This paper analyzes qualitative interview data with a sample of 41 executive directors of human services nonprofits to discover why people become executive directors, what career paths they follow, and how well these career paths prepare them for the job. All became executive directors because they wanted to help others.Less important motivations included influencing how programs operate, wanting to be successful, and wanting a higher salary. The paper proposes a new typology of career paths: founders who started their own nonprofit, fillers from the board or a volunteer position, planners who actively pursued an executive position for years, and risers who worked their way up through the ranks and found that executive director was the next step. Most considered themselves well prepared at the time they took on the position, and there was little difference among the four types of career paths in the level of perceived preparedness. The findings suggest that nonprofit organizations should pay more attention to training leaders who rise up through the ranks, and that management education programs can assist in this mid-career training. Future research should expand the examination of career paths and preparedness to a large and nationally representative survey.