Using a constructivist narrative inquiry approach, this manuscript examined the stories of 10 early-career student affairs professionals to understand how they made sense of their experiences of free speech events at public higher education institutions. Each professional participated in three semi-structured interviews to provide insight on their roles and responsibilities relative to free speech events. Findings highlighted four main characteristics of early-career professionals' sensemaking: (a) referencing educational experiences, (b) wrestling with identity, (c) keeping in mind contexts, and (d) incorporating lessons from supervisors and mentors. As a result of their sensemaking, participants viewed themselves as advocates and bridge-builders for free speech events. However, potential negative ramifications, primarily the loss of employment, tempered the desire to actualize these roles. Implications for research and practice are offered.