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.
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.
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.
Maybe if he was the sort of person who could eat someone else's hash browns, who the hotel wanted to impress so much they sent him someone else's breakfast, maybe then he was the sort of man who could get an audience with the King. (II.78.18)
Alan journeys into the Saudi Arabian desert specifically to create a new life for himself. That also means creating a new identity. But first, Alan has to figure out what kind of a man he is and how to turn that guy into the person he wants to be. And it's pretty clear that Alan wants to be a winner this go-round. If he can just do the thing that all "real winners" do (i.e. take things that really aren't theirs), then things might be okay.
His only weapons against her were silence, truculence; he cultivated an occasional brooding intensity. He had never been as stubborn as he was with her. This was the version of himself who spent six years with her. This version of Alan was fiery, jealous, always on his heels. He had never felt more vital. (IV.15.31)
Our hero has several "out of body" experiences in this work. Whenever he does something that he can't explain, Alan often wonders, "Just who am I?" In his relationship with his wife, Ruby, Alan finds that he becomes a totally different character.
This is not a functional response to another human being, but that's all he has against Ruby's force-of-nature personality. While he says he doesn't recognize himself in this behavior, he kinda likes it. Which just makes us wonder: who are you, Alan Clay?
[…] the key thing is managed awareness of your role in the world and history. Think too much and you know you are nothing. Think just enough and you know you are small, but important to some. That's the best you can do. (XV.42.107)
Alan makes another attempt here to pass some wisdom on to his daughter, Kit. It's interesting that Alan can make such grand existential observations in his letters, but has a miserable time applying them to his actual life.
In this case, Alan seems to understand that a person has to cut himself some slack in the legacy department: not everyone can be great or do great things, but it's all okay in the end. In reality, Alan can't stop being down on himself for his lack of achievement.
Alan wondered, continually, about his own behavior. No sooner had he done something, something like hiding behind a hill of dirt by the Red Sea, when he would wonder, Who is this man who leaves the presentation tent to hide behind a hill of dirt? (XX.20.167)
Most of us have probably had a moment when we've thought, "Did I really do that?" Hey, everybody has regrets and second thoughts. But who wouldn't want to escape a hot tent in the middle of the desert for a place by the sea?
Alan's profound sense of isolation from society makes him question all of his actions ("Do I seem weird?"). We can also see him judging himself through his former, more confident eyes. The result? Alan no longer recognizes himself and has to wonder where "he" has gone.
People worried about our passing over into some robotic state, but we were so much like robots already, programmed and easy to manipulate. We had buttons, we had circuits, and it could all be mapped and explained, reprogrammed and calibrated. (XXII.115.190)
In his struggle to understand who he has become over the years, Alan also contemplates human identity and purpose in the face of evolving tech. It doesn't take much of a leap of imagination to see human behavior as a product of our "wiring": biology, electrical impulses—and in this case, hormones.
Humans may feel sovereign and in control, but really, are we? And are we any more miraculous or mysterious than a robot that really is only a sum of its parts?
Whatever she's done that has displeased you I want you to know that you are who you are because of your mother, because of her strength. She knew when to be the tugboat. She coined that term, Kit. The tugboat. She was the steady, she navigated around the dangers lurking below. (XXIII.50.202)
Alan hits on a moment of truth in his recollection of his doomed family life: he wasn't the man he ought to have been in Kit's life—and that Ruby's response to that has, in fact, shaped Kit's identity. We don't get to see Kit or Ruby on their own terms in this work, so it's impossible to know how accurate Alan's assessment might be. But Eggers does give us a more complex understanding of Ruby's role in their lives in Alan's moments of drunken honesty and loneliness.
This will be good, he thought. It will be good to be the one to see and shoot the wolf. To shoot a wolf in the mountains of Saudi Arabia will be something. The man who pulls the trigger will have done something. (XXVIII.134.277)
Alan has a serious desire to remake his identity on this trip to Saudi Arabia. He has no legacy, no fortune, has done no fabulous deeds, and doesn't really even have a loving family. His desire to murder a wild animal may seem like nothing more than a masculine fantasy (which, hey, it is), but it's also the yearning of a man desperate to have a story and identity that extends beyond his own lifetime.