The first section explores the epistemological similarities between postmodern and conservative thought. I attempt to show the underlying similarities between the assumptions made by each school of thought. The primary focus is on similarities in how each school of thought views the role and limits of reason. Each school of thought is highly conscious of how complex our environment is relative to our cognitive capacities. The next section is an overview of political science literature that addresses the decision making process and the role of various sorts of expertise (policy, political, and cultural) within situations of great complexity. The focus is primarily on foreign policy decision making, especially the Vietnam War. The themes raised are tentatively applied to the current situations in Afghanistan and Iraq. However, the general themes discussed and the questions raised are applicable to domestic politics (on the local, state, and federal levels). In both of these sections, I raise practical and theoretical questions and I argue that an interdisciplinary approach, borrowing much from social and cognitive psychology, would be useful in furthering this research. In addition to helping us achieve a greater understanding of past events, this interdisciplinary approach would be of modest (but significant) prescriptive value by offering policy makers advice on how to best avoid major policy mistakes. The final section examines the Mt. Laurel housing cases and how the judicial branch was assisted by land use experts who were appointed as special masters to the courts. This section gives an example of decision makers (in this case, judges) in a complex situation and how the New Jersey political system has seen fit to supplement the judges' legal expertise through the advice of experts in housing and land use policy. As in the previous sections, questions are raised about how to best calibrate the roles of the educated generalists and the policy experts to achieve more satisfactory policy outcomes.