# DMA#55: Paid to be in trouble with Avi Steinberg

Page: https://stenobird.com/podcast/draw-me-anything-with-jason-chatfield-7482418/dma-55-paid-to-be-in-trouble-with-avi-steinberg
Text version: https://stenobird.com/podcast/draw-me-anything-with-jason-chatfield-7482418/dma-55-paid-to-be-in-trouble-with-avi-steinberg.md
Podcast: [Draw Me Anything with Jason Chatfield](https://stenobird.com/podcast/draw-me-anything-with-jason-chatfield-7482418)
Published: 2026-08-14T11:00:00+00:00
Episode link: https://www.newyorkcartoons.com/p/dma55-paid-to-be-in-trouble
Audio file: https://api.substack.com/feed/podcast/208729739/3efa8c320319c30e8fc0ff7492f6ae06.mp3
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JSON: https://stenobird.com/v1/public/podcasts/draw-me-anything-with-jason-chatfield-7482418/episodes/dma-55-paid-to-be-in-trouble-with-avi-steinberg
Duration seconds: 4790

## Resource

About twelve years ago, a teacher hired me to draw a caricature of her colleague as a gift. The colleague, she mentioned, was a New Yorker cartoonist. I said yes immediately, then realised I had no idea what the man looked like. That’s the whole profession, basically. You know the work, you know the signature, you’ve never seen the face. “It’s the perfect crime,” Avi Steinberg said this week, a decade after drawing him without his knowledge. “You can be famous on paper and still walk around without anyone bothering you.” Avi kept the caricature. I look at it and see only the mistakes, but he tells me it’s a treasured possession. I’m deciding to believe him. Ten years, Ten a week. Avi started submitting to The New Yorker straight out of high school and sold nothing for roughly a decade. I asked whether he hit year seven and wondered if he should pack it in. “I don’t wait till year seven to feel like that…” The turn came when he worked out what the cartoonists he admired were actually doing. “The greats, they drew a batch of ten cartoons every week. And when I really learned that, my heart sank.” So he gave himself a year of ten a week. No more emotional rollercoaster. At the end of it, he could either do this properly or quit. He teaches kindergarten in New York City, which is where he gets his best material on artistic confidence. “My students are the best artists in the world. No one told them how not to draw something.” I told him about being fifteen, getting detention for a savage caricature of my history teacher, then having that same teacher sidle up to my desk during detention and offer me twenty dollars to do a mean one of the retiring school gardener. Avi diagnosed the whole career in one line: being a cartoonist is the balance of being in detention and getting…

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