Transitional diabetes self-management (DSM) for children and their families is complicated. This article was undertaken to provide an exemplar of DSM strategies used by one family that were based on developmental milestones from preschool through college age. Two brothers who were both diagnosed with type 1 diabetes before the age of 2 years reflected on how their parents began a DSM navigation process during their early preschool years. Personal strategies and recommendations successfully resulted in both youths transitioning to college. With the parents serving as DSM coaches to the boys, an interdependent relationship was built. Key recommendations include 1) starting early, 2) being consistent and flexible, 3) using "invisible actions" and "what ifs," 4) incorporating technology and community resources into DSM, and 5) building confidence with shared problem-solving.