Teaching is a complex and challenging endeavor. Teachers are continually faced with difficult choices in which competing values are set in tension with one another. The interests of all students, and of other groups and constituencies, can rarely be served at the same time. Different educational goals, each desirable in and of itself, often place incompatible demands on teachers, especially in light of the limited resources and time available to most of them. Of course, teaching does have its satisfactions and fulfillments, but increasingly those rewards must be sought in the context of challenges that reflect the competing expectations society places upon educators. These essays tackle important aspects of the complex, often conflicted contexts of teaching. Each chapter focuses on a different aspect of teaching, offering candid analysis of the difficulties and trade-offs inherent in teaching practice, while suggesting ways to productively address a given conflict. Together, the chapters speak honestly to the realities and challenges of teaching, without downplaying the ideals that draw teachers into education in the first place.