The paper explores and assesses, through quantitative research and data analytics models, as to how socio-demographic profile, work, and family responsibilities may be associated with motivational level and educational attainment or course completion rate of learners enrolled in the undergraduate courses of Indira Gandhi National Open University (IGNOU), the largest distance education University in India. The models, generated using classification tree methods, show that employed and married learners perform better in distance education. Assessing underlying reasons, an empirical study using the Keller's ARCS (Attention, Relevance, Confidence, Satisfaction) framework reveals that course relevance and level of satisfaction while pursuing the study are the two most important factors in keeping distance learners motivated and achieving better academic performance. The quantitative survey also shows that the employed learners have significantly higher levels of motivation, while the others may have difficulty in maintaining their self-motivation during distance learning. The findings are important for Open and Distance Learning (ODL) institutions to understand students' varied expectations of the distance learning experience and the consequences on their motivation levels and academic performances when these expectations are not met.