Drawing on 25 years of experience, this narrative-driven presentation walks through proven strategies for all aspiring security leaders who may be wondering: how can I have fun and profit whilst hacking the typical systemic challenges that block better security outcomes? The four sections of this talk outline people-driven and culture-conscious methodologies that will enable you to do just that! First, you will learn how to choose the right leadership opportunity that aligns with your professional career goals and your amazing life purpose. Second, you will explore how to harness your “new role energy” to do two simultaneous jobs: making good on your highly visible “30/60/90 day plan” that aligns with the business of security; also an in-depth investigation into what is holding back the security program you just inherited. Third, you will discover how to rebuild your security program step-by-step, including a commitment to excellent security experiences, fostering healthy team culture, and partnering with others in your security ecosystem. And to round out your journey, you will uncover how to deal with inevitable entropy and change in a fast-paced industry through the power of reflection, storytelling, and gratitude.