Understanding the rationale behind a rule when trying to circumvent it

Am reminded reading this of an esteemed and since passed away colleague who had written windows driver code since the dos days and may have had decades of insanely archaic knowledge die with him - when working on a difficult piece of windows driver code years ago, he said to me in a thick eastern europe accent as best i can remember “you make the primary mistake of thinking anything in windows makes sense. once you abandon this bias, you may someday hope to get where i am”

This seems adjacent to Chesterton's Fence, though maybe not the canonical form of it.

For anyone not familiar with the term, Chesterton's Fence is the idea that you should understand why a rule exists before trying to remove it or work around it: https://fs.blog/chestertons-fence/

Here the issue is not that the rule was removed, but that the code followed the wording while missing the reason the rule existed.

Microsoft is so broken that an employee finds it easier to write a blog post about a documentation improvement than simply making that improvement? Explains a lot. "Conway's Flaw?"

of course they had to add dont wait for your worker thread in 2020