The present longitudinal study, based on existing theoretical tenets, explored a conceptual model that depicted four major orientations: optimism, self-efficacy, and academic well-being. An important question for consideration, in this case, involved the testing of different untested trajectories that could explain and predict individuals' mastery-approach goal orientations. This research investigation, in particular, is of significance for its unexploratory nature, and its findings, we contend, would contribute to our understanding of individuals' academic and learning patterns. Data were collected across six separate time points, and path analytical procedures were used to test the hypothesized relationships. M"Plus" 7.3 produced a number of notable findings, emphasizing mediating mechanisms and interesting trajectories, for example: (1) the impact of enactive learning experience on Time 1 optimism and Time 3 self-efficacy, (2) the positive impact of Time 1 optimism on Time 2 motivation towards learning, and on Time 3 self-efficacy, (3) the direct impact of Time 1 optimism on Time 6 mastery-approach goals, mediated by Time 4 optimism and then Time 5 motivation towards learning. This evidence, overall, is substantive in terms of making theoretical contributions, as well as informing sound pedagogical practices for consideration and implementation.