Previous research has indicated the efficacy of mindfulness practices for improving student focus, reducing stress, and regulating emotion in the classroom. However, this workshop demonstrates that optimal student learning involves more than mindfulness by exploring how the additional components of awareness and insight can cultivate emotional intelligence and meaning-making skills through study, contemplation, recognition, and discernment. This workshop addresses the shift from emotional regulation to emotional intelligence, which includes the ability to understand one’s own emotions, and to interpret, act, and respond appropriately. This is the basis for understanding the emotions of others and developing empathy. Drawing from detailed Tibetan Buddhist traditions of mindfulness-awareness, presenters make the case for contemplation-based pedagogy, and lead specific guided contemplations on painful emotions.