In this paper, I wish to offer insight into the role of paradox in teaching. I will do so by analyzing teachers' everyday work, taking a qualitative approach and constructing a small-scale empirical study. Philosophically, my attempt is framed by Heidegger's thought. Drawing from research data, I argue the following: (a) paradoxes and dilemmas are the very basis of teaching, and a teacher cannot see paradoxes and dilemmas if she/he has already made an (unaware) choice of disengagement from the profession. Stated otherwise, the sense of dependency, laceration, and even helplessness experienced by teachers I met and interviewed are not occasional or unwanted outcomes, but rather the very nature of the ethics of teaching. (b) The rationale of teaching-- curricula, objectives, and learning outcomes--is framed by teachers' intentionality, namely, by teachers' "being thrown" and involved in leaving teaching situations. (c) Teachers are simultaneously thrown into the projecting and understanding that constitutes teaching and positioned as the authors of such projecting and understanding. Understanding this ripping condition is a step towards accomplishing the edge situation that teaching can be.