A peril of teaching for a while--and thinking about teaching--is that everything you read becomes filtered through the question "What does this say about teaching and learning?" But here are three short pieces that more-or-less deliberately engage issues of teaching and learning in somewhat parabolic (if not elliptic) ways.
"Shooting an Elephant," by George Orwell, captures the experience of being a new teacher (whether new to the profession, or new to a school) confronted by a discipline problem and a class or hallway full of students what you're going to do about it. I think it also reminds us that we're never really as prepared as we think we are, that first time, and that the chances of things ending well--for the elephant surely, but also for us--are slim indeed.
Sideways Stories from Wayside School, by Louis Sachar, is full of wonderful and off-the-wall tales and fables, but it's the first one that has stuck with me: Joe is held back during recess by Mrs. Jewl because he can't count properly. When Joe counts a set of objects, the numbers come out in any old random order, but he always gets the number of objects right. The (very Wittgensteinian) irony is that whenever Mrs. Jewl tries to explain to him how to count the "right" way, he does exactly what she does, and comes up with the wrong answer. Ever since my mentor Steve Starr read me this story, I've tried to listen more and worry more about whether the student has what appears to be a robust way of getting the right answer than whether he or she is doing it my way.
Finally, Philip Roth's "The Conversion of the Jews" is the hilarious and deeply sad story of Ozzie, a young pre-teen Jewish boy in 1950's New Jersey who has a history of asking his rabbi the wrong--and by that I mean "the hard"--questions. The story's precipitating incident is an argument in which his rabbi asserts the existence of a historical Jesus but says that he couldn't have been the Son of God as the New Testament describes because, as Ozzie quotes the rabbi, "‘The only way a woman can have a baby is to have intercourse with a man." Ozzie asks "if He could make ail that in six days, and He could pick the six days he wanted right out of nowhere, why couldn’t He let a woman have a baby without having intercourse." And the rabbi refuses to give a consistent answer, leading Ozzie to burst out "You don't know anything about God!" What strikes me here is that Ozzie demands only two things of his rabbi: intellectual honesty, and a modicum of kindness. And really, for a teacher, is it reasonable to expect anything less?