The article deals with the connection of psychological well-being with such personal characteristics as tolerance of uncertainty, self-efficacy, and coping strategies. The study aimed to identify psychological predictors of psychological well-being. Employees of commercial organizations (N = 93, 62 men and 31 women) with an average age of 45 years old, participated in the study. The implicit emotional and semantic content of the psychological well-being phenomenon was revealed by analyzing the data of the "unfinished sentences" projective technique that became the basis for interpretation and comparison with the results of the quantitative techniques. The results of pairing the categories of responses to unfinished sentences with the actual level of psychological well-being assessed under the K. Ryff questionnaire (adaptation by T.D. Sheve-lenkova, T.P. Fesenko) showed differences in the perception of this phenomenon in respondents with high and low levels of psychological well-being. Correlation analysis revealed a positive relationship between psychological well-being and proactive coping strategies and self-efficacy, and a negative relationship between psychological well-being and tolerance of uncertainty. The mediator analysis results showed that self-efficacy can be considered a predictor of psychological well-being, while proactive coping strategies mediate the relationship between psychological well-being and other variables. The study was conducted in the context of the cultural-historical approach methodology. The results obtained can be used in personnel selection and assessment tasks and psychological counseling.