Despite extensive research documenting associations between adverse early-life experiences and negative outcomes in later life, little is known about how adverse experiences in late adolescence relate to young adulthood disadvantages. This study examines the role of adverse experiences during late adolescence on young adults’ education and work trajectories in Taiwan. Drawing theories and research from human development and sociology, the study links indicators of disadvantages in young adulthood to measures of adverse experiences in late adolescence using data from the Taiwan Youth Project data (n = 1221; median ages 18, 20, and 22; 49.4% female). The analysis found that running away from home was associated with instability in education or employment and that having cumulative adverse experiences was associated with graduating with debt and instability in education or employment. Some associations were explained by financial pressure, however, taken together, the findings suggest that certain adverse experiences in late adolescence have a significant impact on disadvantaged education and work trajectories in young adulthood.