What is the role of an evaluator (King & Stevahn, 2002), and how far dare an evaluator go toward saving the world (Patton, 2004, 2021)? Despite rich knowledge and well-honed skill sets, evaluators often struggle to articulate their expertise and career goals. Evaluators hold various roles (e.g., as internal or external evaluators) in myriad settings (e.g., within organizations, university-based evaluation centers, academia, evaluation firms, or solo shops). It is no surprise that navigating this diversity of career options can feel overwhelming. Servant leadership is a helpful lens for mapping a career arc that will make a difference in the spaces that matter most. In this session, we will use servant leadership to make sense of our shared professional identity and praxis, and we will walk through a project and some follow-up design thinking exercises to consider a career pathway that advances evaluation as leadership.