Ongoing trends towards more flexible work arrangements (FWA) have been accelerated by the Covid-19 crisis. Whilst research has shown the overall benefits FWA can have, limited research has explored whether use and benefits of FWA are equal across differentiated organisational contexts and genders. We suggest that individuals working in their family’s business face less organizational constraints that typically hinder employees from taking advantage of FWA. It could be suggested that these workers may make higher use of FWA than individuals in regular employment because of their entrepreneurial status and nepotistic privileges. Consequently, the aim of this paper is to explore if family members working in their family’s business, work under favourable boundary conditions which enable them to more freely make use of and benefit from FWAs. Utilising representative data from the German Family Panel (pairfam), our comparative analysis based on propensity score matching, suggests that family members working in their family’s business (N = 337) do make greater use of FWA than those in regular employment. Counter to common assumptions, the findings reveal that FWA leads to higher workloads for owner-managers but not for family employees. Furthermore, families working in their business show no differences in how they divide household tasks compared to regular employed families–yet they perceive that division to be fairer. This study extends knowledge by introducing family ownership and kinship ties as important boundary conditions to existing theories on FWA, such as life-course theory. It also provides new insights into the commonly assumed consequences of FWA use.