Board of Director retreat presentation on transforming cybersecurity programs from a fear of failure to a sophisticated culture embracing failure at the operations level. This is meant for a verbal deep dive, so the work plans are excluded as these are done interactively. The focus to transform an organization is to develop beyond controlled failure (penetration testing) to a robust chaotic, multi-level failure posture. This must address compliance and privacy debt. Leaders leverage AI, machine learning, threat intelligence to achieve these benefits. Upside is higher performance on the financial metrics and those found around culture.