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The literature on precarious and insecure work rarely examines how workers with jobs in large bureaucratic firms experience insecurity. Current theories suggest two approaches. First, workers might focus on their individual occupation and detach their commitment from firms that no longer reciprocate long-term commitments. Second, employees might respond with increased organizational commitment because leaving an employer creates risks of uncertainty. Based on in-depth interviews with 22 financial services professionals, this paper refines our understanding of when workers focus on intra-organizational career development. This happens when large firms offer opportunities for advancement and foster loyalty. I develop the terms spiral staircase and serial monogamy career. A spiral staircase career results when workers take entrepreneurial approaches to advancement that include lateral job changes and vertical promotions within a firm. When the local labor market has multiple firms in their sector, career advancement may take an intermediate form, in which workers spend medium-to-long-term stints with multiple organizations. I call this the serial monogamy career. My research shows how sector characteristics and geography can impact worker commitment and mobility in insecure environments.