The understanding of livelihoods in an economy dominated by informality can benefit considerably from correlations between macro data on employment and detailed studies of ‘work’ and ‘non work’ in select communities. As a modest contribution in this direction, this paper charts the changing profile of myriad occupations, from about the 1930s, in a village called Dhantala (in Meerut, western Uttar Pradesh) and a slum called Aradhaknagar (in east Delhi) through local records, oral history, focus group discussions, and personal interviews. Besides throwing light on the changing patterns of officially acknowledged and unacknowledged occupations in a rural and an urban setting over eight decades, the paper identifies factors that support or constrain economic mobility among the subjects after comparing studied employment trends with those in other micro studies as also national data sets for the said period. The paper highlights changing proportions of students, homemakers, home based workers, employers, entrepreneurs, ‘illegal’ professions, middlemen, activists and ‘multi taskers’ etc. along with standard occupational categories like agriculturists, skilled and unskilled labour and salaried workers in both locations. The study shows that among the five broad phases of policy regimes in the country since the late colonial era, it is the period of economic liberalisation that benefitted the workforce the most in the said locations, contrary to the general left anticipation of pauperisation and proletarianistion growing with liberalisation. The paper concludes with a list of policy imperatives and some pointers for future research in this light.