The present study examined whether and to what degree empathy increased in adolescents who participated in a high-intensity writing program over the course of a year. Data for this study came from writing samples of a randomly selected group of middle-grade students (n = 61) collected at three different time points to answer whether: (1) it was possible to reliably and systematically measure empathy as a complex construct that included both affective and cognitive elements, and (2) empathy increased over one year in an intensive writing practice program. The findings showed statistically significant increases in various aspects of empathy such as reasoning, including multiple perspectives, expressing emotion, and proposals for action, and statistically significant increases in empathy as a latent construct. The high-intensity writing program, an essential component of the school's curriculum, served as an educational tool and provided a showcase for the role of deliberate practice in skill building.