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How to explain Technical Debt to your Boss
(feddit.org)
Hey Boss, look here!
I made a magical X-ray app that displays our code as wiring.
Here is the shiny, neat program that Bob wrote 15 years ago, right before he left us:
And here is what it is today, after Tom took it from Bob, and Jane from Tom, and Mick from Jane, and me from him, porting it to roughly four new platforms, and adding about 240 features from customer requests (150 of which were urgent):
Might be a poor comparison, but that doesn't mean it's necessarily a bad way to present it to thier boss. If the analogy, however flawed, communicates the underlying idea to the listener, then it was effective.
The concept here is very related to why "ceci n'est pas un pipe" is/was compelling.