Drawing people is a funny kind of thing. (I like to start out with an eloquently-rendered atatement, which dazzles the reader with its wisdom and the graceful lilt of its carefully chosen words.) One way to approach it is to try and capture the essence of the subject, something true that emanates from his or her psyche. And the history of art is littered with artists who have excelled at just that. Another is to use the visual image of the subject to create a formal work that's not about the psychology of the person at all, it's about the formal aspects of the picture, or about the act of creating it or whatnot.
The approach that interests me the most is letting the drawing be an unconscious mix of what's emanating from the model and what the model's presence is holy shit what am I writing here? Wake up, sparky! What a rumbling cartload of nonsense! That was almost sounding like an artist's statement, and not a very bright artist's statement at that. Sometimes it seems like all the talk about what things mean and how they came to be and what place this or that thing has in the cosmos is just squid ink in the ocean. Talk and theorizing and all that bullshit just get in the way of interacting with the Oh no! What am I doing now? Playing at being some chickenshit iconoclast? Who am I to dismiss analysis? What a poseur!
This is like a dream or cartoon where you open door after door after door, and never get anywhere, you just keep exposing more empty rooms. Over the years I've built up so many layers of crap, so many useless guises, that I'm not at all sure there's a final room where the goods lie. Maybe that's one reason it's hard to really delve into yourself; you're afraid to discover there's nothing in there. From a buddhist perspective, this is probably a good thing. The self is an illusion anyway, and the sooner you discover that, the better. But how to get there without the crescendo of fear, guilt, self-pity--oh man, listen to yourself, Sparky! Caught in another pose! You really annoy me, you know that?