Much has been written about the challenges of effective transition planning (e.g., Cavendish & Connor, 2018; Landmark etal., 2007; Luft, 2015). In this article, ways to mitigate some of these common challenges are provided, including low or passive student and family involvement, unresponsiveness to family culture, poor communication between the educators and the family, limited parental knowledge of transition services, and inadequate school transition services. Yet, overcoming these challenges also requires commitment and dedication to educating not just students but families who can shape the future for all individuals with disabilities. When educators and families take a future-oriented perspective, they can create seamless pathways toward a life of independence and full participation for individuals with disabilities in today's larger world.