This ethnographic study investigates the experiences of those learning tailoring and trading in Freetown, Sierra Leone via apprenticeships, other on-the-job training or Technical and Vocational Education and Training programs (TVET). I examine these forms of occupational training by investigating the practices underway, how knowledge transmission occurs, as well as why learners engage with and what they get out of these activities. I consider how the job learners utilise occupational training as a manner of increasing social, cultural and economic capital in Bourdieu's sense of those terms to navigate the urban labour market.     I find that the learners aspire fundamentally to social mobility and a sense of self-worth. To achieve this, they use four main tactics: flexibility, reframing, co-operation and diligence. However, I find all tactics are developed in response to greatly circumscribed opportunities to obtain a good and stable income, and increased social status, due to structural inequality. Local political neoliberal discourse on youth unemployment emphasising diligence, belies these inequities and the limited ways in which social mobility is within the individual’s control. Hence, I argue, a focus on training without addressing structural inequality is inadequate.     As the training usually does not lead to paid and reliable employment, I argue it serves more fundamentally as a form of moral education and a vehicle for personal and social development. I argue it helps develop certain personal moral traits and alleviate society's concern about immoral "idle youth". Further, that it helps develop what I term resilience capital; that is, the hard-working and stubborn disposition developed by reframing previous experiences of adversity, which may later assist the individual in acquiring other forms of capital.     Although not its main focus, this study also seeks to contribute to academic scholarship through developing our understanding of knowledge transmission. I find that the process of knowledge transmission is fundamentally social and shaped by hierarchy, subjective positions of power, the inculcation of moral and ethical values, and more dependent for success on various forms of capital than it might at first appear.