Hustling as a concept has travelled through the global soundscapes of impoverished, neglected, racialized and otherwise marginalized urban settings. The widespread rearticulation of the term ‘hustling’ in a broad range of urban languages reveals that its use in particular forms of Black Atlantic music cultures speaks to shared experiences worldwide. Simultaneously, it shows the flexibility of this term to acquire new and unfolding meanings. This article focuses on the modes in which poor young men in Nairobi (re)deploy, translate and practise hustling to fit immediate circumstances and imagine possible futures, and on the meanings these men produce in the process. I argue that interrogating hustling as a practice provides insights into gendered experiences of urban life worlds in the underserved and highly policed areas of Nairobi, which may tentatively resonate with young men in comparable positions worldwide. I specifically examine how positions of (junior) manhood are configured by localized hustling practices to elucidate how navigating fear and hope, while facing extreme uncertainty, simultaneously defines and undermines their sense of manhood.