Except that those who are "proud to be bad at math" exude pride because they've given up, but don't want to feel like a failure. In other words, all attempts at math education have so far failed them, and they have succumbed to learned helplessness.

When people are consistently frustrated using your website, you'd normally look into the UX so that you can make a smoother experience. You then test to make sure your changes actually made your site better. Math and science education is no different, except that those in charge tend to treat it like the bad old UNIX days of "If it was hard to write, it should be hard to understand" and "RTFM".