While much is known about what contributes to teacher attrition, there is less research on those who leave teaching positions to work as a union representative. The purpose of this study was to explore how three teacher union representatives frame their experiences with mobility, leadership, and advocacy in education. The research question was: How do former teachers enter and perform the role of teacher union representative? The sub-level questions were: a) How do they story their transition from teaching students to representing teachers? b) How do they frame the responsibility of teacher unions and teacher union representatives to advocate? Data were collected using semi-structured interviews, examined for story elements and plot, and interpreted using a framework on working conditions (House, 1981). The major theme was that educators left their positions as teachers in response to emotional, instrumental, informational and appraisal factors, namely discrepancies between what they wanted and what was provided as part of their working conditions. The findings are: 1) Working conditions pushed educators to pursue union leadership, 2) Professional responsibilities of a Union Representative varied 3) Issues for which Union Representatives advocated involved the improvement of working conditions. The findings are discussed, as are implications for revising the theoretical framework for use in future studies with regard to the fluidity of the advocacy process, and the long-term sustainability of American Educational Unions. Recommended are longitudinal studies to determine how teacher union representatives’ frame their narratives of working conditions and advocacy in response to changes in legislation, including union decertification, over time. Keywords: advocacy, union representation, working conditions, administrators, teacher’s rights, framing and professional mobility.