[karaterobot]

This describes our legacy codebase, which is quite cleverly optimized for the original business case our company had ~15 years ago, and which is now a massive millstone dragging everything down into a black abyss. Just try to add a feature, I dare you.

I would say: design for flexibility rather than cleverness in most cases.

[gnat]

Fifteen years is a long time for code to remain unchanged. Either you constantly work on it and change as the needs change, or you have a boom and bust cycle of productivity.

Another way to look at it would be: holy shit, this company made it 15 years without investing in rearchitecting their codebase even as they took on new problems. That's amazing! Now we have 15 years worth of use cases to accommodate as we remodel/rearchitect/refactor/rewrite ... do you think that new codebase will last 15 years before it needs major work?