The purpose of this study is to analyze the mediating effects of parent-child communications and self-encouragement on the impact of female high school student’s career stress on psychological well-being. For this purpose, descriptive statistical analysis on career stress, psychological well-being, parent-child communications, and self-encouragement and correlation analysis between the variables were conducted for 367 female general high school students in 3 cities of B, D, and P cities. And the mediating effect of parent-child communications and self-encouragement was analyzed by conducting path analysis according to the procedure of the mediating model proposed by Hayes. The main results are as follows: first, it was found that female general high school student’s career stress affects psychological well-being through parent-child communications. Second, female general high school student’s career stress was found to affect psychological well-being through self-encouragement. Third, parent-child communications and self-encouragement were completely mediated in the impact of female general high school student’s career stress on psychological well-being. The results of this study suggest that in order to increase female high school student’s psychological well-being, it is necessary to help facilitate parent-child communications, intervene to improve self-encouragement, and develop various education and programs to enhance female high school student’s psychological well-being.