Datadog has been addressing the challenges of operating a large, shared relational database by transitioning towards independently owned database instances. This shift is driven by the limitations encountered as the organization grows, where the database's monolithic nature creates operational risks and hinders agile development. The process of splitting the database involves defining functional boundaries, minimizing migration risks, and implementing specialized tooling to ensure a safe transition. Datadog's strategy includes three phases: logical separation, access reduction, and physical separation, supported by platform investments like the Rapid framework and OrgStore managed platform. These initiatives aim to mitigate the operational burden, enhance scalability, and enable more autonomous development, while maintaining collaboration and communication with product teams to ensure the migration's success. Despite the complexity and time required, Datadog's approach highlights the potential for deeply entrenched systems to evolve through careful planning, automation, and partnership across teams.