A Playboy cartoonist and children's book author divulges the hidden-secret to coming up with a never-ending stream of ideas.

Written by Cole Schafer

The late cartoonist, writer and musician Shel Silverstein was an idea machine. He came up with more ideas on a daily basis than most creatives do in an entire year. 

Shel was a horrendous speller, a quality that his editors at Playboy (and later his publishers at HarperCollins) would bitterly complain about. Shel's mind worked so goddamn fast, that his fingers could barely keep up with his constant flow of ideas.

In Lisa Rogak’s stupendous biography, A Boy Named Shel, she loosely describes Shel's process for coming up with ideas in several places throughout the book. I found his approach inspiring. So much so, that I've distilled it down into something a bit more concrete.

Step One: Hunt

Back when Shel lived part-time at The Playboy Mansion (for many years he was Playboy’s go-to cartoonist), he was said to wander its never-ending parties in constant hunt for inspiration. 

He’d move from person to person. If someone bored him, he’d leave the conversation in the middle of a sentence without so much as a wave goodbye. However, when he did find someone that interested him, he was completely and totally present with them. 

Dianne Chandler, a playmate at The Playboy Mansion, described Shel as a heat-seeking missile, "When he was with you, he was with you, intensely concentrating on only you."

Step Two: Capture

After inspiration struck Shel, he was terrified of losing it. 

In A Boy Named Shel, Lisa Rogak describes Shel’s obsession with capturing ideas on the spot, "If he ran out of paper, he’d start in on the napkins in a fancy restaurant, then move on to the tablecloth. When he had that completely covered, or if he was walking down the street, he’d start doodling on his hands, his shirtsleeves."

While Shel ultimately decided not to do anything with many of the ideas he had, it was never because he forgot about them. He always wrote them down.

Step 3: Play

Few people ever actually saw Shel create. He preferred to create alone. However, when they did, they described the experience as transcendent.

Record Producer and music manager Ron Haffkine had the luxury of watching Shel write and draw on a handful of occasions, "He worked, hunched over his desk, his long bony fingers drew and redrew each character as he giggled to himself like a child. There would be quiet for a while, then a burst of laughter. It was as though he were enjoying something that someone else had created especially for him."

Call it play or pleasure, Shel loved not only coming up with ideas but making something out of them, too.  

Step Four: Consciousness

Decades ago, a country music singer by the name of Chris Gantry asked Shel to teach him how to write plays.

While a lot of folks today know Shel for his hugely successful children’s books The Giving Tree and Where The Sidewalk Ends, he also wrote 800 songs (a handful of which were cut by Chris Gantry) and more than 100 one-act plays. 

Both Gantry and Shel owned homes down in Key West, Florida back when it was still a creative haven for writers, artists and musicians alike. 

Gantry had caught wind that Silverstein was having quite a bit of success as a playwright so he asked him how the hell he did it. Shel told Gantry to meet him the following morning at his home with a pen and some paper.  

"Do exactly what I tell you to do," Shel told him. "When I tell you to go, start writing with no preconceived notions about what your play is about. I’m going to time you and give you a little more than an hour. The first thing that comes into your mind is the title of the play."

As Gantry nodded along, Shel continued to divulge his secrets, "Then you’ll write about a man and a woman, use M for man and W for woman. Start writing free-form, free association and don’t take your pen off the page. The key is not thinking about it."

Shel went on to explain that if Gantry found himself stuck, to write the first thing that came to mind, "If… the first thing that comes in your head is 'I have a carrot and stick up my ass’, then you write that down, that’s your line."

Shel smacked the timer and he started writing. 

An hour later, Gantry had written a one-act play.

In closing. 

If, like Gantry, you were to seek out the late, great Shel Silverstein’s advice on the subject of coming up with ideas, he’d tell you to hunt for inspiration, write down your ideas, have a hell of a lot of fun and, lastly, set a timer.