Lessons in Rereading: The Phantom Tollbooth

While I love a good textbook as much as – if not more than – your average gal, I’ve been feeling a little bogged down by my collegiate course-load these days. Looking for an extracurricular remedy to my academic blues, I decided to design myself an entirely new syllabus, and I thought you might want to tag along.

Welcome to Lessons in Rereading, where I’ll return to a childhood classic every month or so and put it to the ultimate test of rereading. Do the works of literature that shaped our early years have anything to offer for a twentysomething on the go? Can we learn something new as we look back on those adolescent page-turners? Do we ever really outgrow the books of our childhood?

First up: The Phantom Tollbooth, published in 1961 by Norton Juster with illustrations by Jules Feiffer.

I still remember plucking a dusty copy of The Phantom Tollbooth off the shelves of my local public library. No one recommended Juster’s masterpiece to me, and I had never heard of the strangely titled book before. To me, it was as if I had discovered some hidden treasure, a story written just for my six-year-old eyes. Little did I know, I had stumbled across one of the great works of children’s literature.

The Phantom Tollbooth recounts the story of Milo, a despondent boy who can’t muster up any enthusiasm until, one day, he receives a strange package containing a magical tollbooth. (In rereading The Phantom Tollbooth, I have a better sense of what a tollbooth actually is, so I’ve learned something in the last fifteen years.) Milo hops in his toy car, drives through the tollbooth, and finds himself in a magical land. While the plot of The Phantom Tollbooth is somewhat secondary to the novel’s revelry in the pleasures of language, you’re still swept up in Milo’s quest to restore Rhyme and Reason to the Kingdom of Wisdom. A triumphant Milo returns home and receives notice that, as mysteriously as it arrived, his tollbooth has disappeared. But that’s okay because, as Milo exclaims in the final words of the novel, “Well, I would like to make another trip…but I really don’t know when I’ll have the time. There’s just so much to do right here.” That’s Juster’s point, really: you don’t have to travel any further than your own backyard to find an adventure, because your imagination can turn even the most mundane of surroundings into a fantastical new world.

From the very start, Juster peppers Milo’s adventures with puns on the intricacies of grammar and language. To an awkwardly bookish kid, the power of language at the heart of The Phantom Tollbooth was mesmerizing. To an only slightly less awkwardly bookish twentysomething, the verbal acumen of Juster’s novel still astounds, reaffirming my own commitment to a life of active learning. Over the course of the tale, Milo learns that anything is possible if you just think. Your mind is a powerful tool, and when used properly, its potential is limitless. Whether you’re counting down the days until graduation, committing yourself to the academy, or just trying to finish that book on your bedside table, Juster has a message for you. Keep learning, keep expanding your mind, and you’ll go far.

The Phantom Tollbooth would be worth a reread on these merits alone. It’s the perfect antidote to boredom, an affliction that infects regardless of age. And if you’re feeling stuck, if you’re trapped in the doldrums of tedious office work, mired in an unfulfilling romantic entanglement, or in the midst of your run-of-the-mill quarter-life crisis, The Phantom Tollbooth reminds you that the key to living an extraordinary life lies within your own mind. And that’s pretty cool.

But for me, The Phantom Tollbooth holds a new meaning this time around, and from the vantage point of my twenties, I feel an even greater kinship to Milo. As I reread the first pages of The Phantom Tollbooth, I felt something click. Like many of my fellow twentysomethings, I know all too well the inexorable, grinding halt of the depressed mind. Nothing seems quite as bright as it once did, nothing is as interesting, as captivating. It seems that Milo knows just how I feel:

There was once a boy named Milo who didn’t know what to do with himself – not just sometimes, but always.

When he was in school he longed to be out, and when he was out he longed to be in. On the way he thought about coming home, and coming home he thought about going. Wherever he was he wished he were somewhere else, and when he got there he wondered why he’d bothered. Nothing really interested him – least of all the things that should have.

And that is how The Phantom Tollbooth opens.

The dullness of Milo’s life has been the texture of my depression, and his struggle has been mine. It is the struggle of reawakening a sleeping mind. Sometimes, it seems as if my mind is actually my greatest enemy, a foreign adversary blocking my path at every turn. But as a twentysomething rereading The Phantom Tollbooth, I’m reminded that my mind is also my greatest strength.

What was your favorite book as a child? Is there anything you’re itching to reread? Got a book I should add to my syllabus? Let me know in the comments!