There is a well-documented developmental decline in engagement among adolescents throughout secondary school. Given this pattern of engagement poses problems for both student well-being and their academic outcomes, it is important to examine potential strategies to address this decline. As a growth-oriented strategy, personal best (PB) goal setting may be one viable option to challenge this decline in engagement. Across 3 years of data collection among a sample of N = 368 Australian secondary school students and using latent growth modeling (LGM), we explored 4 ways that PB goal setting may impact engagement: (a) an "initiating effect" such that initial PB goal setting positively impacts initial engagement; (b) a "contemporaneous effect" such that PB goal setting at each time point positively predicts engagement at that same time point; (c) an "escalating effect" such that at each time point PB goal setting has an increasing impact on engagement; and (d) a "slope effect" such that initial PB goal setting improves the rate of change of engagement (reduces negative slope) over time. Findings confirmed an initiating effect, contemporaneous effect, and escalating effect of PB goal setting on engagement, but not a slope effect. These results suggest that although the developmental decline in engagement seems to be somewhat pervasive during adolescence (i.e., no slope effect), PB goal setting may be a viable strategy to positively impact early levels of engagement (initiating effect), positively impact engagement at any given point in time (contemporaneous effect), and increasingly impact engagement across time (escalating effect). Taken together, this investigation adds to the growth, goal setting, and engagement literatures while showcasing the various ways (and analytical approaches to them) that psychoeducational phenomena can interact and impact one another across time. The findings also provide applied direction for practitioners seeking to assist students through this challenging developmental stage of adolescence.