Self-employment in the Russian Federation is a special tax regime; tax on personal income is a simplified form of entrepreneurship. The self-employed are often associated with freelancers. The exponential growth of information increases uncertainty, and the development of digitalization levels out uncertainty. This work analyses the factors influencing the digitalization development of self-employment as an integral indicator that can affect the sustainability of self-employment. The main method used is a topological method based on the polymerase chain reaction method, as well as the model based on fuzzy sets theory – Mamdani fuzzy inference algorithms. The data for the study were collected through a survey posted on Google Forms. The respondents were experts in the self-employment sector. Eight people participated in the survey (4 – self-employed; 4 – university professors). The self-employed comprised the following areas: developer – 1; service worker – 1; online marketer – 1; musician, event host – 1. Further calculations were performed in Mathlab. According to the study results, the level of factors in the development of self-employed digitalization is 0.502, which corresponds to the third interval of the five-level classifier and has growth potential.