The fostering of a dialectic between Certainty and Uncertainty and the perspectives of reality and "truth" that each engenders is necessary for writing and the teaching of writing. This necessity arises from the fact that a privileging of either extreme, at the expense of the other, is antithetical to work for the progress of not simply the teaching of writing but of the greater society and culture to which it would serve. Whether the pursuit of Certainty that culminated in late-nineteenth- and early-twentieth-century America in the birth of "Current-Traditional Rhetoric" or, conversely, the pursuit of Uncertainty that spread throughout academia during the "Post-Modern" era, either choice is detrimental to those who would strive for that progress within academic writing instruction and beyond. In the end, both possibilities serve the continuation and profusion of the status quo. The strict worship of either of these supposed contraries begets the very same dualistic, "black or white" perceptions. Through my research, I explore those separate pursuits and then examine the possibilities for founding this crucial dialectic between them. I also investigate not simply how I have attempted to pursue that dialectic in my own writing classes but also the results of those attempts.