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Career paths in student affairs generally follow a conventional course: graduate degree to entrylevel position, progressive responsibility until middle management (Renn, 2004; Twombly, 1990), and then a decision to remain, work to advance, or change fields (Mills, 2007; Rosser & Javinar, 2003). This middle management, or director/dean–level career stage has been considered a bottleneck (Belch & Strange, 1995), particularly for women (Jones & Komives, 2001). Research has also shown advancement is increasingly difficult without a terminal degree (Howard-Hamilton & Hyman, 2009). Studies on factors influencing career advancement have enlightened qualitative considerations individuals face when moving up (Jones & Komives, 2001; Marshall, 2009); however, few studies have quantitatively shown which positions and/or experiences lead to the most reliable paths to becoming a senior student affairs …