The Fessler and Christensen (1992) teacher career cycle model provides the theoretical framework for this case study incorporating a narrative design nested within a larger research project examining six teachers' journey across the career cycle (Woods & Earls, 1995; Woods & Lynn, 2001). The current case study sought to gain a greater understanding of why one teacher, Patsy, was unable to negotiate environmental hurdles that are commonplace in physical education and how these factors were being negotiated as a classroom teacher. Data sources included: seven interviews with the participant, multiple interviews with her principals, spouse, and three former university teacher educators, field notes from live lesson observations, and related documents. An interpretative framework was used to understand the perceptions and meanings Patsy gave to her experiences and revealed that she reported being both positively and negatively affected by most of the personal and organizational environmental factors in the teacher career cycle model. Viewing Patsy's teaching career through the lens of the career cycle provides insight into areas of change necessary to motivate and retain quality physical education teachers. (Contains 2 tables and 1 figure.)