The keystone of the blindness rehabilitation process is the emotional adjustment to blindness. Such an adjustment involves building confidence and self-efficacy, comfort with one’s identity as a blind person, feelings of first-class status in society, and an overall willingness to greet the world with pride. Students bring with them to training a culmination of life experiences, including previous employment experiences. This article tells stories of a handful of students, whose previous employment experiences had varied impacts on their emotional adjustment to blindness.