• Dave

The Phantom Tollbooth || The Sand Dollar Ep. 3



I wasn’t planning on doing this episode for a while, in fact I’ve ben spending the month preparing to do an episode on Star Trek the original series. But Wednesday March 10th, my friend Ryan Fossier, who is the ensembles coordinator at Boston Conservatory, an excellent composer and my friend sent me a link. That was when I found out Norton Juster had died, the author of today’s subject, The Phantom Tollbooth.

Phantom Tollbooth is one of those special books that I remember reading when I was younger, but didn’t understand until I reread it as an adult. It is packed with wisdom and humor and love of life. It is one of those books that was so inspiring to me that I wrote an entire orchestra piece about one of the characters while I was in grad school. More on that later.

If you haven’t read it, I am going into a lot of detail about this book, so SPOILER alert! If you are interested, it is a children’s book and isn’t a long read. I highly highly recommend it. Getting to reread it for this episode was an absolute joy, and if you need an easy but inspiring read, it’s a great choice. There is also film/musical version of it out there, though the book is where the magic really lies.

So, this is the first time that I am doing a deep dive like this. I’m excited to give it a shot and share some of the things that I’ve learned from this book and how I think about it in my everyday creation.


The premise of the book is a wild one. There is a boy named Milo, who isn’t interested in anything at all. Everything is boring and a waste of time. One day he comes home from school and finds a mysterious package in his room. He opens it and inside is a tollbooth. Insert a coin and you get to play the game. Milo decides well why not, gets in a little toy driving car, plops in his coins and drives through the tollbooth. But, as soon as he does so, his room disappears and he is suddenly in a different land, driving in the countryside. And from there the adventure unfolds and he travels to various lands, including a place Expectations-(the place you go before you go anywhere else), the Doldrums (a place you go when you stop thinking), Dictionopolis ( a city where you can buy words and letters), Digitopolis ( a city where all of the worlds numbers are mined), The Land of Ignorance (where you choose to live) and many more including my personal favorite: The Island of Conclusions, (which you get to by accidentally jumping).

Milo discovers that the two Princesses, Rhyme and Reason, have been kidnapped to a place called the Castle in the Sky. The Castle in the Sky is in the Land of Ignorance, and is filled with evil and demons. (More on that later). He must go and rescue them, and is joined on his quest by Tock, a watchdog, who is literally both a dog and clock, whose mission is to stop the wasting and even the killing of time.

Now already from all of this you can tell that there is going to be a lot of fun with the English language. We are surrounded by so many strange and unusual phrases in the English language, yet we hardly ever stop to think about what they actually mean. Who thinks about “killing time” and how awful a thing that is once you take the time to look at it. How easy is it to jump to conclusions about something?

And that exactly is Juster’s point. Thats the mission that Milo must go on, is to ultimately see the beauty and joy of everyday life, to not fall into the doldrums by not thinking!

Now on top of this word play and cleverness, Juster packs a sincere message into each and every chapter.

In Chapter 19: The Creatures of the Land of Ignorance exemplify this.

Milo and co. have rescued the Princesses Rhyme and Reason and are being chased by hideous monsters including:

The Triple Demons of Compromise: two of which disagree on everything and the third agrees

The Horrible Hopping Hindsight: whose eyes are in the rear and whose rear was out front. He leaps before he looks and doesn’t care where he is going as long as he knew why shouldn’t have to gone to where he’d been.

The Gorgons of Hate and Malice-who leave slime everywhere and move a lot quicker than you’d like to think

The Overbearing Know-It-All- a demon who is mostly a mouth and is there to spread misinformation.

The Gross Exaggeration-which hunt in groups

The Threadbare Excuse- which mumbles phrases like “well no one else did it” and “I missed bus” and he looks quite harmless but once he grabs you he never lets go.

Now humor aside, there is a lot to be learned in this. Juster has a way of making you laugh while also revealing truths about the human condition. How many of us have at one point or another been Horrible Hopping Hindsight? I know I have. Just about everyone I know at some point spends time overthinking why we shouldn’t have done something or another.

Laughter at the absurdity of our language.

What we can take away from The Phantom Tollbooth as creatives is the love of EVERYDAY MAGIC. That the originality that is found is this book is mystical or created, it is simply looking at what is already here and finding beauty in it.

There is a whole chapter about the love of noises sounds. A chapter on the love of silence. A chapter on perspective, where Milo, Tock and the Humbug all meet the a single man who is the worlds tallest short person, the worlds shortest tall person, the fattest thin man, and the thinnest fat man.

The Phantom Tollbooth is about perspective. It is about taking a step back and seeing the big picture, seeing life for what it is and loving it intensely. It seeks to instill a sense awe and wonder with regards to learning.

Ultimately what hits home about this book for me is its most beautiful mission. This sublime goal for its reader.

Let me read you the first page of Chapter 1. Milo:


“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. Where 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.

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 at all” EQ

Now that is beautiful opening. On the one hand it is something to which we can all relate. On the other it sets a premise that seeks to change our perspective on life itself.

To get us thinking about the EVERYDAY MAGIC that surrounds us, to not just look or hear, but to SEE and LISTEN.

What a noble and magical premise for children’s book.


I have loved this book for a long time in my life. As I will share at the end of the episode, this book is very personal to me and my life.

I get a lot of hope from the fact that even though this is one of my most cherished and loved books, the author, did this in his spare time.

That Norton Juster, wasn’t primarily an author. He was an architect.

This book and many more of his other children’s book was a labor of love. A part time author. In today’s language, a side hustle.

What is even more inspiring about this is that Tollbooth was his first published book. The illustrations were made by his roommate of the time. Jules Feiffer, who would go on to win a Pulitzer Prize and have a career as a cartoonist and an author.

As a creative person, this gives me so much joy to know that something that has mattered so much to me and no doubt has mattered so much to many people over time, was made in his spare time.

What a hopeful thought. That this is a shining example of an artist working on their craft part-time, juggling the everyday realities that many of us deal with, and despite all of it, coming through the other side.

For us as creatives, I think the lesson is clear. You never know how important your work might be to someone else down the road. That work that you do in your spare time, your labor of love always has the chance of resonating with someone.

Would it ever occurred to Juster that one day in the future, almost 60 years after his book would be published that a composer would make a podcast episode about his story? Of course not. Because that is not the point of the work.

Another point about this is the importance of connecting with those around us. The book is made all the better by the illustrations made by Juster’s than roommate: Jules Feiffer.

Now obviously, Tollbooth is a book, and it is mostly about the words and the story. But, the illustrations are such an important part of the story! The book would fundamentally read different if there was a different illustrator!

And that is the funny thing about collaborators. Obviously, you need to be in sync with them. It rarely is about being the best at whatever activity. I’m sure that there were hundreds of more experienced and qualified illustrators out there for Juster to work with. But, by the same token, the were probably thousands of more experience and qualified authors for Feiffer to work with. The point, is that it is almost never about hiring or finding the best person. Its about finding the right person, and the right person may very well be someone you already know.

Even the best person in the entire world, was at one point, a beginner, a newbie. A great collaborator is someone who shares the same vision as you. You don’t have to be the best in the entire world, just the small world that you are a apart of, with each project bringing you into a larger and larger world of connections and contacts.

As always, the people we know, the fellow artists, especially in different disciplines, are the ones we cherish. For everyone’s careers grow and blossom at different times. Your writer friend may turn out to be the next Margaret Attwood. Your director friend might be the next Steven Spielberg. Your composer friend may be the next John Williams. So appreciate the work of those done around you!

The point of the work is finding its audience. That this book as amazing as it is, wasn’t written for everyone. There are people out there that this book simply won’t resonate with, and that is perfectly okay.

Because it isn’t about pleasing everyone, it is about transforming your audience, however small or large it is. And once you take the time to do the hard work, to show up and be vulnerable, to put the time in, then you have the privilege of sharing it with others. Others with whom your work may resonate.

So if you learn anything from Juster, learn the importance of showing up and getting the work out there. You never know how what you are working on today can change and effect someone and their life.

Side hustles matter and they have the potential to create meaning just as much as those fortunate enough to be able to do their craft full-time. Don’t fall into the trap of thinking that just because you aren’t a professional means that somehow your work is less important, that it can’t connect or resonate with others. That’s the fear talking.



“Whether or not you find your own way, you’re bound to find some way.”


Its the trying and the doing that is the art. Don’t fall into the trap of thinking the work that you really want to do is impossible.


“So many things are possible just as long as you don’t know they’re impossible.”


I think the most important lesson for us as creatives, come in the very beginning of the book and the end.

Just after Milo reaches Expectations, he begins driving to Dictionopolis. But, on his way he starts to zone out and stop paying attention.

As his mind wanders, he slips into the DOLDRUMS. A place where everything moves slowly and thought is not allowed! Especially laughter. The land of uninspiration.

This is where he meets is greatest companion, Tock the Watchdog!

To get out of the Doldrums you have to THINK! You have to see life for what it is. And the fastest way to do this is to laugh.

I think for creatives it is easy for us to fall into the doldrums. To find ourselves in a place where we are uninspired, where we can’t think straight. Some might even think of writer’s block. Sometimes we can even fall into the doldrums by overthinking, or focusing to intensely on some aspect of the work.

It is easy to blame ourselves when we just can’t find that next great idea, and we are often our own worst critics. It is easy to think that the work we make while we are in the doldrums (if we are lucky enough to even be able to make at all) is a waste, that is a mistake.

That if it isn’t a great idea its worthless. And we miss an opportunity when start viewing mistakes as a bad thing. Sure, know one likes to make them, it is not a fun experience. But, we start taking everything so seriously, we can forget that failure is a great teacher.


“‘You must never feel badly about making mistakes,’ explained Reason quietly, ‘as long as you take the trouble to learn from them. For you often learn more by being wrong for the right reasons than you do by being right for the wrong reasons.‘” EQ

Juster’s point about laughter being the fastest way out of the doldrums is, I think spot on. Laughter has the power to make thing that are so heavy, that weigh us down, feel just a bit lighter.

Laughter has a way of making the lights in the room just a little bit brighter. .

And most importantly, laughter means we are having fun.

One of the best pieces of creative advice (and really just advice in general) that I have ever heard comes from Jordan Peele, a genius writer and director.


“Follow the fun”


That if we take ourselves too seriously, we may miss opportunities in our work that could see if we’re looking at it through the lens of fun.

And it can be easy to take things seriously, because we love it and it is important to us. Trying deal with the every day struggles of being an artist or creative in the making is a daunting task, and so many of us desperately want to succeed.

But when we lose track of the fun, we can make our work stale.

It may seem at times that what many of us are trying to do is impossible. And sure, many of us, myself included have high expectations and ambitions that we may not ever get.

But Juster reminds us:


“But just because you can never reach it, doesn’t mean that it’s not worth looking for.”


And even there, that’s a call to action. That you may not get everything you original set out for, and it most certainly won’t be perfect. But it is the doing of it all that matters, because it will change you and lead you somewhere that you need to go.


“But someday you’ll reach them all, for what you learn today, for no reason at all, will help you discover all the wonderful secrets of tomorrow.”


The book closes with Milo coming back to his room. He impatiently waits for school to finish the next day so he can race home and go back to the land beyond. But when he gets home, the Tollbooth is gone, with letter left explaining that he now knows the way. And at first Milo is very disappointed, but he slow starts to realize that there is some much going around him right now

Here is the very last page of the Book:

“And, in the very room in which he sat, there were books that could take you anywhere and things to invent and make, and build, and break and all the puzzle and excitement of everything he didn’t know-music to play, songs to sing and worlds to imagine and then someday make real. His thoughts darted eagerly about as everything looked new-and worth trying. “Well I would like to make another trip” he said jumping to his feet; “but I really don’t when I’ll have the time. There’s just so much to do right here.”


What does this mean for us???

That there is beauty and life all around us, if we choose to see it. EVERYDAY MAGIC


That the work that you do as a side hustler, or in your spare time has the potential to resonate.


Remember Milo when you want to get out of the doldrums, remember to step back and look at life. Remember to not just to look and hear, but to SEE and LISTEN.


I’ll end on a yet another quote:

“Time is a gift, given to you, given to give you the time you need, the time you need to have the time of your life. ”




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