The purpose of this study is to examine the effect of personal psychological variables(cognitive flexibility, emotion dysregulation, subjective health condition), family variables(marital satisfaction, father-adolescent communication) and job satisfaction on the psychological well-being of middle-aged men. For this research, questionnaires were administered to 550 middle-aged men residing in Seoul, Gyeonggi and Incheon. Among 352 questionnaires collected, 327 were selected and statistically analyzed by average, standard deviation, frequency analysis, t-test, one-way ANOVA, and hierarchical regression analysis using SPSS Win 21.0. The main results of the study are as follows: First, according to middle-aged men’s social-demographic variables, the level of their psychological well-being differed significantly. Second, cognitive flexibility was the most significant predictor of their psychological well-being. In addition, emotion dysregulation, job satisfaction, father-adolescent communication, and subjective health condition were significant predictors. These results suggest that cognitive reconstruction training or problem-solving intervention could be useful for the psychological well-being of middle-aged men.