Philosophic thought and particularly ‘essentially contested’ concepts improve with understanding of their predecessors, with a sense of context. History helps us to see the value of characteristics or features that otherwise seem arbitrary: when presented in a narrative (i.e., a story that can be followed, in which the crucial developments are contingent and the act of following expresses real interest), trends or ideas are integral to the topic in question and not analytical. Conversely, failure to see the entire range of possibilities (i.e., failure of imagination) undermines understanding of what the principal(s) in fact chose to say or do. Rather than a general set of scientifically discovered rules, history is a public exercise in continuous criticism (revision) combined with advancing interpretation via the discovery of new evidence. Having outlined a dynamic philosophy of history, the author shows that the schools of philosophy themselves – comprising logic (valid inferences), epistemology (objective criteria of different kinds of knowledge), and ethics (individual responsibility to society) – tend to talk past one another, and so their systems and constructs are weakened. As a case in point, the author suggests that metaphysics (Hegel: absolute presuppositions) can only be understood after the unquestioned becomes questionable.