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This theoretical paper takes an aesthetic view of leadership to investigate the leadership needed to make cities more resilient. It sees an urban system as a complex, evolving entity constantly crossed by a variety of inflows and outflows connecting it to other systems, while its constituent elements are in interaction between themselves. Three fundamental dispositions in the aesthetic literature, sensibility, reflexivity and wisdom, seem crucial to ensure that leaders anticipate and cope with a variety of shocks, taking advantage of the opportunities to transform and learn. These dispositions are found fundamental to urban resilience. The paper also discusses the implications for preparation and learning.