Adolescents today are confronted with the compounded stressors of life in our high-pressured society and the cognitive, physiological, and emotional changes characteristic of this stage of development. To explore ways to promote well-being in this population, mindfulness, defined as paying attention in the moment in an intentional and purposeful way, was examined in terms of its associations with aspects of emotional well being. It has been reported to have positive effects on emotional well-being in adults, and shows promise for similar results in research with youth. Moreover, the mechanisms through which being mindful may influence positive outcomes have only recently been explored, and have not been investigated with adolescents. Self-compassion, defined by the three components of self-kindness, sensing oneself as part of a common humanity, and maintaining perspective in challenging circumstances, was examined as a potential mediator of the relationship of mindfulness to various outcome measures. Measures assessing mindfulness, self-compassion, and aspects of emotional well-being comprised an online survey that was administered to 67 adolescents in an urban high school. Path analysis was utilized to explore relationships among the variables. An alternate model with self-compassion as the predictor and mindfulness as the mediator was also investigated. Results suggested that both mindfulness and self-compassion functioned as mediators in the pathway to emotional well-being. A theorized model is presented which depicts a reciprocal relationship between mindfulness and self-compassion and describes an iterative process that takes place between these two constructs, promoting emotional well-being. Implications for research and practice include conducting longitudinal studies, which assess constructs at three time points to definitively establish mediation, and developing a self-compassion program tailored for adolescents to facilitate improvements in emotional well-being.