Draw Me Anything with Jason Chatfield

DMA #47: Naked Kickstarters & Bypassing the Print-pocalypse with American Bystander's Michael Gerber

“You cannot write a line of code that replaces the invisible labour, the thousands of terrible rough sketches, and the deeply human derangement required to make a truly great cartoon.” If you try to launch a print humor magazine in the 21st century, most financial advisors will tell you to just set your money on fire instead; it’s faster, it requires less paperwork, and it keeps you warmer in the winter. We live in the era of the digital churn. We live in an ecosystem where corporate media conglomerates are continuously gutting their editorial staff, pivoting to video, pivoting away from video, pivoting to AI slop, and generally treating the written word and the drawn cartoon as disposable ephemera. The conventional wisdom is that print is dead… But if you’ve been reading this newsletter for more than five minutes, you know I am obsessed with the messy, unglamorous back-end of making a living as an artist. I love pulling back the curtain on the creatives who look at the “churn,” laugh, and figure out how to keep the lights on without selling their souls to the algorithm. This week on Draw Me Anything, I brought in a guy who looked at a sinking ship and decided to build his own lifeboat. I was thrilled to host the brilliant Michael Gerber [https://substack.com/profile/6381031-michael-gerber]. Michael is the publisher, editor, and mastermind behind The American Bystander, a publication that Newsweek literally called “the last great humor magazine.” During the stream, we dug into exactly how you resurrect a print humor magazine in the 21st century without setting mountains of corporate cash on fire. It is a story of grit, absurd luck, and a publishing model that bypasses the corporate overlords entirely. But before we get to the Chinese oligarchs and the naked Kickstarter launch, we have to go back to a very small room in the One World Trade Center. The Everest of Cartooning and the Mouse in the Car My introduction to The American Bystander didn’t happen on a newsstand. It happened in the absolute epicenter of the New York cartooning world. It was late 2014, maybe early 2015. I was a relatively new immigrant to America, still trying to figure out the brutal mechanics of the New York publishing scene. To my brain, the ultimate peak of the industry -the absolute Everest of cartooning- was getting into MAD Magazine and getting into The New Yorker. Those were the twin pillars of the comedy art world. Everything else was just scenery. Related Reading: I was sitting at The New Yorker in the cartoon lounge. Now, let’s be honest about the cartoon lounge at that time: it wasn’t really a “lounge” anymore. It was just a small room off to the side from where cartoon editor Bob Mankoff’s office was located. But the physical space didn’t matter, because of who was in it. The legendary Sam Gross was sitting in the room. He was positioned right below a giant framed picture of his absolute classic cartoon—the one with the mouse driving the wind-up car. If you’re a cartoonist, sitting in a room with Sam Gross was like a guitarist sitting in a room with Keith Richards. Sam was holding a copy of a magazine I had never seen before. “Kid, have you heard of this magazine?” he asked me. I looked at the cover. The unmistakable, beautiful line work of Arnie Roth stared back at me. It was Issue Number Six. “I’m embarrassed to say that I haven’t heard of it,” I admitted. Sam started explaining what it was, and as he flipped through the pages to show me the cartoons, my jaw hit the floor. I was looking at a murderers’ row of comedy art. “This is everyone I love,” I remember thinking. “These are all my favorite cartoonists in here. What the hell? How long has this thing been around?” Sam saw the absolute shock on my face. “Yeah, right?” he smiled. “You should submit to this.” Naturally, the moment he said that, the impostor syndrome kicked in with the force of a freight train. I looked at the names on the pages. I don’t belong in here, my brain screamed. This is ridiculous. These are giants in here. I don’t belong in here. I was so completely enamored with this magazine, yet I had absolutely no idea it even existed. When I told this story to Michael on the stream, he just laughed. “Well, that’s kind of the story of the business right there,” he said. “Everybody loves it. Very few people know about it. We’re always trying to figure out how to get more people to know about it.” Fast forward to today, and I am deeply proud to not only be a contributor to The Bystander, but to have hosted its “re-founder” to talk about exactly how this impossible publication came to exist. The Trifecta and the Pitch To understand The American Bystander, you have to understand the pedigree of the people who originally conceived it. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe [https://www.newyorkcartoons.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

DMA#50: Aussies in New York Getting Sandwiches with Ben Gollan

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com [https://www.newyorkcartoons.com?utm_medium=podcast&utm_campaign=CTA_7] My drawing board is currently covered in a mix of art supplies and aggressively pungent deli meats. I’ve got a puddle of Higgins ink dangerously close to a towering pastrami on rye, and my entire apartment smells of mustard. Outside my window, a sanitation truck is violently reversing down 9th Avenue. The floorboards are vibrating. On my monitor, looking entirely too relaxed for a man navigating the crazy New York City culinary scene, sits Ben Gollan, a fellow Aussie expat making a go of it in the big smoke. If you enjoy my work and would like to support, please upgrade to become a paid subscriber [http://www.newyorkcartoons.com/subscribe](only $1 per week) Ben’s the undisputed Sandwich Tour King of New York. He runs a wildly successful walking tour company called ‘A Man and His Sandwich’, where he guides people through the absolute best, most artery-clogging delis in the five boroughs. But the thing that always short-circuits my brain about Ben isn’t his encyclopaedic knowledge of cured meats. It’s his backstory. It’s always deeply comforting to talk to another expat. We spent a significant portion of the hour just being two Australians with thick accents, complaining loudly about the structural inefficiencies of New York City while simultaneously admitting we’d never live anywhere else. We got into the gritty reality of the New York hustle. If you’re an Aussie expat, you know the exact cultural whiplash we’re talking about. Back home, we have this insidious thing called the tall poppy syndrome. If you try something outside the box, people immediately try to cut you down. Ben mentioned that when he goes back to Australia and tells people he runs sandwich tours, they laugh and ask what his real job is. But here in New York? People look at him and say, “That’s a great idea, I bet you’re the best.” The city runs on that delusional, infectious encouragement. It’s the only place where a hungover, out-of-work chef from South Africa can stare at leftover Indian paratha bread and some banh mi scraps in his fridge, accidentally invent a pulled-pork paratha taco, and suddenly end up running three wildly lucrative storefronts. (That’s the true story of Goa Taco [https://www.thrillist.com/eat/new-york/gao-taco-nyc-paratha-tacos], by the way. A legendary Lower East Side staple born entirely out of desperation and a hangover). As I mentioned, Ben’s a fellow expat Australian. Back in Sydney, he was a crisply dressed corporate lawyer working for the government. He traded the courtroom for the chaotic, unforgiving streets of New York back in 2016, all to support his wife’s career. Somewhere along the line, a single pastrami sandwich at a now-defunct East Village deli completely derailed his professional trajectory. He ate the sandwich, had a culinary epiphany, and decided he was going to dedicate his life to the space between two pieces of bread. There’s something deeply terrifying about abandoning a stable, lucrative law career to yell about sandwiches on a Brooklyn sidewalk. But it’s the kind of unhinged creative pivot I completely admire... During our Draw Me Anything session, I set myself the absurd task of drawing a photorealistic pastrami sandwich while we talked. I quickly realised that drawing bread’s a nightmare. Bread’s just a chaotic sponge. You try to capture the crust with pilot pen, and it just looks like a diseased rock. Ben’s got this incredible, magnetic energy. You can see exactly why his tours are perpetually sold out. The live chat was losing its collective mind over his deli recommendations. You could feel the audience getting hungry through the screen…

DMA#49: Creativity within Confines & the Poetry of the Page with Grant Snider

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com [https://www.newyorkcartoons.com?utm_medium=podcast&utm_campaign=CTA_7] I am sitting at my drawing board in my sweltering Manhattan apartment. Grant is sitting in his room in Wichita, Kansas. The contrast between our two environments is immediate and palpable. His background is calm, lined with books. There is a quiet, steady, midwestern stillness to his frame that makes my own neurotic, constantly vibrating New York energy feel unhinged. I have been a big fan of Grant’s work for a long time. If you have spent any time on the internet looking for art that makes you feel deeply seen, you’ve likely stumbled across his comics. They’re incredibly insightful, minimalist, and poetic. He manages to take complex, abstract concepts like mindfulness, anxiety, the crushing weight of the creative process, and distil them into beautiful, clean, uncluttered panels. His style is a brilliant amalgamation of influences, echoing the whimsy of Quentin Blake and the neurotic genius of Roz Chast, yet entirely his own. But there’s a detail about Grant’s life that always manages to short-circuit my brain. Grant is a practising orthodontist. By day, he is literalizing the mechanics of human smiles. He operates a medical practice in Wichita. He looks into people’s mouths, adjusts wires, and fixes the geometry of their teeth. And if that wasn’t demanding enough, he also has five kids. He is managing a small, highly energetic army of children, running a medical practice, and somehow still managing to be one of the most prolific and poignant cartoonists I’ve ever met. When you spend your life as a working artist in a city that charges you fifty dollars just to leave your apartment, you tend to view time as a hostile currency. The idea of holding down a demanding, highly technical medical career while simultaneously producing emotionally resonant art feels impossible. During our session, I had to ask him how on earth he manages it. Does the day job drain the creative battery, or does it fuel it? Grant’s answer completely flipped my understanding of creative burnout. He explained that his multifaceted skill set is actually the secret engine of his productivity. “You need some kind of natural reset button. For me, my job where I straighten teeth and, you know, talk to people and, you know, do some good work is part of that for me”. It’s a deeply reassuring concept. Instead of draining his creative reserves, his orthodontic work acts as a mental palate cleanser. It engages a completely different, highly analytical, physical part of his brain. When he’s adjusting a bracket on a teenager’s molar, he is not agonising over the narrative arc of a graphic novel. By stepping away from the drawing board to do a job grounded in the physical, real world, he allows his creative side to rest, recharge, and process ideas in the background. We fell into a deep discussion about this, touching on David Epstein’s brilliant book, Range, which argues that generalists -people with diverse, multifaceted backgrounds and varied experiences- often triumph in a specialised world. I mentioned that I was currently reading Epstein’s other book, Inside the Box, which explores the idea of creative thinking within strict confines.

DMA#48: Drawing Sneaky Art in Times Square: AI Slop & the Radical Act of Paying Attention

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com [https://www.newyorkcartoons.com?utm_medium=podcast&utm_campaign=CTA_7] As always, if you want to watch the full replay, please upgrade to Paid. I really appreciate your support. If you want to test the absolute limits of your nervous system, try sitting in the middle of Times Square with a sketchbook, a pen, and an open microphone... It is a sensory assault. It does not smell like inspiration; it smells like roasted nuts, diesel exhaust, and the sweat of ten thousand tourists realising they’ve lost their Marriott room key. The noise is a physical weight. Sirens, pedicabs aggressively looping Alecia Keys, and people dressed as off-brand Spider-Man aggressively demanding five dollars for a photo. “Drawing in New York is combat journalism. You’re trying to capture lightning in a bottle while the bottle is being kicked down Broadway by a guy screaming at his phone.” But this is exactly why I do this. When I started New York Cartoons, the core promise to you, the reader, was that I wasn’t just going to send you polished, sterile drawings from the safety of an air-conditioned studio. The promise was to show you what living, surviving, and creating in New York City actually looks like. The chaos, the invisible labour, and the absurd encounters that fuel the work. So, for this week’s episode of Draw Me Anything, I took the studio to the street! My guest was the brilliant Nishant Jain, better known to his massive audience as The Sneaky Artist. Nishant came down from Canada to sit with me in the blistering epicentre of Manhattan. For an hour, amidst the absolute bedlam of Times Square, we drew the chaos in real-time. Before the stream started, a tall man holding a brown paper bag whipped towards us before locking eyes with me… it was, of course, my neighbour and pal Anthony LeDonne [https://substack.com/profile/1390125-anthony-ledonne]. Because of course it was. (You can see his SYML entry here. [https://www.newyorkcartoons.com/p/18-anthony-and-lauren-ledonne]) When I introduced him to Nishant, I’d mentioned we were nerding out about Derrida last time we spoke. When he asked who that was, I knew he’d be in for an education… Nishant gave him a primer on the arsehole French philosopher and his musings. I could see the hamster in Anthony’s brain begin to sweat, then die in a mad panic. Derrida: It’s one helluva conversation starter. What started as a live drawing session quickly spiralled into one of the most profound, quotable, and vital conversations I’ve had in years. We talked about everything from French philosophy and the existential threat of tech companies to the mindfulness of observation and the stark contrast between Canadian politeness and New York velocity. Here’s what happens when you put two process-junkies in the loudest intersection on Earth… Part I: Vancouver VS. New York There’s a distinct difference in the way a New Yorker observes the world versus the way a Canadian does, and watching Nishant work was a masterclass in pacing. Nishant possesses a terrifying level of calm. He didn’t fight the chaos. He observed it. “In Canada, the environment gives you the space to think,” Nishant told me, his eyes tracking a guy in a chaotic neon jacket. There is a physical and auditory room to breathe. The silence lets you construct the narrative. But in New York, the noise forces you to react. It’s an entirely different muscle. He’s right. Drawing in New York is combat journalism. You’re trying to capture lightning in a bottle while the bottle is being kicked down Broadway by a guy screaming at his phone. But despite the velocity of the city, Nishant’s process is startlingly deliberate. As we talked, he casually built what would become a beautifully complex drawing of the scene. He wasn’t rushing. He was practising what he calls the radical act of paying attention. “...your body and mind are absorbed in the union of an ask, which is to look to interpret and then to put it down, translate it. And in a lot of ways, you shut out a lot of concerns, you stop thinking about time, you stop thinking about your responsibilities of service, and you're just here for a while.” Part II: The Mindfulness of the Pen, and the Radical Act of Paying Attention We spend so much of our time talking about “mindfulness” as this sterile, corporate buzzword. (I’ve written about this before [https://www.newyorkcartoons.com/p/10-profound-insights-from-10-years]) Tech companies have commodified it. They sell us apps that ding to remind us to breathe, which we check on the same glowing rectangles that are actively destroying our attention spans. Nishant’s approach to drawing is the exact antidote to this. For him, drawing isn’t about producing a piece of “content” for an algorithm. It is a grounding mechanism. “Drawing isn’t about making a pretty picture,” Nishant said, his pen moving carefully across the paper. “It is about forcing yourself to sit still in a world that profits entirely off your distraction. When you draw something, you are forced to actually see it. You aren’t just looking at it. You are understanding its geometry, its weight, and its relationship to the things around it. You are acknowledging its existence in a way that taking a photograph never will.” That hit me like a freight train. In the digital mailstrom, we take thousands of photos we will never look at again. We consume the world in half-second swipes. But when you drag a pen across watercolour paper, you’re making a physical record of time spent. You are saying, I was here, and I paid attention. “The modern world wants us to skim,” he added. “Drawing is the refusal to skim.” If you’re a free reader, now is the time to upgrade. A subscription costs less than a bad bodega sandwich, and it directly funds the real, human, unapologetic art that the tech companies are actively trying to automate out of existence. Support the artists who are actually paying attention. Please upgrade to become a paid subscriber [http://www.newyorkcartoons.com/subscribe](only $1 per week) Part III: Derrida, Language, and the AI Plagiarism Machine Naturally, sitting in the glowing neon Mecca of American capitalism, the conversation pivoted to the tech overlords and the looming shadow of Generative AI. If you read my essays, you know my stance [https://www.newyorkcartoons.com/t/ai] on the “AI Slop Machine.” I view it as a cultural parasite. But Nishant brought a deeply intellectual, philosophical lens to the conversation that completely reframed the issue for me. He brought up Jacques Derrida. For those who skipped French Philosophy in college, Derrida was the father of “deconstruction.” He famously argued that language isn’t just a tool we use to describe reality; language creates the boundaries of our reality. We can only understand the world through the vocabulary we have to describe it. “Think about what AI actually is,” Nishant explained. “These tech companies aren’t building ‘intelligence.’ They are building predictive language models. They are machines that guess the next word, or the next pixel, based on a massive, stolen dataset of the past.” He paused to add a shadow to the drawing of an awning. “If Derrida is right -if language shapes our reality- then handing our visual and written language over to a machine is incredibly dangerous. An AI cannot create a new vocabulary. It can only recycle the old one. It homogenises human experience into an average. It regresses us to the mean.” This is the exact problem with AI art. It looks perfect at first glance, but it contains absolutely zero humanity. It has no point of view. It doesn’t know what it feels like to sit on a cold metal chair in Times Square while a siren blares in your left ear. “When a human draws a line,” Nishant said, “even if it’s a wobbly, imperfect line, it contains intention. It contains a decision. The AI slop has no intention. It is just statistical probability masquerading as art. And humans are biologically hardwired to eventually reject things that have no soul.” He added something that I really wanted to write down for a discussion later: “...the point of AI is not to make articles; the point of AI is to make an endlessly spinning mill of content to feed their social media algorithms to hypnotise and make you into addicts so that you become a passive consumer instead of a creative.” Part IV: The Finished Masterpiece By the end of the 50-minute conversation, my own drawings were a frantic, scratchy, high-energy reflection of the anxiety of Times Square. It looked like New York feels. But then Nishant held up his sketchbook. I actually stopped talking for a second. Look at that, I said on the stream. It was incredible. This guy had just casually, while dissecting French deconstructionism and the ethics of tech conglomerates, built the most insanely beautiful drawing of the intersection. It wasn’t just a rendering of buildings and tourists. It had life in it. You could see the deliberate choices he made -what to include, more importantly, what to leave out, what to emphasise. It was the absolute antithesis of an AI-generated image. It was a physical artefact of a human being paying deep, mindful attention to a chaotic world. Watch the Full Replay… Reading these quotes and clips is only half the experience. If you want to actually see the process -if you want to hear the sirens, see the pen hit the paper in real-time, and watch two working artists navigate the muck of New York City while talking about the survival of human art, you need to watch the replay. This is the promise of New York Cartoons. I don’t hide the process. I don’t put a filter on the reality of this job. The full, uncut, 50-minute video replay of our Times Square drawing session is available right now for paid subscribers.

DMA#40 Recap: The J. Jonah Jameson Editor, Surviving the Tech Deluge, and the Rules of Timeboxing with Jeremy Caplan

When I first sat down to chat with Jeremy Caplan [https://substack.com/profile/332836-jeremy-caplan] about artificial intelligence and digital productivity tools, I genuinely did not think we would end up talking about him playing the violin. I certainly did not expect the conversation to pivot into a deep, philosophical appreciation for the irreplaceable magic of humans sitting in a room together, simply enjoying a live performance. But tha’s the funny thing about talking to someone who spends their life evaluating machines. You inevitably end up talking about what it means to be human. The frictionless technological utopia we were promised feels increasingly like a relentless, exhausting deluge. Every week brings a new platform to master, a new algorithm to appease, and a new artificial intelligence threatening to automate us into oblivion. It’s like drinking from a fire hose while someone yells at you to “pivot to video!” This is exactly why I was so incredibly relieved to sit down with Jeremy on this episode of Draw Me Anything. Jeremy is a rare beacon of sanity in the digital miasma. He is the Director of Teaching and Learning at CUNY’s Newmark Graduate School of Journalism. He is a former journalist for Time Magazine. Before that, he was a classical violinist. But more importantly for my own daily survival, he is the creator of the massively popular Wonder Tools [https://open.substack.com/pub/wondertools] newsletter on Substack. Jeremy spends his days wading into the chaotic, deeply overwhelming waters of the internet. He tests, breaks, and reviews new apps, software, and digital features so the rest of us don’t have to waste our precious human hours doing it. Distilling the Chaos We kicked off the stream talking about the exhaustion of trying to keep up with tech news. It is not just about discovering new tools anymore. It is about tracking the constant, aggressive updates to existing tools. ChatGPT has a new voice feature. Gemini just launched a massive update. Claude is now doing something entirely new with your phone. And you can’t opt out of it.. It never stops. Jeremy explained that his superpower for distilling this madness down to accessible, bite-sized pieces actually came from his time writing for Time for Kids. When you have to explain complex global news to an eight-year-old in exactly one hundred words, you learn to cut the jargon immediately. You learn to anticipate a human reader’s questions and preemptively answer them. He also cited the legendary tech writer Walt Mossberg as a major mentor and influence. Mossberg succeeded wildly at The Wall Street Journal because he approached technology not as a deeply entrenched engineer, but as an ordinary guy just trying to figure out how a tool could actually be useful in his daily life. “I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone…” That is exactly what Jeremy does with Wonder Tools. He doesn’t just list fifty new AI tools that launched on Product Hunt this week. He gives you three specific, highly actionable ways to use one feature of NotebookLM to make your Tuesday slightly less miserable. He gives you templates. He shows you what a forty-page deep research report from Gemini actually looks like, so you do not have to spend twenty minutes generating one just to see if it is useful. If you enjoy my work and would like to support, please take out a premium subscription (just $1 per week) Evergreen Processes over Disposable News One of the most fascinating things about Jeremy’s approach is his focus on evergreen content. We’re constantly blasted with disposable news. A tech CEO gets fired, a new app launches and dies in a week, a company changes its name. Jeremy actively avoids the daily churn. He wants to create resources that a reader can save and return to three weeks later, knowing the information will still be fundamentally useful. This really resonated with me. I told him about a post I wrote on Medium over a decade ago [https://jasonchatfield.medium.com/work-from-a-calendar-not-a-to-do-list-9c93ea88fbcf]. People constantly ask me how I manage to juggle cartooning, stand-up comedy, writing, and running a business without completely losing my mind. The answer is timeboxing. I work strictly from a calendar, not a to-do list [https://jasonchatfield.medium.com/work-from-a-calendar-not-a-to-do-list-9c93ea88fbcf]. I estimate how long a task will take, block it out in my iCal, and adjust the time block later if it took longer or shorter than expected. I wrote a simple, straightforward piece explaining this exact process. I thought it was old news. Cal Newport had written about it years prior. But the piece went incredibly viral, and I made two thousand dollars from the Medium partner programme purely off that one specific workflow explanation. Sometimes the most valuable tools are not shiny new apps. Sometimes, they are just fundamentally sound ways of organising a chaotic human brain. The Ethical Calculus of AI We eventually had to talk about the elephant in the room. Artificial intelligence… I frequently get accused of being either a doomer or a total Luddite, but the truth is, I am an early adopter. I was one of the very first cartoonists in my circle to embrace Wacom tablets, Cintiqs, and the iPad Pro. I actively test out tablets for companies like Xencelabs. I do not shy away from folding digital tools into my workflow when they help automate the absolute drudgery of administrative freelance life. However, the rapid acceleration of generative AI requires a lot of mental arithmetic. I told Jeremy about my personal ethical boundaries. I use Grammarly for proofreading. I am currently experimenting with Gemini for deep research. But I absolutely refuse to use Meta AI or Elon Musk’s Grok because I fundamentally distrust the ethics of the people building them. I opt out of the platforms where I find the creators ethically compromised. Putting these streams together, wrangling brilliant guests, manually untangling the spaghetti bowl of a brain to pull out the best insights, and writing these recaps requires a heady cocktail of intense caffeine and sheer willpower. If you value this little digital monastery, please consider upgrading to a paid subscription for just $1 a week. It pays for my time, repays the time and labour of writing these up, and keeps Morris supplied with the unnecessarily expensive dog food he demands… Jeremy had a fascinating, highly pragmatic take on this. He acknowledged the massive macro issues. He is deeply aware of the environmental cost of data centres, the terrifying water usage, and the flawed predictive models being used to evaluate people in hospitals and prisons. But he treats his newsletter strictly as “service journalism.” He used a brilliant restaurant analogy. When we go out to eat, we sometimes evaluate the ethical supply chain of the ingredients, the working conditions of the farmers, and the environmental impact of the transportation. But other times, we just need to eat a sandwich because we are hungry. He doesn’t believe we need to litigate the macro ethics of AI every single time we try to automate a tedious spreadsheet or fix a typo. He leaves the heavy investigative journalism to the experts, specifically citing Karen Hao’s brilliant book Empire of AI, and focuses entirely on practical utility. The J. Jonah Jameson Editor I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone. Because I no longer work in a physical newsroom, I deeply miss having a ruthless editor. When I was coming up in newspapers at nineteen years old, I had a classic, cantankerous, ink-in-his-veins editor. He was a J. Jonah Jameson type who had absolutely no compunction about telling me my work was complete garbage. It hurt my precious feelings constantly, but I learned faster than I ever would have with a polite sycophant. Since I can’t afford to hire a human to yell at me in my apartment, I built a custom AI editor in Gemini. I programmed it with the specific persona of a grumpy, hard-assed, chain-smoking newspaper editor. Now, when I finish a draft by hand, I feed it to the bot. It yells at me about my weak verbs, my terrible grammar, and my overly long paragraphs. I ignore half of its advice because I know the rules well enough to break them, but it forces me to actively defend my choices. Jeremy agreed completely. He relies heavily on Claude Projects for his micro-editing. He feeds it all of his past writing to establish context, background, and tone, and then uses it as a highly critical sparring partner to catch redundant phrasing and double commas. He pointed out a provocative but entirely true reality. There are incredible human editors out there. But the average human copy editor simply doesn’t have the bandwidth, the time, or the willingness to ruthlessly tear apart paragraph four and analyse your four different verb choices on a Tuesday night. An AI will do it instantly, comprehensively, and without worrying about hurting your feelings. Drawing by Hand Before Hitting Undo This brings us right back to the violin. We talked about where different artists draw the line with these tools. I brought up a story from a previous stream with Liza Donnelly, the brilliant New Yorker cartoonist. She mentioned using AI purely as a brainstorming partner to bounce ideas around. Our mutual friend, the wonderful British cartoonist Alex Hallatt, heard that and decided to try it. Alex took some scattered, messy notes from a walk, fed them into an LLM, and started riffing on gag premises. It was a great, highly functional workflow. Right up until the bot cheerfully asked, “Do you want me to draw this for you?” That is the exact moment the panic sets in. It is the moment you realise the tool wants to replace the human element entirely. I firmly believe that the wobble in the line, the physical imperfections, and the distinct human voice are the only things keeping us from being completely swallowed by the generic digital void. When young students ask me if they should learn to draw on an iPad, I always tell them absolutely not… Learn to draw by hand first. Learn the absolute fundamentals with ink and paper. If you draw a bad line with a Hunt 101 dip pen, you cannot hit undo. You have to draw that exact line forty-five times until you get it right. You need those neural pathways to form, and you need to understand the physical mechanics of the craft, before you start relying on digital safety nets. You have to learn how to play the instrument before you let a computer tune it for you. I spent the rest of the stream doing exactly what I love to do. Drawing wobbly, imperfect lines while navigating the absurdities of the modern world. I am deeply grateful for guys like Jeremy who do the heavy lifting in the digital trenches so I can safely retreat to my analogue drafting table. Now, if you will excuse me, I need to go figure out why Adobe is demanding another subscription fee. ‘til next time!Your pal, PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads. The Tools We Discussed * Wonder Tools [https://wondertools.substack.com/]: Jeremy Caplan’s brilliant, incredibly useful Substack newsletter. If you are overwhelmed by tech, start here. * Claude Projects [https://claude.ai/]: Jeremy’s preferred tool for maintaining context and generating ruthless micro-editing feedback. * Gemini [https://gemini.google.com/]: The engine behind my custom J. Jonah Jameson editor, and a powerful tool for deep research generation. * NotebookLM [https://notebooklm.google.com/]: A fascinating tool for organising notes and research that Jeremy frequently writes actionable guides for. * IA Writer [https://ia.net/writer]: A beautifully simple, distraction-free writing tool Jeremy relies on. * Grammarly [https://www.grammarly.com/]: My go-to for catching the embarrassing typos that slip through the cracks at 2:00 AM. * Wacom [https://www.wacom.com/] & Xencelabs [https://www.xencelabs.com/]: The digital drawing tablets that keep my freelance career afloat. The Processes We Discussed * Timeboxing: The absolute lifesaver of a scheduling method where you work strictly from blocked-out calendar chunks rather than a sprawling to-do list. * Macro vs. Micro Editing: Understanding the difference between fixing a structural narrative flaw (macro) and tightening up a weak verb in paragraph three (micro). * Custom AI Personas: Training an LLM with a specific voice and set of instructions to act as a specialised sparring partner for your writing. Resources and Artists Mentioned * Cartooning in the Age of AI [https://alexhallatt.substack.com/]: Alex Hallatt’s incredibly thoughtful Substack documenting her journey and boundaries with digital tools. * Liza Donnelly [https://lizadonnelly.substack.com/]: Legendary New Yorker cartoonist and previous DMA guest. * Walt Mossberg [https://en.wikipedia.org/wiki/Walt_Mossberg]: The legendary tech journalist who proved that writing for the ordinary user is far more valuable than writing for the engineers. * Cal Newport [https://calnewport.com/]: The author of Deep Work and a champion of timeboxing. * AI Snake Oil [https://www.aisnakeoil.com/]: The book by Arvind Narayanan and Sayash Kapoor that Jeremy’s new Wonder Tools book club is tackling first. * Bird by Bird [https://www.penguinrandomhouse.com/books/97395/bird-by-bird-by-anne-lamott/]: Anne Lamott’s absolute bible on the excruciating, beautiful process of writing. This is a public episode. 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