In pediatric malignancies, when a parent(s) and a child are faced with a life-threatening illness, the decision-making process can be quite complex. The purpose of this study was to describe parents’ experiences and their perspectives of transitions that occurred along the trajectory of their child’s illness. A thematic content analysis was performed to identify patterns in the parents’ experiences through their children’s illness. The sample included seven parents, two fathers and five mothers, whose children had died within the previous 2 years. Three overarching themes emerged: parents’ development of multidimensional trust and parents’ transitional knowing, which both occurred along the parents’ journeys of hope. In healthcare, the knowledge gained from these parents’ experiences is beneficial to practitioners to facilitate the best journey possible.