Using data from the first three waves of data (Grades 5, 6, and 7) from the 4-H Study of Positive Youth Development (PYD), the authors assessed among 1,184 youth (58.5% female) the patterns of change associated with indicators of PYD and of risks/problem behaviors. Results indicated that five PYD trajectories represent change across grades, four trajectories were associated with indicators of internalizing problems, and three trajectories were associated with indicators of externalizing problems. Although theoretical expectations associated with the study of both child and adolescent resilience and PYD led to the expectation that most youth across the early adolescent period would show change marked by the coupling of increases in PYD and decreases in risk/problem behaviors, only about one-sixth of all youth in the sample manifested this particular pattern of change. Other youth remained stable over time, showed increases in PYD and risk, and declined in PYD. The multiplicity of patterns of conjoint trajectories for PYD and risks/problem behaviors constitutes a challenge for both developmental theory and applications aimed at enhancing resilience and positive development among adolescents.