The objective of this psychoanalytic case study was to examine what comprises the vicissitudes of hope in five seasoned clinicians over the course of their professional lives. The data was obtained through several interviews with each participant. The data was first analyzed by looking at each individual narrative for the resonant themes that emerged for each participant. The findings then were compared across individual narratives to construct a more detailed psychoanalytic understanding of the meaning of the vicissitudes of hope for these participants. The overarching finding is that the sense of hope of the participants stemmed from a larger and more expansive experience of the self. The state of the self develops over time through the integration of experiences, of which professional experience is one facet. The participants also described a developmental trajectory in terms of the establishment of professional self-esteem and the expansion of professional hope that occurred over time. The vicissitudes of hope in the countertransference was found to be an inevitable and valuable part of the treatment process for the participants. These countertransference expressions of hope were forms of communication from the patient, the psychoanalytic clinicians studied, or how they and their patients come together that could be used to facilitate the treatment or deepen self-understanding of the participants. The participants actively regulated their hope over time to maintain hopefulness through an ongoing process of self-expansion and self-protection.