This chapter explores the third meta-skill of contextual intelligence: leveraging learning through tacit knowledge. Tacit knowledge, often gained through experience but difficult to articulate, plays a critical role in decision-making, leadership, and innovation. Unlike explicit knowledge, which is easily documented and taught, tacit knowledge emerges through lived experiences, intuition, and subconscious pattern recognition. The chapter illustrates how leaders can transform tacit knowledge into explicit insights, using personal reflection, synchronicity, and analogical reasoning to enhance their decision-making capabilities. By leveraging learning, individuals can recognize pivotal moments in their lives, extracting deeper lessons that shape their behaviors and leadership styles. The chapter also explores the importance of both firsthand and vicarious experiences in developing wisdom and fostering cognitive flexibility. Innovation, a natural byproduct of leveraging learning, emerges when individuals recognize incongruities, adapt to changing perceptions, and integrate new knowledge. By embracing these principles, leaders can enhance their contextual intelligence, make better decisions, and drive meaningful change in an increasingly complex and uncertain world.