This chapter narrative traces the roots of Rhona S. Weinstein's development as a community psychologist just as the field was beginning and emerging interests in the dynamics of negative self-fulfilling prophecies as a source of educational inequality. Critical personal influences included being the child of immigrant parents living as a Jewish minority in French Quebec, developmental opportunities provided by a unique summer camp setting, and obstacles encountered as a woman aspiring to an academic career. Rhona S. Weinstein's graduate training in clinical and community psychology took place both at McGill University and Yale University. She was greatly influenced by two significant mentors, the late M. Sam Rabinovitch and Seymour B. Sarason, as well as their visionary clinical settings, the McGill-Children's Hospital Learning Centre and the Yale Psycho-Educational Clinic, respectively. From both mentors, she developed a passion for understanding and creating social settings that enhance human development.