Rereading this also has led me to believe that Usopp’s problem has never been about taking accountability for mistakes (he VERY MUCH admits when he feels he’s done something wrong! He says so outright! And takes responsibility to try and fix it). Instead it was about taking a step back and making sure his own insecurities don’t affect his reasoning. I don’t think his problem was pride or stubbornness. It was insecurity & not feeling like enough.
I was gonna wait til I have more sketches to put them in a bigger post, but I most likely won't have time to do these for a while! I just wanted to post this now because it was my favourite suggestion:]