The Missing Piece Meets the Big O: Shel Silverstein’s Lesson on Self Reliance & Mentorship


Shel Silverstein was an American writer, poet, cartoonist, songwriter, and playwright. He is known for his cartoons, songs, and children’s books. His books have been translated into more than 30 languages and have sold more than 20 million copies, and he was the recipient of two Grammy Awards (“A Boy Named Sue” as popularized by Johnny Cash, and a recording of his famous “Where the Sidewalk Ends

For her first Christmas, my parents got my niece Shel Silverstein’s Where the Sidewalk Ends (apparently expectations are high for the six-month mark). I grew up reading its collection of poems, over and over. I even – to the horror of some of my readers, I am sure – used colored pencils (because I didn’t yet appreciate the waxy beauty of crayons) to color in some of Silverstein’s famous illustrations.

The gift sent me down memory lane. Re-reading a selection of those poems from all those years ago, I was struck by just how much more there is to much of Silverstein’s writing than his characteristic style and funny words.

Take the namesake of that book – Where the Sidewalk Ends – for example. As a child, reading the poem brought to me images of running out into a grassy field somewhere. And that is what Silverstein is writing about.

But why didn’t I realize that the place “before the street begins” was so radiant? It is “soft and white,” burning “crimson bright,” with a mint-sweet smell in the air. What happens, once we arrive in the city, that changes nature into a place where the “smoke blows black” and the winding “dark streets” are pitted and cracked?

Are the “asphalt flowers” supposed to be nature succumbing to industry? Or are we even talking about nature?

Maybe we are the flowers, trapped in cracks of a toiling modern life – meaning we never grow into what we were meant to be? Why is it that only the children see the “chalk-white arrows” and know they lead to “the place where the sidewalk ends,” while adults might have forgotten how to get there altogether?

Where the Sidewalk Ends

There is a place where the sidewalk ends
And before the street begins,
And there the grass grows soft and white,
And there the sun burns crimson bright,
And there the moon-bird rests from his flight
To cool in the peppermint wind.


Let us leave this place where the smoke blows black
And the dark street winds and bends.
Past the pits where the asphalt flowers grow
We shall walk with a walk that is measured and slow,
And watch where the chalk-white arrows go
To the place where the sidewalk ends.


Yes we’ll walk with a walk that is measured and slow,
And we’ll go where the chalk-white arrows go,
For the children, they mark, and the children, they know
The place where the sidewalk ends.

And what about the unhappy crocodile with a toothache? Isn’t it true that we often run through life not listening to other’s difficulties because of our preoccupation with solely our own lives, meaning others have no option but to do the same?

The Crocodile’s Toothache

Oh the Crocodile
Went to the dentist
And sat down in the chair,
And the dentist said, ‘Now tell me, sir,
Why does it hurt and where?’
And the Crocodile said, ‘I’ll tell you the truth.
I have a terrible ache in my tooth.’
And he opened his jaws so wide, so wide,
That the dentist he climbed right inside,
And the dentist laughed, ‘Oh, isn’t this fun?’
As he pulled the teeth out, one by one.
And the Crocodile cried, ‘You’re hurting me so!
Please put down your pliers and let me go.’
But the dentist just laughed with a Ho Ho Ho,
And he said, ‘I still have twelve to go —
Oops, that’s the wrong one, I confess.
But what’s one crocodile’s tooth, more or less?’
Then suddenly the jaws went snap,
And the dentist was gone right off the map.
And where he went one could only guess…
To North or South or East or West…
He left no forwarding address.
But what’s one dentist more or less?

And we all need to remember to not take ourselves too seriously because creativity doesn’t come without the chance of looking at least a little bit silly.

Put Something In

Draw a crazy picture,
Write a nutty poem,
Sing a mumble-grumble song,
Whistle through your comb.
Do a loony-goony dance
‘Cross the kitchen floor,
Put something silly in the world
That ain’t been there before.

But then I came across one of Silverstein’s works that I had not read before – thanks to the power of Google and the endless curiosity of Maria Popova. Flipping through the pages of The Missing Pieces Meets the Big O, I landed on a little bit of a different takeaway than Maria did.

She is probably closer to correct, but I thought I would share the story and my own thoughts anyway – which is related to Charlie Munger’s ideas on dealing with adversity: “If you just take the attitude that, however bad it is in any way, it’s always your fault and you just fix it as best you can – the so-called ‘iron prescription’ – I think that really works.

Pictures sourced from Open Library.


We meet a lonely, pointy shape that wants nothing more than to be able to roll. Unfortunately, its shape is not quite right for rolling – or so that is what it believes. Thus, it is constantly searching for something outside of itself to solve its inability to roll.

It looks to all these other shapes, trying to find a way to fit in with them so that those shapes can carry it along. But the fit is never quite perfect, and it even has to put on a false exterior to try to attract attention.

But even after finding what looks like a good fit, the missing piece runs into trouble as it changes over time – and thus it is left alone, again.

But then the missing piece meets a shape very different from those it has met before – a solid piece that can roll completely on its own – the Big O!

Unlike the other pieces, the Big O is not looking for anything from the missing piece.

“What do you want of me?” asked the missing piece.
”What do you need from me?”
“Who are you?” asked the missing piece.
“I am the Big O,” said the Big O.

Much to the disappointment of the missing piece, the Big O says it cannot help the missing piece roll.

In fact, according to the Big O, it is up to the missing piece to go through the effort of trying to roll in order for it to start rolling!

“By myself? A missing piece cannot roll by itself.”
”Have you ever tried?” asked the Big O.
“But I have sharp corners,” said the missing piece. “I am not shaped for rolling.”
“Corners wear off,” said the Big O, “and shapes change. Anyhow, I must say good-bye. Perhaps we will meet again…”

Well, that is annoying, isn’t it? The missing piece has wasted all this time and effort trying to find something it was in control of the entire time.

And after some effort and practice, the missing piece is no longer a missing piece at all. In fact, it is now the Little O!

The potential to do what it wanted to do was inside the missing piece the entire time, but it was easier to look at other ways of solving its problems – to other shapes to solve its pointedness – than it was to go through the effort of changing itself to achieve its goal.

But that never seems to work out, at least over the long term for most people.

This is also a beautiful metaphor for the importance of mentors and understanding how others got to where they are today. Sitting alone, only seeing pieces missing something, the missing piece might never have understood what its potential was or how to achieve it.

Remember to face your problems with an ownership-mentality, and try to surround yourself with people better than yourself so that you can learn from them. If you happen to have made some progress, don’t forget to humbly help those looking for guidance on how to do the same.

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