Freud? Jung? Bettleheim? Aristotle? Psychology books? Something that delves into understanding human motivation. Specifically, right now I need more info on the id, ego, and superego. Anything in particular stand out to you?
I was going to suggest Gervase Phinn, Yorkshire School Inspector, he has a wonderful philosophy towards life and the people around him. Alan Bennett is another. They are not scholarly texts but they teach me more about real life than psychology can. More non fiction would be the Continuum Concept by Jean Liedloff, Making Babies Christina Hardyment and Baby Wisdom by Deborah Jackson. Wonderful anthopology/history attempts to show how we are formed. Thomas Aquinas has always been my favourite philosopher I love Plutarch the stories of ancient greek and romans Pliny The Younger is also fun to read.
The topological Freud (with id etc.) is later than the Interpretation of Dreams Freud (1900) or the Mourning and Melancholia Freud (1914, I think). The topology is from around 1923 (and later) I seem to recall. In approaching Freud I recommend: 1) read a few books on Freud in his context as a biologist 2) read a few on Charcot and Freud's trip to France in the early 1880s 3) read about the collaboration between Beuer (? co-author of Studies in Hysteria) 4) Read some early Freud Papers 5) Read Studies in Hysteria 6) Read the Interpretation of Dreams And then...well, you're on your own.
Where do you start? Well, as noted if you want to know about the id, ego and superego then Freud would be a good place as those are Freudian concepts. Totem and Taboo is a good first work on Freud, though there are a thousand 'introductions to Freud' books out there. Otherwise, take your pick. What aspect of the human condition do you want to know about? Historical? Biological? Psychological? Sociological? Philosophical (by far and away the most interesting - not biased at all)? Religious and spiritual? If you want something short and sweet, but a primary text that is insightful and controversial I would recommend J.P. Sartre's Existentialism is a Humanism (aka Existentialism & Humanism). It's readable in a day and you'll either hate it or love it.
Eastern philosophy is fun. Lin Yutang's The Importance of Living is a nice book written back in the 1930s, I think.
The newspaper. But that is slanted toward the worst of human behavior, so I have to remember to focus on the stories of people going the extra mile fo fellow human beings. You are specifically talking about Freudian psychology now, which is not "the human condition." Freudian psychology is not particularly in favor these days.
Freud is very good when tackling broad themes. Civilisation and its Discontents might be a nice place to start (and is admirably short). If your's is a layman's interest, approaching some of Freud's ideas through his successors and interpreters might prove very fruitful. Erich Fromm is my favourite. Wonderfully wise and insightful and not rigidly Freudian - which is a good thing.
nhope, at 57 I must admit that the shine is off the human condition. I think the best description of the human condition was by an invisible man character named Claude in the first year of the TV drama Heroes: I spend a lot a time moving around people's homes, their bedrooms. You get to know people if you see them when they think they're alone you see them for what they truly are: Selfish, Deceitful... and Gassy. If you don't mind learning about people's motivation via analogy, there are two books about two biggies in the human condition: power and seduction (which is power by another means). Both are by the same author: Robert Greene. The 48 Laws of Power and The Art of Seduction. He uses examples from the 1600 - 1800s of the behavior of royal courtiers where the path to power took guile, subtlety, and determination. I want to be clear I'm not a cynic of human nature by any means. I just believe from experience that the safest take on your fellow being is that Claude is probably right.