Finding fit between work and family responsibilities is challenging for parents, especially when raising a child with mental health difficulties. The purpose of this study was to investigate the relationship of children’s problematic behaviors to maternal employment and difficulty combining work and family obligations. Data were analyzed from 174 mothers parenting a child with a diagnosis of attention deficit hyperactivity disorder who completed child problem behavior (child behavior checklist), family functioning, and employment measures at baseline and 12 months later. Results from logistic regression analysis indicated that children’s problematic behaviors predicted maternal employment. Structural equation modeling showed that children’s higher baseline scores on the child behavior checklist internalizing scale were related to difficulty combining work and family at 12 months, even after controlling for difficulty of combining work and family at baseline. Children’s externalizing scores were not found to predict difficulty combining work and family responsibilities. Further analysis did not confirm mediation between children’s externalizing and internalizing behaviors, family conflict, and difficulty combining work and family. Given these results, service providers need to more comprehensively address the intersection of children’s mental health difficulties and work–family fit in order to better support caregivers as parents and employees.