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The bulk of teacher attrition literature pointed to job satisfaction and working conditions as reasons teachers leave their building or the profession (Cha & Cohen-Vogel, 2011; Clotfelter et al., 2008; Gardner, 2010; Grissom & Keiser, 2011; Horng, 2009; Johnson et al., 2012; Loeb et al., 2005). The purpose of this qualitative study was to investigate factors teachers and administrators perceive to influence teacher career decisions. Semi-structured interviews were conducted with 14 teachers and nine administrators in nine districts across six states. Teachers and administrators believed work environment and social conditions impacted teacher attrition and retention, but administrators and teachers had disparate views in their descriptions of these factors.