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This talk from RailsConf 2019 describes how our team made deep changes to the data model of our production system over a period of 2.5 years.
Changing your data model is hard. Taking care of existing data requires caution. Exploring and testing possible solutions can be slow. Your new data model may require data completeness or correctness that hasn't been enforced for the existing data.
To manage the risk and minimize disruption to the product roadmap, we broke the effort into four stages, each with its own distinct challenges. I'll describe our rationale, process ... and the lessons we learned along the way.