The present study seeks to advance understanding of the interaction of work and family roles. Typically, while the intersection of these domains is established as either being detrimental (i.e. work-family conflict) or beneficial (i.e. work-family enrichment), we argue there is a fundamental issue with timing. Specifically, we offer zigzag working as an approach to understanding how work and family interact. We suggest, rather than roles operating separately (e.g. work to family or family to work), the reality of work is where employees have work and family roles intersecting simultaneously. We believe this provides unique insights for those with dependent responsibilities, representing potentially both a unique challenge and benefit. Our study has two samples (n = 318 employees and n = 373 managers) and we find support for zigzag working at the day-level and while it is positively related to work-family conflict dimensions it is also positively related to happiness. Overall, our paper offers a new lens on work-family border negotiation, providing empirical evidence showing that zigzag working does occur and that it appears to have unique properties. Importantly, zigging and zagging around work and dependents during a typical day represents both positive and negative effects, highlighting a unique occurrence within the literature.