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Impactful leadership requires an investment in the self and others. Blinded by past success, this leader’s story explains examples of a failed attempt to learn how to navigate a new industry culture with hidden political landmines in the organization, communicate effectively in a hierarchy, and ultimately realize she might not have been a fit for the organization. This chapter will provide examples of the leader’s story of challenging organizational politics and relational aggression in the workplace. Through many conflicts and barriers to effective leadership, this chapter provides key insights of leadership self-awareness, wellness, communication blind spots, and organizational strategies to build trusting leader–follower relationships. Living in a volatile, uncertain, complex, and ambiguous (VUCA) world today, the ability to build strong trusting relationships between leaders and followers and peers is vital to success as a leader and organization. The leader must learn from failure and innovate from lessons learned. To lead within a VUCA world, the time to invest in continuous leadership development is strongly recommended.