This study investigates the factors that draw working professionals towards distance education programs, and the factors that sustain their distance education experience. The study is conducted in difficult terrains of Uttarakhand, a hilly state in India which helps us investigate the phenomenon in difficult geographies. Through interviews of ten working professionals in this difficult geography these factors are deduced and a conceptual model is then developed. We also tried to find theoretical linkages to the factors identified. The findings are of value to distance educators and students alike. © 2015: Jatin Pandey, Manjari Singh, and Nova Southeastern University.