Brain Pickings

Secrets of The Phantom Tollbooth: Norton Juster and Jules Feiffer on Creativity, Anxiety, and Failure

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“Failure is a process … you have to fail over and over and over again to get anything that’s worthwhile.”

In 1961, a young architect by the name of Norton Juster received a grant for a book on urban perception and settled down at his house in Brooklyn Heights to write it. Struggling with the process, however, he began toying with a playful story about a boy named Milo in an effort to distract himself from the burden of his workload, and showed his drafts to his neighbor, an emerging political cartoonist named Jules Feiffer. Juster never wrote the urbanism book — instead, he teamed up with Feiffer and together they dreamt up The Phantom Tollbooth, which went on to become one of the most celebrated children’s books of all time, brimming with timeless philosophy for grown-ups — its map of The Kingdom of Wisdom alone is a profound metaphor for curiosity and the human condition.

Map of The Kingdom of Wisdom from ‘The Phantom Tollbooth’

In 2011, to mark the 50th anniversary of the beloved classic, Brooklyn-based filmmaker Hannah Jayanti set out to capture the book’s remarkable legacy by offering a rare glimpse of its creative process in a documentary that follows Feiffer and Juster, both 82 at the time, as they reminisce about their historic collaboration and the lesser-known challenges of the project. The documentary, funded on Kickstarter, has now come to life. Hannah has kindly offered two exclusive clips from The Phantom Tollbooth: Beyond Expectations — one of Juster and one of Feiffer, each reflecting on the core of his creative philosophy — for our collective enjoyment. In the first clip, Juster explores the reverse bell curve of pleasure that stretches across what he considers to be the three stages of writing — a notion that maps almost perfectly onto Malcolm Cowley’s four-step model, only fusing the first two steps into one — as he looks back on writing The Phantom Tollbooth:

It was a wonderful experience — wonderful in an odd sense, in that I always felt there were three steps in writing:

The first step, which is the anticipation of writing — wonderful, because there you are with an abstract idea, and you’re quite sure that you can do it, and it’s going to be quite wonderful, and you can visualize all the wonderful sales, the interviews, the reviews; you start to write your Nobel acceptance speech. And so that’s great, because there’s nothing real there, in the anticipation of writing.

Number three is the other end of that, having finished — and that’s a wonderful feeling, because number two is an agony all the way.

Juster echoes Kierkegaard on anxiety as an essential part of creativity, reminding us of John Keats’s notion of “negative capability” — the uncomfortable skill of tolerating uncertainty and the prospect of failure, so very crucial to all good art — and harking back to Tolstoy’s notion of “infectiousness” as the ultimate litmus test for creative success:

I find that writing … it’s so anxiety-making, it’s so tense, it’s so scary, it’s so full of danger of failure, that you wake up every morning and you’re not sure what’s going to happen, and you don’t know whether you’re going to be able to do it… You can feel what you want in the back of your head but can you and are you going to get it down on paper so someone else can feel the same.

Juster’s closing remark, however — the revelation that someone as magnificent as Maurice Sendak experienced the same cauldron of creative anxiety — is strangely yet immutably comforting.

In the second clip, Feiffer reflects on his experience as an art educator and the importance of teaching his students the art of making mistakes — and reminds us that the fear of failure so core to the creative experience, while toxic, is also our greatest chance for transcendence:

Failure is a process … you have to fail over and over and over again to get anything that’s worthwhile, and to try everything.

The full film premieres at the 2013 New Yorker Festival and is available for pre-order online. Complement it with the magnificent The Phantom Tollbooth 50th Anniversary Edition, which features reflections from such beloved authors and artists as Philip Pullman, Suzanne Collins, and Maurice Sendak.

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