This chapter investigates why organizations and leaders themselves often find it difficult to change during turbulent times, focusing on both organizational- and individual-level obstacles. Organizations often fall victim to management fads, pursuing superficial trends without aligning them with specific needs, leading to failed implementations and missed opportunities. Leaders, central to facilitating change, are sometimes the primary barriers due to entrenched behaviors, resistance to adaptation, or the urge to cling to their power. Crucially, structural changes in organizations, like hybrid working or self-managing teams, demand shifts in leadership behaviors that are often inconsistently adopted. The chapter underscores the critical role of self-awareness and adaptability in overcoming these barriers, emphasizing that effective change requires two roles from leaders. They not only need to direct and facilitate change processes in their organizations, but they also—and even more importantly—need to change themselves.