This brief presents findings from an analysis of young adults in the US who successfully moved beyond initial career pathway steps to attain middle-skill jobs. Using the 1997 National Longitudinal Survey of Youth, we examine the postsecondary and employment trajectories of the young adults through their early thirties who earn more than one postsecondary credential, compared to those who don't. We also explore the challenges young adults may face in advancing their schooling and careers beyond a first credential. The brief concludes with implications for career pathways relevant to policymakers and practitioners supporting young adults' advancement toward middle-skill jobs.