Time-management technologies and their adoption into daily working life have been discussed as solutions for managing individual productivity and as problems that intensify individualised productivity, enhance the norms of busyness and disconnect colleagues from one another. However, drawing on the case study of a company that implemented a four-day workweek, this paper argues that this is not always so. In our case company, a digital marketing agency, the Pomodoro time-management tool led to the personalisation of productivity and instances of collective working towards better work-life balance. We end the paper by suggesting that this fruitful adoption of time-management habits can be understood through John Dewey's notion of habit. Deweyan habit allows us to know how time-management habits are plastic and open to change while always being part of a material and social assemblage. We argue that these two features explain why time-management tools might lead to personalising productivity and enhanced neoliberal self-discipline. At the same time, these features point to how time-management habits under the right circumstances can be part of cooperation and better work-life balance.