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Integrative strategic management for urban regeneration involves reconciling conflicting demands and translating abstract concepts into concrete actions. This article examines how public-sector strategists address these dilemmas by developing a dynamic perspective that helps in understanding how they ‘strategize’. This perspective was applied to two urban regeneration projects in Gothenburg (Sweden) and Antwerp (Belgium). Our findings illustrate how actors strategize at different locations and times, putting middle-management strategists, in particular, on the horns of a dilemma. Acting quickly through establishing experimentation spaces could result in innovative outcomes, but politicians and local residents may feel bypassed; however, waiting until strategic visions are translated into detailed actions may eventually result in no action at all. This article helps us understand the disconnect between planning …