEO of Principal Matters, LLC, an organization dedicated to encouraging and empowering education leaders. Find more free resources like this one at williamdparker.com