The chronically high rate of special educator attrition across U.S. schools creates a dilemma for educational leaders because special educators provide direct services to students with special needs. Attrition exacerbates already high special educator shortages reported in most districts, and nearly one million schoolchildren with disabilities receive fewer or no services as a result. Given this dilemma, the purpose of this article is to advance a research-based model to provide guidance for school administrators and researchers. Adapted from previous conceptual models and perspectives, the proposed model combines five thematic, contributing factors and a sixth, relatively understudied factor, workplace decision-making, to illustrate factor effects on special educators’ perceptions of job satisfaction and, ultimately, career decisions.