Trait anxiety, emotion regulation strategies, and metacognitive beliefs influence executive functions (EFs) and academic achievement. This study examines their interplay and impact on academic success. In total, 275 adolescents (10–17 years) and parents completed an online questionnaire assessing trait anxiety, emotion regulation strategies, metacognition, parent-reported behaviors related to executive functioning, and overall school average. Preliminary analyses confirmed consistency with the existing literature for each variable and their interaction. Furthermore, we conducted a network analysis among the main variables. This analysis supports the need to pay more attention to reflective variables—maladaptive emotion regulation strategies and metacognitive beliefs about worry—when studying trait anxiety. These variables were linked to problematic executive functioning in adolescents, and the latter was negatively linked to academic achievement. This study offers innovative insights by investigating relationships less explored in the scientific literature. It reveals high and significant correlations between metacognitive beliefs, maladaptive emotion regulation strategies, and trait anxiety (r > 0.500, p < 0.001) but also between these variables and both executive functioning and academic achievement. These findings offer new perspectives for research and underscore the importance of holistically examining the psychological factors related to academic success.