A student's lack of belief in his or her own ability to do well in school can be a driving component of disengagement. In response, the author created art activities aimed to build students' confidence in their ability to learn, carry out a given art task, and identify a competence; such asset-based thinking approaches encourage students to reach a new level of engagement, undertaking positive action and achieving traction in the present moment (Buckingham & Clifton, 2001). In this article, the author explores how students perceived their ability to carry out a given art task and to discuss how their perception of their own artistic competence changed through participation in an after-school art program. Finally, the author describes the educational implications of therapeutic art activities, such as expressive drawings, which use the imagination to identify and develop the motivation and competence of students. The author's experiences with these students emphasized the significant role that a teacher can play in establishing a conducive and caring learning space by providing mutual and reciprocal interactions that promote artistic engagement and expression. A teacher who respects a student's sense of autonomy also optimizes his or her opportunities to take the initiative and explore potentials (Legault et al., 2006). It is quite a significant benefit for students to achieve something using their own skills; it motivates them toward further engagement with learning and competence development. Through such experiences, students become more aware of their own abilities, and able to draw on a range of alternatives when coping with daily challenges. This ultimately makes them feel empowered rather than vulnerable.