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Research on job precarity and job instability have largely neglected the labor market trajectories in which these employment and non-employment situations are experienced. This study addresses the mechanisms of volatility and precarity in observed work histories of labor market entrants using the National Longitudinal Survey of Youth of 1997. Several ideal-typical post-education pathways are modeled for respondents entering the labor force between 1997 and 2010, with varying indicators and degrees of precarity. A series of predictive models indicate that women, racial-ethnic minorities, and lower social class labor market entrants are significantly more likely to be exposed to the most precarious early careers. Moreover, leaving the educational system with a completed associate’s, bachelor’s, or post-graduate degree is protective of experiencing the most unstable types of career pattern. While adjusting for these individual-level background and education variables, the findings also reveal a form of “scarring” as regional unemployment level is a significant macro-economic predictor of experiencing a more hostile and turbulent early career. These pathways lead to considerable earnings penalties 5 years after labor market entry.