A little over a year and a half ago, we had a dramatic rethink of the technologies and development workflows for building with WordPress. Our existing codebase and workflows had served us well, but ten years of legacy was beginning to seriously hinder us from building the modern, fast, and mobile-friendly experiences that our users expect. It seemed like collaboration between developers and designers was not firing on all cylinders. So we asked ourselves the question: “What would WordPress.com look like if we were to start building it today?” A New Beginning: Prototyping and Iterating We’d asked ourselves this question before, and had our fair share of initiatives that didn’t result in useful change. Looking back, we were able to pinpoint our biggest mistakes: we’d been starting with a muddy vision, and were trying to solve an ill-defined problem. These insights really helped us change our approach. One of the original Calypso prototype screens, listing all of your WordPress sites. Calypso, the codename for this new WordPress admin interface project, started differently. To present a clear vision, we built an aspirational HTML/CSS design prototype — based on clearly defined product
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