School is sometimes framed as a place for preparing, a place for becoming college and career ready. At times this approach positions school as an important space "within" the world of college and careers, envisioned perhaps as Dewey imagined it, as a safe place to try things, a space where real work of participation in society could be done but in which there was some protection from serious consequences of a misstep or two. Other times school gets characterized as a place apart, yes, but with a more negative connotation: on graduation students will enter the real world from which, it follows, school is quite separate (and thus unreal). Each of these views suggests different approaches to engaging students in literacy; what counts as authentic work in an English classroom depends in part on what kind of space one takes the classroom to be and how one sees its relationship to the rest of the world. In this article, the author uses some moments in her own uncomfortable history as a student as entry points to reflection on a problem she finds at the heart of some of the more uncomfortable moments she has had in her practice as a teacher and teacher educator as well. (Contains 1 figure.)