Norton Juster’s The Phantom Tollbooth is a classic. It’s whimsical, sharp, and dripping with creative brilliance. But if you’re the kind of person who likes to dig deeper, theologically or philosophically, you start to notice that there are a few places where the story doesn’t quite hold together. Here are three big incongruences that stand out, and what they reveal.
Wonder Without a Foundation
At the beginning of the story, Milo is bored and disinterested. By the end, everything is magical and full of purpose. On the surface, it’s a beautiful arc, but here’s the problem: nothing external actually changes. Milo’s “new world” is just a shift in perspective, and while that’s inspiring, it’s also hollow. If wonder is only based on a feeling, what happens the next time Milo wakes up bored?
Feelings are great, but feelings also change, therefore, the reader has to ask the question, “Without an anchor for meaning, something outside of herself or himself, where does a person find something more stable than feelings?” I love “wonder” but “wonder” alone is temporary at best.
The Rhyme and Reason Dilemma
The whole plot revolves around restoring Rhyme and Reason to the kingdom, which I appreciated. Once they’re back from their journey, everything is balanced again. But pause for a second: why were they exiled in the first place? And why does their mere return magically fix a broken kingdom?
The story never digs into those questions. It wants the satisfaction of resolution without the complexity of wrestling with why wisdom was lost, or what sustains it in the long run. It’s like patching a leaky roof with duct tape: it works for now, but it won’t hold when the next storm of life rolls in on someone.
In short, you could make the argument that this book could do spiritual harm to someone, which is what the authors are trying to avoid. It’s great to ask questions but simply fanning the flame of deconstruction could lead a person to a place of confusion. How’s that helpful?
Growth Without Real Community
Milo matures throughout his journey, no doubt about it. He goes from apathetic to engaged, passive to proactive, which is great! But he mostly does this alone as an individual. Sure, there’s Tock and the Humbug tagging along, but the story doesn’t show deep, transformative community shaping Milo.
In real life, and certainly in a biblical framework, real transformation usually happens with people, in relationship, through accountability and shared experience. Milo grows in isolation, which makes for a clean narrative but a shallow reality.
Why These Gaps Matter
None of these incongruences ruin the book, far from it. In fact, they make it a great conversation starter. They reveal that while The Phantom Tollbooth offers brilliant observations about curiosity, courage, and wonder, it struggles to ground those truths in something unchanging. That’s where a biblical worldview shines: it takes the good questions the story raises and points to a better answer — one rooted in the life, death, and resurrection of Jesus.
What do you think? Where have you noticed moments in The Phantom Tollbooth that feel a little thin? Or are these the very things that make the book such a timeless read?

