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Milo is a boy who does not know what to do with himself. He is bored senseless by practically everything in his life and is constantly trying to find something exciting or interesting. Milo especially dislikes his schoolwork because he cannot understand the use behind learning geography or math and thinks that learning is "the greatest waste of time of all."
One day, Milo goes into his bedroom to find a strange package waiting for him. The box is not quite square but not quite round and is addressed to "MILO, WHO HAS PLENTY OF TIME." There is no return address on the package, and Milo has no idea who might have sent it to him—it is not his birthday or Christmas. Deciding that there is no way he can return the box, he opens it. Inside he finds an unassembled turnpike tollbooth, a map, a book of traffic rules, and an instruction manual. He puts the tollbooth together and gets into a small electric car, one of the many toys he is usually too bored to play with. As he approaches the tollbooth he is told to have his destination in mind, so he randomly picks the city of Dictionopolis from the map and passes through the turnstile.
Once through the tollbooth, Milo finds himself speeding along a country highway. He is shocked to discover that the tollbooth was no toy at all. Since it is a beautiful day on the road, he continues on his trip. Before long, he arrives at Expectations where an excitable little man rushes up to his car. The Whether Man, has a habit of saying everything three times. In response to Milo's questions about how to reach Dictionopolis, the Whether Man talks nonstop about navigation and the weather.
Milo presses on, leaving Expectations. The road gets increasingly curvy and repetitive. Bored by the seemingly endless circles, Milo's mind begins to wander and he becomes very drowsy. The car also seems to tire and grinds to a halt. As he sits, almost asleep, a distant voice informs Milo that he is in the Doldrums.
After looking around, Milo realizes there is a tiny man sitting on his shoulder who changes color to match it. He then notices a number of little people around him hiding like chameleons. They introduce themselves as the Lethargians and describe their idle lives in the Doldrums, explaining that thinking and laughing are both outlawed.
Suddenly a large dog with a clock for a body comes running up, frightening the Lethargians away. The watchdog whose job it is to make sure nobody wastes time, suspiciously asks Milo what he is doing in the Doldrums. When Milo replies that he is "just killing time," the watchdog becomes furious and tells Milo that the only thing worse than wasting time is killing it. He tells Milo that if he wants to leave the Doldrums he only needs to do the opposite of what got him there. Since Milo drifted into the Doldrums by not thinking, he concentrates on thinking and his car begins moving. Soon he is back on his way to Dictionopolis with the watchdog.
In Chapters 1 and 2, Juster sets out the major theme of the book in two forms, one general and the other more specific. Milo's character represents all bored children; note that Juster gives us no specifics about Milo's classes, friends, or parents. Milo is generic, and thus can be seen as representing a whole category of character, or an archetype. In this case, the traits Milo symbolizes are boredom and laziness.
Juster sets up the premise so that there is a drastic contrast to Milo's moping around the house-something has to happen to shake up Milo's world. That something is the anonymous package. The gift-giver does not have a name, which makes him or her as nonspecific as Milo. Here Juster sets out the theme of the book on the first, broader level: The Phantom Tollbooth is largely about discovering and appreciating what is interesting in everyday life. Milo finds something—in the most common place, his bedroom&mdashthat at first seems nondescript but then, once opened, reveals a gateway to a magical land.
It is also important to notice that Milo's feelings of boredom disappear as soon as he leaves his old world behind. Instead of being frightened by the sudden transportation from his bedroom to a country highway in an unknown land, Milo is so busy noticing what a beautiful day it is that he forgets to be scared. His brief stop in Expectations highlights the excitement he feels and Milo becomes eager to see more. To linger in Expectations, Milo realizes, is pointless since all one can do is wonder (asking "whether" questions) about where he can go next and what he can do.
When the distance between Expectations, where he comes up with ideas about the land he is about to tour, and the city of Dictionopolis proves to be very long and winding, Milo loses interest and begins to daydream. Here we see Juster's more specific theme: Milo allows his mind to wander, and so he physically wanders into the Doldrums, the land of ultimate boredom and laziness. The physical and the mental become one. Not only do Milo's physical surroundings jump-start his mental process, but here his mental processes change his physical surroundings. Juster suggests that a person can affect one with the other, exciting a boring place by thinking exciting thoughts or getting excited by finding an exciting place. The introduction of the watchdog—who eventually becomes Milo's closest friend in the Lands Beyond—and his suggestion that Milo can escape the Doldrums simply by putting his mind to work, underscores Juster's larger theme of finding interesting things everywhere, including seemingly boring places. All Milo has to do is use his imagination to get him back on track and speeding towards a more exciting and interesting place.