Parents and educators are expected under IDEIA to work together on educational decision-making for students with disabilities. While collegial relationships in this process are intended, partnerships are not always formed because both parties can struggle to understand each other's perspective. Parents may hold their view, while educators may have another. What happens when parents are also educators? Can stronger partnerships be forged when parent-educators exist in both roles? This paper presents the cases of three parent-educators and their struggles in advocating for their own children with disabilities. From those experiences we provide parents and educators lessons to carry forward as well as resources for improving parent-school relationships in special education.