The article is based on the results of the research devoted to the activities of self-employed citizens. The purpose of the study was to analyze the nature of self-employment as a socio-economic phenomenon, the extent of its prevalence, the measures taken by the state to legalize the self-employed and create favorable conditions for their activities, as well as generate proposals for their correction. The informational and empirical base of the study was constituted by reference materials, scientific publications and the results of opinion polls, including those conducted by the authors. The analysis shows that selfemployment is a special type of entrepreneurial activity, but it is difficult to regulate due to its predominantly “shadow” nature. The scale of self-employment is significant both abroad and in Russia. According to a sociological survey, the share of the self-employed in the total number of employed Russian population is 22%, while 64% of the self-employed work without registering their activities, without paying any taxes or insurance contributions. In recent years, the state has taken various measures to legalize the activities of the self-employed, which at the moment are mostly experimental in nature. As a rule, they are related to taxation, simplification of their registration with tax authorities and further communication with them. The state regulation of the activities of this group of citizens is hindered by the absence in Russian legislation of a uniform definition of “self-employment” for the entire legislative system, as well as generally accepted criteria for classifying citizens as self-employed. The results of a sociological survey show that state initiatives at the moment do not find   tangible support from the self-employed citizens themselves, which is largely due to their distrust of state authorities, as well as the lack of real incentives for moving to a legal fi eld, in particular, providing social guarantees. The article provides suggestions for improving the mechanism of legalizing the activities of self-employed, taking into account the opinions and assessments of citizens themselves, working on the basis of self-employment.