School well-being for adolescents is a condition that is expected to be one form of educational success. Many personal factors certainly play a role in producing the well-being include positive character of the student. This study aims to look at the role of optimism in mediating the influence of wisdom & knowledge virtues consisting of the character of creativity, curiosity, open-mindedness, love of learning, and perspective on school well-being. The quantitative research design was used involving 339 respondents selected by non-probability sampling techniques. The results showed that optimism plays a significant role as a mediator of creativity, curiosity, open-minded, and love of learning for school well-being adolescents. While the strength of character curiosity, creativity, open-mindedness, and perspective become significant predictors that influence optimism itself. This study explains that the importance of developing these positive characters in daily activities at school.