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DON: I think it'd be a good idea if we took along my typewriter
DON: I'm going to write there, get started on that novel.
Spoiler alert: Don isn't actually planning to get started on that novel. As we'll learn over the course of this section, he has a tendency to not finish what he starts, and the resulting disappointment drives him <em>mad</em>.
DON: Helen, will you stop watching me all the time? Let me work it out my way. I'm trying. I'm trying!
Personal disappointment aside, Don is wracked with guilt over how his actions affect Helen and Wick. To be honest, it's almost worse that they're so sympathetic in spite of everything.
WICK: Who are we fooling? We've tried everything, haven't we? We've reasoned with him, we've babied him, we've watched him like a hawk.
After he returns to find Don missing, Wick's finally fed up. He's done everything he could for his little brother and all he's gotten in return are broken promises and unmet expectations. It might sound harsh, but could you honestly say that you would act differently if you were in Wick's shows?
DON: I'm a writer. I've just started a novel. As a matter a fact I've started several, but I never seem to finish one.
As we see in this flashback, Don's terminal case of writer's block has been afflicting him for some time. This is also our first real hint that his failure as a writer might be the root of his addiction.
DON: The reason is me—what I am. Or rather, what I'm not, what I wanted to become and didn't.
HELEN: What is it you want to be so much?
DON: A writer. Silly, isn't it?
The fact that Don sees his dream of becoming a writer as "silly" shows that he's all but given up. That's a real bummer. Instead of picking up the pieces and moving on with his life, however, he starts falling down a deep, dark hole of depression that just so happens to filled with whiskey. The rest, as they say, is history.
DON: I reached my peak when I was nineteen, sold a piece to the Atlantic Monthly, reprinted in the Reader's Digest. Who wants to stay in college when he's Hemingway?
Interestingly, Don feels so dissatisfied about his failed writing career because he was once a real literary hot shot. He's like the star high school athlete who tries and fails to make it in the big leagues. What's more, these early successes gave him such high expectations for the future that they could never hope to be met.
DON: I moved right in on New York. Well, the first thing I wrote, that didn't quite come off, and the second I dropped—the public wasn't ready for that one.
As you can imagine, this chain of half-baked and unfinished novels leads us all the way to the present day and The Bottle. It's also worth noting that Don rushed to New York City immediately after dropping out of college, which is a classic example of "too much, too soon" if we've ever see one.
DON: I'd sit in front of that typewriter, trying to squeeze out one page that was halfway decent, and that guy would pop up again.
That "guy," btw, is Don's alcoholism. This quote confirms something that we had already suspected—that Don turned to booze after his first, failed attempts at writing novels. This leads to a nasty Catch-22 in which he drinks to write, but ends up drinking so much that he can't.
DON: Sure, take a nice job. Public accountant, real estate salesman. I haven't the guts. Most men lead lives of quiet desperation—I can't take quiet desperation.
In other words, Don couldn't live with himself knowing that he completely failed to achieve his dreams. It would be too great a disappointment. Still, we'd argue that he's failing to achieve his dream even without the "nice job," so it shouldn't make that much of a difference, right?
DON: Let's face reality. I'm thirty-three, living on the charity of my brother, room and board-free, [...] all out of the bigness of his heart.
In many ways, Wick's generosity only makes Don feel more like a disappointment. After all, he's a thirty-something who still gets an allowance from his older bro—there's no way to frame that so it doesn't seem lame. Once again, we see Don's little vicious cycle back in action.
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