This commentary considers the psychic impact of analytic work as we engage with the all-too-real, potentially overwhelming aspects of living and dying. I use Kaplan’s narrative about his patient’s illness and death to think about the strain caused by the analyst’s need to contain experience and maintain boundaries, when such requirements conflict with the analyst’s personal need for relational engagement in the context of grieving. I suggest that the analytic community has both the potential and obligation to create holding environments for its members that help sustain them as they metabolize experiences like those described by Kaplan.