This paper addresses the varied and often contradictory emotions that accompany living with multiple disabilities. The author incorporates his personal experiences (e.g., as a middle school teacher, as a doctoral student, and as a researcher) with disability as he attempts to reflect upon his perceptions of the world as a disabled individual. In particular, he expounds on the notion that segregation be considered and re-conceptualized as a strategy, recourse, or even as a retreat of sorts from a profound level of ableism that is perpetuated within an unsupportive and unforgiving society. But in addition, to further problematize the concept of segregation, the author examines how some of his students have dealt with their own segregation in school.