Graduate training in psychotherapy can be an exciting but challenging time in terms of both personal and professional development. This developmental trajectory can be significantly altered by challenging life experiences. The impacts of such experiences on professional development in psychotherapy trainees is not often discussed in the literature. Through this article, we hope to generate a much-needed conversation about the experiences of graduate trainees who encounter challenging life experiences, and the importance of supervision in facilitating professional and personal growth. To do this, we present vignettes inspired by the actual experiences of early career trainees and tie these stories to larger issues related to professional development. (PsycINFO Database Record (c) 2019 APA, all rights reserved)