Creative stress test: A bestselling humorist’s guide to letting go

This season on the Write Away with Nat & PJ podcast, we interviewed NYT best-selling author, humorist, and cartoonist, Bob Eckstein, about staying creative in hard times, how he finds a punchline, and where he gets his inspiration for projects like his latest book, The Elements of Stress, a parody of The Elements of Style.

In the spirit of Bob’s knack for communicating with both words and pictures, we wanted to talk to him because we thought he might have advice for writers about how to play with messy ideas until you have something ordered and meaningful to share.

As with any writerly journey, our conversation wound through the twists and turns of Bob’s magical mind, uncovering the tips and tricks he uses to conjure his humor, while also revealing advice for writers who are trying to get or stay creative. Questions and answers have been edited for clarity.

Write Away: How do you get into a creative space where you can play with your ideas?

There are techniques that I use from different people. One that comes to mind immediately is Monty Python’s John Cleese. The technique is to find yourself in a state of playfulness, so that your mind can experiment and be creative. And you want that playfulness because you want to allow yourself to make mistakes.

It’s by mistakes that you come across accidents – pleasant accidents that could work. If you stay on course and do everything exactly the way it should be from A to B, you’re not going to explore the best opportunities for your story. Instead, you’ve got to freeform in your head, try different things. Most of it you might throw out, but then find the thing that works. That’s worked for me.

cartoon by Bob Eckstein - "if the Bronte sisters wrote science fiction"
Write Away: You decided to attack the topic of stress during one of the more stressful events of our lifetime. How did you manage to make it so funny?

Bob: The North Star I had for the book was to try to entertain, get people through this period in a way that lightens the mood. I’ve been saying, “Things cannot get worse. But they can get funnier.” That was a goal.

At the same time, there’s always a point anytime you’re trying to make a joke. I tried to first lay out principles that I thought would help people, just see what people’s problems were and come up with a different approach of how to resolve that stress. What’s a creative way to eliminate what we are all going through? And from there, the jokes just sprung up.

You pick apart how ridiculous certain things are, the contrasts. You contrast the normal with maybe some kind of abstract suggestion, and then at the intersection is the comedy. You find the comedy within that weird juxtaposition of ideas.

As a giant fire-breathing dinosaur wreaks havoc in the background on a golf course, Jim's golfing buddy tells him, "Just put that hole behind you."
Write Away: We saw what you did there, going after The Elements of Style.

Bob: Most writers had to use Elements of Style and had it on their side, had a copy at the house. I’ve read it over and over a zillion times. And when you read something that much, you want to make fun of it in some way too, tear it down as well as make an homage. You want it to be freshened up.

Cartoon by Bob Eckstein. A waiter approaches table littered with food remnants and a laptop. He asks the writer sitting there, "Are you still working on that?"
Write Away: And what does being “the world’s leading snowman expert” have to do with all of this?

Bob: I traveled the world for seven years to try to find out who made the first snowman. To me, the whole interest surrounds trying to solve a mystery, seeing if there’s something interesting beyond the obvious. What I found was that the snowman was an early form of political commentary, an early form of pornography in the middle ages – all these secrets that that were just amazing.

From there, I wrote a book called The Illustrated History of the Snowman, and I often do talks around the world on snowman-making being one of the few activities we still share with our ancestors.

Snowman-making, I should mention too, is one of the few times you’re going to, as an adult, make something that’s a life-sized replica of a human, a sculpture. And make it so public that everyone can see your artwork. Because it’s usually in your front yard – so everyone can judge you.

Bob Eckstein's cartoon about the snowman job interview. The interviewer asks, "So where do you see yourself in five months?"

Listen to the full interview wherever you consume podcasts.

Cartoons used with permission from Bob Eckstein. Thanks, Bob!

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