As women on parole and probation transition from correctional facilities to the community, they face many threats to reintegration. Reintegration counsellors offer support to individuals on parole and probation who are re-entering the community. Working closely with a marginalized population places counsellors at risk for burnout and hopelessness. Research indicates that hope can serve as a sustaining and motivating factor when facing difficult working contexts. Further, a large body of research consistently confirms the importance of hope in the human change process, both for clients and clinicians. The current study investigated how reintegration counsellors fostered and maintained hope in their work, including their personal descriptions of hope. Employing Merriam’s (2002) basic interpretive inquiry, five reintegration counsellors participated in semi-structured interviews about their work experiences. Thematic analysis indicated that hope played an important role in these counsellors’ experiences of work and their belief in their clients. The overarching theme of the findings, Maintaining a Hope-Seeking Orientation, elucidates the complexity of maintaining a hope-seeking orientation in the challenging context of reintegration counselling. Specifically, participants in this study were understood to hold a hope-seeking orientation to their worklife that included, viewing life as a journey, maintaining a hopeful perspective, holding ‘down-to-earth’ expectations, and viewing hope-seeking as a learnable skill. Participants associated hope with both motivation and meaning, believing that hope was a necessary ingredient in their work and a resource to combat work-related exhaustion. Implications for counselling include sustaining hope at work through a variety of means, including perspective change.