Central to many psychological schools of thought is the notion that self-reflection leads to self-insight which, in turn, leads to enhanced well-being. However, empirical research has found that although self-insight is typically associated with well-being, self-reflection is frequently not associated with self-insight or well-being. Past attempts to understand this conundrum have tended to focus on the role of ruminative self-refection. Using a different approach this study investigates the roles of dysfunctional attitudes and positive core self-evaluations. Using data from 227 participants, two key findings are reported: first, dysfunctional attitudes suppress the relationship between self-reflection and self-insight; and second, positive core self-evaluations mediate the relationship between self-insight and subjective well-being. These two findings imply that a path exists from self-reflection to subjective well-being through self-insight and positive core self-evaluations. This path model was found to be a good fit. Implications for future research and positive psychological practice are discussed.