Numerous factors have been posited to promote desistance from criminal offending in late adolescence and early adulthood. Research in this area has generally examined these factors for their impact on offending for a period shortly after the occurrence or shifts in possible predictors. The current study takes a slightly different approach. It examines the broad relation of life changes and developmental patterns to wholesale shifts in offending behavior. The current study uses data from the Pathways to Desistance study to compare the developmental patterns of two groups of serious adolescent male offenders: those who are “system successes” with no subsequent criminal justice system involvement and a matched sample for a 7‐year period after court involvement for a felony offense. Findings from growth curve analyses indicate that patterns of change in criminal attitudes, psychosocial development, and legal employment over this extended follow‐up period are related to an absence of offending. These results support further investigation of the synergistic effects of psychological changes and entry into the job market as possible mechanisms promoting desistance during this developmental period. The policy and practice implications of these findings are discussed.