How sufficiently precise must we be?

I have a little sister, albeit being an English professor, who could not comprehend a Chris Rock joke:

>> When you're white, the sky's the limit. When you're black, the limit's the sky.

Is that so hard to understand? I remember her making a big deal of it when I was in university saying the two sentences mean exactly the same thing. It's a shift in implied emphasis. The first emphasizes the sky, and the second emphasizes the limit. How do I know that? I don't know. Maybe from socializing with people?

How does this elude an English professor? I've come across much similar confusion in my career with the most technical types of people as an engineer. I don't have time for this tedium.
2 mo
This is actually the biggest source of frustration in my career... this need to disambiguate all forms of human communication... except human communication is riddled with ambiguities. People are supposed to be able to somewhat interpret intentions.
How sufficiently precise must we be?
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