Regretting one's career path (in fiction)

I have to say I am not enjoying Maugham's Of Human Bondage.  It is very hard for me understand why it is often considered one of the top 100 books of the 20th Century, aside from the fact that there are lots of people who like watching car crashes -- but only if it is sufficiently high-minded (i.e. they wouldn't be caught dead watching reality TV but they'll read books like Madame Bovary or Anna Karenina or Of Human Bondage).  I really don't like Philip Carey as a character.  He is portrayed as a thoroughly unpleasant young man, who goes out of his way to snub his uncle and generally only hangs out with people he can look down on.  Maugham seems to justify everything because Carey lost both parents as a child and has a physical handicap as well (a clubfoot).  The only section of the book that was bearable (so far) was when he was off in Paris trying to become an artist.  Now he is back in London, doing a fairly poor job of studying to be a doctor.  And he falls hard for a waitress, essentially only because she snubs him, thus instantly becoming forbidden fruit.  I know the heart wants what it wants, and I have to admit that there were times in my youth where I preferred the "unapproachable" women the best.  After all, isn't that the primary reason Dante fell so hard for Beatrice?  He never got close enough to get to know her as a person and see some wrinkles and spots, which would force him (or allow him, depending on one's take) to take her off the pedestal.

So some small credit must be given to Paul for at least speaking to Mildred, the waitress, even though he is acting pretty stupidly in falling for a woman solely because he wants what he can't have.  I think that's still further than Dante ever got, though he certainly put a lot of words into Beatrice's mouth when it came time to write The Divine Comedy.  On a side note, this waitress-customer dynamic is somewhat reminiscent of Gabrielle Roy's The Tin Flute, though that was a case where both the waitress and customer got entangled and played a bit hard to get at different times, though in the end it was the waitress (Florentine) who fell harder for the customer (Jean), which is the reverse of Of Human Bondage. 

However, as I learned in my 20s, it gets really boring reading about anyone who doesn't have enough self-respect to be treated well.  A mature person doesn't even fall for someone or something just because it is out of reach, and that is a hard standard to live up to.  But most of us can at least manage to have that smidgen of self respect where we would have broken things off after only one or two of the truly terrible scenes that Mildred creates where she tells Paul just how little she thinks of him.  Obviously that would have meant a short book, and Paul is an extremely weak character who keeps crawling back to her.  You really want to shake him and say how hard would it be to find another restaurant and another waitress to ask out.  There are so many other fish in the sea.

It is really hard to fathom how Maugham is going to keep this going for another 300+ pages.  I find it tedious and not at all compelling, and indeed this is exactly why I disliked Vargas Llosa's The Bad Girl. (In fact, I dislike it even more now, seeing how it is close to a carbon copy of Of Human Bondage.)  I am kind of dreading these last 300+ pages actually, and would not finish the book except I am going to be seeing a play at Soulpepper based on the book in a few weeks.  Though if this book ends the way I think it will, I should probably skip it (the play) and try to get my money back.  I do have to wonder if they are basing the play a bit more on the movie, which I have to assume is a bit better balanced (I haven't seen it).  In the book, Maugham gives a disinterested person (like the reader) absolutely no reason to even want Philip to succeed in wooing Mildred -- she's common, fairly stupid, sickly, a liar and basically an all-around unpleasant young woman.  Of course, I don't like Philip either, so maybe they are meant for each other, just to keep the dating pool clear for nicer people.  (In this sense, it is similar to Taylor's A Game of Hide and Seek, where I didn't like either of the romantic leads, though Of Human Bondage is 2.5 times as long!)  In the movie, Mildred is played by Bette Davis, so at least one can imagine why there are some obsessive longings on Philip's part.  However, they seem to have tweaked the plot and have him give up his art career due to her, whereas in the novel it was already over by the time he met her.  That may have been the only truly difficult or even semi-noble thing he did in his life -- agree to give up the career of an artist when it became clear he didn't have what it would take to be a great artist.  He is told this (his lack of skill) by an art teacher who actually admits that he wishes he found out when he was younger that he didn't have the raw talent to become great.

I'm having some trouble thinking of comparable cases in literature where a young person gets career advice and then takes it.  (Or even ditches a career and switches to something else unprompted -- Don DeLillo's Americana sort of falls into this category, but not completely.*)  I think part of the problem is that the first 200+ years of the novel, they are written for (and often by) the leisured, monied classes who didn't have to work.  That changes with the Victorian novel, where Dickens and Trollope write about various professions.  I suppose in the States there was never as much of a leisured class to begin with, and Mark Twain in particular knew just how much money meant.  Still, you have books written by Edith Wharton that barely acknowledge that money (and the obtaining of money) is something to be worried about.  However, this is well-balanced by Theodore Dreiser and Sinclair Lewis and even John O'Hara to an extent.

I can certainly think of cases where an individual is placed in a job they don't like very much.  There are numerous examples of that in American and European literature to say nothing of Russian literature.  There are also examples of people striving to do well or reasonably well at work, even though they have temperaments (artistic or otherwise) that make this a struggle.  I'm thinking of Bazarov in Fathers and Sons for one, but quite a few of the figures in Dos Passos's USA Trilogy are not well-suited for the work they do.

I'm sure I can come up with more after I think about it, though I am blanking on this early career advice angle.  Part of the problem is that professional writers just often know so little about the world of work that it isn't that convincing, and they focus far more on emotional truths and affairs of the heart and not so much on office politics.  This seems even more true of playwrights, with Arthur Miller being an honorable exception and Mamet a partial exception.  Well, if I can think of some other good examples I will list them later, and feel free to add some in the comments.

* I'm struggling to remember the details, but the main character throws away a career as a television executive but to become a film-maker, which is still in the same general category of arts production, even though his economic status is far more vulnerable.  In the same way, in Steven Shirrell's The Minotaur Takes a Cigarette Break, the minotaur is going to go from working in a diner to being his own boss at a hot dog stand.  Not exactly a radical career change, even though there is some uncertainty (and potentially some personal growth) involved.