Youth today spend years moving in and out of different education and employment statuses until they settle into stable employment. This 14-year Canadian longitudinal study reveals how month-to-month fluctuations in employment and educational statuses from age 19 to 25 predict employment success at age 32. Early employment instability was linked to lower income at age 32 and, among men, to lower occupational status and career satisfaction. However, for those who had made at least one career change, employment fluctuation had a positive effect on income and career satisfaction. Greater fluctuation in educational status was associated with higher occupational status at age 32. In general, labor market instability in the early 20s might best be described as floundering, while educational status changes more often reflect exploring.