Relation between self-esteem and creativity (as a cognitive ability) highlights the regulative function of the self-awareness. Self-esteems of different kinds and different generality function in interaction with other components of intellectual and personal potential of a person, and they take leading role in psychological regulation of person’s productive activity. Tolerance for uncertainty and intuition are such components, and they are connected to the productive choice and other types of novelties. In this paper we describe a study of creativity (as a result of subject’s creative behavior assessed by experts), its self-assessment, intuitive style, and tolerance for uncertainty among creative professionals (writers, composers, and directors, n = 53) and control group of psychology students (n = 593). With correlation analysis, we show that psychologists base their self-esteem on acceptance of uncertainty, whereas creative professionals orient toward the objective results of their creative activity. Using the confirmatory factor analysis we verify structural model of Creativity, integral Self-esteem of creativity and intelligence and Acceptance of uncertainty and risk. The positive connection of integral Self-esteem with Creativity and Acceptance of uncertainty and risk was shown as well as the negative connection between Creativity and Acceptance of uncertainty and risk. According to the results, unlike self-esteemed intelligence, integral self-esteem is connected both to acceptance of uncertainty and success in creative activity.