Self-insight has been identified as an important predictor of psychological well-being, and it is commonly believed that self-insight is achieved through self-reflection. However, findings regarding the relationship between self-reflection and self-insight remain largely inconsistent warranting further examination of the determinants of the outcomes of self-reflection. This thesis examined the relationship between self-reflection, self-insight, and psychological wellbeing as a function of individual differences in identity styles, while also considering the roles of rumination and self-compassion. Two hundred and twenty-six emerging adult women (N = 165) and men (N = 61) completed self-report measures of identity styles, self-reflection, self-insight, psychological well-being, rumination, and self-compassion via the University of Northern British Columbia (UNBC) Psychology Research Participation System in the time from September 2020 until April 2021. Self-insight and self-compassion partially mediated the positive relationship between informational identity processing and psychological well-being. For users of the diffuse-avoidant and normative identity styles, rumination negatively predicted psychological well-being. This relationship was fully mediated by self-insight and self-compassion. The results are discussed in terms of the roles of self-reflection, self-insight, and self-compassion in fostering psychological well-being. Findings highlight the importance of self-compassion as a precedent in order to adaptively self-reflect, gain self-insight and increase psychological well-being. Any attempts at increasing self-insight that are not done in a self-compassionate way pose a risk to an individual’s psychological well-being; this risk is especially high when diffuse-avoidant or normative identity processing is used. The primary implication is that a consideration of self-compassion is warranted in therapy and other practices relying on self-reflection.