Some people struggle to take no for an answer so at times, as a freelancer, I have had to paint the picture of the most likely outcome if they push forward and evidence it being highlighted.

I then do as the client asks as the "customer is always right" and highlight the issues, more often than not predicted by many people including myself, as they arise in the most professional manner (no one likes to hear "I told you so").

The client then makes a call of how they want to proceed which is another opportunity to discuss the most likely outcome.

Unfortunately, it is a cycle that some people struggle to break out of.