This inquiry explores the educative meaning of interruptions or breaks in teacher's experiences by looking at their role in reflection and listening. Reflection and listening are not only two vital and distinct aspects of teaching, but are also interrelated and as such can serve to productively inform one another. In this context, I develop the notion of "negativity of experience" to describe the space that opens up when our experience has been in some way interrupted, the space where we dwell between old and new experiences and where new thoughts and ideas emerge. I demonstrate throughout my discussion that it is in this space that listening and reflection take place. To begin, I analyze the works of John Dewey and Donald Schon to take up a few particular aspects of reflective thinking and its relation to the practice of teaching. In this context, I point out similarities and important learning-theoretical differences between the notion of "negativity of experience" and Schon's notion of "messy situation." The second section examines the role of negativity of experience in listening. Here, I seek to explore ways to include listening in the contemporary discussion on reflective teaching and practice. The inquiry concludes by considering the meaning of reflection, listening and negativity for the education of professional teachers.