Employees in the outdoor recreation sector account for 3.2% of the U.S. workforce, contributing to over $1.1T in national economic output. As awareness of the sector's economic strength has grown, interest in promoting outdoor recreation careers has expanded. Research on outdoor recreation careers has not kept pace with workforce development initiatives, however, and existing data and research reports provide only aggregate figures that neither reflect the new employment landscape nor track how careers are navigated by the people who occupy them. This article reports on an interview study of 15 established outdoor recreation professionals in executive or management positions to gain insights into career trajectories in outdoor recreation. Their narrative responses were assessed using the Psychology of Working Theory, a career counseling framework organized around the concept of decent work. Findings are presented along with points for outdoor recreation career advocates to consider in future research and workforce development initiatives.