We keep buying tools. We keep writing policies. We keep getting breached. The uncomfortable truth is that cybersecurity’s biggest failures aren’t technology problems; they’re culture and incentive problems. This talk explores why high-performing sports teams and expedition mountaineers succeed where security programs fail: they align incentives with outcomes and treat culture as a measurable playbook, not a poster on the wall. Attendees will leave with a practical framework for diagnosing culture rot, identifying misaligned incentives, and building the “expedition behavior” mindset that transforms security from a department into a team sport.