Mandy Andress reflects on her journey as a security leader since the early days of the internet and highlights the lessons learned and the challenges faced in the evolving role of Chief Information Security Officer (CISO). The position is characterized by a complex blend of technical skills, business acumen, and interpersonal abilities, requiring CISOs to engage in both strategic and operational tasks. Beyond the day-to-day responsibilities, successful CISOs emphasize the importance of internal communication and collaboration to align security initiatives with business objectives, which involves engaging with executives, department heads, and stakeholders. By fostering a collaborative security culture and aligning with organizational goals, CISOs can significantly enhance their organization's cybersecurity resilience and their own effectiveness. Andress draws on insights from industry experts and fellow CISOs to outline the principles that distinguish exceptional security leaders.