Big technical migrations - like switching databases - can feel like you're swapping out the engine of a bus while continuing to drive down the freeway (with all your users screaming in the back). However, there are ways to make these transitions safe, incremental, low-stress. In this talk we'll walk through a real-world case study of switching a production system from one database to another with no downtime, and no tears, using techniques like Expand/Contract, Dark Launch and Parallel Run. We'll also see hands-on examples of using CNCF open standards like Open Feature and Open Telemetry to manage this migration.