Utilizing a relational developmental systems approach to examining character strengths, this article examines the connection between adolescents’ intentional self-regulation (ISR) with youth sense of purpose, using data from a large-scale evaluation of a youth development program in Scotland. Data were triangulated from multiple sources, including youth surveys and interviews as well as teacher assessments. Surveys were collected from 783 S2 (approximately seventh grade) pupils; teacher survey data were collected for 732 of these pupils. Telephone interviews were conducted with a subset of 29 adolescents. The data were analyzed with an innovative mixed-methods technique that allows qualitative interview data to underscore consistencies and disconnects with quantitative findings from both teacher and adolescent surveys. Results demonstrate a strong connection between ISR and purpose and many consistencies across measures of purpose.