It's fair to say that Moses Herzog spends an awful lot of time in his own head, and the results are usually none too good. Herzog endlessly thinks about…well… the way he thinks about things. Talk about a vicious circle.
And even though the goal of all this thinking is to become a better person, it usually sends him running in (vicious) circles. Moses' trying to think his way out of self-obsession is kind of like trying to dig your way out of a hole.
Herzog tries to diagnose his character at one point, thinking,
What sort of character was it? Well, in the modern vocabulary, it was narcissistic; it was masochistic; it was anachronistic. His clinical picture was depressive—not the severest type; not a manic depressive. (1.22)
Yikes. So he thinks he's the best thing since sliced bread, but he also loves pain. And the weird cherry on top of this DSM-researched self-involvement sundae (yum, yum!): he's out of place in time. No wonder he needed to hole up in his country house for a quick second.
Herzog feels cut off from the world but doesn't know how to get over himself. Is it any wonder that his aunt Zelda tells him that he's "Overbearing, gloomy. (He) brood(s) a lot" (2.55)? But, knowing Herzog, this bit of wisdom from Auntie Z just sends him further into the "Woe is me" rabbit hole.
But we can't hate the guy. He wants to make himself better…but he has no clue how.
Herzog has always lived inside his own head, but things get out of hand after his split with his wife Madeleine. She has humiliated him by sleeping with his best friend (oof. Ouch.) and kicking him out of his own house (oof. Ouch again.).
So Herzog deals with his pain by—you got it—retreating even farther into his own head and writing imaginary letters to all kinds of people. As the narrator tells us,
He knew his scribbling, his letter-writing, was ridiculous. It was involuntary. His eccentricities had him in their power. (1.57)
Oh, come on, Herz. Can't you just cuddle up in a quilt, eat a couple of pints of Phish Food, go through a box of Kleenex and sing sad songs like the rest of us do post-breakup? But no—Herzog wants to skip the whole wallow-and-cry phase and go straight for the intense-self-improvement phase of brokenheartedness. He doesn't just join a gym and do some retail therapy, though:
Moses wanted to do what he could to improve the human condition, at last taking a sleeping pill, to preserve himself. (4.17)
Herzog is so amped up on the thought of "improving the human condition" that he needs to take a pill to shut his brain down for the night. Let's mark this as Reason #4,324 That Herzog Isn't Doing Too Great. Other reasons include: the fact that he's willing to bankrupt himself to ruin his ex-wife's good name and that he seriously contemplates killing his ex-wife and her new manfriend… even though that would leave his young daughter with no family to speak of. Hmm. Yeah, maybe that sleeping pill is a good call, H.
For all his (serious) flaws, Moses Herzog is a good guy deep down. One of his great goals in life is to become a better person, but he doesn't really know how to go about doing this. He thinks about a lot of big philosophical questions, hoping that some wisdom will lead him to a new perspective on things.
But in the end, he realizes that—despite his flaws, or even because of them— he's appealing to some people (like his new ladylove Ramona):
He was beginning to see that his particular brand of short-sightedness, lack of realism, and apparent ingenuousness conferred a high status on him. (5.77)
Ramona likes the fact that he's a bumbling professor with his head in the clouds. And it's just this kind of acceptance for who he is that gives Herzog the love he needs to make changes for the better.
Toward the end of Herzog, Moses can feel himself changing. He's so happy about this development that he wants to shout about it from the mountaintops:
Thus I want you to see how I, Moses E. Herzog, am changing. I ask you to witness the miracle of this altered heart. (5.100)
Now to be fair, Herzog is still self-indulgent in thinking that the whole world will care about his change (and in referring to his change as "miraculous"). But hey, it's unrealistic to think that he'd become a whole new person overnight. Baby steps are what are often needed when a person's trying to change, and that's exactly what Herzog takes toward the end of this story.