This study was conducted for the purpose of providing basic data for understanding emotional changes according to the development process of middle school students in counseling and education fields by verifying the mediating effect of self-esteem in the relationship between parenting attitudes and school life adjustment, focusing on middle school students. It has been done. For this purpose, a survey was conducted on 389 middle school students located in N City, and descriptive statistics, correlations, and mediation effects were analyzed using SPSS 23.0 and Model 4 of PRECESS Macro. The research results First, positive parenting attitude and school life adjustment showed a significant positive correlation, and negative parenting attitude and school life adjustment showed a significant negative correlation. Second, self-esteem showed a partial mediating effect in the effect of positive parenting attitude on school life adjustment. Third, self-esteem showed a partial mediating effect in the impact of negative parenting attitudes on school life adjustment, but caution is needed in interpretation due to low explanatory power, so groups according to self-esteem level (top 25%, middle 50%, bottom 25%), and as a result of additional analysis, it was confirmed that each group’s negative parenting attitude may have different effects on school life adaptation depending on the individual’s level of self-esteem. Based on the research results, limitations and suggestions for follow-up research were discussed.