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Lessons from 14 Years at Google
(addyosmani.com)
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That has some really insightful advice and even something I hadn't considered. They mentioned that with enough users, even bugs become features that are used. People rely on the way a system works, whether it was intentional or not and maintenance could mean disruption.
I am not a dev but I am in IT and think quite a few of these ideas could be applied outside of code.