Subject. This article considers the self-employed as a subject of economic activity, and it discusses the participation of the self-employed population in the system of social and pension insurance. Objectives. This article aims to analyze the development of the pension and social insurance system of the self-employed people. Methods. For the study, we used the general scientific research methods. Results. The article presents an author-developed algorithm of actions of the self-employed in terms of relations with government agencies on registration, taxation and insurance, and it offers certain approaches to the development of the system of voluntary social insurance of the self-employed. Conclusions and Relevance. Based on the analysis of the current regulatory documents, the article concludes that it is necessary to determine the legal status of the self-employed, the list of obligations to pay taxes and fees, and the specification of their social guarantees and rights. The practical application of the results of the study can improve the mechanism of employment management, which is important for the development of Russia as a social State.