How we cite our quotes: (Chapter.Paragraph.Page)
Quote #1
He had not planned well. He had not had courage when he needed it.
His decisions had been short sighted.
The decisions of his peers had been short sighted.
These decisions had been foolish and expedient. (I.6-9)
Alan is good at beating himself up for the choices he's made in his professional and personal life—and we can't say that we disagree with him. But Alan also has a tendency to equate his financial/professional worth with his personal value, something that drags him into a dark and desperate place in this work. His decisions have been short-sighted, but it's Alan's hyper-optimism that keeps him believing that tomorrow, everything will be better.
Quote #2
Now he was fifty-four years old and was as intriguing to corporate America as an airplane built from mud. (II.44.12)
Alan almost makes a life-and-death error much later in the story, when he's on a wolf hunt with Yousef. He does so because he's desperate for some kind of achievement that will at once define him and proclaim his worth as a man. This need for external validation is at the very core of Alan's being. It makes it really difficult for him to separate his professional failures from who he is as a person.
And that's the real question for Alan as he tries to work things out in the desert: who is he, anyway? Without the crutch of a career, Alan's really grasping for an answer.
Quote #3
His eyes had retreated and people were noticing. At his last high school reunion, a man, a former football player whom Alan had despised, said, Alan Clay, you've got a thousand-mile stare. What happened to you? (II.55.13)
With a steady stream of failures and rejections at his command, Alan finds himself withdrawing from society. He can't participate any longer as an active, working person so he feels that there may be no place for someone like him. It's just adding insult to injury that the jerk football player from high school is the one to notice this—out loud.