Satisfying and meaningful relationships depend on the ability to take the perspectives of others. Empathy, the process of considering the thoughts, feelings, and behaviours of another person from their point of view, results in other-oriented emotions and behaviours, such as compassion, forgiveness, and altruism. A central way in which we take others’ perspectives is through imagining ourselves in their place, a process made easier by having experienced similar situations in our own past. As such, understanding our similar past experiences influences the ability to connect with another’s misfortunes and traumas. In this poster, we examine the relationship between self-reflection and empathy. From this examination, we argue that when reflection on our own experiences involves a ruminative focus on past events, perspective taking is inhibited, as personal distress, inaccurate perceptions, and negative emotions predominate. By contrast, when individuals work towards developing insight and take a self-compassionate approach to their experiences, understanding of one’s own experiences and those of others, as well as compassion for others, is improved. Ways in which insightful processing of experiences may be increased are discussed, as well as how this approach is useful for understanding important positive psychology concepts such as subjective wellbeing and posttraumatic growth.