In this paper, two psychotherapy trainees who lost a parental figure to cancer during graduate training discuss this shared experience. We explore the literature on bereavement and how loss has been tied to psychotherapist growth while interweaving the ways in which the literature coincides with our experience. Within this exploration, we center our experience around the wounded healer literature. We also highlight areas of growth and challenge and narrow in on what others may take away from our lived experience. Specifically, we discuss cultural values in the context of bereavement, bridging the personal and professional self with colleagues and supervisors, feelings of relief and guilt, psychotherapist escapism, appropriate self-disclosure, and unexpected takeaways. To conclude, we tie together the ways in which our experience of loss impacted our growth as psychotherapists. (PsycINFO Database Record (c) 2019 APA, all rights reserved)