The document describes a company's multiple attempts to transition to cloud native technologies. It introduces Jenny, a technical manager, who has three "wakeup calls" as past approaches fail to successfully modernize their systems. They first try adopting new tools but deliver only incremental changes. A second attempt plans a full rewrite but delivers even less. With an ultimatum from the CEO, they work with an expert to design a new approach using cloud native patterns to gradually transition while maintaining delivery of features. This balanced approach allows them to successfully innovate while gaining proficiency in the new technologies over time.