As industries digitally transform their existing business models to fend off competitors or disrupt new markets, they find their IT to be a limiting factor. In this session, we cover the trends of disruptions and opportunities of digital transformation, and the evolution of IT monoliths to microservices and now cloud native services. We also explore dependency management, or lock in, through a 'choosing, using, and losing' mental model. Finally, we explore chaos architecture as an evolving method for exposing weaknesses before they become real problems.