The Quiet Accounting Teachers Do in May

Kelli and I are spending a little time at our place in Florida right now, catching our breath after the usual busyness of home—yes, still busy, even in retirement.

The weather has been one of those gentle Florida stretches: sunny skies, the temperature settling comfortably in the mid-70s, just warm enough to make a walk along the beach feel like exactly the right pace for the day. We’ve had time to sit by the water, take long walks, and enjoy the kind of unhurried conversations that seem harder to find during the rest of the year.

And as often happens when life slows down a little, my mind has started wandering back through old memories from my years in the classroom.

May always comes to mind.

Anyone who has taught knows that May carries its own particular rhythm. The calendar fills quickly: end-of-year testing, school activities, final projects, and the long list of tasks that come with closing out a school year. For Kelli and I, those weeks were even fuller. We both served as advisors for several clubs, so May meant planning for the Senior Prom, helping organize scholarship assemblies, preparing for graduation ceremonies, and, somewhere in the middle of it all, finishing grades.

It was a busy time, no question.

But it was also a reflective time.

Because somewhere in the middle of all that activity, something else quietly began happening in a teacher’s mind.

And that’s where the real story of May begins. We started looking back over the year. May has a way of turning teachers into reflective accountants of their own work. In many ways, it echoes something I wrote about earlier in [What Teachers Need to Receive], where I explored the quiet nourishment teachers themselves need in order to keep giving year after year.

Somewhere around May, something quiet begins to happen in a teacher’s mind.

It usually doesn’t arrive all at once.

More often it slips in slowly, sometime between the last round of grading and the first hint that the school year is beginning to loosen its grip.

You might be driving home after school.

Or sitting in the classroom after the students have gone, the hallway noise fading into that familiar late-afternoon stillness.

And without quite meaning to, you begin reviewing the year.

Not formally. Not like a report.

More like a quiet accounting.

Sitting here in the Florida sun, with time to slow down and think, I realized that what teachers experience in May has very little to do with the official calendar.

It has more to do with the quiet way we begin adding up the year.

The Quiet Accounting Teachers Do in May

Years ago, toward the end of a spring semester, I remember sitting alone in my classroom after most of the building had emptied out. The windows were open just a little, and the breeze carried in that unmistakable late-spring smell—cut grass, warm pavement, and the faint sound of a baseball game somewhere down the road.

My gradebook was open on the desk, but I wasn’t really looking at the numbers anymore.

Instead, my mind had wandered back through the year.

I thought about the student who never quite found his footing in the class, despite all the encouragement I could offer.

I thought about a lesson that I had been excited to teach, only to watch it fall flat in ways I hadn’t anticipated.

And then, almost unexpectedly, I remembered the quiet moment when a student who had struggled all semester suddenly raised her hand and explained a concept clearly to the class.

Moments like that stay with you.

But so do the others.

If you’ve been teaching for any length of time, you know this quiet ritual well. May has a way of turning teachers into reflective accountants of their own work. We begin adding things up—not in spreadsheets, but in memories.

The lessons that landed.

The conversations that mattered.

The places where we wonder if we could have done more.

Why the Mind Does This

Psychologists actually have a name for this habit of looking back and wondering how things might have gone differently. They call it counterfactual thinking.

It’s the mental habit of replaying events and imagining how they might have unfolded differently: If I had explained that concept another way… If I had noticed that student earlier… If I had handled that moment differently.

In one classic line of research, psychologists Neal Roese and James Olson found that people often engage in this kind of reflective thinking after meaningful experiences because the mind is trying to learn from them. Counterfactual thinking isn’t simply regret—it’s part of how human beings refine judgment and grow wiser over time.

Teachers experience this especially strongly because our work involves people, not products. Every day in the classroom contains dozens of small decisions that ripple outward in ways we can’t fully see.

And so in May, the mind revisits those moments.

Not because teachers are failing.

But because teachers care.

The Trouble With the Ledger

The problem, of course, is that the inner accounting system teachers use is rarely fair.

When educators review a year, they often hold themselves to a standard that no human being could realistically meet. They remember the student who struggled more vividly than the dozen who quietly found their way. They replay the lesson that faltered more often than the many that worked.

Psychologists have looked at. our tendency to give more weight to what went wrong than to what went right. They have found that negative experiences tend to stick in our memory longer than positive ones. Roy Baumeister and others have written about this tendency, which they call the negativity bias.

For teachers, that bias can quietly shape the end-of-year reflection.

The mind flips through the year like a ledger, and somehow the columns labeled not enough begin to feel heavier than the columns labeled good work done here.

Seeing the Year With More Grace

Over time—usually with a few more seasons of teaching behind us—many educators begin to see this quiet accounting differently. That shift is closely connected to something I explored in [The Courage of Enough], the realization that teaching was never meant to be measured by perfection.

They start to realize that teaching isn’t something that can be measured cleanly at the end of a semester. The real outcomes of the work often unfold long after the year has ended.

I’ve heard from former students years later who remembered a brief conversation I had completely forgotten. Something that felt small in the moment had quietly stayed with them.

Which is a humbling thing to realize.

And a comforting one.

The truth is that most teachers influence far more lives than they ever get to see.

Scripture captures this beautifully in Ecclesiastes 11:6:

“Sow your seed in the morning, and at evening let your hands not be idle, for you do not know which will succeed, whether this or that, or whether both will do equally well.”

Teachers spend a year sowing seeds they may never fully see grow. And May is often when we start wondering which of those seeds mattered.

A Different Way to Close the Books

If May brings with it this quiet accounting, perhaps it’s also a moment to change the way we balance the books.

Instead of asking only What didn’t I do well enough? we might also ask:

• Where did I show up faithfully for students?
• When did I offer encouragement that someone might have needed more than I realized?
• What moments in the year quietly mattered, even if I never saw the outcome?

Teaching was never meant to be perfect work.

It is human work.

And human work always contains unfinished edges.

But that doesn’t make it less meaningful. In many ways, it makes the work more sacred.

A Few Questions to Carry Into May

As the school year begins to wind down, it might be worth sitting with a few gentle questions:

• What moments from this year still stay with me?
• Which students might I underestimate the influence I had on them?
• What did this year teach me about patience, presence, or persistence?
• Where might I offer myself a little more grace?
• What seeds did I plant that I may never fully see grow?

May has a way of inviting reflection.

Teachers naturally begin adding things up.

But if there is one lesson many educators learn with time, it is this:

The true measure of a year in teaching rarely appears in the columns we keep in our heads.

More often, it shows up quietly—years later—in the life of someone who once sat in our classroom.

And by then, the teacher may never even know.

But the seed was planted.

And sometimes that is more than enough.