Currently, a difficult stage of institutionalization of self-employment in the Russian economy is taking place. The authors conducted a study of the ways of legalizing the self-employed in conditions of the development of digital technologies and assessed its role in innovative development. Self-employment, according to the authors, acts as a way of adaptation of employed and unemployed to changing socio-technical systems in the labor market. Using historical, statistical and regulatory analysis, the authors investigated the problem of determining self-employment and ways to legalize it in Russia and other countries. The article explores the relationship between its distribution and innovative development by means of the analysis of legislation regulating self-employment in different countries. Using the analysis of official statistics, the article reveals a tendency towards an increase in the number of citizens wishing to legalize their self-employment status. The article studies the legislative pilot related to the legalization of self-employment in Russia, assesses the prospects for the expansion of this pilot in terms of the appropriateness of the proposed measures. According to the professional structure, based on statistical data and expert estimates, a low proportion of people receiving professional income from intellectual work was identified and the causes of this phenomenon were determined.