The Phantom Tollbooth by Norton Juster

Kit Teguh
4 min readAug 4, 2023

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The Phantom Tollbooth’s iconic cover may well be one of my favourite book covers ever. A young boy is face to face with a dog at least three times his size, and the dog doesn’t look none too impressed at him. They’re staring at each other nose to nose. There is a huge clock on the side of the dog. You’d only learn later and perhaps you should’ve guessed that the dog is a watchdog. Peppered generously, the rough illustrations in the book complements the linguistic pandemonium that is The Phantom Tollbooth.

Thinking that it’s a good airplane book, I brought the book over for a short trip to Singapore where I finished it on the second day. To be fair, if you have enough time, you can finish the whole thing in one sitting, but who’s got the time these days? The front cover of my copy was already falling apart by the time I read the first page, and was already entirely separated by the time the flight arrived an hour later, but I guess the torn and browning pages add some charm to the book, like the tollbooth itself, found amidst the attic dust.

Image by Goodreads

A young and apathetic boy, Milo came across a gift from a mysterious entity in the form of a tollbooth in his attic which will take him to the worlds beyond. Jumping on his long, unused electric car he ventures through to look for the city of Dictionopolis. The land has long been chaotic and furtive ever since the princesses Rhyme and Reason were exiled away by their callous brothers, Azaz the Unabridged who rules Dictionopolis and Mathemagician, who oversees Digitopolis. It is Milo’s quest along with his companions Tock the watchdog and the Humbug to bring them back so stability reigns in the land.

Right off the bat, I knew the book was pretty special on Milo’s first encounter with the Whether Man in the Land of Expectations:

“What kind of a place is Expectations?” inquired Milo, unable to see the humor and feeling very doubtful of the little man’s sanity.

“Good question, good question,” he exclaimed. “Expectations is the place you must always go before you get to where you’re going. Of course, some people never go beyond expectations, but my job is to hurry them whether they like it or not.”

In so doing, my expectations of this book was also blown out of the water. There is so much intelligent wordplay and profound thoughts of how we do things — mundane things, our own limitations, our ambitions, which words are able to show our strengths and limitations.

And an absolute gem when our heroes find themselves somehow jumping to the Island of Conclusions:

“But how did we get here?” asked Milo, who was still puzzled by being there at all.

“You jumped, of course,” explained Canby. “That’s the way most everyone gets here. It’s really quite simple: every time you decide something without having a good reason, you jump to Conclusions whether you like it or not. It’s such an easy trip to make that I’ve been here hundreds of times.”

Many people are stuck in the Island of Conclusion and finding it hard to make their way back, to swim back is to get wet and not many want to get wet while the way back is long. After all you can “swim all day in the Sea of Knowledge and still come out completely dry”. I feel attacked with this line, as sometimes this is how I feel about my insatiable reading.

The world of the Phantom Tollbooth is a land where people eat their words (literally), the concept of words and numbers battle for the pursuit of truth, boys growing from the air to the ground, 0.58 of a boy shows up out of nowhere, the sunset is orchestrated, well, by an orchestra. There are monsters which haunt the book as well as our lives: The Everpresent Wordsnatcher, the Terrible Trivium, the Demon of Insincerity, the Giant, and the Senses Taker. As an allegory, The Phantom Tollbooth doesn’t carry too many flaws.

Though seemingly written for children, perhaps you’d only appreciate it better as an adult with its intense wordplay and moral allegories, but it is a book that children should have a taste of in their younger years. Bunyan’s Pilgrim’s Progress comes to mind if you have read that, with its overt symbolisms. But this book is much, much, much, much, much better. It is a joy to read and who knows, you might get something more out of it than the preachiness of Pilgrim’s Progress.

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Kit Teguh
Kit Teguh

Written by Kit Teguh

A full time project manager who loves to read on the side. Connect with me to chat anything tech and lit.

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