In the crisis conditions of entrepreneurs business functioning in Russian, it is important to develop critical thinking in conjunction with the skills of self-regulation of behavior. It is assumed that entrepreneurs with different styles of self-regulation differ in the level of critical thinking, and there is also a relationship between the styles of self-regulation and the level of critical thinking. The theoretical basis of the study is the idea of the relationship between the degree of formation of individual self-regulation and the productivity of performing various types of professional activities. The sample of the study consisted of 140 individual entrepreneurs engaged in entrepreneurial activity for more than two years, aged from 30 to 50 years. We used techniques to analyze the style of self-regulation of behavior, volitional self-regulation, critical thinking and mental abilities. The study allowed us to expand the understanding of the relationship between critical thinking and self-regulation, to reveal the content aspects of critical thinking of entrepreneurs with different levels of self-regulation of behavior. We found out that in the group of entrepreneurs with a high level of self-regulation of behavior, there is a high level of volitional self-regulation, perseverance, self-control, information processing skills and critical thinking skills. We came to conclusion that there are differences at the content and semantic level among entrepreneurs, differentiated by the type of self-regulation. For entrepreneurs with a low level of self-regulation, it is planned to conduct a program for the development of critical thinking.