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Research of teacher dissatisfaction often focus on the perspectives of novice or former teachers. Rather, in a secondary analysis of interview data, collected for a broader inquiry of urban Title I high school teachers, we examined mid-career teachers’ expressions of workplace dissatisfaction and what motivated/moderated their turnover intentions. Using Johnson’s schools as workplaces framework (1990), we found that teachers’ job persistence was most challenged when structures that reified teacher specialization and autonomy were disrupted. Teachers committed acts of defiance, individual (e.g., transferring schools) and collective (e.g., designing new schools; joining the teacher’s union), to remain in the profession. We revised Johnson’s model to illuminate how to strengthen morale and resolve workplace issues to retain teachers in urban Title I schools.