When you start something new, it's not a big deal. Everybody loves to work on something new. Nobody loves working on legacy products, because they don't have enough documentation and full of bugs, driving up costs of support and becoming a pain in the ass of some CIO. Yet somehow all those fancy new tools focus on creating great experience for building something new. Plenty of decent software was written in the last 50 years, but we are burning the money, electricity and silicon to replace it, because we could not come up with methods and tools for building on top. Why it is always about integrating something like requirements and context into planning? Why not doing it the other way, integrating planning into requirements and context, being product-centric rather than work-centric?