The purpose of this study is to examine the mediating effect of self-esteem and depression between social stigma and living satisfaction, and future optimism among youth after dropping out of school. A total of 318 data youth from the panel of school dropouts wave 5 conducted by the National Youth Policy Institute, was utilized for analysis. A hierarchical regression analysis was conducted to examine the mediating effect of self-esteem and depression. The findings are as follows. First, social stigma was found to have a negative impact on living satisfaction and future optimism. Second, social stigma was found to have a negative impact on self-esteem and a positive effect on depression. Third, the partial mediating effect of self-esteem and depression was found in the relationship between social stigma and living satisfaction, and future optimism. Based on these result, implications and suggestions were provided.