The authors’ goal has been to show the need to improve both the general level of education of self-employed citizens, and, mainly, the actual level of specialized competencies. The modern world does not tolerate an unskilled approach in any business. Therefore, special education for self-employed citizens is their internal need that has direct impact on their well-being and relevance in the modern labor market. Real digital technologies aim at improving comfort for self-employed citizens while realizing their need in specialized education. For efficient forecasting, the inductive analysis method has been chosen. This is when the current and previous situations in the self-employed market are examined, then the main factors of the market development are revealed, and the main reasons for the formalization of self-employment are considered. Based on this, the prospects for increasing the self-employed citizens’ groups as consumers of general and specialized education are defined. Sociological instruments of this study include expert surveys, in-depth interviews, analysis of Internet publications of central print media, and content analysis. The main results of the study are as follows: • There is an exponential increase in the number of registered self-employed citizens – consumers of specialized education in the medium term. • Self-employed citizens specializing in such areas as IT, tutoring, online courses, beauty industry may become the most promising in the market of additional specialized education. • Self-employed citizens aged 35 – 45 are the most promising in the market of general education, mainly in pension legislation. • The accessibility of self-employed citizens as potential consumers of educational services can be ensured mainly through their official registration. The official registration of self-employed citizens can be stimulated by a) more favorable tax regimes for self-employed citizens, b) a simplified registration procedure, and c) the introduction of harsh administrative penalties for evading the registration.