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A large body of research has shown that the returns to four-year college degrees are very high, even (and sometimes especially) for low-income students. Nevertheless, pursuing “some college” without receiving a credential or degree is now the modal outcome for high school graduates who begin higher education. Despite its rapid growth, our knowledge about the population of students with “some college” remains limited. Why do so many young adults who begin college leave without a credential? And why are increasing numbers of low-income and minority youth turning to for-profit trade schools with high costs and dubious returns? To address these questions, we examine the postsecondary educational choices and decision-making processes of 150 low-income youth in Baltimore. Drawing on narrative interviews, we find that many of our respondents factored an expectation of shock-induced derailment into their educational investments and postsecondary decision-making. Youth perceived and anticipated high probability of derailments stemming from neighborhood violence, ill family members, and unanticipated caretaking responsibilities, among others. Factoring this anticipation of shocks into their postsecondary decision-making process, these youth opted to enroll in short-term occupational certificate programs or for-profit postsecondary institutions which they felt were less likely than longer-term degree programs to be interrupted by unforeseen adverse life events. While previous research has contended that students’ seemingly “bad” educational choices are due to financial constraints, lack of support, and poor information about costs and returns, we argue that disadvantaged youth approach postsecondary decisions with a seemingly rational consideration of the perceived likelihood of shock-induced derailment.