This article deals with different semantic interpretations of freedom in philosophy’s history, such as necessity, (in) dependence, grace, fate, estrangement, responsibility, choice. We consider choice to be a semantic interpretation of content of the category of freedom and offer a new theoretical model of choice as a phenomenon In order to study the nature of choice more completely, today it is necessary to analyze the concept of choice from the positions of phenomenology and synergetics. Thus, this article describes some new approaches to understanding a choice phenomenon, namely, phenomenological and synergetic approaches, which allow marking out three stages in the mechanism of a choice’s realization. They are immersing into chaos, being in chaos and going out of chaos.