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I wish languages were more willing to release breaking versions, like a C++ v2 or such. That’s not to say languages don’t already have breaking changes between versions (Python comes to mind), but it would allow people to start fresh and clean up obsolete designs and libraries.
You know the cleaning up probably won’t happen. If some dependency doesn’t work anymore because Python introduced a breaking change, then you stick with the old Python version.
Python is actually a good example of this: see the mess that the transition from 2.6 to 3 generated.
Python 3.7 is another good example. The new await and async keyword broke a lot of programs.