Does it seem to be less of a caricature now that you've read a version in which you identify with the writer, rather than one in which the writer is analyzing and criticizing you from outside?

Honestly, no. The only thought that passed my mind when the context was changed was 'Watch out Kaj! Make sure you've secured the aliances and status necessary to make that sort of honest observation. That's a recipe for getting yourself bullied and ostracised!"

Sometimes it might be necessary to go ahead and damn the torpedoes

Damn right.