Collective Reading and Historical Perspective

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 you follow-up questions. That conversation forces you to articulate ideas you haven’t fully formed.

* Teach your AI assistant to be a critic, not a ghostwriter. Ask it to challenge your structure, suggest sections to cut and to explain why, and to point out your blind spots. Your friend might be too polite to tell you a section of your piece you’ve worked on for hours is redundant or dull. Your AI assistant will, if you train it to.

* Let’s read books collectively. We’re reading 10 AI books in 2026 through the Wonder Tools Book Group. (For WT paid subscribers). We started with AI Snake Oil, whose co-author was a surprise guest at our first gathering. Reading together allows us to benefit from dialogue. And we can learn more deeply from books than we can from a random diet of posts and videos.

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Tips Jason shared during our conversation

* Work from a calendar, not a to-do list. Sometimes what’s most valuable is a workflow, not a specific tool. Like timeboxing. Jason predicts how long a task will take, blocks time in his calendar (iCal), then learns from the difference between his estimate and how long the task actually took. His timeboxing Medium post about the process went viral.

* Build a grumpy editor. Jason created a J. Jonah Jameson–style editor persona in Gemini. If you’re not familiar with the Spider-Man character, he’s a cantankerous, chain-smoking newspaper editor who tears apart a writer’s drafts. Jason says he takes about half of the suggestions.

* Choose your tools based on who built them. Jason uses Grammarly and Gemini, but refuses to use Meta AI or Grok. If he doesn’t trust those building a platform, he opts out.

* Learn the analog way before you go digital. Jason suggests students draw by hand first, not on an iPad. If you draw a bad line with a dip pen, you can’t hit undo. You learn through that process.

* Use AI to brainstorm, but know when to stop. Cartoonist Alex Hallatt of Cartooning in the Age of AI used an AI assistant to riff on cartoon premises from messy notes. Jason said she was intrigued by the results, until the bot offered to draw the cartoon for her. 👇

Tools & Apps We Discussed 👇