The article is dedicated to the theoretical study of the process of convergence, integration of two types of activity - playing and working in the information society. The author’s classification of the stages of research of playing as a philosophical, psychological and social phenomenon is proposed. There are three stages in the development of research of playing starting from the research of Immanuel Kant and Johann Christoph Friedrich Schiller to modern-day authors. Based on the analysis of modern authors’ study, it is shown that functions of working are increasingly filled with playing methods, and vice versa playing partially acquires the characteristics of work behaviour. The transformation of the main functions of playing in the conditions of the information society is also shown; i.e., the information environment acts as a factor of change. The results of the study can be used in the study of digital environments, in theoretical and empirical studies, to explain the transformation of work behaviour of a subject, as well as in the practice of various pieces of training in the field of human resource management.