Do capital and skills endowments drive occupational choice and poverty among the world’s poorest? To answer this question we provide evidence from a large scale and long term randomized control trial of a program that simultaneously provides assets and training to the poorest women in rural Bangladesh. The evaluation tracks 7000 eligible women over four years, as well as 16000 households from other wealth classes in the same communities. We find the program transforms the occupational choices of the poor: treated women spend 92% more hours in self-employment activities, and 26% less hours in insecure/seasonal wage employment. This shift is associated with a 38% increase in earnings, and the share of eligibles living below the poverty line drops by 9pp. The eligible women, who were largely assetless and illiterate agricultural laborers at baseline, overtake women in near-poor households and begin to close the gap with middle class women on dimensions such as occupational choice, regularity of earnings, household per capita expenditure and happiness. Inculcating basic entrepreneurship, where the most disadvantaged women take on business activities which hitherto had been the preserve of non-poor women, is shown to be a powerful means of transforming the economic lives of the poor through changes in occupational activity.