There's merit to this position. You can think of this as the process/organization equivalent to technical debt. Every problem that you introduce a hacky work-around, that root problem sticks around and keeps generating more and more hacks and work-arounds. The end result is incompetent management.

That doesn't mean it's always the wrong decision, though. Sometimes, technical debt is the right trade-off. Sometimes the trade-off of teaching your boss just isn't worth the effort, and getting the job done quickly works out.

And, just like technical debt, doing this results is more problems for other people (including future-you) as your bad boss looks good and calcifies his bad habits and rises in the ranks.

Personally, my preferred solution is malicious compliance. If someone makes a stupid decision, they have them suffer the consequences of that stupidity rather than covering for them and letting them delude themselves that their bad decision was good. This only works on new decisions, though; if you try to remove existing work-arounds for old bad decisions, you're the one that looks bad.