The Phantom Tollbooth Questions and Answers
by Norton Juster

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Why is it fitting that Milo's journey started with the Land of Expectations?

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It is fitting that the first place Milo goes to is the Land of Expectations because Milo's standards are so high that nothing meets his expectations. Everything feels like a waste of time.

In the first chapter, he talks about how much he hates school and what a waste of time it is. He says “the process of seeking knowledge is the greatest waste of time of all.” It isn't just school, however. He says he owns nothing interesting, he never goes anywhere interesting and he never does anything interesting. Even when he is putting together the tollbooth he is disappointed that it doesn't include a highway

After the Land of Expectations, Milo gets stuck in the Doldrums where "nothing ever happens and nothing ever changes.” and where it is against the law to think. He is helped by a watchdog called Tock who takes him to the capital city of Dictionopolis. Here they find a word market selling words and letters that can make you stronger. After many adventures in Dictionopolis, including getting arrested and thrown into a dungeon, Milo travels to the mathematical world of Digitopolis.

On his return home, Milo is a changed person. He misses his friends and his old way of life and looking out of his window realises how beautiful the world is.

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