Within the context of increasing precarity in the labor market, this study seeks to understand how young, racialized and economically disadvantaged jobseekers make sense of opportunity. While studies show that American white-collar workers embody self-blame instead of structural critique in their assessments of the modern labor market, we show the complicated, sometimes contradictory ways Black disadvantaged jobseekers think about unemployment and the broader economic landscape. Using 66 in-depth interviews with Black sub-baccalaureate job seekers, we expose a complicated picture of how these workers understand the modern economy. Contrary to previous studies, we find respondents who are deeply critical of social structures, calling out schools and educational systems as failing Black communities. At the same time, in other domains, respondents do showcase deep self-blame and even a deeper, racialized group-blame in their viewpoints on job availability and unemployment. Finally, in simultaneous system-critique and self-affirmation rather than blame, respondents are extremely enthusiastic about what they see as the next frontier of social mobility: namely, online entrepreneurship. In considering this unsettled approach, we understand how race, class, and extended-periods of unemployment and marginalization influences the subjective experiences of jobseekers, how self-blame and system-blame can co-exist, and where opportunities and challenges to Black worker power lie.