Death and debilitating illness can have a significant impact on one's understanding of self, others, and society. When a counseling or clinical psychology graduate student experiences such hardships during the course of his or her clinical training, there can be several potential implications. The stressors of graduate school may exacerbate the emotional responses to an already painful situation. Additionally, clinical skill development can be negatively affected if the student has difficulty acknowledging how hardship influences his or her capacity to be an effective therapist. However, the same tribulations can also help new therapists to realize their inner strength, develop beneficial coping skills, and apply this knowledge when working with clients. Highlighted in this article are three cases of loss and hardship that underscore the importance of supportive clinical supervision, psychological hardiness, humor, and optimism during times of personal crises.Keywords: supervision, grief, training, clinical internship, counselor development The experience of death or debilitating illness is a salient issue for most clinical and counseling psychologists. The presence of death or illness in our own lives can make navigating the day-today demands of life and work difficult. Yet, in the presence of such extraordinary difficulties, we can continue to learn and grow by reconciling and integrating these painful experiences. Considering such issues is a process that not only affects us on a deeply personal level but can also affect the therapeutic work we do. If our own struggles are dealt with appropriately, these experiences can actually make therapy more powerful and dynamic. However, learning to use painful personal experiences with clients/patients is a high-level clinical skill that requires substantial insight, intensive training, and strength-based clinical supervision. Moreover, the clinical training experiences that typify graduate training programs use a developmental process whereby psychologists-in-training treat clients/patients who are appropriate for their level of training and then are able to gradually move on to more complex cases as clinical skills are mastered.An experience with death or debilitating illness at any point during the course of graduate-level clinical training presents both a potential obstacle and a source of tremendous growth, for it forces the novice psychologist to grapple with how personal issues affect his or her clinical work to a degree that is far beyond what is typically expected during the graduate training experience. We propose that it is the responsibility of students to identify how personal grief and loss impacts their clinical skills and to use the emotional pain to become better clinicians. This insight-oriented journey requires dialogue and introspection. These discussions should be facilitated by a supportive supervision process, peer support, and active self-reflection.This article first broadly examines the stressors related to graduate school as well as the gener...