The present study considered "global self-esteem" and "academic self-efficacy" as two contrasting precursors and distinctive pathways that could account for effective schooling experiences: (1) the "social pathway" (e.g., the predictive effect of teacher-student social relationship) and (2) the "personal pathway" (e.g., the predictive effect of a child's recognition of realistic best practice). This theoretical-conceptual model for examination, which we tested with a cohort of secondary school students from Taiwan (N = 750 Year 11) affirmed the direct and potential mediating effects of "social relationships," "personal well-being," "best practice," "positive emotions," and "academic striving." Causal modeling techniques used showed a number of significant findings--for example: the direct effect of teacher-student social relationship on a student's experience of positive emotions, the direct effects of a student's belief of optimal best practice and academic striving on his/her academic achievement, and the potential mediating role of personal well-being between global self-esteem and a student's recognition of realistic best. This evidence, overall, makes substantive theoretical and methodological contributions to the study of positive schooling experiences, using social psychology and educational psychology theories as a basis for further development. One distinction, in this case, entails our intricate conceptualization of two contrasting courses of action that a student may experience. Moreover, from an applied practice point of view, our research inquiry has informed educators, researchers, and stakeholders of different viewpoints that could foster proactive social relationships, subjective well-being, positive emotional functioning, and academic performance at school.