This article aims to delineate several issues raised by an historically based approach to understanding the present and the future. Beginning with a discussion of the profound impact that drastic changes have had on the international environment, the article then outlines what history suggests about human nature’s influence on the course of future events; the future of war; the nature of governance and the United States. This essay does not attempt to provide answers, but rather suggests how policy makers, strategists, and military leaders might think through the complex political and cultural questions they need to be asking in the making of strategy. This is the essential first step for Americans. If they fail to ask the right questions, most answers will prove irrelevant to the challenges of the future.