I explore the history, theory, tools and benefits of dialectical thinking, a way of thinking adults grow into to different degrees after mastering formal logic (Basseches, 1984, Laske, 2009). My goal is to show that dialectical thinking is a natural outcome of adult cognitive development and that, pragmatically speaking, it is learnable. In order to give the broadest possible introduction to dialectical thinking, I detail the reverberations of the dialectical tradition in developmental psychology and introduce a set of hypotheses as to the nature of dialecticism. My outline is based on the notion of Four Quadrants of Dialectic (Laske, 2009) each of which is associated in human thinking with a particular “class of thought forms”, or ways of making sense (rather than meaning) of the world. With regard to Wilber’s work, the Four Quadrants of Dialectic are seen as inhering each of the four integral quadrants. In a short Appendix, I briefly detail how dialectical thinking can be learned today, extrapolating from my work at the Interdevelopmental Institute (IDM).