The last time I felt like a failure was during the final meeting of an ostensibly three-week-long workshop on Constrained Writing. I pitched the workshop to the directors of 826 Chicago, and, weirdly, at least one of them seemed enthusiastic about it. (Note: if you don’t know about 826, you should check it out – it’s a pretty great program [co-founded by author / publishing maverick Dave Eggers], and anybody who finds themselves despondent over the state of literacy, public funding for the humanities, or plain old written English should support it with time, money, or both).

While I naively assumed that untold hordes of high school students would go bonkers over the prospect of learning about lipograms, chronograms, pangrams, and the like, in reality they, well, didn’t.

The workshop was sort of a failure. The first week, three students showed up. Two students showed up for the second week, and, finally, the last workshop saw a TA and myself sitting around, awkwardly chatting for 40 minutes until it became apparent that that nobody was coming. As failures go, this one was as unqualified as I am.

Thing is, I didn’t feel unqualified. I’ve sat through enough workshops to know what makes some of them great and what makes others utterly flatline. The good ones are based on mutual respect, which manifests as a willingness to take other people’s work completely seriously, but also to exercise judiciousness in criticism. In this case, “judicious” means, “Keep your vocab civil and your comments work-bound.” On the other hand, a real flatliner of a workshop is usually the result of some or all of the following: an incompetent or apathetic instructor, rampant competitiveness among the students, a dearth of proffered niceties, and the misanthropic tendencies that tend to crop up in “creative writers” who feel they have been misunderstood.

(Full Disclosure: I am guilty of contributing to the going-down-in-flames of at least one workshop. I had, in my weaker moments, a tendency toward virulent misanthropy, which was often directed at people who, for one reason or another, I believed were utterly full of it and in need of deflating. When you’re in the high-pressure context of a workshop, where people are offering up for public and critical consumption the very works into which they’ve sometimes literally poured their hopes and dreams, virulent [and highly vocal] misanthropy will vaporize any remnant of mutual respect.)

So, knowing full well what happens when good workshops go bad, I resolved that this workshop, my first teaching experience ever, would not go out like that. These were high school students, after all, and probably ambitious at that. Who else but very ambitious, smart students, I reasoned, would want to sign up for a workshop that made writing (which is difficult enough as it is) exponentially more difficult? And plus I’m not actually that much older than these students. There is the possibility that I will be teaching someone a mere four years younger than myself – therefore I’ll be easier to relate to, and the students will maybe look at me less as a tentacle of the panoptic Educational Apparatus and more as what I actually believe myself to be: just some guy who wants to show them something pretty neat.

During the first workshop, I actually believed that was the function I served. The kids seemed to be paying attention, they were writing, they were blown away by the excerpt from Perec’s A Void I had them read, and at least one of them seemed to have a pretty intuitive grasp on the idea of constraint. All seemed to be going well, and I found myself utterly exhausted by the end of the class, which I took to be a good thing. Having a class of three rather than a class of, say, ten (which was my original plan) seems much more difficult – each of those students demands a positively numbing amount of concentration. Rather than being able to address a “group,” there is pressure to address three individuals, which is pretty literally a pedagogical juggling act. A friend of mine likens teaching to being on a weird drug – your consciousness of your surroundings dilates, forcing you to absorb even the most miniscule behavioral tics of everyone sitting in front of you. Even as you’re talking, you notice a stealthy clockward glance, a stifled yawn, a covert cuticle examination. And the fewer you have to concentrate on, the larger those tics loom, like the tap dripping in the Cure’s 10:15 Saturday Night.

I knew things were going wrong a few days after that first workshop. I had asked each student to dream up their own constraint, and to start writing something utilizing that constraint. After some inquiring emails, it was pretty clear that, by the middle of the week, nobody was planning on doing the writing, which, when you’re trying to run a writing workshop, starts to conjure nightmares linear and 2-D in nature.

Sure enough, those students who did show up hadn’t done any writing. In a moment that would have been funny, had it not also sounded the death knell for the class, one of them proposed writing a story with no J’s, a constraint pretty clearly made up on the spot. Not exactly the kind of linguistic muscle-flexing I was hoping for. I found myself actually kind of upset, though I covered it up. These kids, I realize, have real classes, and real teachers, who will give them real grades. Might it be too much to expect them to take on an entirely new bundle of work just because some guy in Asics and a blazer tells them to? Especially when this guy is barely even older than they are?

Clearly, on some level, it is too much. And I think about what I would have done had I been in their position, about to go to college, a new dimension of papers and homework and deadlines. Here’s some guy who wants you to work, and you know that in some abstract sense the work will be “good for you.” But this idea of work-as-cure, it’s just a bit too abstract for you, what with your entire concept of academic achievement being pretty much alphabetic and standardized in nature. And here he is in his black sneakers and black blazer, obviously trying to make it look fun. But the future is looming like a black cloud, and you, who are young, have a good sense of what fun really is, and even now you’re starting to realize that fun actually won’t be accessible for too much longer, at least in the form you know it. There’s letters to earn, and for now those letters signify knowledge, something you can touch and see.

This is the way education works in this country, at least until the university, where independent pursuit of knowledge is encouraged, if only as an afterthought. Were it different, there’s no guarantee these kids would have done the work, or turned backflips over the prospect of writing a clept poem for fun. At the start of the workshop I said that, more than anything, I wanted the experience to be fun, thinking that the concept of intellectual flexing and stretching as a form of pleasure might be something new to these kids. Afterwards, thinking back on all the of the “learning is fun” clichés I heard as a kid, all I could do was roll my eyes at my own personal use of the oldest pedagogical groaner in the book. A groaner, like all others, sapped by the perpetual failure that is misuse.