The main purpose of this study is to verify the relationship among regulatory focus fit, value from fit, and psychological well-being of subordinates, and also the mediating effect of value from fit between regulatory focus fit and psychological well-being. For this purpose, we conducted an experimental study for undergraduate and graduate students (160 pairs) and a survey method for office workers (182 pairs) to verify the relationship between study variables. In the experimental study, as a result of data analysis through one-way MANOVA, the result showed that the more supervisor and subordinate coincided with each other in regulatory focus, the higher value from fit and psychological well-being improved. In survey study, as a result of data analysis through polynomial regression analysis, it was found that prevention focus fit showed a positive relationship with value from fit, but did not have a significant relation with psychological well-being, similar to the results of experimental study. On the other hand, promotion focus fit showed positive relationship with value from fit and psychological well-being, respectively, and it was also found that there was a significant mediating effect of value from fit between promotion focus fit and psychological well-being. This study is meaningful to increase the reliability of the study by showing a consistent result between the effects of state regulatory focus fit through experimental design and chronic regulatory focus fit through survey method. Based on the results of these empirical analyses, the theoretical and managerial implications were discussed.