At the outset: “since no one bothered to explain otherwise, he regarded the process of seeking knowledge as the greatest waste of time of all” (pg 9).

In the beginning, Milo could not see the purpose of learning to subtract, to identify a country, or to correctly spell words. Thus, he does not have the motivation to participate in these activities. He perceive these activities as pointless, mundane, and unnecessary in life. But he also wonders what is life supposed to be about. Because of this lack of meaningfulness, Milo is not happy and nothing ever gets him to be happy. Certainly not his room full of toys or going to school would uplift his low spirits. But as the story progresses, we can see that his queer journeys and experiences through the Tollbooth are meant to help him to discover this hidden purpose.

Milo’s travels through the land of Expectations, the Doldrums, and on to the Kingdom of Dictionopolis is reflective of his progress to go beyond his low expectations, to get out of doing nothing, and to advance toward finding a purpose in life and in learning. The turning point is when he decides to start thinking, to start moving. Along the way, he unconsciously develops a fascination/interest for the different elements of knowledge. For example, letters and words are the essential mediums to acquiring knowledge.  Without these basic building blocks, one would find it difficult to comprehend concepts and truths, which is knowledge itself, from a bunch of strange looking words. Near the end of chapter eight, Milo is committed in a quest to save the two Princesses of Rhyme and Reason. We finally see Milo take an interest in something other than doing nothing. And through each of the events, we can see very clearly the change that Milo successfully went through from his original indifferent attitude.

I see the Tollbooth experiences as a journey for Milo to discover the purpose in seeking knowledge. I also see the experiences as an exposure to the way to knowledge, which is through words and sentences and meaning. These inferences are based on the fact that Norton Juster’s direct focus on the idea of knowledge. He structures his settings and contents in terms of the “Foothills of Confusion”, the “Mountains of Ignorance”  and the “Sea of Knowledge”. These are meant to distinguish the stages of knowledge; you either stay or move beyond ignorance and into perhaps confusion and onto having knowledge. But in order to get to the sea of knowledge, one must acquire words before sailing to the Sea of Knowledge (pg 45). Juster’s emphasis on this specific chronology led to the idea that Milo is to find purpose in seeking knowledge.

In conjunction to the stages of knowledge, Juster’s literal play on words such as “you eat your own words” at King Azaz’s banquet or the “Watchdog” and the “Spelling Bee” provide further emphasis on the role of grammar. He also integrates sarcasm in the dialogues to exemplify that meaning can be taken differently when spoken literally and sarcastically. For example, Sheriff Shrift thought the Humbug implied that “boys are the cause of everything” (pg 62). Thus, Juster purposefully illustrates the different ways that meaning can be conveyed as in sarcasm, literally at face value, or implications. I thought these are brilliantly integrated into the random yet structured world of the Tollbooth.

On the last note, I want to applaud the way Tollbooth is exceptionally written as a children’s book. I believe children can easily be drawn into Milo’s journeys because of the random twists of events, the queer characters and the play of words. Even as an adult, I find this book very amusing and I have a high level of interest to keep reading. The Phantom Tollbooth is one rare combination of amusement and education (alphabets, words, conveying meaning through words, etc).