The neo-liberal reforms are advocated and lauded for strengthening efficiency, creating white-collar professionals in the private sector, and expanding job opportunities in the market. The transformations introduced by the new economic policies in the free-market economy are simultaneously criticised for surging casualisation of paid work. Youths are one of the key demographic groups to have drawn significant attention in developing countries to gauge the consequences of the transformed economy. The conceptual theorisation of “waiting,” “timepass,” “precarity,” or “neo-liberal subjectivity” shows how youths negotiate to overcome their precarious status in the contemporary labour market and reconfigure the meaning attached to the category of youth. Continuing the discussion on intergenerational mobility, the chapter primarily attends to the occupational aspirations and engagement of youths from different caste groups.