Essays | Lit

The Staples Letters: Daydreaming About My Class

Lizzie Smith

Inspired by C.S. Lewis’s The Screwtape Letters, the Staples Letters are a series of essays in the South Side Weekly written in the form of letters from a veteran teacher, Staples, giving advice to a young teacher, Ms. T. All events in the Staples Letters are drawn directly from real-life experiences in Chicago schools, and names and identifying details have been removed in the interest of privacy. Though fictional in form, the letters are used to address a variety of issues in education, from quotidian classroom considerations to national policy.

Ms. T—

Yes, I do that, too! I call it “daydreaming about my class.” I’ve done it since my first year teaching, and every principal I’ve ever had has found it a completely ridiculous, useless idea. They read it as just sitting around, wasting time. They want ACTION ITEMS. They want DELIVERABLES. They want a designated note-taker and sign-in sheets and all the other pieces of evidence that prove work is occurring at the appointed times. They want seven-page lesson plan templates, hideous graphic organizers, page after page of mandated rubrics.

I don’t really know about anyone else, but I find stuff like that to be totally harmful. It’s not just that I don’t get good ideas using them—the ideas I do get are terrible! The medium is the message, you know? Those tools, that process, totally warps my thinking and almost inevitably reproduces the same sort of bureaucratic grossness the tools themselves embody. It makes me start thinking, “Hm, maybe I should have the students monitor their own engagement levels with a series of worksheets, while self-assessing themselves on a district-issued rubric filled with incomprehensible jargon…and maybe I should be really mean about it for no reason?”

I’ve internalized the mumbo-jumbo.

I find that to successfully plan for my classes, I’m forced to engage in a sort of shadow-process, out of view of the administration and their initiatives and resources. In other words: I lie. I literally write out a bunch of stupid B.S. and jargon in the organizers that the principal has decided are useful this year (with absolutely no mention of last year’s life-changing rubrics and worksheets). I submit those documents to the proper authorities, then promptly forget about them and get down to the real work—the dreaming.

I hesitate to describe this process in too much detail, in part because it’s sort of magical and intuitive rather than completely logical. I find the best, most inspired ideas reside in a place that language can’t quite get to. And the whole point is that this works for me. Demanding every other teacher to work this way is just the sort of silliness principals go for. The last thing I want to create is some “best practices for daydreaming” document. I had a friend go to Berklee College of Music in Boston. He said the professors would have them transcribe a wild solo Thelonious Monk improvised, then create a bunch of rules based on it. Sort of missing the point, right? Like hilariously, completely, one hundred percent missed? Imagine codifying an act of total inspiration and creativity into a series of dos and don’ts—yuck.

But I do think it helps to think of planning—planning a semester, a unit, a day, or a single activity—as an act of creation. It is, to me, closer to writing a poem or short story than it is…oh, I don’t know, following a recipe to bake bread? Sometimes I picture a student who absolutely hates school, despises reading and writing, wants to stare at a screen for as much time as possible. What kind of class would be capable of engaging that student? What about the student who loves to read and write? How can I make my class an absolute dream come true for them? Other times I imagine the sharpest, most interesting person I know is coming to visit my class. I ask myself: what would I most want that person to see? To hear? To feel? What lazy habits have I allowed myself to slip into that would outrage me if I saw them in another teacher’s class?

I’ve worked with teachers, on the other hand, who’ve been turning in and executing the same lesson plans for literally decades. “Why mess with perfection!?” I heard one joke to his department chair in the hallway once. Well? Why mess with it?

I’ve been reading a book lately about Thelonious Monk—I guess I’ve got Monk on my mind. I think his example can be instructive. The book talks about a song called “I’m Getting Sentimental Over You,” a song Monk would’ve played hundreds of times. But if you listen to him play it, it’s almost as though he is figuring it out for the very first time— the author describes the playing as “groping.” Monk is striving to experience the song as though it is his first time because he is determined to find something new. It’s as though he is allergic to playing the same old licks.

Now I’m not suggesting you recreate the wheel each and every semester. Certainly there will be ideas, themes, activities, projects, etc. that you can hold on to and refine year by year. But you never step into the same river twice, you know? Your loyalty ought to be with the students in front of you—all totally unique and different from every other group of students you’ve ever worked with before—and not with the plans you’ve used (even successfully!) in the past. Find the new licks.

It’s too easy to get in a rut otherwise. That’s what happens when the plan itself becomes the highest authority in the room. I mean, I get it. You might’ve spent hours on that lesson plan! Came up with all sorts of activities and questions and prompts. Carefully mapped out how each lesson leads into the next and culminates with some wonderful project. There’s nothing necessarily wrong with any of that.

But it’s hard to show much emotion when you’re just following a well-worn script. And when you’ve accounted for absolutely every second of the class, you’ll end up speeding past those magical moments: when a student asks an unexpected question, when a powerful topic organically presents itself, what people who need to constantly name things have named “teachable moments.” You’re too eager to get back to your 387 PowerPoint slides or whatever.

My advice is to instead intentionally under-plan your class, to build in spots for improvisation. I don’t necessarily want to know every single question I’m going to ask, every single move I’m going to make. It’s too hard to keep classes like this electric, too easy to just go through the motions, to play the same old licks. There are days where my lesson plan, were I to write it out, would have a chunk of time that literally says “(something inspiring).” I’ve essentially set myself a challenge: find something meaningful in the first twenty minutes of class and use it to create something new, or else.

Today, a student, for seemingly no reason whatsoever, rose her hand and asked: “How can I be a more patient person?” Shit! That’s a good question! Why didn’t I ask it? We talked about it for an hour. Did I have activities for some other lesson ready to go? Of course. Had I given any recent thought to the idea of patience? Well, uh, no. But this conversation was better, more important, and more organic than anything I could have planned. It came from the students, so it automatically took precedence. The articles got bumped. I’ll get to them another day, or not.

Now, think: what would that conversation have looked like if it’d been conceived using the tools the district enforces on us, weeks or maybe months in advance? Well, it wouldn’t have existed at all, because patience is not one of the “skills” considered important enough to teach students. It’s not testable, not really, so it’s meaningless to the powers that be. But even if it were, the lesson plan would have sucked all the spontaneous joy out of the conversation; in fact, it undoubtedly would’ve been patronizing as hell. Just another adult trying to trick students into behaving. It would’ve centered around some horrible article off some scam website that provides standards-aligned lesson plans ( or or There would’ve been multiple choice questions involved. There would’ve been a rubric. It would have looked like an important lesson to people on the outside, far from the actual classroom—but totally miserable to any actual participant.

There are topics that students are desperate to investigate; conversations they’re absolutely starving to have; thoughts, emotions, and memories they are dying to express. It might be possible for you to anticipate some of these, and students might be able to specifically articulate others. But they most often appear like fireflies during the in-between moments of class, while you’re passing out papers or waiting for the projector to warm up, and unless you are explicitly seeking these opportunities, they will pass unremarked upon.

Using our approach, the start of each new semester can be a deeply exciting time. Everything is new again. Anything is possible. I often feel this is the semester I really put it all together, that this is the semester I figure it all out. Maybe this is the semester we all fall in love with our writing journals, I think. Maybe this is the semester we stare at poetry more often than screens. Of course I know it will never go as wonderfully as my imagination, but conceiving of that ideal is important, permanently elusive as it may be.

I mean, if you can’t imagine your own classroom as a better place, how can you imagine a better world? And if you can’t imagine a better world, why are you in a classroom to begin with?

Your affectionate cousin,


✶ ✶ ✶ ✶

Support community journalism by donating to South Side Weekly

The Weekly is a volunteer-run nonprofit written for and about the South Side of Chicago. Our work is made possible through donations from our readers. If you enjoyed this article, please consider making a one-time or recurring donation. Donate today.

Leave a reply

Your email address will not be published. Required fields are marked *