We draw on generative mechanisms to study how managers cope with a tension inherent in flexible work: the opportunity to determine when, where, and how to work can give employees the opportunity to flexibly address their personal and professional needs, while simultaneously placing new demands for structuring their activities and relationships. Drawing on a longitudinal case of a Danish pharmaceutical company and its transformation towards flexible work, we analyze how middle managers balance out flexibility and structure in a way to achieve an unstable equilibrium of the work practices that unleashes adaptability by generating continuous change. We discuss how the identified managerial practices reconnect two contradictory and yet complementary patterns of individualization and socialization, in a way to reduce the inertia of existing structures while also providing employees with the conditions to safely experiment with new ways of working.