Why May is the Cruelest Month for Teachers (And What We Can Do About It)

Several years ago I wrote the the following about the month of May:

“T.S. Eliot states in The Wasteland that “April is the cruelest month.” He is close, but he misses the mark by a month, at least in my opinion…May [is] the cruelest month…at least when it comes to my teaching life. The problem is that after a long Michigan winter, the extra summer sunlight of the north makes everything lush and leafy, seemingly overnight. This might not seem like a bad thing, but the appearance of summer is a serious problem when it comes to my students, as en masse and like clockwork they begin to checkout in uncharacteristic ways once the trees suddenly burst with leaves, despite the fact that over a month of school remains.

A lot has changed in the two years since I wrote that, but something that hasn’t changed is the cruelty of May from the standpoint of planning lessons and running a classroom. I have found this cruelty to be especially true this year, where after a school year set against a backdrop masks and variants and societal discord, my students are more ready than I’ve ever seen to reenact that scene in Dazed and Confused where they sprint through the school doors, as papers (and in this case masks too) explode into the sky and flutter like giant snowflakes to the ground.

There isn’t much that we as teachers can do about the summer weather that brings such changes or the time-honored tradition of students growing antsy as the long days of summer appear on the horizon. Still, there are things that we can do in this beautiful and cruel month of May to keep our classes meaningful and engaging, even as the countdown begins in student heads.

I know and have written about what I tend to lean on in the last month of school, but given how strongly my students are eyeing the exit this year, I wanted to learn more about how other teachers approach May. Unfortunately, not much has been written or researched around keeping student engagement once it becomes t-shirt weather, so to get a better sense for the options, I put this tweet out into the universe, and to my delighted surprise, I got dozens of brilliant responses, many from educators who I have admired for a long time.

What was interesting about the responses is that they fell into a handful of distinct categories, each a potentially useful slice of the overall answer to the question of how to navigate May:

Creativity and Choice

The most common responses I got focused on some intersection of creativity and choice. For example, Matthew Kay, author of one of my all-time education favorites Not Light, But Fire (and with whom I have a new book coming out in just a few weeks. Check it out and order now for 25% off with code IMPACT25; I’m really excited about it!!), kept it simple but full of creativity:

Blogger and assessment expert, Shannon Schinkel offered one of my new favorite terms, “competency-based freedom,” as an argument for letting students pursue a topic and genre of their own choosing:

And teacher and poet Lesley Clinton has her students do a character talk show and podcast roundtables:

All of the responses that focused on creativity and choice reminded me of two posts I wrote this year about the often underrated role of joy and choice. Both are often cast as being at odds with rigor, but the truth is that both joy (and especially the joy of creation) and choice, when used well, are two of the most potent accelerators of rigorous work. Much like a soccer player might not notice that she has run five miles during a game or an actor might not notice that he has done dozens of hours of deep character analysis in preparing a role, creativity and choice can help students to secretly continue to work hard even as they outwardly claim to be done working hard for the year.

Novelty and Practicality

Alongside creativity and choice, another major theme was novelty and practicality. Christopher Butts, co-author of Planning Powerful Instruction, shared a novel way of discussing texts he uses late in the year (for more about how to do it, see this post on The Cult of Pedagogy here).

Podcaster Joe Ferraro shared his senior interview unit idea:

And educator Allison Seitz shared this idea:

Along with these I also got suggestions for units on humor, identity projects, Greek mythology, and website creation. What these novelty and/or practical suggestions have in common is that they are a content-driven approach to keep students interested. If students feel that they are learning something strikingly outside the norm or something that will be useful to them someday, they will be more likely to stay tuned into a class right up until the end.


The last theme was reflective work, which makes a lot of sense because regular reflection is a prerequisite for students remembering the things from our classes longterm. The trouble with reflection is that it doesn’t quite have the panache of many of the choice/creativity/novelty/practicality suggestions. That is fine—not everything can or should be flashy after all—but Syd Korsunsky, a writer and educator from Manitoba, shared a wonderful idea for making reflection fun and meaningful through the creation of “yearbook” zines:

My students always do an end of the year reflection, but this year I am definitely going to try his zine idea in some form or another. It is a clever twist, especially the physicality of the zine (as opposed to a digital portfolio) because I think tangible items can have a certain appeal now even more than ever in this otherwise mostly digital era.


May is probably never going to be easy as a teacher, but that doesn’t mean it has to be cruel. On that note I want to end with a suggestion from award-winning teacher Annie Syed, who shared the following suggestions:

Everything she lists is great and brings together all of the themes above, but what I love the most is the last line: No “crunch time” vibes!

I’ve definitely been guilty of leaning into crunch time vibes at the end of the year in an effort to keep kids engaged. It is hard not to when one only has 14 or 17 days left. But like many external motivators, that approach always felt limited in both its effectiveness and the number of students it motivated. So this year, after a whole year that felt like crunch time, I am channeling Annie and the rest of the teachers above and leaning into joy and freedom and curiosity and self-reflection instead. As always, I will let you know how it goes! 

If you have anything you are doing that is helping May to be less cruel, I would love to hear about it and pass it on, and thanks as always for reading.

Yours in teaching,


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