This article presents the text of the author's presidential address, delivered at the National Council of Teachers of English (NCTE) Annual Convention in Philadelphia, Pennsylvania, on November 22, 2009. For the author, the title of this president's address, "Sailing over the Edge: Navigating the Uncharted Waters of a World Gone Flat," calls to mind that most famous seaman, Christopher Columbus. The author suggests that teachers may be venturing now into unknown waters--a world in which the tools of literacy are multiplying and evolving more rapidly than ever before, in which the social fabric is complicated by social networking tools, and in which sources of information and misinformation have exploded from three channels to 300. But we know that some principles will hold true even in these new oceans. Teachers still want their students to learn to use language to make sense of their experience, they still hope that students will read to sharpen insight and deepen understanding, that they will write and speak ethically and honestly. Some fundamentals remain true. But teachers' most threatening dragons are the educational policies and classroom practices that reduce our understanding of what it means to live a literate life to a score on a bubbled-in exam. We have got a lot to fix in education as we sail past those dragons. To sail over the edge, we must remember that the best teachers are thoughtful, creative, independent thinkers--not passive, restrained script-followers; the best teachers teach from a cornucopia of pedagogy, choosing the right instructional strategy for each student; the best teachers value the probing question from the curious--even angry--student far more than the right answer from the passive one. The best teachers, like good leaders, have the courage to overcome obstacles, the courage to sail into the unknown, even though, here, there be dragons. (Contains 1 note.)