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1
Why do you think Milo was chosen to receive the Phantom Tollbooth?
The Phantom Tollbooth leads to an adventure that forces a person to notice the world around them - not just the big, obvious things, but also the little, everyday things that sometimes are taken for granted. Milo was a child who didn't really notice anything and who was bored by everything. In fact, he always felt like he had nothing to do and would spend every minute of the day wishing he was doing something else. From the start of his adventure he is forced to look at everything differently and not just see it but appreciate it and understand its purpose. For example, he would see the different colors of a sunrise every day but not pay them any attention until he tries to conduct the orchestra of colors himself and finds that everything is the wrong color entirely.
Milo does not really know why he needs to learn many of the subjects he is studying, and this experience shows him that one never knows when particular knowledge will be useful and that you must retain it for when it is needed. He is the ideal child to receive the Phantom Tollbooth because when his journey is over, he is transformed: the formerly bored child is now excited and energetic and unsure of how he will fit everything into his day because there is just so much to see, do, and play with.
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2
What does the Island of Conclusions teach Milo?
The Island of Conclusions can only be reached by jumping and it becomes clear that by jumping to Conclusions one will never find the right answer for anything. By jumping, one also avoids swimming in the Sea of Knowledge which surrounds the island, because if one had already taken a dip in the Sea of Knowledge one would not need to jump to Conclusions at all. The island shows Milo that it is better to study something and gain some real knowledge about it than it is to assume you know something and not experience the best of it.
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3
Do you think the Mathemagician and King Aziz will continue to live in harmony?
King Aziz and the Mathemagician have fundamental disagreements about words and numbers and which is more important. This is why they need the Princesses Rhyme and Reason to maintain accord. The king believes words are much more important than numbers and is offended that the Mathemagician thinks numbers are even close in their importance. The Mathemagician believes numbers to be superior to words and is mortified by any suggestion that they are equal. Fortunately they will never agree on anything and so will be unable to banish the princesses again as this can only happen if they are on complete agreement. They will therefore maintain an accord which would be unlikely if they were without Rhyme and Reason again.
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4
What does Juster suggest about words and their power?
Words are incredibly important. They create meaning, make life vibrant and colorful, and help achieve goals and desires. They form questions and answers, and, as King Azaz, says, "With them there is no obstacle you cannot overcome. All you must learn to do is use them well and in the right places" (99). Words help discover and explore, connect and decipher. Of course, words are very powerful. They have to be chosen properly and precisely or their meanings can be obfuscated. Too many of them can also obscure meaning.
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5
What does Juster suggest about numbers and their power?
Milo also learns about the power of numbers. He realizes that numbers can make his world knowable. Numbers help measure, estimate, and make things precise. They help you travel places, know how long something will take, and find a way to make something like time concrete. Numbers are powerful because they provide truth and clarity; on the other hand, they also can give us a sense of the infinite.