The right to request for flexible working legislation (sections 80F–80I, Employment Rights Act 1996) attempts to reconcile the demands of employees’ jobs with those in their personal lives. It does this by detailing a procedure whereby employees can request an adjustment to the amount of time spent working and the timing of those hours. The duration of work time and the timing of work time are indeed critical factors in employees’ ability to manage their work and personal lives. But it is questionable whether these purely quantitative features of work time capture the temporal issues that feed into the work–personal life problem. This article reviews the temporal assumptions implicit in the flexible working legislation and critically evaluates them in light of broader theoretical perspectives on time. In particular, it highlights the role of temporal subjectivities, which employees develop at work, and the relationship of these to new emerging patterns of work. A case study focusing on software engineers and managers is presented to demonstrate these theoretical viewpoints in practice. The article concludes that the legislation’s failure to address the social and collective nature of time is problematic, and that this hinders real progress in achieving flexible working.