AI, Art, and Drawing the Line 🖌️

AI, Art, and Drawing the Line 🖌️

From Wonder Tools by Jeremy Caplan

March 27, 2026 · 47 min · Season 2 · Episode 1

About this episode

The episode features a conversation with cartoonist Jason Chatfield about the intersection of AI and art, focusing on editing and creative processes.

This is a free preview of a paid episode. To hear more, visit wondertools.substack.com I recently talked with Jason Chatfield a New Yorker cartoonist and creator of the lively New York Cartoons Substack. He sketched while we talked, as part of his video series Draw Me Anything . We traded ideas about writing, editing, tools, and where to draw the line with AI. 📺 Watch the conversation above, or read highlights below. Takeaways from Our Conversation 🛠️ * Teach your AI assistant to offer personalized editing suggestions. I’ve trained a Claude Project to learn from my past writing and editing. It catches typos like double commas, cliches, redundant language, weak verbs, and sloppy copy. Instead of having it make changes, I ask it for a punch list of suggestions. * Talk before you type. I turn on my AI dictation app, Letterly , and just start talking. The AI-enabled transcription and summary I get helps me make sense of ideas rolling around in my mind. Then the next part of the writing process becomes more about shaping and editing those ideas, rather than staring down a blank screen. * Ask AI to interview you. After a conference or a day of meetings, get your AI assistant to ask…

People in this episode

Host: Jeremy Caplan

Guest: Jason Chatfield

Topics covered

  • AI
  • art
  • drawing
  • editing
  • technology
  • creativity

Keywords

  • AI
  • art
  • editing
  • cartoonist
  • technology
  • writing
  • transcription

Mentioned in this episode

Organizations: New Yorker, New York Cartoons Substack

Products: Claude Project, Letterly

More episodes of Wonder Tools

Explore listener stats, chart rankings, contacts and more on the Wonder Tools podcast page.