The article is based on the report “The Transit of Civilizations: Methodological and Prognostic Aspects of Civilizational Competition”. It is devoted to the analysis of methodological and prognostic aspects of diachronic civilizational competition in the process of the current transformation of Modernity into the new historical state, defined as Postmodernity. Methodological and prognostic aspects of this historical transit are analyzed. The general aim of the study is to observe effective strategies for behavior while in situations of complexity, volatility, uncertainty and ambiguity. Different methods of orientation, action and management in post-war period are described and the possibility of their further transformation up to the next epistemological revolution is discussed. There is also an attempt to present certain analytical tools. Civilization is a dynamic concept, a social analogue of evolution. The globalization of modernity is accompanied by post-modern individuation, the antipode of industrial culture and mass society. The process of splitting of political structures, genesis of technical and anthropological complexity, creation of cloud structures – all this distorts the modern World Order. System approach is usually used to study complexities, while view of the future is based on a combination of transdisciplinary analysis, global context and long-term perspective. New methodological approach is produced for replacing the globality with fractality, long-term prognostics with non-linear dynamics, and transdisciplinary generalizations with uniqueness. The article also analyzes the latest generation of methodologies that possibly will allow us to make decisions and effectively act in this complex environment full of wicked situations and processes as well as non-classical approaches, such as the mode of action based on the analysis of deep codes of evolution, the art of non-classical operative, synergetic behavior, phenomen of serendipity etc. Research of the innovative methodological and predictive tools is an imperative for sustainable development, taking into account the upcoming turbulence of the social environment.