The study of childhood bereavement is a crucial domain of developmental psychology as it explores the impact of loss on attachment, personality, and behavior in children. Through the lens of a personal narrative, this paper examines the author's own experiences of grief from infancy to adolescence, integrating the work of developmental theorists including Anna Freud and Martha Wolfstein. Further, it integrates contemporary perspectives on childhood bereavement found at "Judi's House," a grief care organization based in Denver, Colorado. These contributions are explored through interviews with senior clinicians at "Judi's House," serving ultimately to bridge the gap between psychoanalytic theory and clinical applications. Through this integration, this work highlights that young children, even at a preverbal age, experience and express grief throughout multiple stages. This includes disrupted feeding patterns and modes of attachment in infancy, as well as feelings of isolation and fractured identity during adolescence. As such, this paper underscores the importance of tailored therapeutic interventions, emphasizing the importance of family systems and attachment theories in fostering healthy emotional adjustments. This lens offers a human-forward perspective, validating the lived experience of individuals while highlighting the importance of the integration of personal insight with academic and clinical discourses to advance our understanding of grief in development.  This paper calls for longitudinal efforts for understanding the effects of parental loss, whilst advocating for a compassionate, nuanced approach to grief support.