We introduce this chapter by describing the context of our work and the various ways that systemic ideas have affected it. Three systemic ideas inform our transition interventions: “side-step autonomy”, “keep multiple realities alive”, and “expect engagement and disengagement”. These ideas organize the structure of subsequent sections. We summarize the research literature that supports and explains the ideas, some of which may be unfamiliar to professionals working in intellectual disability services. Vignettes illustrate the issues and give some ideas of how we engaged with families or systems seen within our clinic. We conclude by pulling together our thoughts about this work, including some personal reflections.