Limited qualitative research exists on the experiences of outdoor education leaders. The purpose of this phenomenological study was to explore the job-related experiences of outdoor education leaders within and outside the workplace. Five participants who had experience as outdoor education leaders completed in-depth, one-on-one interviews about their experiences. Transcripts of the interviews were coded and analyzed. Five common theme clusters about leader experiences emerged from the data: life cycle, relationships, transition, leadership, and health and wellness. This study is an important contribution to the overall outdoor education literature as it provides an opportunity to add the voices of outdoor education leaders to the quantitative literature currently available.