Benjamin seems to be doing pretty well. The narrator tells us right off the bat that he is "by nature obliging" (1.3.7), and we see this in the way Benjamin responds to his father's absurd demands that he shake a rattle periodically, dye his hair brown, go to Kindergarten, and so forth. In fact, part of the reason we root for Benjamin as a protagonist is that he's so intent on making others particularly his father happy.