Despite the recognition of labour as important for productivity and sustainability in rural economies, its constraints have often been neglected in district studies. This paper has conducted labour-related challenges in agriculture and micro enterprises at the micro level for the district of Chittorgarh, Rajasthan. From a sample of 385 respondents, the primary data for this study has been gathered and seasonal unemployment, skill mismatches, wage insecurity, and weak “foundations” are highlighted as the key obstacles. The data discloses these obstacles are not homogenous in character, for they are differentiated by gender, occupational sectors, and education. EFA and reliability provide evidence for the multidimensionality of the labour challenges, and the integration of ANOVA and regression analyses answer the productivity decline and local economic recalcitrance. The paper ends by drawing attention to the need for more decentralized and targeted skill development, rural employment, and innovation to close the gaps identified. This study adds primary information to the literature of labour economics from one of India's neglected agricultural districts.