In 2010, "Intervention in School and Clinic" undertook a project to interview "giants" in the fields of learning disabilities and emotional/behavioral disabilities. The purpose of the interviews was to document the perspectives and reflections of leaders who had contributed to their respective fields over several decades (i.e., in most instances spanning back to the 1950s or 1960s) in order to provide a historical context for current and future professionals to envision a successful future. Contributors were asked to discuss their careers and their historical perspectives about their fields and to focus on areas of success and struggles. Interviews from 29 contributors were reviewed for this article, which focuses on concerns and reasons for optimism in both fields. Themes across interviews are described, along with highlights of contributors' observations.