How are universities conceptualizing and mobilizing well-being on their campuses? Our qualitative inquiry explores growing challenges of addressing educator mental health and well-being on university campuses. As part of an effort to increase awareness and support around issues of mental health and well-being at one university, a campus-wide strategy was announced in 2015. This article follows up on that strategy to understand how university educators come to identify with well-being. We collected composite anonymized data from a World Café discussion with a range of educators. The goals of the World Café discussion were to: (a) highlight campus-wide conversations on educator mental health and well-being; (b) explore multiple perspectives and make sense of how educators experience mental health and well-being; (c) create a space to nurture meaningful relationships; (d) inform the continued development of research, strategies, and policies to support educator mental health and well-being. We share four themes that emerged from the discussions to consider well-being and life in the university: (a) affective, relational and holistic aspects "in search of well-being"; (b) working through the messiness of well-being: risks and vulnerabilities; (c) inviting people into a culture of well-being; and (d) the role of leaders in moving beyond policy towards enactment.