Family business studies exploring intergenerational dynamics often suggest that the offspring of business-owning parents typically follow a career path within the parent’s business or start their own ventures. While this literature is extensive, it typically treats offspring as a homogeneous group, overlooking potential personality differences. In this study, we address this gap by drawing on birth order theory to examine the differences in the early career choices to join and leave the parent’s business among siblings of business-owning parents. Using a unique sample of offspring in Sweden, we employ hazard models and show that later-borns are more likely to join their parent’s business compared to earlier-born siblings during their early career stages. However, when the offspring join the parent’s business, later-borns are also more likely to leave the parent’s business unless the parent’s business is underperforming.