From time to time, every educator asks the question "why am I doing this?" Some of the answers may relate to personal goals or needs, but some are invariably focused on beliefs about the impact their work has on learners. For postsecondary educators, those answers may include thoughts about increased employability or better citizenship or mastery of a body of knowledge or a set of skills. In a recent "College Quarterly" article, Susan Johnston (2011) suggested that the "fear and anger" stemming from the combined effects of the attacks on the World Trade Towers and international economic disruption have created a kind of "collective disorienting dilemma" that has "drawn individual adult learners into a reflective process and created a focus on the need for dialogue which addresses the crisis in the systems world." Clearly, massive social and political events may serve to alert large numbers of people that their current frames of reference may need revision. Is it possible that less catastrophic social change might also constitute system wide disorienting dilemmas? Johnston's piece had the author thinking anew about the impact of technology on teaching and learning. Obviously, new technologies have not infiltrated every postsecondary classroom, but where they do, can one profitably regard them as creating disorienting dilemmas? The larger issues of social change that drive Johnston's thinking demand a kind of open and trusting communication. In this article, the author discusses the smaller issue of adapting to technological change which may be a useful "sandbox" for creating collective disorienting dilemmas and fostering the learning that they enable.