This article is a reflection on the lack of systemic and holistic “dialectical” thinking in a world in which more than ever human actions have strong and immediate repercussions in the natural, and thus also the social, environment. It is suggested that present notions of teaching, coaching, and consulting are hopelessly anachronistic since they are built on theories and algorithms of a purely formal logical nature that hinder individuals’ potential for dialectical thinking to emerge. Human Systems in the Anthropocene