This study examines the experiences, over 6 years, of 73 managers and high level professionals who reduced their workloads to achieve more sustainable career and family outcomes. We compared personal, family, and career success outcomes for people who maintained reduced loads over time with those who went back to full time work, and we found few differences, except for more promotions for the full-timers. To further understand our results, we identified four groups with all four possible combinations of extreme success (either very high or very low) on our two measures of success, objective and subjective. The groups were labeled Aligned Achievers, Alienated Achievers, Happy Part Timers, and Hard Luck Strivers. Subsequent qualitative analysis of group members’ reflections on the meaning of career success as well as the occurrence of significant life events helped explain the variation in their success in sustaining desired career and life arrangements over time.