Fully 60% of Americans suffer from mathematics anxiety, resulting in math avoidance and impaired learning. Unconscious psychological and emotional processes can disrupt students’ cognitive learning, and negatively “charged” feeling-toned memory associations can derail the learning process. Math can become associated with a psychological inferiority complex, low motivation and self-efficacy, poor self-directed learning strategies, and feeling unsafe or anxious. Analytical psychology’s useful heuristic theory explains how an unconscious or “shadow” prejudice that favors culturally preferred learning styles (Kolb) and psychological types (Jung) can cause stress in math learning domains. In this study, a positive experiential learning (Kolb) intervention was designed in accordance with current knowledge of brain functioning to depotentiate math-associated inferiority complexes and improve learning. Two studies were undertaken, one correlational and one experimental, involving 388 students and 55 higher education faculty using standardized psychometric instruments, specifically: Kolb Learning Style Inventory (Kolb, 2005), Psychological Type Indicator (Myers, 1998; Jung, 1977), Motivated Strategies for Learning Questionnaire (Pintrich, Smith, Garcia, & McKeachie, 1993), Mathematics Anxiety Scale (Betz, 1978), Psychological Safety Scale (Edmondson, 1999), and the Transformational Leadership Behavior Scales (Podsakoff, MacKenzie, & Bommer, 1996). The data are analyzed using appropriate ANOVA, correlations, and regressions to determine the relationships between variables. Advanced level math students and faculty displayed similar Kolb learning style preferences for assimilating or converging, which share the abstract learning mode, as well as a typological preference (Jung) for extraverted judging, which involves the rational psychological functions. These particular preferences dominate higher education mathematics culture, and therefore correlate with higher psychological safety, higher motivated strategies for learning and increased math learning performance. In this study with developmental math students—those less associated with these dominant preferences—an experimental experiential learning community, in contrast to a traditionally taught control group, reported significantly improved math learning, decreased math anxiety, increased psychological safety, increased motivation and cognitive strategies for learning, higher levels of teacher transformational leadership behavior, a higher rate of persistence in continued math courses, and heightened consciousness as evidenced by greater self-efficacy. Implications for conscious attention to unconscious processes by teachers and leaders in both academic and business learning organizations are discussed.