Let's say you're running a software company with moderate success. The problem is you've built your product on technologies that are now rather old, and support for the tools is long gone, and there aren't many people around anymore with those skills.
Every tool was the hot new thing at some point. When do you flip the switch on the old thing?
There are several companies that bought your product -- maybe even very recently. Do you give them the new version for free? How do you tell them what they got wasn't bad, but the new thing is better?
Do you do a full rewrite of your huge platform to catch up with the present? How do you better future-proof for the next time you hit this threshold?
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