This article addresses a key contrast in how teachers may regard the uncertainties of their work, considering how an orientation to uncertainty can be regarded as a decision-making style. Through the use of case studies, the author contrasts two teachers. One is oriented "toward" uncertainties in her work and describes her herself as being always "on the edge" of her capabilities, constantly seeking out perspectives that differ from and challenge her own and remaining vigilant to the need for improvising to respond to the circumstances of the moment. The other is oriented "away from" uncertainties and describes herself as prepared and deliberate; committed to achieving outcomes in line with her articulated goals and purposes; and purposeful about which unresolved questions she chooses to pursue. This contrast has implications not only for how these teachers make decisions and view their professional growth, but also for how some teachers may be understood, and misunderstood, by others. In a culture that often seeks to ignore pervasive moral ambiguities and focuses instead on questions for which there are easily identifiable answers (Cuban, 1992), an orientation toward uncertainty is more likely to be devalued or seen as an indication that one is not teaching well. Identifying these different approaches to decision-making styles enables us to appreciate the integrity and strength of each, as well as the limitations of each, suggesting new possibilities for research and for teachers' professional development.