The art of a good question is always to draw out the thoughts and feelings of the one being questioned…(and for the most part…to avoid yes/no answers).
Here are 20 questions to get your student chatting up a storm (of course the student must have read the book closely in order to answer them, so you’ll find that out too.)
To read a review of THE PHANTOM TOLLBOOTH, click here
To order THE PHANTOM TOLLBOOTH, click here.
- What is Milo like in Chapter 1. How would you describe him?
- Would you want to be Milo’s friend, the Milo of Chapter 1? Why or Why not?
- When Milo sees the mysterious gift, he makes a pretty big effort to put it together (the tollbooth) and then decides to use it. Does this surprise you? Why or Why not? Would you go through all the trouble to put the tollbooth together and use it?
- In Milo’s initial travels, he gets stuck in the Doldrums. Who helps him get out? What does Milo have to do to get his car moving again?
- How would you describe Dictionopolis?
- In chapter 6, we learn about two Princesses. What are their names and how did they get banished?
- Milo starts thinking about the idea that he will rescue the Princesses. Where are the Princesses being held and what hardships will Milo face if he tries to rescue them?
- How would you describe the banquet in Dictionopolis? Did any of the foods make you laugh? Which one(s)?
- Chapter 9 introduces us to a boy called Alec and the idea of Point of View…How would you define “point of view” based on the discussion Alec and Milo have?
- In Chapter 10, the chapter that features Reality, Milo realizes “…the many times he’d done the very same thing; and, as hard as he tried, there were even things on his own street that he couldn’t remember…” What was Milo’s mistake? How has he made the same mistake people in Reality made long ago?
- Alec tells Milo in Chapter 11: There’s a lot to see everywhere, if only you keep your eyes open. What do you think Alec means when he says this to Milo? What is Milo supposed to see?
- Are noises and sounds important to you? Which ones and why? What do you think it would be like to live in a place where there was no sound?
- Milo steals a sound from the Soundkeeper…How does he do it and what are the results?
- Is the Island of Conclusions a good place to jump to? Why or why not?
- Who helps Milo reaches Digitopolis (see Chapter 14)?
- How does Milo outsmart the Mathemagician?
- What does the Demon of Petty Tasks and Worthless Jobs, Ogre of Wasted Effort and Monster of Habit ask Milo, Humbug and Tock to do?
- What are the demons that protect Ignorance? Come up with a list of the demons in this book, to the best of your ability (hint…end of Chapter 16 to middle of chapter 19)
- Which demon scares you the most and why?
- Look back to your Chapter 1 answer…How has Milo learned from his adventure? How would you describe him now? Would you want to be Milo’s friend, the Milo of Chapter 20?
THE PHANTOM TOLLBOOTH is a Gateway Book for Digging into a Values Discussion with your Children or Students
To order this classic, click here.
To access 20 questions on the book, click here
This post is especially (but not only) for folks who have kids or teach kids. I loved my re-read of THE PHANTOM TOLLBOOTH. Here are four reasons why you ought to read this book with a child today (or tomorrow if the child is already asleep). And, for the record, this story does NOT fall into the category of sci-fi…more aligning with fantasy than science fiction.
- The story introduces ideas that unearth values we have (or need) about education and learning.
- The main kid character starts out flat and plain, but makes simple choices that thrust him into hero status…In many respects, he reacts to problems in a childlike way…he is very relatable…he also wants to do what is right. He discovers that doing what is right will require courage. He relies on his friends to accomplish the heroic task. These are all important values put forward by THE PHANTOM TOLLBOOTH.
- Imaginative characters, whose names reflect an aspect of their character, that you can discuss with your child, thus leading to more thorough discussions on everything from friendship to politics. This is a timely story for our kids. (No, really…you CAN talk with your kids about politics after reading this book…In fact, you should!)
- Lovely illustrations by Jules Feiffer scattered throughout.
Now for the longer review and musings about stories that provoke discussions…which is a very old way to teach deep lessons.
How does one discuss serious real-time issues with kids? Stories help a lot. I remember showing our children (and at a pretty young age) the Star Wars trilogy…at the time it was episode 4, 5 and 6. Star Wars is an archetypal good versus evil narrative. It features a character, Darth Vader, who though evil, still has the potential for redemption. This was an idea my husband and I wanted our 6 and 8-year-old kids to understand. The story raises the issues: What is evil? The Empire shows what evil looks like in a variety of ways. What is good? The rebellion shows us good and what it’s like when good battles evil. The force is a neutral entity in the universe, but seems to be used most powerfully (ultimately) by those who are good. Star Wars also raises this important question: Can a person be pure evil without the possibility for reform? This story tells us about Luke, Darth Vader and the deep power of love (sometimes love that costs us our lives, as it did for Anakin, Darth Vader) and how that love counters evil…(not to mention the sacrificial love of the friends, Han, Leah, R2-D2, C-3PO and Chewie.) This is a friendship story as much as it is a family story.
For me and my husband, the above ideas were important to us in particular because of our values that also have to do with our faith. We wanted to discuss the reality of evil with our kids, but also help them understand that people ALWAYS have the possibility of breaking free from the evil that grips them and as they do so, help themselves and others achieve goodness…much as (spoiler alert) Darth Vader does at the end of Return of the Jedi.
THE PHANTOM TOLLBOOTH is definitely less scary than Star Wars, but the reader still finds a good versus evil narrative. Milo, a boy, disinterested in life and education is our protagonist. This is how the reader sees him in Chapter 1.
“It seems to me that almost everything is a waste of time,” he remarked one day as he walked dejectedly home from school. “I can’t see the point in learning to solve useless problems, or subtracting turnips from turnips, or knowing where Ethiopia is or how to spell February.” And since no one bothered to explain otherwise, he regarded the process of seeking knowledge as the greatest waste of time of all.
Milo is given the gift of a magic tollbooth that takes him into an imaginary world, a place that will transform him. While there, he learns that words sustain life. He learns that numbers too are essential to life and he learns that the conflict between two brothers (the king of words and ruler of numbers or the Mathmagician) cannot be solved until he helps them bring back their sisters from banishment. They are the Princesses Rhyme and Reason. In the world Milo is visiting, there is currently no rhyme nor reason to anything that takes place and it that has caused much misery across both kingdoms.
Milo isn’t a bad kid…initially, he’s just bored and disengaged…In today’s world…Milo might be a tv junkie or video game addict, but in the 60s…he was simply lethargic, lying around and doing nothing because nothing seemed interesting to him. In the new world where he travels, he is confronted with an adventure that captures his passion. Milo then begins to appreciate and notice the world around him, including the importance of education and learning. Milo’s transformation is an example of a child who decides to be curious and walks toward/into an adventure. That little step opens him to a world of learning. He even gains friends along the way.
A key for Milo is that he figures out his purpose. He decides to rescue the two princesses. He persists until he achieves the goal, despite many challenges.
The evil characters (Juster calls them demons) in this story resonate with today’s evils and dare I say…some of our current events. The demons live on the Mountain of Ignorance and include monsters such as Compromise, Hopping Hindsight, the Gorgons of Hate and Malice, Overbearing Know-It-All, Gross Exaggeration and Threadbare Excuse. Each creature described on the mountain could spur a conversation about values. Parents, consider yourself primed for a discussion of politicians, ad agencies, media or news organizations and grownups, in general…We adults could all use a refresher course on the “demons” that dull our wits in postmodern society. Good lessons for all.
Milo is a relatable kid character, even for kids today. He starts out bored and boring until he accepts the invitation to enter the tollbooth. His curiosity spurs him forward. He emerges into the new world and continues to be curious. He learns along the way that he must engage his senses and make friends. He slowly grows in appreciation of beauty around him and all the goofy characters he meets who are passionate about one thing or another. However, Milo’s own passion is not fully engaged until he decides to rescue the princesses. Then, his journey takes on a new vitality and without being fully conscious of it, he has stepped into the hero’s journey. His purpose, which has become his passion enables him to persist.
Through his determination and action, Milo is healed of his boredom…At the close of the story, Milo grieves that he (spoiler alert) no longer has access to the tollbooth, but he notices that
…the sky was a lovely shade of blue and that one cloud had the shape of a sailing ship. The tips of the trees held pale, young buds and the leaves were a rich deep green. Outside the window, there was so much to see, and hear, and touch–walks to take, hills to climb, caterpillars to watch as they strolled through the garden. There were voices to hear and conversations to listen to in wonder, and the special smell of each day.
*For a suggested list of questions for teachers, see my post on THE PHANTOM TOLLBOOTH, discussion questions for educators.