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Supported by media technologies, today’s employees can increasingly decide when and where to work. The present study examines positive and negative aspects of this temporal and spatial flexibility, and the perceptions of control in these situations based on propositions of self-determination theory. Using an exploratory approach, we conducted semi-structured interviews with 45 working digital natives. Participants described positive and negative situations separately for temporal and spatial flexibility and rated the extent to which they felt autonomous and externally controlled. Situations appraised positively were best described by decision latitude, while negatively evaluated ones were best described by work–nonwork conflict. Positive situations were perceived as autonomous rather than externally controlled; negative situations were rated as autonomously and externally controlled to a similar extent.