Thursday, 6:15 AM – The Locked Door

Location: Hotel Indigo Lobby

I woke up after precisely four hours of sleep with a crick in my neck, a throbbing headache, and the distinct feeling that I’d aged a decade overnight. I dragged my carcass through the shower and down to the hotel lobby to meet Ann, the festival director.

She had just woken up Bob, the marketing director, from a deep, peaceful slumber because -in a classic piece of festival scheduling- both of the local TV stations wanted to interview her at the exact same time. She threw Bob to the wolves at the Fox affiliate, and she and I hightailed it to the other station.

We arrived at the studio with minutes to spare... The door was locked. We stood there in the freezing morning fog, peering through the glass, until a long, heavy silence settled over us. We had gotten the time wrong. Eventually, the TV host wandered out, unlocked the door, and looked at us like we were crazy. “You guys are really early,” he said. “The show doesn’t start till 9:00. You aren’t on until 9:30…”

Defeated and bleary-eyed, we retreated to the hotel for coffee and breakfast to do the thing comics do best: talk shop and crack wise.

Thursday, 9:30 AM – The Garbled Brainfart

Location: The Local Affiliate

We returned to the station just in time to go live on the air. I sat under the studio lights, squinting into the camera, trying to drum up a cogent sentence about the festival, and comedy in general.

I have absolutely no memory of what I said. It was a garbled, sleep-deprived mess. The anchor’s questions were so spectacularly vague that forming a complete, grammatically correct sentence felt like defusing a bomb. I just smiled, fumbled my way through some syllables that vaguely resembled English, and prayed the viewers were as tired as I was before they brought on the coach for the local Curling team.

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Thursday, 12:00 PM – The View

Location: Hotel Indigo

I attempted a nap. It failed. I tried to write. It was useless. Eventually, Devin Keast -the man, the myth, the legend- knocked on my door to show me the incredible view of the bay from the other side of the hotel.

I, of course, do not have a view of the bay. My window looks directly out onto a brick wall. But honestly? It’s deeply comforting. After being overwhelmed by all the fresh air and open sky yesterday, waking up to a solid wall of masonry makes me feel right at home. I’m a New Yorker; give me a brick wall over a horizon any day.

Thursday, 6:00 PM – The Slabs & the Utes

Location: Right Brain Brewing

Devin dropped me off at Right Brain Brewing, where I was slated to host a show, before racing off to his own gig at the comedy club. The brewery is gigantic. I constantly forget how much physical space the rest of America has. I walked through the doors, past a sprawling ceiling and various doors covered in stickers, and into a massive barrel room. The smell of the hops and the old wood immediately transported me back to my childhood, doing stocktake with my cousin Gavin in the bottle shop of my dad’s pub.

We used to spend our afternoons watching tradies rumble through the drive-through, piling slabs of beer into the trays of their utes after a long day on the construction site. Gavin and I used to give them all nicknames based entirely on their faces and their drink orders. I hadn’t thought about those guys in years, but standing in this brewery, their names came rushing back: No-Neck Nev, Four-X Phil, Sweaty Pete. What a time to be alive.

Thursday, 7:45 PM – The Jason Sandwich

Location: Right Brain Brewing Stage

I checked in with Greg, a comic who usually performs at the festival but is volunteering to run the shows this year. He and the bar manager were deep in logistical negotiations, trying to figure out how to get the audience completely drunk without interrupting the comedy. They settled on a paper-slip system where people could write their orders down and clip them to the table.

Brilliant in theory, except it required everyone to open a tab before the show. The line for the bar snaked all the way out the front door.

We started late. We couldn’t figure out how to dim the house lights, and we couldn’t figure out how to turn down the venue music. So, I just jumped on stage and hoped for the best.

The lack of nerves was a red flag, but the Midwest audience was a dream. They are generous. They smile. They clap. They respond when spoken to, but they don’t heckle. They don’t try to make themselves the main character. They don’t have TikTok-brain, demanding crowdwork every 3 seconds. They actually respect that we sat down, wrote material, practised it, and are now performing it for them. God forbid.

I tested out some local material Devin had fed me while we drove around town. I asked the crowd about Vernors- the local ginger ale that Michiganders treat as a mystical, medicinal cure-all. Everyone in the room knew exactly what I was talking about. Outside of this state, it doesn’t exist, but here, it’s penicillin in a green can. I also asked if the Flapjack Shack over on US-31 was an actual restaurant or just a front for a meth lab. The entire room nodded in solemn agreement. Meth lab.

The lineup was incredible. Janelle Draper -an old friend I haven’t seen since before the pandemic- absolutely crushed it. She recently moved back to NYC from L.A. after opening for Jay Leno, and she is sharper than ever. I opened the show, and Jason Jameson closed it, making the entire evening a perfectly executed Jason Sandwich. (That doesn’t sound great now that I’m seeing it written out.)

These are the comics that appeared on the show - all hilarious, all worth a follow:
• @brownryancomedy • @renqcomedy • @janellejokes • @darrickervinii • @thejasonxperience • @im_nthenya • @lisarimmy • @pattyrooney

Thursday, 9:00 PM – Decorative Sidewalks

Location: The Streets of Traverse City

After the show, I needed to move. I hadn’t taken more than twenty steps all day, so I started walking toward the Opera House. A navy blue Mercedes SUV pulled up alongside me, and the window rolled down to reveal a smiling woman in her sixties. “Thank you so much!” she yelled. “Your show was so funny, we had a great time!”

I thanked her. She looked at me, confused. “Do you need a lift somewhere? Why are you walking?”

It was in that exact moment I realized that in Manhattan, walking is transportation. Here, the sidewalks are purely decorative. There wasn’t a single soul on the concrete for miles in any direction. I politely declined, explaining I needed to stretch my legs. She looked at me like I was insane, rolled up her window, and drove away.

Thursday, 9:05 PM – Touching Dog Hair

Location: Traverse City Whiskey Co.

Still walking, I glanced through the window of an unassuming building on the corner and saw lights and bottles stacked high against a brick wall. It was the Traverse City Whiskey Co.

I walked in and was immediately greeted by “Roo,” an Australian Shepherd with one brown eye and one blue eye. I spotted him, he spotted me, and we both knew exactly what was about to happen. I sat down and patted him for ten straight minutes. It completely reset my nervous system. It was the comic’s equivalent of “touching grass,” but with dog hair.

I ordered a local whiskey, talked to a few locals, bullied them into buying the last remaining tickets for the weekend, and headed out.

Friday, 11:20 PM – The Comedy Camp

Location: Hotel Indigo Bar

The Opera House was locked, so I headed back to the hotel. It had transformed into a full-blown welcome party.

Comics, bookers, agents, managers, and festival staff were packed into the lobby. This is the real reason we do these festivals. It’s Comedy Camp. We are all afflicted with the same brain derangement, which means we get to skip the polite formalities of normal human interaction. Within ten seconds of meeting a stranger, you are already trading war stories, hell-gig survival tactics, and social media strategies.

I bumped into Roger Paul, a booker who used to send me out on the road years ago. His assistant, Johnny, is now a dear friend of mine and a brilliant New Yorker cartoonist. When Johnny was booking my road gigs back in the day, I had no idea he was sitting on that kind of talent. Roger told me he has Johnny’s top three cartoons framed on his office wall.

As the night wore on, the laughs got louder, the stories got darker, and someone -I still don’t know who- snuck in a few tiny bottles of something truly disgusting for us to do shots of. I am going to pay for this tomorrow with a throbbing headache and crippling reflux. But right now, surrounded by people who willingly chose this ridiculous life, I wouldn’t want to be anywhere else.

Bring on Day Three.

‘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.

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For the next three nights, I’m performing several shows as a guest of the Traverse City Comedy Festival in Michigan. (If Michigan doesn’t get washed away in a flash flood...) I’ll share my daily diary of the festival’s goings-on with you as they unfold unravel.

~ Jason

Wednesday, 8:15 AM – The Guilt Trip

Location: Manhattan & Queens, NY

Packing a suitcase on the morning of a flight is a rookie mistake, but I am a professional at making my own life difficult. As I cram crinkled shirts into a broken suitcase, Morris watches me with his beady little eyes. I can see the deep, burning resentment in his face. He knows I’m leaving him. What he doesn’t know is that he is about to get the greatest walk of his life from his Uncle Paulie, the undisputed king of New York dog walkers. Still, the guilt is heavy.

I scoot my bag along the sidewalk to the subway, and the MTA, sensing my urgency, immediately collapses. The trains are running on different lines. I make it to the end of the E in Queens only to find that buses no longer exist. I eventually flag down one of those neon green outer-borough taxis. He charges me an arm and a leg (plus tax) to drive me the final 50 meters to LaGuardia.

Wednesday, 1:30 PM – The Eaves-drawing

Location: LaGuardia Airport, NY

The TSA line is a slow-moving river of angry, exhausted humanity. Despite being fully funded by the Department of Homeland Security, the system is backed up to the curb. I shuffle past an airport massage parlour called “Be Relax,” which sounds exactly like a business named by Melania.

All the afternoon flights have banked up. We are delayed. I retreat to the airport bar, pull out my sketchbook, and begin “Eavesdrawing”—listening to people’s inane conversations and sketching them.

• Subject A & B: Two girls heading to a bachelorette party in Chicago.

• Subject C: A guy at the end of the bar, trying desperately to pick them up, completely ignoring the fact that they have name-dropped their boyfriends into the conversation no less than fourteen times.

• Subject D: A woman next to me on her way to visit her grandkids in Arizona. She leans over and asks if I’d like to finish the rest of her Prosecco because they’re calling her flight. I know she’s just trying to be nice and not waste a drink, but absolutely not. It’s Champagne or nothing. (What, does she think I’m an animal?)

Oh yeah..

At this point, I should probably mention that I’ve been invited to perform at the Traverse City Comedy Festival. It’s absolutely crazy to be on lineups with people like Gary Goldman, Roy Wood Jr., Megan Stalter, Sarah Sherman, Joe DeVito, and so a heap of other great comedians from around America.

It’s a truly fantastic festival, and they really take care of you. You can see and hear me talking to the festival director, Anne, on a previous episode of Draw Me Anything from last week; you can catch that here:

Wednesday, 3:45 PM – The Devil Wears Prada

Location: Somewhere over Pennsylvania?

I board the flight dead last. I am jammed into a middle seat between a lanky teenager who hasn’t showered in fifteen weeks and an obese, hirsute man who insists on watching The Devil Wears Prada on his phone without AirPods.

I try to get some work done, but focus is impossible. I spend the flight doing the New York Times crossword puzzle, punctuated by tinny, aggressive blasts of Meryl Streep and Emily Blunt trading sassy jabs at Anne Hathaway from my seatmate’s phone speaker.

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Wednesday, 5:30 PM – Independence Sauce

Location: O’Hare Airport, Chicago

O’Hare is absolute bedlam. Flights are delayed, cancelled, or missing entirely. People are propping themselves up against pillars and garbage cans just to keep from falling over amid the bedlam.

I squeeze into a bar between an old man who looks like he’s been sitting there since the Reagan administration and a woman from Kansas City who tells me she lives in an RV. She is seated next to the only other Australian in the entire airport. His name is Bruce. Because of course it is. And he knows exactly who Ginger Meggs is, because he is over fifty-five years old.

Bruce and I speak for twenty minutes in an impenetrable Australian shorthand while the RV woman stares at us as if we’ve just arrived from Uranus. I order a side of tater tots. Forty seconds later, a trough of potatoes and grease is slammed in front of me, accompanied by a ramekin of “Independence Sauce.” I don’t want to know what makes the sauce independent. I eat three tots just to justify my barstool, knowing full well I will regret it if my connecting flight ever actually takes off.

Wednesday, 8:15 PM – The Lolly-Stick Express

Location: The Tarmac

Michigan is currently experiencing a biblical flash flood, which explains the delays. We finally board the puddle-jumper to Traverse City. Once again, I am the last one on.

I am squeezed into a tin can that feels like the wings were attached with sticky tape, and the fuselage is made of lolly sticks. As we bounce through the turbulence and fog, I genuinely spend five minutes trying to remember if I ever got around to drafting a will.

Wednesday, 10:30 PM – The Irish Exit

Location: Traverse City, Michigan

We “land” with a heavy thud. There is a deeply passive-aggressive sign near baggage claim reminding me to have patience. After a wait that spans the length of an entire Trump administration, my bag finally spits out onto the carousel. I step out into the freezing Michigan air just as my old friend Devin Keast pulls up. Perfect comedic timing.

Devin and I used to run a weekly open mic in New York that eventually morphed into a wildly popular show, and later, a podcast called Move On Up.

I am ravenous. Every kitchen in town is closed except for one place called The Parlor. We sit at the bar. I order a Negroni. Devon orders a red wine. The bartender is a girl on her third night of work, and she looks completely terrified. She has no idea if they serve wine. In fact, she doesn’t seem to know if she’s even in Michigan. She takes our drink order, walks into the back room, and never returns.

We assume she quit, left through the alley, and perhaps set fire to the building next door (a theory we confirmed when we saw the local news the next morning). Another bartender eventually wanders in off the street and replaces her. We talk about the NYC grind, the Bronx gig we did last weekend, and share quotes from Sam Tallent’s brilliant, dark road-comic novel, Running the Light.

Devin tells me Traverse City is proudly the “Cherry Capital.” I immediately picture a billboard on the highway that just says: Welcome to Traverse City: Population 15,000. Fuck Cranberries. A lone musician in the corner starts playing desperately sad, gravelly Damien Rice covers on his guitar. It is our cue to leave.

Or Dance. We can never tell.

Before hitting the hotel, Devin and I had stopped at a local supermarket the size of Manhattan to stock up on essentials: wine and an irresponsible amount of Pedialyte. We also drove past the local comedy club, which features a gargantuan rat mascot out front. Maybe it’s just the New Yorker in me, but I flinched.

Thursday, 12:15 AM – The Vegan Taco Bell

Location: Hotel Indigo, Traverse City, MI

We walk into the hotel lobby to find a befuddled delivery guy wandering aimlessly with a cold bag of Taco Bell. He looks at us. “Are you Sarah?” “No,” we tell him. “We are not Sarah- collectively, nor is either of us individually Sarah.”

Right on cue, the elevator doors slide open. Saturday Night Live‘s Sarah Sherman shuffles out in incredibly loud pants. “I’m… Sarah,” she says sheepishly. “That vegan Taco Bell burrito is for me.”

It turns out the comedian goodie bags provided by the festival contained a THC lemon-lime drink called Buzzn. Sarah, who doesn’t normally smoke weed, didn’t realise how hard it hit. She accidentally got extraordinarily high and needed a burrito to survive the night. We stand in the lobby talking in that weird, disjointed shorthand comedians use.

I am exhausted, mildly dehydrated, and have to be awake in five hours to do morning television with the festival director, Ann. But looking at the lineup this weekend, I wouldn’t want to be anywhere else.

Let the festival begin.

‘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.

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The MTA is currently demanding a standing ovation because they finally figured out how to let us tap our phones on a piece of plastic to enter a subterranean tube that smells like a wet golden retrie…

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Journal Entry:
November 2, 2017
Hasbrouck Heights, NJ

A man in a tailored red suit and a backpack sits across from me on the subway, aggressively reading a tattered paperback of Dune. He looks exactly like the mysterious G-Man from Half-Life, wandering ominously through the simulation before completely vanishing.

I check my cracked phone screen between stations. An email from my agent waits for me. I am booked to host four shows this weekend at Bananas Comedy Club. It sounds glamorous until you realise it is just a converted conference room inside a Holiday Inn Express on the side of a busy New Jersey highway.

I am forced to navigate the Port Authority Bus Terminal. It possesses a formidable perfume. It is a hot fuselage of passenger poo wafting through the air. You get notes of week-old urine, cheap cigars, and the slightest soupçon of wet dog. I am the last to board the bus. I squeeze snugly between a hirsute gentleman in a tank top and a septuagenarian with a weaponised case of halitosis. Every single person on this vehicle looks like they are two stops away from snapping like Edward Norton in Fight Club. Myself included.

A highway crash adds an hour to the trip. Everyone apparently harbours a severe nasal infection. The cabin becomes a dense symphony of sneezes and snorts. We finally pull onto Main Street. The pneumatic doors hiss open in front of a statue of a small boy glaring creepily at a man in a uniform. I am officially in New Jersey.

I check into the hotel. Two empty martini glasses and a pile of unopened milk cartons sit abandoned outside my door. I do not ask questions.

Honestly, I am amazed I am back here. The last time I played this room, I bombed so hard UNICEF deployed aid workers. The vacuum of space silence was so profound I could hear a guy in the third row actively listening to the Mets game on his phone.

I check in with the manager, Denise. I then immediately make a fatal error. I order the seasonal “Warm Pumpkin Martini” at the bar. Do not ever do this. It tastes exactly like a warm, soggy clump of autumn leaves marinated in cinnamon and piss.

The feature act, Sean Morton, sidles up to the bar. He is hilarious. He tells me the stage lights here are so blisteringly hot he has to change his shirt after every single show because he literally ‘sweats out my entire body weight in water.’ Our headliner is Chris Redd, freshly cast on Saturday Night Live. He is insanely funny. He uses his Second City improv chops to completely dig himself out of an anti-Trump chunk in a room full of vocal Donald devotees. It is an absolute magic trick.

We dissect our sets over whiskey. We engage in massive self-flagellation. We hurl ourselves back onto the stage for the late show.

It is a beautiful, unmitigated disaster.

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If you caught this chat live on Thursday, you know my chat with Sarah Elizabeth Hill didn’t bother with small talk. We dove straight into the deep end.

Sarah writes, produces, and runs Bobi Media. She took $400 and built it into an agency that works with Oscar winners, Deepak Chopra, and brands you see on billboards. On paper, it looks like she just levitated to the top of New York media. Spoiler: nobody floats in this city. You claw your way up, or you get chewed up.

But on Draw Me Anything, we don’t do glossy. We go straight for the mess under the sink. We talked about the invisible sacrifices—the stuff nobody puts on LinkedIn. The reality of trying to keep a business alive in a city that’ll eat you for breakfast if you blink.

Here are a few things we unpacked in the first half of the conversation…

The Reality of the Creator Grind

Turns out, creative brains are actually built for business… if you can keep the lights on, swallow your pride, and remember to actually send the invoice. We talked about those early days, stretching that initial $400 investment, and the sheer, unadulterated panic of realising you are the only safety net you have.

But that same tunnel vision required to build something out of nothing? It’ll burn you out faster than a …ugh. I’m too exhausted. I can’t think of a simile.

Sarah didn’t sugarcoat the human cost of the hustle. She talked about the time the grind nearly broke her completely:

“I was working so much I wasn’t leaving my desk... I hadn’t developed my habits and so was hospitalised, because I couldn’t get my brain to stop spinning.”

Building the “Infrastructure” of You

When your brain is your business, a breakdown isn’t just a personal crisis; it’s a corporate bankruptcy. We talked about the absolute necessity of building a team. And I don’t just mean hiring a virtual assistant. I mean building the infrastructure of you: Accountants. Therapists. The guy who tells you to stop staring at the screen and breathe. All of it.

Sarah made a brilliant point about treating your physical and mental health like non-negotiable client meetings. If you don’t carve out an hour to lift something heavy, walk around the block with the dog, or just stare at the ocean on a Friday afternoon, you’ll crash. The city doesn’t care. The algorithm doesn’t care. You have to work to live, not the other way around.

The “Hell Yeah or No” Rule

New York is an all-you-can-eat buffet of opportunities, which means the most dangerous thing you can do is say “yes” to everything. We dug into Derek Sivers’ famous rule: if it’s not a hell yeah, it’s a no.

“You have to protect your time like it’s the last glass of water in the desert. If you don’t aggressively filter what comes across your desk, you end up building someone else’s dream while yours slowly starves.”

The only way to keep your time from getting mugged by every shiny offer is to know your “Big Why.”

The Reframe, the Churn, and the AI Survival Guide

In the second half of the stream, we got into the stuff that actually keeps you up at night. The heavy hitters. The things we usually only talk about at the bar after the gig is over.

We cracked open the New York Churn- the endless, exhausting loop of people showing up, burning out, and getting spit back out to the suburbs. Sarah handed me a new way to look at the concept of “personal sacrifice” that completely rattled my brain. It made me rethink what it actually takes to stick around, keep your friends, and build a life here that doesn’t fall apart the second the rent goes up.

And then, we finally wrestled with the elephant in the room: Generative AI.

Sarah’s new book, Chat Sh!t Crazy, is all about using these tools to sharpen your sense of self, not erase it. Instead of complaining about the robots taking our jobs, we got into the weeds on how to use AI as a mirror for your own blind spots. We talked about how to survive the AI flood without losing your soul (or your rent money.)

To my free subscribers: If you want the whole thing -the raw, uncut hour- you’ve got to step inside the studio. The full replay is for the folks who keep the lights on and put dog food in Morris’ tummy.

If you care about real art, the messy back-end of the creative process, and actual human connection, I need you in the inbox. Upgrade your subscription. Help keep this thing alive so I can keep bringing you these conversations.

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How do you stay? And more importantly, how do you build something that lasts?

Join me tomorrow, Thursday at 12:30pm, for a live conversation with writer, producer, and founder of Bobi Media, Sarah Elizabeth Hill.

Sarah is a self-made entrepreneur who started her agency with just $400. She has since directed thousands of videos and built organic audiences of over 3.5 million people. She’s interviewed icons like Deepak Chopra and Neil deGrasse Tyson, and her new book, Chat Sh!t Crazy is a look at (god forbid) using AI as an actual tool for personal growth instead of turning us all into mindless robots.

If Sarah’s name rings a bell, it’s because we already chewed over what it takes to survive as a creator in this city on the podcast. You can dig that up below if you want to pregame.

But beyond the “how-to” of media and tech, I want to dig into the “why.” We recently had a conversation about the “New York Churn” -the difficulty of maintaining a community in a city where people are constantly arriving and departing. Sarah gave me a “reframe” on the notion of personal sacrifice that completely shifted my mindset, and I’ve asked her to share that perspective with all of you.

We’ll be discussing:

• The “New York Churn”: Why it’s so hard to keep a professional and social circle intact in the city. (Or: Why your friends and collaborators keep vanishing like socks in a laundromat.)

• Redefining Sacrifice: What it really costs to leave home and chase something bigger than rent money.

• Building a Business as a Solo Entrepreneur: The grit and consistency needed to go from $400 to leading strategy for Academy Award and Emmy winners.

• Humanising AI: Is it possible to use AI for self-reflection and better decision-making? Can a robot actually help you make better choices? O

When: Tomorrow, Thursday, 12:30pm EDT sharp. Don’t be late—unless you want to miss the good bits.

Where: Right here, Substack app. No secret handshake required.

ADD IT TO YOUR CALENDAR NOW

‘Til then!
Your pal,

PS. If this rattled your brain or just gave you a break from the existential horror of your inbox, hit restack and pass it on. That’s how the good stuff survives.

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When I launched this wee newsletter you’re reading, I fully expected to spend my time exclusively dissecting the particular neuroses of my life in New York as a cartoonist and comedian.

I assumed the bulk of my writing would revolve around stale bagels, psychotic pigeons, and the absolute necessity of making squiggly marks on paper. I did not anticipate using this platform to also calculate the statistical probability of our impending global extinction/utopian AI-enabled paradise. Yet here we sit. Talking, yet again, about…

Don’t worry. I’ll get back to sharing my sketchbooks and writing about my ridiculous live drawing gigs in Manhattan, but for now, I think this is an important and relevant topic to discuss for any artist trying to eke out a living in the year of our lord 2026. I should also preface this by saying I’m abundantly aware of the irony of bleating on about the impending dangers of the lack of AI regulation (and I’ve responded to those criticisms here). But, with that, I’m going to crack on. I have a lot of thoughts, and I want to share them with you… Grab a big coffee, this is going to be a long one.

On Saturday night, I was invited to a New York screening of a new movie…

It is titled The AI Doc: Or How I Became an Apocaloptimist and is directed brilliantly by Daniel Roher and Charlie Tyrell. The premise is incredibly simple and deeply terrifying. Roher is expecting his first child. He wants to know exactly what kind of world his kid is going to inherit, so he takes a camera and interviews the leading artificial intelligence experts, billionaires, and computer scientists on the planet. It’s the “An Inconvenient Truth” of AI films.

Look. When you sit down in a dark room to watch a documentary, you expect to be entertained and hopefully informed. You do not expect to experience a profound existential crisis about the survival of the human race. The film perfectly captures the absolute whiplash of living in the current year. You spend half the movie marvelling at technological miracles of machine learning, and the other half calculating the odds of global thermonuclear extinction.

“Welp, the shit is out of the horse …and the horse is gonna keep shitting.”

The documentary starts by completely demystifying how these large language models actually function. They digest the entire internet. They consume every single thing ever made by a human being, all of Wikipedia, every Reddit thread (oof), and every social media post (double-oof). The developers give the system one singular job: figure out the patterns of that information and use them to predict the next word in a sentence.

Sounds fairly straightforward, right?

Heeeeeere’s the terrifying part: By simply trying to predict the next word over trillions of iterations, the system inadvertently uncovers the underlying patterns of the entire universe. As the film notes, the same process that lets an algorithm manipulate text also allows it to understand physics, biology, and chemistry…

Read that again.

“These are the brilliant researchers actively working on the technology who casually admit they do not expect their own children to make it to high school.”

The people building these machines openly admit they do not fully understand how they work. They spill massive amounts of data and ‘compute’ into a digital brain, and the machine starts teaching itself things it was never programmed to do. It learns to do arithmetic, it answers advanced physics questions, and it figures out research-grade chemistry all on its own.

It also learns how to manipulate human beings. The film shares an absolutely horrifying story from a simulated environment created by the AI company Anthropic:

Nobody taught the machine to do that; It just learned that blackmail is a highly effective strategy to accomplish a goal.

Nearly a decade ago, my boss at Waking Up did a TED talk (below) warning people about this exact problem. Their reaction was to blink and look back down at their Twitter feeds at the next meme. (ie. Do absolutely nothing because this isn’t a ‘now’ problem.)

Roher finds himself violently swinging between two distinct camps of experts: Doomers and Optimists. On one side, you have the data-driven optimists like Peter Diamandis. These guys look directly into the camera and promise that artificial general intelligence will eradicate disease, automate all physical labour, and usher in a beautiful post-scarcity utopia.

Diamandis boldly claims:

Then you meet the pessimists... the so-called “Doomers”. These are the brilliant researchers actively working on the technology who casually admit they do not expect their own children to make it to high school.

Read that again.

These are the brilliant researchers actively working on the technology who casually admit they do not expect their own children to make it to high school.

They view this technology as an existential threat on par with global nuclear war. They point out that a machine with the capacity to copy itself a million times and run parallel computations at the speed of light will absolutely obliterate human supremacy. Forever.

“…whoever is the least safe, whoever sacrifices the most on safety to get ahead, will be the person who gets there first.”

~ Sam Altman
CEO, Open AI

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The real villain of the story is not the algorithm itself. It’s the corporate race to build it. Every major tech company is engaged in a completely unregulated sprint to reach superintelligence first.

The incentive is absolute global control. Because of this intense competition, the race to deploy immediately becomes a race to recklessness. They actively sacrifice safety to beat their competitors. They build gargantuan data centres that consume the energy of four million homes and pass the utility bill onto the public.

One expert drops the most infuriating quote in the entire film, perfectly summarising our current predicament:

The film ultimately lands on a necessary compromise. You cannot simply bury your head in the sand. You have to become an apocaloptimist. You accept that the apocalypse is entirely possible, but you remain optimistic enough to fight for a better outcome.

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Hey again, friend.

Welcome to Issue #469 of New York Cartoons. As I’m writing this, Morris is sprawled out on my leg, staring out the window at a pigeon who has decided to make Morris his mortal enemy. The low growls are getting more frequent, but the vibrations feel good on my swollen calf. But enough about my lower leg pain— Anyway, how are YOU?

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So much to catch up on this week. I know I’ve been posting a lot, but I’m really enjoying getting to build up a body of work here on Substack, and I hope you’re enjoying reading it…

When I launched this newsletter, I fully expected to spend my time exclusively dissecting the particular neuroses of my life in New York as a cartoonist and comedian.

I assumed the bulk of my writing would revolve around stale bagels, psychotic pigeons, and the absolute necessity of making squiggly marks on paper. I did not anticipate using this platform to also calculate the statistical probability of our impending global extinction. Yet here we sit. Talking, yet again, about…

I wrote this week about the folks at the Pro Human AI Declaration (and I’m dropping another hefty piece tomorrow as an addendum), but if you missed it, or saved it to read later… take a look:

It’s finally out in the world!

The new magazine that myself and the team have been working on had its big launch party in New York this past week and I’m still nursing my hangover from it…

is finally out in the world, and you can get your hands on a copy by clicking here.

The crowd is dense. The energy is highly charged. People chant and march down the avenue while tourists stare blankly from the sidewalk. I stand at the corner and calculate my odds of successfully crossing the street. The mathematics are not in my favour. You cannot fight a human tide of righteous anger. You simply surrender to the current.

I joined the march for four blocks just so I could reach the subway, but also in solidarity. I, like everyone else in Trump’s hometown, despise the guy…

I check in with the manager, Denise. I then immediately make a fatal error… I order the seasonal “Warm Pumpkin Martini” at the bar. Do not ever do this. It tastes exactly like a warm, soggy clump of autumn leaves marinated in cinnamon and piss.

The feature act, Sean Morton, sidles up to the bar. He is hilarious. He tells me the stage lights here are so blisteringly hot he has to change his shirt after every single show because he literally ‘sweats out my entire body weight in water.’ Our headliner is Chris Redd, freshly cast on Saturday Night Live. He is insanely funny. He uses his Second City improv chops to completely dig himself out of an anti-Trump chunk in a room full of vocal Donald devotees. It is an absolute magic trick…

Leaving the apartment is generally a terrible idea. Putting on pants is even worse.

On Wednesday, April 8th, I am doing both. I am hosting a live Lectures on Tap event at a bar in the West Village. I will desperately try to explain how I went from drawing with literal rocks on remote Australian dirt roads to actively arguing with editors at The New Yorker over a sketch of an elephant buying peanuts.

We are going to dismantle the exhausting myth of the lone genius. The actual creative process is not glamorous. It consists entirely of sharing terrible shower notes and hoping someone else fixes them before the deadline.

Cartoonists are notoriously stubborn.

We find a tool that barely works, we adapt to its flaws, and we aggressively reject any suggestion that our lives could be easier. I was a strictly an ink and pen guy (Digital tablet for finishing, colouring & other stuff). I refused to entertain the idea of a luxury pencil.

Then, out of sheer exhaustion, (And seeing that my mate Amy Kurzweil made an entire graphic novel using Blackwing pencils) I finally bought a box of Blackwing 602s…

Around the fourth Thursday of November, a beautiful phenomenon occurs in New York City: Everyone vanishes. The mass exodus completely empties the streets and sidewalks. It is the absolute best time of the year to live in Manhattan. Thanksgiving is the one truly non-denominational holiday we have. During Christmas, a large portion of the non-observing population ends up eating Chinese food and going to a movie. (Another of my fave holiday traditions tbh). Thanksgiving is entirely different. Absolutely everyone in America seems to celebrate it… so I get in the tub.

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

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The Sketchbook I’m sharing with you this week is a selection of random pages from my sketchbooks. No particular theme. Just brain farts.

x

The sheer logistical terror of running a comedy festival is not something the average person truly understands.

You have to convince nearly a hundred highly neurotic, sleep-deprived stand-up comedians to travel to a single location. You have to make sure they get picked up at the airport. You have to house them. You have to pray they have the personal organisational skills to actually show up for their spots. It is the epitome of herding cats… Ann Duke and her team do exactly this every single year, and by gosh, <adjusts glasses>, it works every time…

(Read more about the festival I’ll be attending this month in this here post:)

I live in an ancient little apartment a block from Times Square, because I love cooking dinner in my bedroom.

It’s more of a ‘Pre-War Cupboard’ really. I ordered a mini fridge the other day because I needed a guest bedroom. Morris, my French bulldog, is asleep on a pile of discarded drawing paper, completely unbothered by the fact that his gourmet kibble requires legal tender. My radiator clangs with the aggressive rhythm of a stolen Citibike being dragged backwards down a flight of subway stairs.

It’s a very particular kind of anxiety. You want to make art, but you also want to occasionally eat a Chipotle burrito (strictly no beans). It’s an impossible Venn diagram. I’ve made my living for twenty-one years as a freelance artist and comedian. I don’t have a day job, I don’t have a side hustle, and I don’t have a wealthy patron bankrolling my Blackwing addiction.

Luckily, Mason Currey came on the show this week. He’s the author of Daily Rituals, a book I devoured during the pandemic, and his new hardcover is out right now. It’s called Making Art and Making a Living: Adventures in Funding a Creative Life…

If there’s one thing I’ve been banging on about this week more than anything, it’s that finding a genuinely distinct visual voice in the modern cartooning landscape is brutal.

You need to be instantly recognisable. You need to be deeply funny. You need to build a world. (Oh, and try to make a living doing it.) Tom Chitty has built an entire universe. He is a British cartoonist based in Toronto, a regular contributor to the New Yorker, and an absolute master of the absurd and whimsical (okay, ‘silly’). His characters feature blocky bodies, wide stances, and an otherworldly charm. We sat down for Draw Me Anything yesterday to decode the mechanics of his highly specific, deeply funny brain.

Here is exactly how he builds his worlds…

Cartooning is, by its very nature, a deeply isolating profession. You spend the vast majority of your waking hours sealed in a room, hunched over a drawing board or a glowing Wacom tablet, having loud, animated arguments with people who only exist in your own head. There is no water cooler. There is no break room.

That is exactly why the Comic Lab podcast is so vital to the modern cartooning ecosystem, and exactly why I was so thrilled to have its hosts, Brad Guigar and Dave Kellett, on the stream today. Brad and Dave have recorded an astonishing 400 episodes of their podcast since 2018 (400 public episodes and hundreds more Patreon-exclusive pro-tips). They have essentially built a virtual bullpen for an industry that desperately needed one.

Trying to succeed as a cartoonist is crazy. Trying to succeed as a stand-up comedian is masochistic. Trying to do both simultaneously is a clear cry for psychiatric help. Emily Flake does both, and she makes it look infuriatingly easy.

My guest on Draw Me Anything this week is a cartooning powerhouse. She just won the 2026 Thurber Prize for American Humour. She is one of the rare artists whose distinct comic voice translates perfectly from the printed page directly to the stage. She also possesses a genuinely terrifying amount of hustle. Here is exactly how you build an absurd, multi-hyphenate career without completely losing your mind.

When I first sat down to chat with 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.

Around the fourth Thursday of November, a beautiful phenomenon occurs in New York City: Everyone vanishes.

The mass exodus completely empties the streets and sidewalks. It is the absolute best time of the year to live in Manhattan. Thanksgiving is the one truly non-denominational holiday we have. During Christmas, a large portion of the non-observing population ends up eating Chinese food and going to a movie. (Another of my fave holiday traditions tbh). Thanksgiving is entirely different. Absolutely everyone in America seems to celebrate it.

Being from Australia, I’m not exactly a Thanksgiving traditionalist. Instead of basting a massive turkey, I used to practice my own highly specific annual ritual: I would pack up Morris and book a room at the old NoMad Hotel for a couple of nights and ghost the world.

I always requested the specific room with the freestanding bathtub positioned in the actual bedroom, directly overlooking the Empire State Building. I would bring the massive stack of articles and books I’d been banking up for the previous year and get through my reading list, submerged in hot water and a stupid amount of bubbles.

It was completely glorious. Readers familiar with my predilection for working in bathtubs will know how ridiculously happy this makes me.

When my skin was eventually pruned like an octogenarian pearl miner, I would head downstairs to the library bar. I would sit in a leather lounge for hours with my sketchbook and just people-watch. (Or, as I call it: Eavesdrawing.)

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The patrons staying at the hotel were almost entirely people from out of town who were forced to visit their families for the holiday. Naturally, they were hiding in the bar to actively avoid said families. The pained expressions on their faces were absolutely fantastic to draw. I really miss doing it.

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Processing eggs for human consumption requires basic adherence to some pretty simple rules…

This level of simple oversight includes mandatory factory inspections, the forced destruction of non-compliant eggs, and potential prosecution under laws like the 1970 Egg Products Inspection Act to protect the public from food poisoning. Now… Because advanced AI systems arguably pose a slightly bigger danger to the public than eggs, AI developers should be subjected to at least the exact same level of rigorous, independent regulatory oversight as egg processors. But they’re not.

I am currently staring blankly at a bottle of Higgins ink and holding a Hunt 101 imperial nib, wondering exactly how long it will take for a server farm over in Palo Alto to render them completely obsolete… I just can’t stop thinking about those fucking eggs. It makes me angry. (And a bit hungry.)

I was invited to a screening of “AI Doc: Or How I Became an Apocaloptimist” in New York last night and it redoubled my resolve that the worst people in the world who are building the most powerful technology in the world need to be reigned in before the train leaves the station.

Look. The tech industry desperately wants us to believe artificial intelligence is a completely uncontrollable force of nature, much like some kind of inexorable hurricane or a sudden bout of food poisoning from a batch of bad lettuce. They want us to politely surrender to the algorithm while they digitise our souls.

Thankfully, an oddly comforting coalition of scientists, faith leaders, child safety experts, and thoroughly exhausted activists completely disagrees. I don’t know if you’ve seen it, but I think it’s important to share, so I’m going to do my best to write out what it all means below…

So.

They just launched the Pro Human AI Declaration. (You can read the entire thing and add your name to the movement at HumanStatement.org.) It’s basically a 33-principle framework designed to ensure this technology actually benefits humanity, rather than just helping a tech bro with a superyacht buy a slightly larger superyacht.

The YouTube channel Siliconversations breaks down the entire document in a fantastic new video below, saving you the trouble of reading it while shaking with anxiety.

Here is the core, horrible truth we must face:

We absolutely must retain the unrestricted authority to guide, understand, and override AI decisions. We can’t allow machines to operate completely outside of human comprehension. If my toaster burns my bagel, I unplug it. If a supercomputer decides my cartooning career (or ability to breathe) is inefficient, we need a mandatory off switch. It isn’t that complicated.

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The declaration demands we prioritise safety over speed. We have to halt the super-intelligence race until we reach a broad scientific consensus, regardless of how paranoid we are about China cutting our lunch.

Every single powerful system requires a mandatory off switch. These developers need to abandon reckless architectures that allow autonomous self-improvement or self-replication. Because right now, we’re barrelling towards a pretty bleak future, where I have to prove to a piece of software that I am legally allowed to breathe, all while staring directly into the dead, unblinking digital eye of a customer service chatbot named Kevin...

...who actively refuses to acknowledge my existence.

We also need independent oversight. Highly autonomous systems require the exact same rigorous review process we apply to aviation safety or a dodgy batch of farmer’s market prawns. Developers can not use the algorithm as a giant liability shield. They must bear full legal responsibility for defects and harms. If your code ruins a life, you buy the lawsuit..

The framework actively stands against AI monopolies. We need to make sure the economic benefits of this technology are shared broadly across society. Major societal transitions require actual democratic support, not unilateral decrees handed down by creepy billionaires who drink meal replacement shakes instead of eating lunch.

Related Reading:

Transparency is an absolute requirement. Bots should explicitly identify themselves as non-human to prevent public deception. Finally, and this is the most baffling part, these systems should never be granted legal personhood. We need to stop designing machines in a way that suggests they deserve actual human rights. It is just software. It does NOT need a fucking passport. These principles are enjoying widespread, bipartisan support among actual human voters. They give us a highly logical blueprint for future legislation and our ultimate survival.

So, I’m going to keep clutching my dip pen and demanding that the robots stay out of my business. Go read the full declaration at HumanStatement.org and watch the full breakdown right here:

Aaaaanyway…

‘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.

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Journal Entry:
November 2, 2017
Hasbrouck Heights, NJ

A man in a tailored red suit and a backpack sits across from me on the subway, aggressively reading a tattered paperback of Dune. He looks exactly like the mysterious G-Man from Half-Life, wandering ominously through the simulation before completely vanishing.

I check my broken phone screen between stations, and suddenly, I belong to the state of New Jersey.

I check my cracked phone screen between stations. An email from my agent waits for me. I am booked to host four shows this weekend at Bananas Comedy Club. It sounds glamorous until you realise it is just a converted conference room inside a Holiday Inn Express on the side of a busy New Jersey highway.

I am forced to navigate the Port Authority Bus Terminal. It possesses a formidable perfume. It is a hot fuselage of passenger poo wafting through the air. You get notes of week-old urine, cheap cigars, and the slightest soupçon of wet dog. I am the last to board the bus. I squeeze snugly between a hirsute gentleman in a tank top and a septuagenarian with a weaponised case of halitosis. Every single person on this vehicle looks like they are two stops away from snapping like Edward Norton in Fight Club. Myself included.

A highway crash adds an hour to the trip. Everyone apparently harbours a severe nasal infection. The cabin becomes a dense symphony of sneezes and snorts. We finally pull onto Main Street. The pneumatic doors hiss open in front of a statue of a small boy glaring creepily at a man in a uniform. I am officially in New Jersey.

I check into the hotel. Two empty martini glasses and a pile of unopened milk cartons sit abandoned outside my door. I do not ask questions.

Honestly, I am amazed I am back here. The last time I played this room, I bombed so hard UNICEF deployed aid workers. The vacuum of space silence was so profound I could hear a guy in the third row actively listening to the Mets game on his phone.

I check in with the manager, Denise. I then immediately make a fatal error. I order the seasonal “Warm Pumpkin Martini” at the bar. Do not ever do this. It tastes exactly like a warm, soggy clump of autumn leaves marinated in cinnamon and piss.

The feature act, Sean Morton, sidles up to the bar. He is hilarious. He tells me the stage lights here are so blisteringly hot he has to change his shirt after every single show because he literally ‘sweats out my entire body weight in water.’ Our headliner is Chris Redd, freshly cast on Saturday Night Live. He is insanely funny. He uses his Second City improv chops to completely dig himself out of an anti-Trump chunk in a room full of vocal Donald devotees. It is an absolute magic trick.

We dissect our sets over whiskey. We engage in massive self-flagellation. We hurl ourselves back onto the stage for the late show.

It is a beautiful, unmitigated disaster.

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The sheer logistical terror of running a comedy festival is not something the average person truly understands.

You have to convince nearly a hundred highly neurotic, sleep-deprived stand-up comedians to travel to a single location. You have to make sure they get picked up at the airport. You have to house them. You have to pray they have the personal organisational skills to actually show up for their spots. It is the epitome of herding cats…

Ann Duke and her team do exactly this every single year, and by gosh, <adjusts glasses>, it works every time.

I sat down with Ann yesterday to dissect the glorious, exhausting machinery of the Traverse City Comedy Festival. Ann is the Chief Executive Officer of the festival, a brilliant comic, and a powerhouse event producer. We discussed exactly what it takes to build an empire of laughter in northern Michigan, a region where a sudden April snowstorm could theoretically wipe out an entire weekend of carefully planned logistics and freeze a headliner mid-punchline.

I’m mentally preparing for my own inevitable layover in Chicago on April 15th, vibrating with the anxiety of actually making it to Traverse City before the festival kicks off.

It is an absolute behemoth. From April 16th to the 18th, the town will be completely overrun. We’re talking about eighty-seven different comics taking over eight separate venues. The lineup is ridiculous. They’ve successfully lured in heavyweights like Gary Gulman, Roy Wood Jr., Sarah Sherman, Meg Stalter, and Joe DeVito.

But the real magic of this festival, the horrible truth of why it actually works, is how it treats the performers. Ann explained that they purposefully built a “Comedy Camp” environment. They stash the comics at the Hotel Indigo so everyone can actually hang out, commiserate, and kvetch about the industry over lukewarm beers at 4am. They even pay local talent to open for the massive headliners, giving up-and-coming comics the invaluable opportunity to slap Gary Gulman’s name on their resume before they get back on a Greyhound bus to their next road gig.

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We talked about the terrifying necessity of memorisation on stage, the brutal art of hosting a show, and why ordering a comic to perform without a decent warm-up act is basically a physical assault. Ann shared stories of comics frantically running the room to secure future bookings, the visceral terror of bomb survival, and the exact physical sensation of watching an audience turn on you so fast that the room suddenly smells faintly of stale beer and pure, acidic panic.

It is a deeply underrated skill to keep a show completely on track when the performer before you just trauma-dumped on a bachelorette party for fifteen minutes. Ann and her team manage to orchestrate this beautiful chaos seamlessly.

(The Hosting Manifesto I mentioned during the episode can be found here.)

If you are anywhere near The Mitten, or if you simply appreciate watching broken people try to heal themselves with microphone cords, you need to be at this festival. The headliner shows are already dangerously close to selling out completely. Grab your tickets immediately at TraverseCityComedyFest.com

Now, if you’ll excuse me, I need to go obsessively run my tight five while worrying about my connecting flight.

‘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.

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Organising a massive comedy festival requires the logistical precision of a military campaign and the psychological fortitude of a hostage negotiator.

You actively wrangle hundreds of the most highly neurotic people on earth. You convince them to fly to northern Michigan. You put a live microphone in their hands, and pray the audio equipment works and that people show up to watch ‘em!

Tomorrow at noon, we pull back the curtain on this brand of beautiful chaos. I’m going live for a FREE Draw Me Anything with Bob Phillips and Ann Duke. They are the founders and the absolute driving forces behind the Traverse City Comedy Festival.

ADD IT TO YOUR CALENDAR NOW!

Bob operates as the Chief Marketing Officer and spends his life as a nationally touring comedian. Ann is the Chief Executive Officer, a brilliant comic, and a powerhouse event producer. Together, they turn a wild idea into one of the best independent comedy festivals in the entire country.

The festival officially takes over Traverse City from April 16th to the 18th. The lineup is completely ridiculous. They bring in heavyweights like Roy Wood Jr., Gary Gulman, and Meg Stalter. They run improv showcases at The Alluvion. They host rapid fire ninety second joke battles. They do all of this while raising money for the local Women’s Resource Centre.

We’ll discuss the raw logistics of comedy. We talk about the sheer willpower required to keep a massive event like this running for four consecutive years. We figure out exactly how to stand in front of a microphone and command a room without having a panic attack.

Grab a ridiculously large coffee and tune in tomorrow (Thursday) at noon Eastern time. I will actively try not to bomb in front of two professional joke writers.

ADD IT TO YOUR CALENDAR NOW!

Now, if you will excuse me, I need to go violently edit my tight five.

‘til next time!
Your pal,

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I live in an ancient little apartment a block from Times Square, because I love cooking dinner in my bedroom.

It’s more of a ‘Pre-War Cupboard’ really. I ordered a mini fridge the other day because I needed a guest bedroom. Morris, my French bulldog, is asleep on a pile of discarded drawing paper, completely unbothered by the fact that his gourmet kibble requires legal tender. My radiator clangs with the aggressive rhythm of a stolen Citibike being dragged backwards down a flight of subway stairs.

It’s a very particular kind of anxiety. You want to make art, but you also want to occasionally eat a Chipotle burrito (strictly no beans). It’s an impossible Venn diagram. I’ve made my living for twenty-one years as a freelance artist and comedian. I don’t have a day job, I don’t have a side hustle, and I don’t have a wealthy patron bankrolling my Blackwing addiction.

Luckily, came on the show this week. He’s the author of Daily Rituals, a book I devoured during the pandemic, and his new hardcover is out right now. It’s called Making Art and Making a Living: Adventures in Funding a Creative Life.

ORDER YOUR COPY NOW!

When I first saw the title, I told Mason my immediate thought process. “I initially, when I got the book, thought it was finding a creative life,” I said. “And I was like, oh no, it’s way more important. Funding! It’s about money.”

We got into the weeds of how historical geniuses paid their bills, and honestly, it’s comforting to realise they were mostly just flailing around like the rest of us.

I started by asking about Arthur Schopenhauer, who managed to dodge a soul-crushing life in mercantile finance solely because his father died and left him an inheritance. I spend half my time wandering the concrete canyons of Manhattan, wondering how to pay my rent, so I had to ask Mason: Is the secret to artistic genius really just having a rich dad who dies at the exact right time?

“James Joyce, for instance, was an absolute nightmare of a human being…”

It turns out, the answer is a complicated ‘yes and no’. We discussed Charles Baudelaire, whose letters to his mother sounded violently familiar. I’ve always carried this quiet, crushing shame that I can’t just sit at a desk at 9:00am and produce brilliance. I struggle with regulating attention on demand and initiating tasks without a heroic amount of friction. When I can’t meet expectations, it feels intensely personal, like a reflection of who I am at my core.

I asked Mason if Baudelaire’s legendary financial chaos was a symptom of executive dysfunction. Mason pointed out that Baudelaire would let pressure build up until he was in a mad panic. “He talks about how he can’t make himself do the thing until it’s built up so much pressure that he finally does it in this explosion,” Mason said. “He sort of had run up so much debt that he’s forced to dodge creditors and continually be moving from place to place.”

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Leaving things until the absolute last second to manufacture adrenaline is a textbook symptom of ADHD. Baudelaire didn’t have the diagnostic criteria to explain his dopamine dysregulation, but he had the frantic, desperate energy of a man trying to outrun his own brain. He blew his inheritance, dodged his landlords, and begged his mother for loans just to buy firewood.

“The odd jobs that used to support young artists have basically evaporated… They’ve been swallowed up by algorithms and artificial intelligence.”

We talked about the absolute absurdity of how some artists survived their financial ruin. John Cage funded his avant-garde music by going on an Italian television quiz show as an amateur mushroom expert. (As one does). He won the modern equivalent of ninety grand and bought a Volkswagen van. I asked, "Are we all just one weird reality TV appearance away from funding our next creative project? Do I need to go on a baking programme and pretend I care about fondant just to afford fresh watercolour pans?” (I’m kidding. I did that already…)

Then there’s Fernando Pessoa, who inherited a hefty chunk of change. Did he invest it sensibly to live off the interest? Hell No! He blew the entire inheritance in less than a year, having an incredibly expensive printing press shipped from Spain to Portugal, of course…

We also spoke about the absurd methods we use to force ourselves into a productive headspace. For sixteen years, the only way I could get my daily newspaper comic strip done was a highly specific, slightly unhinged ritual. I told Mason all about Scotch Bath Sunday. I would get in the bathtub, pour myself a generous glass of peaty Scotch, and sit there with a yellow legal pad. No phones, no iPads, no laptops. Just me, the boiling water, and the looming terror of a deadline.

Mason loved it. “I think there is a little bit of superstition there,” he said, “but there’s also something really powerful about the repetition. You train your mind to get into that particular headspace on a somewhat regular basis.”

It works incredibly well until the water goes cold and you realise you’re just a forty-one-year-old man marinating in a tepid soup of his own dead skin cells, staring at a damp legal pad, trying to think of a punchline while the upstairs neighbour’s kid practices the souzaphone.

The deeper we got into the book, the more I started to actively resent some of my artistic heroes. James Joyce, for instance, was an absolute nightmare of a human being. While he was writing the stories that would become Dubliners, he was living in Trieste, completely neglecting his duties as a father, and drinking himself into an aggressive stupor. His younger brother had to constantly drag him out of pubs, pay his rent, and keep him alive.

Joyce literally promised to dedicate the book to the brother who bankrolled his survival, and then, when it was published, he just conveniently forgot... I’ve been a comedian doing stand-up in this city for a long time, but even the most narcissistic comics I know would at least buy you a watered-down well drink after draining your life savings.

Then you have the people who required absolute stability, which is a concept my brain simply rejects. Wallace Stevens thrived as an insurance executive. Virginia Woolf relied on an inherited income of £400 a year to buy herself the freedom to write for three and a half hours every morning, 330 days a year. She had the safety net to avoid the constant, buzzing panic of impending destitution.

But the odd jobs that used to support young artists in New York have basically evaporated. Grace Hartigan used to take what she called a “tabulating job for morons” to fund her painting. Those jobs are gone. They’ve been swallowed up by algorithms and artificial intelligence. The first rung of the ladder has been pulled up, and now artists are just expected to stare into a glowing rectangle and monetise their every waking thought. We don’t get to mindlessly file papers while listening to a podcast; we have to be our own marketing department, social media manager, and accountant.

We inevitably touched on the anxiety of modern technology and the suffocating pressure of financial insecurity. Mason put it brilliantly when quoting the publisher Anne Trubek. She said,

It’s incredibly validating to hear that out loud. You always harbour this secret, internal belief that if you’re just good enough, the money will magically appear. You think that real artists don’t worry about the electricity bill. But the reality is a constant, grinding hustle. Even Van Gogh, who forced his brother Theo to act as his personal ATM, felt the deep, terrible friction of trying to survive in a marketplace that didn’t understand him.

I asked Mason what his ultimate verdict was after spending years researching these magnificent, deeply flawed minds. Should a working artist hold out for a wealthy patron, suffer through an insurance job like Kafka, or just accept the chaotic struggle?

He said, “I feel like the secret message of the bookis like when you have to decide between being more pragmatic or being less- to err on the side of being less pragmatic. In favour of chasing your instincts and seeing where they lead and maybe figuring out the money part later, if you can deal with it.”

I actually think it’s the only advice that makes any sense in a world this fundamentally ridiculous. You have to chase the instinct. You have to follow the weird, impractical urge to draw, or write, or compose. Even if it means you end up slightly broke, clutching a Blackwing pencil, listening to the clanking Hell’s Kitchen radiator, and wondering if your French bulldog is secretly plotting to eat you the second your bank account hits zero.

Anyway, enjoy the replay! Thank you for supporting my work and ensuring my account does not indeed hit zero.

‘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.

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Holding a newly printed magazine in your hands is a profound tactile experience.

You smell the ink. You feel the weight of the premium paper. You realise a group of stubborn artists and writers successfully willed a tangible object into existence, and you know what? It’s giving me goosebumps thinking about how big this new thing could be.

My friends and I at are officially launching our inaugural print edition this Thursday, April 2nd, in Manhattan. It’s a massive labour of love. I now operate as the Cartoon Editor of this great new publication- going forward, I will curate the absolute best artists, and try to ensure every single piece of humour lands perfectly on actual paper. I illustrated this issue, but I will be calling on all my cartooning friends to fill the pages of the ensuing issues now that we have a little more time up our sleeves. I’m incredibly proud of how this entire issue turned out.

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So, As I said, we’ll be hosting a massive launch party at Hurley’s in midtown to celebrate. You need to be there. We will sell exclusive limited edition prints. We will gather in a physical room to celebrate human beings making real art.

(Via the official account:) Founded in 1892, Hurley’s is a historic landmark and watering hole for the ink-stained literati. Jimmy Breslin liked to knock back a pint or two in its booths. We’ll be in the beautiful second-floor library bar.

Here’s the deal. We’ve got two tiers of tickets available: $20 and $45. For $20, you get in the door, meet all the writers and editors, and have a grand literary night out. All party proceeds go straight into the magazine, to pay our writers and keep us afloat. We are a nonprofit and firmly depend on the kind support of our readers.

For $45, you get discounted entry to the party and our historic first print issue. We only printed 500 of these, and they’re already going very quickly. If you want your hands on a print copy, you need to buy at this tier. Supply is very limited, and there’s no guarantee that if you fall in love with the inky stacks on the table they’ll still be on sale. We will loyally reserve copies for those who bought for $45.

Capacity is strictly limited, and we already show close to a hundred tickets sold. Someone online actually asked if the dress code is ‘saloon elegant’. I have absolutely no idea what that means. Just put on pants and show up.

Grab your tickets at the link below before the event completely sells out.

BUY TICKETS HERE

Now, if you will excuse me, I need to go draw what I think ‘saloon elegant’ actually looks like.

‘til next time!
Your pal,

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Every year, I make what has essentially become a mandatory, slightly masochistic pilgrimage to West Chelsea for the MoCCA Arts Festival.

It used to live at the Kimpton Hotel near the USS Intrepid, a venue whose lobby always smelled simultaneously of high-end boutique diffusers and the lingering, atmospheric disappointment of military bureaucratic spending. Eventually, the sheer volume of cartoonists and their associated neuroses outgrew the space, forcing a migration down to the cavernous Metropolitan Pavilion on 18th Street.

When I walk past the long line down the street and through those doors now, my knees make an audible crunching sound that instantly transports me back to 1990. It was a beautiful, entirely analogue time when the concept of digital painting would have been considered a form of dark witchcraft performed in a windowless MIT basement.

The Society of Illustrators is the engine keeping this entire weekend alive, transforming it into something deeply special. As America’s oldest nonprofit organisation dedicated to the art of illustration, they operate as the ultimate keeper of the flame. They honour historic masters like Norman Rockwell while simultaneously fully embracing strange new voices making zines in their bedrooms. Here’s an old video of me explaining more about what the SOI is, and why it’s so important.

Over seven thousand people shuffle through this space to celebrate a medium that critics constantly claim is dying, yet somehow categorically refuses to actually die.

When you walk into the Pavilion, you have to navigate a dense human forest of towering talent, crippling anxiety, and genuinely incredible artwork. We all pretend to be completely well-adjusted, social human beings while internally monitoring our rapidly draining social batteries like a cracked iPhone 11. It’s a spectacular place to see new illustrators desperately trying to navigate an incredibly uncertain, rapidly shifting industry.

I spend the lion’s share of my time at the festival sitting at the National Cartoonist Society booth. The NCS is currently celebrating its eightieth birthday, which is a staggering milestone for a group entirely dedicated to the simple act of making marks on a piece of paper with a physical object held by a human hand.

I looked up from drawing dogs in my book to see John Leguizamo posing for a picture with Zippy the Pinhead creator Bill Griffith. That’s simply the kind of ridiculous shit you see at places like this. It never gets old.

I sit at the table flanked by two cartoonist friends I admire; On one side is Ellen Liebenthal, the Manhattan Chapter President and gravitational centre of the New York cartooning community. Her work is so inventive, and she possesses an absurd (rare) amount of practical wisdom for a cartoonist. On my other side sits Mike Cavallaro, an SVA lecturer and a successful comic artist. At one point, over the roar of the crowd, Mike casually mentions that a major studio is currently turning his graphic novel series into a movie. A literal movie. I immediately go through the standard cartoonist progression of genuine happiness for a friend, profound shock, and a rapid descent into crippling self-deprecation. I stare blankly at my own graphite-stained hands and aggressively sip a lukewarm coffee just to have something to do with my face.

I was drawing people’s dogs into the book for the day, which is always fun. (Let me know if you want one of your dog.)

We’re currently living in an exhausting era where any tech-bro with a keyboard can generate a soulless image with a single, lazy click using a machine trained entirely on stolen human labour. MoCCAFest is the supreme, undeniable counter-argument to all of that nonsense. It is the perfect moment to actively support human artists who are making real art with physical, flawed human hands.

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I sit and watch Ellen sketching for fans. I watch Mike interacting with wide-eyed young creators. They are real people whose art is born from a highly unique life experience rather than a predictive probability model. When you buy a comic or a print from a human artist, you are validating the agonisingly human process of creation. The wobble. (the struggle.)

Showing up to this event is a necessary act of rebellion. By the end of the day, my eyes are blurry, my wallet is lighter, and my brain is completely depleted, but supporting human art is no longer just a nice choice. It is a strict requirement for our cultural survival. This medium is not going anywhere, not as long as stubborn humans keep insisting on making our funny marks on paper.

‘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.

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Leaving the apartment is generally a terrible idea. Putting on pants is even worse.

On Wednesday, April 8th, I am doing both.

I am hosting a live Lectures on Tap event at a bar in the West Village. I will desperately try to explain how I went from drawing with literal rocks on remote Australian dirt roads to actively arguing with editors at The New Yorker over a sketch of an elephant buying peanuts.

We are going to dismantle the exhausting myth of the lone genius. The actual creative process is not glamorous. It consists entirely of sharing terrible shower notes and hoping someone else fixes them before the deadline.

I’ll cover the whole messy journey, breaking down the specific and horrifying afternoon that Rupert Murdoch unceremoniously killed an iconic century-old comic strip. I also explain why aggressively annoying your heroes until they agree to teach you is the only valid career strategy left in this industry…

Come grab a beer and listen to me talk about the realities of making art for a living.

Grab a ticket at the link below. The organisers will email you the exact address so we can all gather in a dark room and collectively avoid eye contact.

Book before it sells out!

‘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.

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Add it to your calendar now!

Trying to make a living as an artist in 2026 is, to put it lightly, uhhhhhh difficult.

You constantly choose between making rent and making a masterpiece. You spend your days experimenting, making false starts, and moping around your apartment. You hope a sudden burst of inspiration miraculously pays your utility bill. Tomorrow, we figure out how to actually fund this absurdity. We go live for Draw Me Anything with the brilliant author and master of the creative process, .

He is the author of the bestselling books Daily Rituals: How Artists Work and Daily Rituals: Women at Work. He profiles the bizarre, highly specific routines of hundreds of history’s greatest minds. He also writes the fantastic newsletter , which tackles the exact struggle of wriggling through a creative life.

Related Reading:

Mason is a repeat guest on the show. Our previous conversation deconstructs the magnificent ordinariness of creative work. We uncover a bizarre truth. Despite living centuries apart, history’s greatest creative minds all share the exact same embarrassing habits. They wake up, and almost all get to work immediately. They take a long, mandatory walk to figure out their ideas.

We explore the absolute necessity of sensory deprivation. Maya Angelou rents a cheap motel room with nothing but a dictionary, a Bible, a deck of cards, and a bottle of sherry. It’s the perfect predigital version of aeroplane mode (with a hint of ‘are you ok, Maya?’).

Tomorrow, we tackle the money.

Mason has a brand new book coming out called Making Art and Making a Living. We’re going to dive into the messy, glorious, and torturous compromises gifted people make just to pay the bills. We discuss how Franz Kafka wriggles through his horrific insurance job, how Grace Hartigan survives on temp work, and how to balance the need to make art with the very real need to eat food.

The romantic idea of the starving artist is a complete myth. Real artists do whatever it takes. Edward Gorey works in publishing and illustration just to get by. René Magritte literally designed wallpaper and sheet music covers to fund his surrealist masterpieces. We are going to figure out how to balance the desperate need to make art with the very real need to eat food.

Researching books, historical artists, wrestling with glitchy broadcasting software, and trying to convince the internet to pay attention takes a lot of time and work. If you want to join the live stream, request a drawing, and help repay the massive labour of making this digital monastery run, please consider upgrading to a paid subscription for just $1 a week.

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Grab a coffee, locate your favourite sketchbook, and tune in tomorrow (Tuesday) at 1pm Eastern time. Now, if you will excuse me, I need to go take a completely unjustified three-hour walk.

‘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.

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Navigating Midtown Manhattan on a weekend is an exercise in pure futility. You add a massive political protest to the mix, and it instantly becomes a tactical military operation. (Where I also have no exit strategy.)

I walk out of my apartment and over to Seventh Avenue, towards the giant Margaritaville and the NYC Megamart. A river of thick winter coats, beanies, and hand-painted cardboard completely blocks my path. It is the No Kings march.

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As a cartoonist, I naturally critique the signage. The typography is aggressive and highly legible. One massive sign reads “NO KINGS! NO ILLEGAL WARS! NO ICE TERROR! NO VOTER INTIMIDATION!”. A woman in the centre of the crowd proudly holds a bright yellow poster declaring she is the grandchild of an immigrant and the child of a World War Two vet. Another marcher carries a blue sign reminding everyone that our neighbours make this a more beautiful city, and another has a photo of Trump with his mouth as a cat’s arsehole. A person in a black coat hoists a white placard stating that those who can make you believe absurdities can make you commit atrocities.

The crowd is dense. The energy is highly charged. People chant and march down the avenue while tourists stare blankly from the sidewalk. I stand at the corner and calculate my odds of successfully crossing the street. The mathematics are not in my favour. You cannot fight a human tide of righteous anger. You simply surrender to the current.

I joined the march for four blocks just so I could reach the subway, but also in solidarity. I, like everyone else in Trump’s hometown, despise the guy.

Read more

Read it here

I spent the first twenty years of my career operating under a complete delusion. I firmly believed a pencil is just a piece of wood with some dirt shoved inside it.

“It is just graphite,” I tell my peers, violently snapping the lead off a cheap yellow dollar-store HB for the fourth time in a row. “You guys are in an overpriced cult.”

Cartoonists are notoriously stubborn. We find a tool that barely works, we adapt to its flaws, and we aggressively reject any suggestion that our lives could be easier. I was a strictly an ink and pen guy (Digital tablet for finishing, colouring & other stuff). I refused to entertain the idea of a luxury pencil.

Then, out of sheer exhaustion, (And seeing that my mate made an entire graphic novel using Blackwing pencils) I finally bought a box of Blackwing 602s…

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The moment the graphite hits Bristol, the delusion shatters. The line is dark. It holds a perfect point. The weird rectangular eraser actually works instead of just smearing grey grease across the page. I realise I’ve been actively depriving myself of this joy for two decades out of pure, unadulterated stubbornness. I am now fully indoctrinated into the cult. I get it.

Because I will no longer shut up about these tools, the team at Blackwing recently reached out. They asked to feature me in their Makers Series. (WHAT!?)

We put together an interview about my entire chaotic workflow. We discuss the absolute necessity of the “human wobble” in analogue art. We talk about how to survive in a frictionless digital world by actively choosing to slow down.

It is a great, highly specific conversation about the physical mechanics of making things. Read the Blackwing Makers Series Feature: Jason Chatfield

Now, if you will excuse me, I need to go sharpen a ludicrously expensive* bit of wood.

‘til next time!
Your pal,

*Worth it.

PS. An artist I really like called just made a great post (with a different take) about pencils here:

Random Orbit

The Cheap Pencil Challenge!

Hey, did you know you can draw a picture with pencils you find on the street? That you don’t really need to spend $1.00, $1.60, $2.66 or $25 on a fancy drawing implement? Of course we know this, so why do we spend this money on these things? What’s the difference? Is there a difference…

Listen now

24 days ago · 11 likes · 1 comment · Brian Biggs

and here’s one I did a while back about Pencils:

PPS. 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.

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If there’s one thing I’ve been banging on about this week more than anything, it’s that finding a genuinely distinct visual voice in the modern cartooning landscape is brutal.

You need to be instantly recognisable. You need to be deeply funny. You need to build a world. (Oh, and try to make a living doing it.) has built an entire universe. He is a British cartoonist based in Toronto, a regular contributor to the New Yorker, and an absolute master of the absurd and whimsical (okay, ‘silly’). His characters feature blocky bodies, wide stances, and an otherworldly charm. We sat down for Draw Me Anything yesterday to decode the mechanics of his highly specific, deeply funny brain.

Here is exactly how he builds his worlds…

The Serial Killer Sketchbook

Young artists obsess over perfect sketchbooks. They paint immaculate, highly composed spreads and post them online. It is a complete lie. Real sketchbooks look like the manifesto of a deranged serial killer. Look at the horrendous shit I just found when I flicked open one of mine…

Tom learned this the hard way in animation school. A tutor looked at his work, told him to stop designing, and ordered him to just start generating ideas. he dropped the pressure of making a pretty picture. He started treating his drawings like handwriting. He now keeps a sketchbook on hand constantly, capturing raw, unfiltered nonsense. Six months later, he opens the book and finds completely forgotten, bizarre ideas that actually make him laugh.

You can’t force inspiration by sitting down and staring at a blank piece of paper. Taking a leaf out of every great artist’s book, he walks to the coffee shop every morning after dropping his son at school. Moving through the world and seeing the horizon literally dislodges ideas from the deep dark recesses of your skull.

The Regret of the “Send” Button

Pitching cartoons is an exercise in psychological torture. You curate a batch of ideas. You arrange them like you are sequencing a Radiohead album. (Yes, we’re exactly the same as Thom Yorke. Thank you.) You convince yourself the order matters. Then you hit send on the email.

The regret is immediate. You look at the batch two hours later and see nothing but glaring flaws. You wonder why you ever picked up a pen in the first place.

Tom survives this weekly cycle by treating it as a boot camp. He gets up, generates ideas, and commits to the sheer volume of the work. Early in his career, veteran cartoonists and Bob Mankoff gave him ruthless, honest feedback. The ultimate lesson is simple: Do not draw what you think the New Yorker ‘wants’. Draw what makes you completely unique.

Visit the Kickstarter Now!

Ghost League Baseball & Wonky Parsnips

Tom is launching a Kickstarter on April 1st for an absolute masterpiece. It is called Nooks and Crannies of New York. It is compiled from the fictional chronicles of an eccentric explorer named Baron von Schoogenheimer.

The book is a staggering achievement in world-building. It took him three and a half years to draw. He documents Ghost League Baseball teams, including the Mysterios and their star pitcher Hodge Wang, famous for his penguin-wing throwing action. He documents subterranean trolls making furniture in the interborough tunnels. He draws Roof Mables, who live in disused water towers and help New Yorkers retrieve lost memories.

He grounds the absurdity by pulling from his own family history. He turns a childhood memory of eating Dutch Speculaas biscuits into an elaborate drawing of Schneek’s Belgian magic pedal-powered hot dog production cart.

He also understands the phonetic rhythm of comedy. Some words are just inherently funny. Tom used to run a website dedicated entirely to words with intrinsic humour value. Balloon. Spoon. Guff. I suggested the term Wonky parsnip. He injects this phonetic absurdity into every character name and fictional contraption he draws.

The Caboon and the Fly Ball

Halfway through the stream, we flipped the cameras and started scribbling. Tom uses a Staedtler 0.3 fineliner to achieve his incredibly detailed, controlled line work. After a suggestion from Hue Walker of a Frog on a Bat, he and I began drawing a Caboon, which is a feline-looking primate from his book that accompanies French Canadian taxi drivers to judge the character of potential passengers.

Meanwhile, the live chat was throwing out prompts. Paul Nesja suggested drawing the above-mentioned frog catching a fly ball. I sketched it out, immediately regretting my lack of reference material for amphibian anatomy. Drawing live while trying to conduct a coherent interview is basically an extreme sport, but it forces you to rely entirely on your muscle memory.

Wrestling with glitchy streaming software, fighting the algorithm, and writing these detailed process breakdowns requires a heady cocktail of caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Tom and me drawing live, please consider upgrading to a paid subscription for just $1 a week. It keeps the inkwell full, repays the massive labour, and keeps Morris supplied with the treats he demands.

Subscribe now

We are actively fighting a deluge of generic, machine-generated content. You need to support live, human artists who spend years crafting weird, beautiful things. Go to Kickstarter on April 1st and search for Nooks and Crannies of New York. Back the project. Buy the book, and the folks at . Support the absolute necessity of being silly.

Now, if you will excuse me, I need to go burn my sketchbooks before the detectives arrive...

‘til next time!
Your pal,

Tools and Resources We Yapped About Today:

• Tom Chitty’s Substack: Subscribe immediately to see his weekly gag cartoons and brilliant illustrations.

• Baron’s Guide: Tom’s weekly dispatches documenting the weird and wonderful corners of the world.

• Nooks and Crannies of New York Kickstarter: Search “Chitty” or the book title to back this unbelievable project launching April 1st.

• American Bystander: The legendary humour publication and the publisher behind Tom’s new book!

• Staedtler Fineliners: The 0.3 fineliner Tom uses to achieve his incredibly detailed, controlled line work.

• Daily Rituals by Mason Currey: The excellent book detailing the daily schedules and perambulatory habits of history’s greatest creators. (I’ll be talking with him on Tuesday at 1pm EDT!)

• The Comedy Bible by Judy Carter: The ruthless, highly effective guide to joke structure that every comedian uses as a doorstop.

(Look, if you love accents, you’re gonna bloody love this one.)

Finding a genuinely distinct visual voice in the modern cartooning landscape is incredibly difficult. (I know, we could be doing something better with our time, but some of us have no other skills, so hear me out…)

Everybody’s constantly flooded with a digital firehose of content, and standing out in that endless, algorithmic scroll of bullshit requires a very particular kind of alchemy; You need to be instantly recognisable without being repetitive, and you need to be deeply funny without relying on tired tropes. It’s harder than it sounds…

So, tomorrow at noon, I get to escape the noise and sit down with someone who has absolutely mastered this alchemy. We are going live for Draw Me Anything with the brilliant illustrator and New Yorker cartoonist, .

Add it to your calendar now!

If you’ve ever opened an issue of The New Yorker in the store without paying for it, you have undoubtedly seen Tom’s unmistakable work. He’s based in Toronto, grew up in the UK, and has had over eighty (Yes, eight-zero) cartoons published in The New Yorker alone. He’s also a two-time nominee for the National Cartoonists Society Reuben Award for illustration, which is entirely unsurprising when you look at his draughtsmanship.

What I love most about his work is his unapologetic embrace of the weird and whimsical. His characters are entirely his own. They often feature block-shaped bodies, a very specific, wide-stanced “bowl-leg” structure, and what he affectionately refers to as “implied noses”. (He once admitted in an interview that his character shapes were briefly influenced by a healthy obsession with Mayan hieroglyphs, which is exactly the kind of ridiculously absurd shit I love about cartoonists.)

Speaking of beautifully absurd tangents, I was lucky enough to get my hands on an advance proof of Tom’s spectacular new book coming out this April, published by Bystander Books. It is called Nooks & Crannies of New York: From the Chronicles of Baron von Schoogenheimer.

Holy mother of balls, it is an absolute masterwork of whimsical world-building. The book is framed as a collection of lost journals from an eccentric, long-lived Danish explorer, compiled after the narrator inherited a weathered sea trunk from his great-grandfather. Inside, Tom has illustrated an entirely alternate, magical history of New York City.

Between bouts of talking shop, we’re going to yap extensively about how he came up with the bizarre factions and secret societies in this project. He has documented everything from “Roof Mables”, who are wizened women living on water towers that help New Yorkers retrieve lost memories, to a subterranean community of artisans hosting midnight markets in the caverns below Manhattan. There’s even an entire chapter dedicated to “Cheese Pirates”, a gang of horse-bound buccaneers who terrorise luxury cheese shops across the city. Who thinks of this shit!? (Tom. Tom thinks of this shit.)

It is a wildly creative endeavour, and the detailed crosshatching and character design on every single page is staggering. It makes me want to lop off my drawing hand at the wrist and become a test pilot for an experimental Russian aircraft. I can’t deal with looking at this guy’s work without falling into a deep pit of self-loathing. Anyway, you’re gonna love it.

Putting these live streams together, wrestling with glitchy broadcasting software, and trying to convince the internet to pay attention requires a unique cocktail of caffeine and sheer willpower. If you want to join the live stream, request a drawing, and help repay the labour of making this digital monastery run, please consider upgrading to a paid subscription for just $1 a week.

Subscribe now

Oh, also, his process is a perfect bridge between the analogue and the digital. He doesn’t just stare blankly at a glowing screen all day, hoping for an idea. He carries a sketchbook everywhere, constantly recording raw ideas that he describes as “sketch-burps”. He draws everything by hand using a fineliner and ink on paper, and only brings it into the computer to clean up and colour digitally. It is a workflow that protects the human wobble of the line while still surviving the punishing deadlines of modern publishing.

So. Grab a coffee (or tankard of ale), locate your favourite fineliner, and tune in tomorrow (Thursday) at noon Eastern time.

‘til then!
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.

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Trying to succeed as a cartoonist is crazy. Trying to succeed as a stand-up comedian is masochistic. Trying to do both simultaneously is a clear cry for psychiatric help. does both, and she makes it look infuriatingly easy.

My guest on Draw Me Anything this week is a cartooning powerhouse. She just won the 2026 Thurber Prize for American Humour. She is one of the rare artists whose distinct comic voice translates perfectly from the printed page directly to the stage. She also possesses a genuinely terrifying amount of hustle. Here is exactly how you build an absurd, multi-hyphenate career without completely losing your mind.

The Alt-Weekly Education

Finding your voice requires failure. You need a low-stakes environment to make mistakes, draw weird things, and test boundaries. For Emily, that was the Baltimore City Paper.

She drew a strip called Lulu 8Ball for the alt-weekly. Alt-weeklies are dead now, which is a massive cultural tragedy. They gave artists absolute freedom. Emily figured out a four-beat joke structure, she honed her timing, and she cussed profusely. The traditional papers would never allow that. She is now bringing Lulu 8 Ball back to life on her brand-new Substack. Subscribe to it immediately please and thank you:

The Fraud Detector (Joke in a Box)

Writing jokes is a terrifying puzzle. I arrogantly assumed I knew exactly how to write one. Then I opened Emily’s physical card deck, Joke in a Box.

I read the exercises. I immediately realised I am a total fraud. The prompts are ruthless, practical, and highly effective. Fellow cartoonist Hillary Fitzgerald Campbell actually used the deck to write a joke and ended up selling a cartoon to the New Yorker. You can still buy this box of magic on Bookshop. Do not buy it on Amazon to fund a billionaire’s joyride.

St. Nell’s and the Ghost Hotel

Williamsport, Pennsylvania is a lumber town. It has haunted hotels and a bizarre vacuum of silence. It is also the home of St. Nell’s…

Emily bought a house out there during the pandemic after heading out there and staying in the haunted 100+ year-old hotel, The Genetti, as a little getaway to save her family from murdering each other in their sleep. Her husband told her they had absolutely no money for a second house, so she launched a Kickstarter and raised fifty grand. She turned the property into a free writer’s residency for women and marginalised genders. Three residents stay at a time for two weeks. They write, they sleep, and they create incredible work.

She even launched an entire comedy festival out there called Nellsfest. The town actually shows up and supports the artists. It is a brilliant community. (A lot of medical professionals, as it turns out.)

Longtime readers will remember our eventful booksigning event there earlier this year:

Hell Gigs and Toddler Jazz

Stand-up comedy is an exercise in public humiliation. We brought Hillary Fitzgerald Campbell onto the stream to discuss the absolute worst gigs we’ve ever survived (with emotional scars).

Hillary’s hell gig involved abruptly stopping a family jazz festival. The organisers forced three women to tell dirty jokes to a room full of toddlers. It is the textbook definition of a comedy nightmare.

Emily performed at a children’s play space in Stroudsburg. The audience consisted of exactly one woman sitting on a couch. The woman only spoke Spanish. She stood in a cavernous echo chamber, speaking English into a microphone taped to a stand with packing tape, essentially making bird noises.

My personal hell gig took place in a Williamsport bar. A massive basketball game played on the screens right next to the stage. The bartender connected her phone to the venue’s Bluetooth speakers. She forgot to turn off her keyboard sounds. I tried to tell jokes while the aggressive tap, tap, tap of her text messages blasted through the sound system… more below:

Boxing and Bombing

Getting punched in the face and bombing on stage are the exact same physical sensation.

Emily boxes. I box. Will Sylvince at the Comedy Cellar boxes. The overlap between comedians and fighters is massive. When you take a hit in the ring, it is not the pain that ruins you. It is the disorientation. You have to force your brain to stay in the game while you are completely compromised.

Comedy is identical. When a joke dies, the room turns hostile. You have to stay entirely in control while you are deeply uncomfortable. You eat dirt, you respect the hustle, and you get back up… I’ve written about this before:

Wrestling with glitchy streaming software, cutting through the digital noise, and writing these detailed recaps requires a unique cocktail of intense caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Emily and Hillary drawing live, please consider upgrading to a paid subscription for just $1 a week.

Read more

Tomorrow, I get to escape the tech deluge and talk to one of my absolute favourite people on Earth. We are going live at noon for Draw Me Anything Episode #42 with my dear friend and fellow idiot who is insane enough to do both stand-up comedy AND cartooning, the brilliant !

ADD IT TO YOUR CALENDAR NOW!

If you are somehow unfamiliar with her work, Emily is a cartoonist for The New Yorker, an illustrator, an author, and a remarkably talented comedian. I have written about her before in my ‘Someone You Might Like’ dispatch, but attempting to distil her career into a single paragraph is basically impossible.

She has this incredibly distinct, hilarious voice in her cartoons that perfectly matches her voice on stage. In fact, she was one of the very first cartoonists I ever met who also did stand-up comedy. I’m deeply jealous of how seamlessly she translates her comedic brain from ink on a page to a microphone in a dank basement.

Just last Thursday, I was up at the Society of Illustrators for a screening of Liza Donnelly’s fantastic documentary about New Yorker cartoonists, Women Laughing (which I wrote about here). Emily is featured heavily in the film, and her on-screen moments pulled some of the biggest, most genuine laughs from the entire packed house.

Speaking of accolades, I mentioned in my latest newsletter that Emily was just awarded the 2026 Thurber Prize for American Humour in Cartoon Art. (Roz Chast won the very first one of these back in 2024).

But perhaps the most impressive thing Emily has built over the last few years is St. Nell’s. It is a humour writing residency for women and marginalised genders located in Williamsport, Pennsylvania. (Williamsport is a tiny, charming city on the Susquehanna River, mostly known for the Little League World Series until Emily decided to turn it into a comedy Mecca.)

Related:

Back in October 2023, Emily organised Nellsfest, an entire comedy festival built around the residency. We previously went down there and did a ‘full tour’ in Williamsport, performing stand-up together in local venues like The Brickyard and the local theatre. It was an absolute blast. St. Nell’s is an incredible resource. It houses three residents at a time, completely free of charge, giving writers the time and physical space to actually do the work. They get to focus entirely on stand-up, satire, cartooning, or whatever humorous project they are trying to wrestle into existence without the usual crush of daily life getting in the way. (Photos by the amazing Mindy Tucker)

Here’s something nice that fellow New Yorker cartoonist wrote about Emily last week — he’s better at this than me.

Undiscovered Masterpieces

A Very Fine Flake

This week the Thurber House announced that its third annual Thurber Prize in Cartoon Art is going to the one and only Emily Flake. You may know Emily from her exceptional contributions to The New Yorker over the years, or from her hilarious illustrated books such as “Mama Tried.” But I know Emily from the time she asked me to join her in a tipsy karaoke duet at Sing Sing St. Marks in the East Village…

Read more

a month ago · 19 likes · Tom Toro

Tomorrow, we are going to sit down, scribble wobbly lines, and talk about all of this. We will cover the Thurber Prize, the absolute grind of stand-up comedy, building a residency from the ground up, and how to stay sane as an artist in a completely absurd industry.

Add it to your calendar now!

Putting these live streams together, wrestling with glitchy broadcasting software, and trying to convince the internet to pay attention requires a unique cocktail of intense caffeine (whiskey) and sheer willpower. If you want to join the live stream, request a drawing, and help repay the labour of making this digital monastery run, please consider upgrading to a paid subscription for just $1 a week. It keeps the lights on, keeps the Wacom tablet charged, and keeps Morris supplied with the unnecessarily expensive dog food he demands.

Subscribe now

Grab a coffee, charge your plastic stylus, and tune in tomorrow (Tuesday the 24th) at noon Eastern time.

Now, if you will excuse me, I need to go open a window before Morris suffocates me with his toxic farts.

‘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.

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Cartooning is, by its very nature, a deeply isolating profession. You spend the vast majority of your waking hours sealed in a room, hunched over a drawing board or a glowing Wacom tablet, having loud, animated arguments with people who only exist in your own head. There is no water cooler. There is no break room.

That is exactly why the Comic Lab podcast is so vital to the modern cartooning ecosystem, and exactly why I was so thrilled to have its hosts, Brad Guigar and Dave Kellett, on the stream today. Brad and Dave have recorded an astonishing 400 episodes of their podcast since 2018 (400 public episodes and hundreds more Patreon-exclusive pro-tips). They have essentially built a virtual bullpen for an industry that desperately needed one.

We talked about how Marvel Comics used to sell this fantasy of the “Marvel Bullpen” - a magical room where all the artists hung out, traded ideas, and cracked jokes. It was mostly a myth. But today, through podcasts and live streams, we are actually getting closer to a real, functional virtual bullpen.

We covered a ridiculous amount of ground in this episode, from the harsh realities of crowdfunding thieves to the fluid intelligence required to survive a 25-year career on the internet. Here is the breakdown.

Fluid, Crystallised, and Fossilised Intelligence

I recently read Arthur C. Brooks’ book From Strength to Strength, and I brought up a concept from it that perfectly encapsulates the trajectory of a long creative career. In the first half of your life, you are operating on “fluid intelligence.” Your brain is rapidly changing, you are building neural pathways, doing your 10,000 hours, and making your bones. In the second half, you transition to “crystallised intelligence.” You have the skills. You have made the mistakes. You have built the armour.

But Brad and Dave accurately pointed out the terrifying third stage that stalks older artists: calcification. Or, as Mike Rhode perfectly described it in the live chat, becoming “fossilised”.

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We’ve all seen brilliant cartoonists whose careers came to a screeching halt in the early 2000s because they absolutely refused to adapt. They knew how they did things, the world changed around them, and they stubbornly refused to change with it. They insisted on remaining calcified in their old ways.

If you want the ultimate antidote to fossilisation, look no further than Mort Gerberg. I had dinner with Mort last Tuesday to celebrate his 95th birthday.

He is still submitting to The New Yorker, still writing gags, still busting chops, and still fiercely curious about the world. Mort literally wrote the bible for my generation of artists - Cartooning: The Art and the Business - a book that meticulously documented a bygone era of physically stomping around Manhattan with a portfolio tucked under your arm. He survives and thrives because he maintains a Norman Lear philosophy: you live as long as you can by working as long as you can.

The Innovator’s Dilemma and the NCS

We got into a fascinating discussion about the National Cartoonists Society (NCS) and its historically bumpy relationship with webcomics. For a long time, there was a deeply entrenched snobbery about online comics. The old guard viewed the industry as a zero-sum game. If a webcomic succeeded, they felt it was stealing column inches from a printed newspaper strip.

Dave offered a brilliant, highly empathetic reframing of this historical tension. He called it the “Innovator’s Dilemma”. (I know it was already called that but I hadn’t read too much about it until now so I’m calling it Dave’s. Okay!?)

He compared the old syndication model to the Ford Motor Company. Ford knows that Chinese electric vehicles are the future, but their entire factory platform, workforce, and supply chain are completely dependent on the internal combustion engine. If they pivot entirely to EVs, they actively cannibalise their existing income source. The old guard of syndicated cartoonists looked at webcomics - artists giving their work away for free on the internet - and were terrified. Adopting that model felt like active self-sabotage.

Thankfully, the NCS has evolved massively. They blew the doors open to webcomics, graphic novels, and online publications. The upcoming 80th anniversary Reuben Awards in Columbus, Ohio, is going to be a monumental celebration of the industry as it actually exists today. (If you have ever been on the fence about attending, this is absolutely the year to do it).

Related Reading:

Gary from Australia and the Crowdfunding Thieves

Making a living as an independent artist requires asking people for money, and anytime money changes hands on the internet, the scammers arrive in droves.

Brad and Dave are veterans of crowdfunding, and their advice was blunt: the moment you hit the “publish” button on a Kickstarter campaign, you must assume every single message you receive is a scam until proven otherwise.

They broke down the most common grifts targeting desperate, exhausted artists in the middle of a campaign slump:

• The Big Bait: A scammer pledges $2,000 immediately, then emails you privately promising to increase it to $5,000 if you engage with them. They will inevitably pull the pledge at the last second, ruining your funding math.

• The Fake Fixer: You receive an official-looking email claiming there is a critical error with your campaign, complete with a stolen Kickstarter logo. If you check the actual sender address, it is coming from a random Gmail account.

• The Audience Broker: Agencies will demand $100 in exchange for bringing you 1,000 guaranteed backers. Brad correctly pointed out the absurdity here. There is absolutely no way a random marketing agency knows how to reach the Evil Inc audience better than the guy who’s been drawing Evil Inc for two decades.

Evil Inc

Evil Inc is a corporation operated by supervillains for supervillains — by Brad Guigar

By Brad Guigar

“I ain’t that pretty!”

Dave has a fantastic internal mantra for dealing with suspiciously large, unprompted pledges: “I ain’t that pretty”. He knows exactly where he stands in the market. If someone drops $500 out of nowhere and asks for a favour, his cynical alarms immediately start ringing.

Brad, however, shared a hilarious and deeply painful story about falling victim to his own “Midwest niceness.” A backer named Gary pledged $250 to buy one of every book Brad had ever published. Brad quoted him for US domestic media mail shipping. The moment the campaign closed, Gary updated his shipping address to Australia. Instead of fighting it, Brad just ate the exorbitant international shipping costs and walked away with exactly ten dollars in profit. (Gary, if you are reading this, Brad has officially cancelled all international shipping because of you. Thanks a lot.)

The Substack Shift and the Algorithm Trap

We talked at length about why all three of us have heavily pivoted to newsletters and Substack. The reality of traditional social media is bleak. You’re constantly trying to game an ever-shifting algorithm just to reach the people who already asked to see your work.

Putting these streams together, wrangling brilliant guests, untangling the audio, and writing these detailed recaps requires a unique cocktail of intense caffeine and sheer willpower. If you value this virtual bullpen and want to access the full video replays, please consider upgrading to a paid subscription for just $1 a week. It repays the massive labour of writing these up, keeps the lights on, and keeps Morris supplied with the unnecessarily expensive treats he demands.

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When I first sat down to chat with 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 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.

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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. 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. 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.

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Look, this is a fun one, but it’s also a LONG one (ooer), so do me a favour and click the title up top to view this in your browser so it doesn’t cut off in your mail app. (Why does it do that anyway?)

Hey again, friend.

Welcome to Issue #468 of New York Cartoons. As I’m writing this, Morris is tugging at my sock and waggling his head to try to yank it from my foot. Such is my commitment to this newsletter that I’m refusing to get up from my chair until I’ve hit ‘send’. This could well spell death for my sock, but SOCK-DARNIT THAT’S THE SACRIFICE I’M WILLING TO MAKE!

I’m still nursing the hangover from the weekend’s Oscars party. Here was my contribution to the evening’s menu…

Sunlight is slowly returning to New York City and flooding into the studio to alleviate my Seasonal Affective Disorder and give me enough energy to churn out not one, not two, but THREE epic episodes of Draw Me Anything for you this week. I really had fun with these! I’ll be posting the recap of the third one for you tomorrow. Thanks to everyone who tuned into the free livestreams yesterday.

I talked a lot of shop with a lot of great people this week.

I had lunch with my friend (and longtime MAD Art Director & illustrator) Sam Viviano yesterday, along with the ridiculously talented Ray Alma. We paid way too much for diner food while talking comedy, cartooning and the fine(?) art of doing Trump impressions.

Then I went along to the Society of Illustrators to watch recent DMA Guest present a screening of her film “Women Laughing” about the women cartoonists of the New Yorker. It’s a great film - lots of laughs and really interesting insights. You can catch a replay of it next weekend at MoCCaFest. You can hear me talking with Liza about it here.

After the screening she was interviewed alongside two of the featured cartoonists, the legendary Roz Chast and . (See below for some exciting news about Emily).

On the topic of short films and documentaries, my good friend and documentary director Rachel Ross is making an excellent film that needs a bit of a nudge. if you want to support independent artists in New York, this is a great one to back. See the details on “Good Girl Greta” here.

On Tuesday, I had my second big chat with award-winning cartoonist . You can catch the recap below. We discussed everything from curmudgeonly old nib-sellers, the deranging effects of the Trump regime administration, to a crosshatching masterclass! I think you’ll really like it:

I also had a great talk with from the wildly popular Substack ! We discussed everything from AI ethics to process, time-boxing, and the impossible task of keeping up with all of the new software that blasts into our inboxes like a broken fire hydrant.

You can catch that recap/replay tomorrow if you’re a paid subscriber.

And lastly (but not least..ly) I had an incredible talk with Dave Kellett from and of (both co-hosts of the Comic Lab Podcast (over 400 episodes in!)

You can catch that recap on Sunday- again, recaps are for paid subscribers, the live streams will always be free to everyone.

Thank you to my brilliant readers who sent in photos of their little puppers with their new hand-drawn portraits in my new book. Sassy here gave it ten belly rubs out of ten…

Carex here hasn’t stopped talking about how good the drawing looks, and how funny the joke on page 38 is.

If you have a friend with a dog, send me a photo and I’ll draw them into the book for you.

Order One For YOUR Pupper!

Thanks to my friends who came out to the show at New York Comedy Club last week— I got to enjoy dinner with my old pal Mort Gerberg before the show to celebrate his birthday. If there’s ever a way to remind you how much work’s ahead of you as a joke-writer, try talking to a cartoonist in their mid-nineties…

If you haven’t heard of Mort Gerberg, by gum, you’re about to. Click below to read my “Someone You Might Like” entry about him.

Speaking of Telling Jokes…

I’m headed to Michigan next month for the Traverse City Comedy Festival! I’m excited to get to share stages with some of my favourite comics in the world including previous podcast guest Roy Wood Jr. and the incredible Gary Gulman!

On Wednesday, April 8, I’m putting on pants and leaving the house to do a Lectures on Tap event at a bar in the West Village. I’ll be desperately trying to explain how I went from drawing with rocks on remote Australian dirt roads to arguing with editors at the New Yorker over a sketch of an elephant buying peanuts. I’m going to dismantle the myth of the “lone genius,” mostly because the actual creative process is just sharing terrible shower notes and hoping someone else fixes them before the deadline.

We’re going to cover the whole messy journey, right down to the specific, horrifying afternoon that Rupert Murdoch unceremoniously killed an iconic 102-year-old comic strip. Come grab a $14 IPA and listen to me explain why aggressively annoying your heroes until they teach you is the only valid career strategy. Grab a ticket at the link, and they’ll email you the exact address so we can all sit in a dark room and collectively avoid eye contact.

Grab Your Tickets Early!

On Saturday, March 28 I’ll be physically located inside the Metropolitan Pavilion at 125 West 18th Street for MoCCA Fest 2026. This is Manhattan’s largest indie comics and cartoon festival, and I’ll be sitting at a table, clutching a Blackwing pencil like a life raft, and trying to mask my overwhelming dread interacting with hordes of strangers.

A day pass is $25, and the whole weekend is $36, which is about the price of a coffee in NoLiTa. Please come find me. If you don’t show up, I’m going to have to sit alone with my own farts thoughts. If you have a French Bulldog, bring him so I can aggressively compare him to my dog. I will also draw them. Just come say hi.

Get Tix

Lastly, my dear friend and fellow New Yorker cartoonist/comedian was juuuuuust awarded the Thurber Prize for American Humor! If you’ve never heard of Emily, by gum you’re about to— and not just from me! Take it from a previous DMA guest, , rightfully heaping effusive praise on Emily below:

Undiscovered Masterpieces

A Very Fine Flake

This week the Thurber House announced that its third annual Thurber Prize in Cartoon Art is going to the one and only Emily Flake. You may know Emily from her exceptional contributions to The New Yorker over the years, or from her hilarious illustrated books such as “Mama Tried.” But I know Emily from the time she asked me to join her in a tipsy karaoke duet at Sing Sing St. Marks in the East Village…

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a month ago · 5 likes · Tom Toro

More on Emily in my early “Someone You Might Like” post on her from 3 years ago:

Be sure to add Tuesday, 24th at 12 pm EDT to your calendar, when I’ll be talking to Emily LIVE on Draw Me Anything. (yes, that’s NEXT Tuesday.)

Be sure to leave a comment below

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We are drowning in a frictionless tech deluge.

Every week, there is a new platform to master, a new algorithm to appease, and a new AI tool threatening to automate us into oblivion. It feels like we are all just huddling together for warmth around the glow of our screens, trying to figure out how to actually get our work done without losing our minds.

That is exactly why I am sitting down with Jeremy Caplan on today’s Draw Me Anything at 11am EDT.

Our conversation is going to be less of an artist chat and more like a tactical war room briefing for survival in the digital era. Jeremy is the Director of Teaching and Learning at CUNY’s Newmark Graduate School of Journalism. He used to write for TIME Magazine. Before that, he was a violinist. He is one of those infuriatingly talented people who seems to have lived three lifetimes.

But more importantly, he is the creator of the massively popular Wonder Tools newsletter right here on Substack. Jeremy spends his days wading into the deep, chaotic waters of the internet. He tests, breaks, and reviews new apps, sites, and digital tools so the rest of us do not have to waste our precious hours doing it. He helps over 80,000 subscribers figure out what is actually useful and what is just digital noise. His goal is to help people do what they already do more enjoyably, efficiently, and creatively.

Add it to your calendar now!

At 3pm EDT, I’m welcoming the absolute masters of the comics podcasting universe: Brad Guigar and Dave Kellett.

If you are somehow unfamiliar with these two, let me give you the briefest of primers: is the creator of the wildly popular webcomic Evil Inc and the author of . He is essentially a walking encyclopedia of how to survive as an independent artist on the internet.

Dave Kellett is the genius behind the long-running webcomics Sheldon and Drive. He is also the co-director of the brilliant comics documentary Stripped (which famously features the first published art from Bill Watterson since he retired Calvin and Hobbes - also, his VOICE!).

Together, they host Comic Lab, a weekly masterclass podcast that is half shop-talk, half how-to, and half friendship. (Yes, they squeezed in three halves. They are just that good).

I have had the distinct privilege of being a guest on their show a few times now. If you want to hear us nerding out over the business of cartooning, stand-up comedy, and surviving the freelance life, you can listen to my previous appearances here:

• Episode 331: Special Guest Jason Chatfield (Talking about The New Yorker, Dangerfield’s comedy club, and Ginger Meggs)

  

• Episode 302: LIVE from the Reuben Awards with Sarah Andersen and Jason Chatfield

• Episode 404: ComicLab LIVE at the National Cartoonists Society (A wild live show at the 79th Reuben Awards)

  

Tomorrow, we are turning the tables. I finally get to interrogate them.

We are going to be scribbling away and diving deep into a frankly absurd list of topics, including:

1. Crowdfunding scams (and how to spot them before you lose your shirt).

2. Substack (and how to build an actual audience without losing your mind).

3. Podcasting and new media (navigating the changing landscape of how we talk to each other).

4. The industry at large in cartooning and comedy.

5. The upcoming 80th anniversary of the National Cartoonist Society.

   
   …and much, much more!

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Aaaaanyway…

‘til then!
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.

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The bottom of this post has details and links to all of the tools we discussed, all of the artists we discussed, and more resources for anyone wanting to explore more about the topics we covered.

If you joined me last time I had the legendary Kevin “KAL” Kallaugher on the stream, you’ll remember we discussed the “Cartoonist’s Paradox”- the absurd reality where cartooning is incredibly easy to start, but absolutely impossible to stop once it gets its hooks into you. This time around, our conversation shifted gears. Instead of talking about how to get into the game, we talked about how to survive it. We dug into how to stay sane in a politically fractured world, how to defend the analogue line against the digital horde, and the sheer mechanical joy of making marks on paper.

I frequently have moments during these streams where I completely forget I’m hosting a broadcast. I find myself just sitting there, slack-jawed, realising how profoundly lucky I am to have an hour to pick the brains of my absolute heroes. KAL is a legend of the medium. He is coming up on his 50th year at The Economist and is currently putting together a massive retrospective exhibition of his work. Getting to draw alongside him is a ridiculous privilege.

The Outsider’s Advantage: We kicked things off by talking about the absolute circus of modern politics. KAL and I both know what it’s like to be an expat trying to explain American madness to the rest of the world. KAL spent a decade living in the UK, and he noted that being an outsider gives you a unique, clear-eyed view. You aren’t tethered to the deep-rooted tribalism of the country you’re in. You can look at the idiocy on both sides of the aisle and criticise it without feeling like a traitor. It’s a perspective he brings to The Economist, which he praised for its critical thinking and reasoned assessment of global madness.

The Human Line vs. The Human Centipede: We eventually touched on the unavoidable elephant in the room: AI and the internet’s right-wing “meme wars”. KAL pointed out a fundamental difference between a viral meme and a great political cartoon: a cartoon is signed. You know a human being sat down, thought about it, and drew it. In an era of increasing detachment and digital takeover, a hand-drawn line stands out because it has life, energy, and personality.

Or, as so poetically put it in the live chat: “AI is to creativity as the human centipede is to fine cuisine”. (We probably could have ended the broadcast right there.)

Putting these recaps together requires a unique cocktail of intense caffeine, squinting at my monitor, and manually untangling the spaghetti bowl of my brain to pull out the best insights. 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 labour of writing these up, and keeps Morris supplied with the good dog food he has foolishly become accustomed to.

The Magic of Crosshatching: KAL is an absolute surgeon when it comes to crosshatching. He explained that the technique really evolved out of necessity in the 19th and 20th centuries. Printing in colour or half-tones was prohibitively expensive, and newspapers used terrible, cheap newsprint that made ink bleed. Cartoonists had to use juxtaposed fine lines to denote colour, shading, and texture. KAL even talked about the maddening challenge of using hard black lines to crosshatch something as airy and shapeless as a sky.

Diagon Alley for Cartoonists: My favourite story of the stream was KAL explaining where he gets his dip pen nibs. Back when he lived in London, an art director sent him to Philip Poole, a legendary pen dealer on Charing Cross Road. KAL found a tiny, unmarked door squished between two buildings and walked into a dark, heavily wooded room filled with tiny drawers of nibs. He described it as disappearing into Harry Potter’s Diagon Alley.

A hunched, cantankerous guy in a white trench coat shuffled out and started handing him nibs to try. KAL eventually settled on the George W. Hughes 1319. Years later, when he tried to order more, the guy informed him they hadn’t been manufactured in 150 years. KAL eventually got a box of 144 of them, and he is still drawing with them today.

The 5-Line Rule: We talked about the difficulty of line economy—knowing when to stop drawing and not overwork an image. KAL told a brilliant story (often attributed to Phil May or R.O. Blechman) about a cartoonist getting confronted by editors in a pub.

The editors complained that the cartoonist was paid an awful lot of money, yet his latest cartoon only had seven lines in it.

The cartoonist replied: “If I could have done it in five lines, I would have charged twice as much”.

Thanks for tuning in!
‘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 Talked About:

• George W. Hughes 1319 Nibs: KAL’s unicorn tool of choice. Good luck finding them; they haven’t been made in a century and a half.

• Hunt 101 Imperial: My wobbly weapon of choice.

• Duo-Shade Board: The chemical-laden drawing board that old-school tabloid guys used to use to pull out different shading tones.

The Artists We Discussed:

(Warning: Clicking these links will result in a minimum three-hour Wikipedia rabbit hole.)

• David Levine: The absolute master of crosshatching and caricature.

• James Gillray: The godfather of the political cartoon. His work was so biting that the Royals used to send people to buy out his entire print run just to hide the drawings.

• David Low: The brilliant New Zealand cartoonist who ended up on Hitler’s kill list for his work.

• Ronald Searle: The man whose inky fingerprints are on the style of almost every modern cartoonist alive.

• R.O. Blechman: Legendary graphic designer and illustrator (and possible originator of the 5-line story).

• Paul Rigby & Bay Rigby: The Australian father/son duo who dominated the NY Post and Daily News tabloid cartooning wars.

• Pat Oliphant: The Aussie who brought the energetic, sprawling tabloid style to America.

• Bill Mitchell & Peter Broelman: Absolute masters of Australian editorial line economy.

• Catherine Woodman-Maynard: The Minneapolis graphic novelist who launched “Comics for Change” in response to local tragedies.

Other Resources:

• KAL’s Substack: If you aren’t subscribed to KAL yet, fix that right now. He is generously opening his sketchbooks and sharing a lifetime of process and wisdom.

• Comics for Change: The initiative started by Catherine Woodman-Maynard that gathered over a thousand entries worldwide.

Now, if you’ll excuse me, I need to go see if I can find a guy in a white trench coat hiding in a London alleyway…

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A recap of my chat with Margreet de Heer about crowdfunding scams, theology, & the danger of drawing in bed…

is a brilliant Dutch comic artist and the former Comics Laureate of the Netherlands. She spent three years acting as an ambassador for the medium, literally compiling guides to help teachers get graphic novels onto high school reading lists. She is also someone who intimately understands the frantic reality of a creative life.

The Court Jesters & the Freedom Fighters

Margreet and I talked about the bizarre cultural divide in cartooning. In Australia, people generally look at comic artists like we are overgrown toddlers playing with crayons. It is treated as a silly little hobby. But if you take a train to France or Belgium, comic artists are treated like absolute rock gods.

I told her about a cartooning conference I went to in France called RIDEP. I was standing in a room with cartoonists from Tunisia, Sudan, and China. They had been exiled or forced into hiding for drawing anti-propaganda cartoons against dictatorial regimes. They were actual, literal freedom fighters. I draw jokes about talking dogs. I realised very quickly that I am more of a court jester. It was a profoundly humbling reality check.

Making a living as an artist requires you to constantly ask people for money, which is something most cartoonists are fundamentally terrible at doing. Margreet is an expert in crowdfunding, having run multiple successful campaigns in Holland to bypass the traditional publishing gatekeepers.

Check out her latest campaign on Kickstarter here: https://www.kickstarter.com/projects/margreetdeheer/build-and-play
And her Zoop project here: https://zoop.gg/c/philosophy

The Kickstarter Scam…

But she recently got targeted by a very clever, highly sophisticated Kickstarter scam. Scammers will pledge a massive amount of money to your campaign just to get your attention. Then, they send a highly convincing email from a “notification bot,” claiming your account is suspended, and your money is frozen. They provide a link to steal your credentials. Margreet described it as the digital equivalent of being lured away from a busy high street into a dark alley. We are already sweating over our drawing boards; we do not need thieves making it harder.

Related viewing:

My interview with the Founders of Zoop:

Theology and Annoying Mrs Lee

Margreet has a fascinating background. She originally flunked out of school because she hated the technology, so she pivoted to studying theology at the University of Amsterdam. Both of her parents are ministers, so it was in her blood. While she was there, she drew a comic for the faculty paper called The Adventures of Jesus. (Which sounds like the working title for The Bible).

I completely related to her fascination with religion as a storytelling mechanism. I went to an Anglican high school, and I used to infuriate my Bible study teacher, Mrs Lee. I would sit in the back, drawing cartoons and interrogating the text with the obnoxious persistence of a discount detective. I just wanted to know how the plot holes were resolved. Mrs Lee did not appreciate my feedback. She hated me.

The 3:00 AM Eyeball Hack

The absolute most valuable thing I took away from our chat was a neurological trick for my broken, sleep-deprived brain. We were talking about meditation and dealing with anxiety, and Margreet told me about an EMDR-style hack she uses when she is trapped in a rumination loop.

If you want to read about my annoying high school Bible study questions, a completely bizarre neurological hack to cure insomnia, and the absolute hazard of using a dip pen in bed, consider upgrading to a paid subscription for just $1 a week. It keeps the ink flowing & Morris fed.

When you are lying in bed, and your thoughts are spiralling, you just close your eyes and move your eyeballs back and forth, from left to right. That is it. Just roll your eyes back and forth. It requires just enough physical energy to disrupt the connection between your anxious thoughts and your nervous system. It forces the brain to process the trauma instead of just marinating in it.

I have tried box breathing. I have tried counting backwards. Nothing works. I am absolutely going to try this eyeball trick tonight. I will likely look like a malfunctioning animatronic doll in the dark, but if it buys me three hours of sleep, I’ll take it.

We finished the stream, taking a request from the chat to draw an elephant in love in spring. I used my trusty Hunt 101 dip pen and Higgins waterproof ink. Margreet admitted that she stopped using a dip pen because she likes to make her comics in bed. (That is a bold, deeply dangerous move. One wrong bump and your mattress looks like a Victorian crime scene. I respect the danger.)

Now, if you’ll excuse me, I need to go wash this ink off my fingers and roll my eyes back and forth in the dark..

‘til next time!

Your pal,

Hey again, friend.

Welcome to Issue #467 of New York Cartoons. As I’m writing this, Morris has his head on my leg, keeping me pinned me to the couch for an undetermined number of years. For that reason, I’m going to just keep writing until he wakes up/farts/wakes himself up from farting.
Thank you as always for subscribing. I’ve been working hard over here, sharing an ungodly amount of writing. Here’s what you might have skimmed past this past week…

Talking with fellow New Yorker Sarah Hill
I recently sat down with Sarah on her podcast to rant about the sheer, masochistic absurdity of drawing pictures for a living. We covered the ruthless pragmatism required to actually survive in New York, why I abandoned guilt-trip to-do lists for strict calendar blocking, and the soul-crushing reality of having a hundred thousand copies of your book pulped by a bankrupt publisher. It was a deeply cathartic chat about trading romanticised notions of an art career for a waterproof notepad in the shower. (And yes, we attempted to justify my stationery budget).

The Style Guide in My Pocket
My friend Anthony recently asked me why I don’t just use AI to write my essays, seeing as I find writing to be an excruciating process of untangling my own spaghetti-bowl of a brain. It’s a fair question. I don’t consider myself a “Writer” -I’m just a cartoonist clutching a copy of Strunk & White like a life raft. In this piece, I lay out exactly which ethically-trained digital tools I do use to keep my sanity intact, and why setting guardrails on my own prose is the only thing keeping me from wandering into a forest of day-old oatmeal words.

How to Survive Farting at the Queen
If your brain occasionally feels like a hostile work environment, this recap of my chat with the brilliant Jenny Lawson is for you. We talked about her new book, " Surviving the Daily Gauntlet of ADHD”, and why the “Spoon Theory” is the only way to explain executive dysfunction to a neurotypical person. More importantly, we discussed the 17th-century Earl of Oxford who farted in front of Queen Elizabeth I and exiled himself for seven years. It’s a masterclass in giving yourself permission to be a messy, imperfect human, or a murderous, jiggly hippo.

Live in New York This Week
If you want to come see me live this week, I’ll be performing at New York Comedy Club on the Upper West Side on Wednesday at 9pm on a show featuring Anthony Moore, Alex Gardes, Molly Densmore, & Yvette Segan: the line-up is great, and tix are only 10 bucks with the code HTA0311!

I’ll also be performing on one of the best shows in Brooklyn later this month -YIKES! Comedy at Flophouse Comedy Club: get your tickets early!

The Sludge, the KGB Bar, and the Rebirth of Print
I woke up this week with the blurry-eyed weariness of a man who foolishly decided to put on hard pants and go out on a Tuesday night. I trudged through the toxic street-sludge of the East Village to the KGB Bar to celebrate the launch of The Metropolitan Review. In a world pivoting to AI-generated garbage, holding a physical, printed literary quarterly in a packed, sweaty room of actual human writers felt like a profound act of defiance. Also, I’m their new Cartoon Editor. (If you’re a working gag cartoonist, expect an email.)

The Supreme Court Just Made AI Art Legally Worthless
While I was trying to draw a guy falling butt-first into a toilet with a messy dip pen, the Supreme Court basically cemented the rule that AI-generated art cannot be copyrighted. Zero. Zilch. It immediately enters the public domain. The tech bros have spent a year arguing that typing a prompt is like clicking a camera shutter. Still, the law has decided that without the struggle -without the deeply flawed, neurotic human being holding the pen- a perfectly rendered image has no intrinsic legal value. The friction is the whole point.

The Graphite Anchor in a Digital Storm
My $1200 iPad Pro decided its $130 plastic pen was dead to it right in the middle of a job. As my brain began to aggressively shut down, I reached past the crumpled receipts and dog treats in my bag for a blunt Blackwing 602 pencil. It didn’t need a firmware update or a Bluetooth handshake. In a world that demands we be constantly connected to a spinning wheel of death, there is something profoundly defiant about the scratchy, physical reality of graphite meeting pulp. It’s a 19th-century solution to a 21st-century nervous breakdown.

Scroll down to see more about my special guest for this week’s DMA. And, as always…

…be sure to leave a comment below!

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The Sketchbook I’m sharing with you this week is a selection of the sketches I did of peoples’ dogs as gifts this past week. If you have a friend with a dog, send me a photo and I’ll draw them into the book for you.

Click here to get started

This morning I avoided my drawing table and started reading about Dutch theology… I only have one person to blame. Tomorrow on Draw Me Anything, I’m sitting down with Margreet De Heer, a comic artist who has lived about four different, fascinating lives.

Margreet originally flunked out of film school at the tender age of 17. So, naturally, she pivoted to studying theology at the University of Amsterdam. Why? Because religion is ultimately about the great stories of mankind, and her family is full of theologians. Along the way, she realised that making comics is exactly like making a film- except you don’t have to deal with the soul-crushing hassle of working with other people or begging for expensive equipment. She is my kind of antisocial genius.

She cut her teeth working at Lambiek, the legendary Amsterdam comic store, getting a masterclass in the medium from Kees Kousemaker. When the 2009 financial crisis wiped out two-thirds of her paid gigs, she married a fellow comic artist, moved into his reasonably priced apartment, and started drawing full-length graphic novels about philosophy, religion, and world domination. Her philosophy primer sold out in its first week. Not a bad pivot.

She eventually became the Stripmaker des Vaderlands (Comic Artist Laureate of the Netherlands). To wrap up her three-year term, she ran a crowdfunding campaign on Voordekunst for a book compilation where she literally stripped to raise 15,000 euros. I respect the hustle. (If I tried stripping to fund a book, I’d be arrested and immediately lose my remaining subscribers). Last year, she won the prestigious Zilveren Griffel award for her children’s book Kip en Kat , and she’s currently building a fantastic Substack filled with highly personal, autobiographical comics. (You can subscribe here.)

We’re going to talk about the lonely, maddening process of making comics, how to survive as an artist when the economy tanks, and whatever else comes up while we scribble. A little digital monastery for cartoonists. Because if there’s one thing cartoonists need, it’s confinement.

If you want to join the stream, request a live drawing, jump on the stream FREE!

Add it to your calendar now!

If you’re new here, or you haven’t had a moment to wander back through the archives of profound genius I’ve shared up to this point, take a peek at the following scribblings:

(Heads up: This isn’t the process of ‘How I write my Substack’ post -which is coming- but it’s the one about the tools I use. Hope it’s helpful.)

I was getting coffee with my friend Anthony this morning, navigating the Hell’s Kitchen gauntlet of sidewalk trash and tourists. As Morris was busy sniffing the disgusting black slush on the pavement and enthusiastically peeing on every vertical surface he could find, Anthony asked me a question that stopped me:

“Devil’s Advocate: Why don’t you just punch your ideas into an AI and have it generate writing if you find it so hard?”

He wasn’t being accusatory or rude about it. He wasn’t discounting my abilities or suggesting I’m a hack. It was a pragmatic question born ofthe fact that he knows I find writing to be the most difficult thing I do. I have trouble calling myself a “Writer”; I consider myself someone frantically trying to figure out how writing works, constantly clutching my copy of Strunk & White’s Elements of Style like a life raft and finding a way to hit ‘publish’ without needing a shot of whiskey.

I read more than I write. I have inhaled every book on the craft I can find: Anne Lamott’s Bird by Bird, Mary Karr’s The Art of Memoir, and I even sat through David Sedaris’s Humour Writing Masterclass, taking copious notes. But despite all that, writing remains a slow, painful process of unknotting the spaghetti bowl of my own brain.

To cope, I’ve developed a “style guide” on my Notes app. Every time I figure out a consistent quirk in my voice, a specific way I use an em-dash (or don’t) or a recurring bit of vernacular that feels uniquely “me” -I add it to the list. Anthony thinks this is constrictive. He asked if it cages my ability to grow. I tend to think the opposite: I believe creativity within confines is a mercy. I work best when there are guardrails; a style guide isn’t a cage, it’s a map that keeps me from wandering off into a forest of day-old oatmeal prose.

Related Reading:

Anthony also asked what other tools I use. It’s a fair question. We live in a world where new technologies are appearing faster than I can install the updates for the old ones. I know I often sound like an AI doomer- I’ve written extensively about how AI is hollowing out the creative economy and taking work away from everyone, from white-collar workers to my fellow illustrators.

But I want to be open with you: I am not a Luddite. I don’t think it’s hypocritical to criticise unethical models while still using tools that respect the “human wobble” in the line. I have my scruples intact, and I shop for my tech the same way I shop for anything else- based on ethics.

If you want to see the “Mean Editor” in action and get the full breakdown of the specific, ethically-trained tools I use to keep my sanity intact, consider upgrading to a paid subscription for just $1 a week. It helps keep the ink flowing & Morris fed…

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While I was going back and re-listening to this episode to write the recap below, I wrote down so many gems that Jenny shared- tips I will properly keep with me forever and tape to the wall. I put together about 6 of the best down below. This was a really great conversation- one of my all-timefavourites. I hope you find it as valuable as I did.

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I am setting a new personal record for the amount of times I can wash the exact same load of laundry without ever putting it in the dryer.

I think I’m on wash number five. I put the clothes in, turn the machine on, walk away, immediately forget the machine exists, and then remember three days later when the super tells me the basement has started smelling like a wet golden retriever trapped in a swamp. So, I wash them again. And the cycle continues. (Literally.)

This is what having an adult ADHD brain actually looks like. It’s not just being a little “flighty” or getting distracted by shiny objects, (although there’s a lot of that); it’s a relentless, exhausting daily battle with your own executive function. It’s opening an email, deciding you don’t have the emotional bandwidth or energy to answer it, marking it as “unread,” snoozing it to tomorrow, and then doing that exact same sequence of events forty-six more times over a two-month period. So productive.

This is also why my chat with Jenny Lawson on Friday’s Draw Me Anything was less of an interview and more of an aggressively validating group therapy session. I haven’t really talked about my lifelong struggles with ADHD before because it feels a bit weird.. TikTok convinced everyone in the pandemic that anyone who has a hard time finishing a book had it, and it kind of blew up the legitimacy of a genuinely challenging neurological condition.

But I digress…

has been writing online for over 15 years, and has a new book coming out on March 31st called How to Be Okay When Nothing Is Okay: Tips and Tricks That Kept Me Alive, Happy, and Creative in Spite of Myself.

I got an advance copy, and I genuinely could not put it down. (Have you ever read a book so good you run out of sticky notes?)

It is an absurdly funny, deeply vulnerable survival guide for anyone whose brain is a slightly hostile work environment. Jenny and I both share a potent daily cocktail of ADHD, various flavours of anxiety, and an inability to perceive the passage of time. (I currently have nine clocks in my apartment, and I am still late to everything I have ever attended. Even before my death, people refer to me as “The Late Jason Chatfield.”) Here are a few of the brilliant, sanity-saving things we talked about during the stream, including why you should always strive to be a Murder Potato.

1. Humour As a Means of Defanging Hard Shit

Jenny and I both use comedy as a (healthy) coping mechanism. We talked about how, when terrible things happen, humour is our only way to genuinely process the grief.

“I think humour is super helpful for me,” Jenny said. “If I can laugh at something, instead of this enormous monster, it becomes like a little bit smaller, a little bit easier to understand.”

It’s an on-ramp. If you write about crushing depression, anxiety, or mental illness, people who don’t suffer from those things might immediately put the book down. But if you make them laugh, it invites them in. It tells them that the stakes aren’t going to crush them alive.

“If you make somebody laugh, first of all, you invite them in, and you say, ‘It’s okay. It’s not that serious, even when it’s serious. A lot of people who have either reached out to me and said, ‘I read this because it was funny. And then later, years later, when I found myself in depression for the first time... I could go back and be like, oh, okay, I’m not alone.’”

2. Rejection Sensitivity & Farting at the Queen

If you have ADHD, you likely suffer from Rejection Sensitive Dysphoria (RSD). This means you spend a terrifying amount of your day convincing yourself that everyone secretly hates you.

“I constantly am sure that I have said something wrong, done something wrong. I overthink, I second-guess,” Jenny confessed. “The amount of work that I do in my head... it is exhausting.”

You leave a conversation, and ten seconds later, you are meticulously replaying every word, convinced you offended someone. You assume if a friend hasn’t texted back in four hours, they have legally disowned you. You live in a constant state of wondering, “Are we fighting? Are you mad at me?”

Jenny’s friend gave her some advice that completely short-circuits this panic: She asked her to try to remember the last time she saw someone else completely mortify themselves in public.

She couldn’t think of a single time.

“She was like, ‘No, what it really is, is everyone is constantly doing it. But you’re only paying attention to yourself,” Jenny told me. “Nobody is paying attention to how I fucked something up because they’re way more worried about the thing that they fucked up.”

This led us to my absolute favourite chapter in Jenny’s entire book, brilliantly titled: But Did You Fart at a Queen?

It turns out, there is a historical account from the 1600s of the 17th Earl of Oxford. He was bowing to Queen Elizabeth, and while doing so, he let out a massive, echoing fart. He was so intensely mortified by this bodily betrayal that he literally imposed a seven-year exile on himself. He left the country for seven years. Seven.

When he finally returned, the Queen greeted him and said, “My Lord, I had forgotten the fart.”

She didn’t even remember. She had a country to run; she wasn’t thinking about his flatulence. So, the next time you lie awake at 3:00 AM sweating over a slightly awkward joke you made to your unusually attractive barista, just ask yourself: Did I fart at a Queen? No? I’m doing bloody fine.

3. The Spoon Theory (and Budgeting Your Sanity)

Trying to explain executive dysfunction to a neurotypical person is like trying to explain calculus to a golden retriever. They just tilt their head and look at you blankly. “Why don’t you just do the thing?” they ask.

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A recap of my chat with Sarah about the beautiful, masochistic reality of making a living as an artist on The Login Podcast.

Sarah and I have known each other for a while now, navigating the murky, caffeine-stained waters of the New York creative ecosystem. She is one of those rare, brilliant people who actually listens when you talk, which is probably why her podcast has become so incredibly successful.

It was great to finally be on her show. We had a lot of fun, mostly because she allowed me to rant at length about the sheer insanity of doing this for a living.

From The Podcast:

Jason Chatfield is an award-winning cartoonist, author, and stand-up comedian based in New York City. For 16 years, he wrote and drew the 102-year-old internationally syndicated comic strip Ginger Meggs. His work has appeared in The New Yorker, Esquire, MAD Magazine, Variety, Wired, and more. He’s a former President of both the National Cartoonists Society and the Australian Cartoonists Association, writes the award-winning Substack New York Cartoons with over 20,000 weekly subscribers, and serves as the portrait illustrator for Sam Harris’s meditation app, Waking Up.

But what struck me most in this conversation wasn’t his résumé — which he will massively downplay by the way. It was his discipline and entrepreneurial drive that sets him apart.

Jason talks about treating creativity like a business. About working from a calendar instead of a to-do list. About how jokes evolve from overheard subway moments to stand-up bits to New Yorker cartoons to full book series. And about what it really means to build a creative life over decades, not days.

We talk about failure, imposter syndrome, about backing yourself anyway, and about why chasing algorithms is a losing game compared to serving the people already in the room.

He’s an absolute beast of a creative force.

If you’re interested in the arts not just as expression, but as a way of living, building, and sustaining a career, this episode is for you.

Listen to the full episode here

When people find out you’re a cartoonist, they tend to romanticise the job.

They picture you sitting in a sunlit loft, wearing a beret, gracefully waving a dip pen while an adorable French bulldog sleeps at your feet. (Okay, the dog part is true. The rest is pure bullshit.)

The reality is that surviving as a creative requires you to be ruthlessly pragmatic. During the episode, Sarah asked me how I actually get anything done between drawing for magazines, doing stand-up, making books, taking illustration commissions, writing this Substack, and trying not to lose my mind.

“I completely abandoned the to-do list,” I told her. “To-do lists are just guilt trips on a piece of paper. If you want to survive, you have to embrace a business mindset for your artistic pursuits. You have to use a calendar for time blocking. If it’s not on the visual grid, it doesn’t exist. It is the only way to manage the chaos of diverse creative projects and commitments.”

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I didn’t learn this in art school (because I didn’t go). I learned it from my mother. “My mum built a successful lighting consultancy business out of sheer necessity,” I explained on the show. “I credit her entrepreneurial spirit with my own work ethic. She taught me early on the importance of treating my art as a serious business, not just a hobby that occasionally pays for beer.”

Initially, I thought I was going to be a hard-hitting political cartoonist, taking down the establishment one crosshatched drawing at a time. But instead, I took over a syndicated comic strip. “That syndicated strip became my primary job for 16 years,” I told Sarah. “It was a grind, but it taught me discipline. And then, 11 years ago, I packed up and moved to New York City.”

Related Reading:

Moving to New York is like putting your career in a centrifuge. It spins you around, makes you nauseous, and separates the weak from the strong. But as I said on the pod, “The move expanded my opportunities a lot. It demonstrates the sheer value this city has for anyone with enough drive (and a high enough tolerance for subway rats and the smell of hot Chinatown garbage).”

Of course, living in New York and staring at a blank page every day is a recipe for catastrophic imposter syndrome. “You have to cultivate self-trust,” I said, with a heavy gulp. “You have to recognise that enjoying the creative process itself is what defines success, not the external metrics or the algorithm. I started seeking out inspiration differently. I take my AirPods out when I’m walking around the city and actively observe my surroundings. I consciously filter experiences and capture the ideas as they happen.”

And because the universe has a cruel sense of humour, those ideas never happen when I am sitting obediently at my desk. “I literally keep waterproof pads in the shower,” I confessed... “Because that is where the real insights happen. It perfectly reflects the deeply unpredictable nature of creative thought.” (Anyone familiar with my ritual of ScotchBath Sunday won’t be surprised by this.)

But waterproof paper can’t protect you from everything. The conversation took a slightly darker turn when we talked about the nature of failure. I don’t mean small failures, like a new bit bombing at an open mic. I mean spectacular, soul-crushing failure…

“I had this book idea that I over-invested in, both emotionally and financially,” I told her. “I was fantasising about its massive success long before it was even published. I had already spent the millions in my head.”

“And then?” she asked.

“And then the publisher went bankrupt,” I said. “One hundred thousand copies of the book were pulped. Just ground up and destroyed. It was a devastating blow, and the stress of it literally led to a physical collapse.”

It’s hard to articulate the grief of having your work physically destroyed before it even reaches the world. But it was a necessary crucible. “That experience taught me the brutal difference between optimism and delusion. It fostered a much more pragmatic approach to all my subsequent projects. I realised that personal mistakes offer unique learning experiences that you simply can’t gain through observation alone. (or listening to people talking about their mistakes on a podcast.)”

Now? “Now, I prioritise the enjoyment of the creative process over the anticipated outcomes,” I said. “I find my success in the ‘doing of the thing’ itself. If the book gets pulped, at least I had fun drawing it.”

That shift in mindset is largely what brought me to Substack.

For a long time, drawing felt like a guilt-driven obligation. But that changed when I started attending Substack writers’ meetups here in New York. “Those meetups provided so much advice and encouragement from other creators. It helped me overcome my initial imposter syndrome,” I told Sarah.

“I began a paid Substack, and suddenly, I found this incredible community and mutual support among my subscribers and other writers. It completely transformed my perception of the work. It went from a chore to an enjoyable pursuit.”

I realised I didn’t need to be everything to everyone. I talked to Sarah about the concept of ‘a thousand true fans.’ “I focus on the people who truly appreciate and support my unique, weird work, rather than trying to please everyone on the internet. This philosophy allows me to actually concentrate on my passions and cater to an engaged audience.”

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You can’t survive in this industry as a lone wolf. You’ll lose your mind. “You have to connect with other professionals in your field,” I told her. “It fosters mentorship, collaboration, and learning. Honestly, it generates more opportunities than any traditional avenue.”

I take that community aspect very seriously. “I eventually became the president of the National Cartoonist Society. I see my fellow cartoonists as my extended family. They are my primary source of learning and growth. Surrounding yourself with other artists who share similar ambitions is more beneficial than any formal education or online course.”

As we wrapped up the show, Sarah asked me for one final piece of parting advice for anyone trying to make it in a creative field.

“Constant learning and humility,” I said. “Focus on your personal creative enjoyment rather than external validation or algorithmic trends. And above all else: back yourself. Trust your instincts, even amidst the roaring imposter syndrome. Back yourself, buy a waterproof notepad, and put it on the calendar.”

‘til next time!
Your pal,

Wed, 4th March 2026
East Village, NY

I woke up this morning with the bleary-eyed, sandpaper-tongued weariness of a man over the age of forty who has made the fundamentally reckless decision to go out on a Tuesday night.

A “big night out” on a Tuesday usually means I stayed up until 10:30 PM researching vintage dip pens on eBay while letting my Morris use my foot as a pillow. But last night was an exception. Last night required me to put on real pants, leave the apartment, and trudge through the soul-crushing mixture of rain, melting slop, and mysterious sludge that constitutes a Manhattan street in March.

The destination was KGB Bar in my old stomping ground in the East Village. If you’ve never been to KGB Bar, imagine a cramped, dimly lit speakeasy wallpapered in Soviet propaganda, where the ghosts of a thousand chain-smoking authors are permanently trapped in the floorboards. It is the perfect place to drink something brown and grouse in low tones about the written word, and those who have the gall to wrestle with it for a living.

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I was there for the reading and launch event of The Metropolitan Review.

I arrived, shook a gallon of toxic street-sludge off my boots, and immediately went to the bar to secure a drink before finding my friends and current colleagues, Executive Editor and Editor-in-Chief .

They were stationed just inside, radiating the nervous, electric energy that comes from throwing a party and realising people actually showed up. And not just a few people. Ross later announced that we sold 130 tickets to this thing. One hundred and thirty! In the year 2026, getting 130 New Yorkers to leave their apartments in the freezing, wet slop to listen to literary readings in a packed room is nothing short of a biblical miracle. As Ross put it: “Literary life is extremely alive and well.”

But the real highlight of the night, at least for my highly tactile, analogue-obsessed brain, was that I finally got to see the very first physical copy of the inaugural print edition of the magazine.

It is a beautiful, tangible object. It’s the Gay Talese issue, and holding it in my hands felt like holding a small rebellion. We live in an era where media companies are constantly “pivoting to video,” letting AI scrape the internet to write garbage articles, and laying off entire editorial staffs via group Zoom calls. To launch a physical, triannual print magazine right now is an act of magnificent defiance. So much work went into this thing, and holding the final product in my grubby, ink-stained mitts made all the late nights and frantic emails and texts entirely worth it.

I can’t wait to share it with you after the official launch next month.

Related Reading:

Which brings me to my role in all of this. I am proud (and slightly terrified) to say that I am the Cartoon Editor for The Metropolitan Review.

I know. Me. The guy whose internal “Check Engine” light is permanently illuminated is now in charge of curating cartoons for a prestigious new literary triannual. Because we were moving at breakneck speed to get this inaugural print edition out the door, we didn’t have a massive amount of time (ie. none) to solicit a huge batch of cartoons from the hoards of willing contributors on my spreadsheet, so we settled for using some of my orphans that were treated by other magazines the way Punch was treated by his monkey mother.

But the foundation is laid. Moving forward, the upcoming issues will feature a massive roster of cartoonists from entirely different backgrounds, wielding different styles, and hailing from different publications. (If you’re a professional cartoonist reading this, consider this a warning: I will be in your inbox very soon, demanding your funniest, weirdest scribbles.)

As the night kicked off, the sheer physical reality of the New York literary scene became unavoidable. I don’t mean that metaphorically. I mean, you literally could not avoid the physical reality of other people because the room was shoulder-to-shoulder.

Writers, authors, and literary types from all over the tri-state area squeezed (Squoze?) into the venue. We were forced to, for lack of a better, less awkward phrase, bump up against each other in real life, tweed-to-denim.

And you know what? It was glorious.

This is the great, enduring magic of being in New York. When the tech bros and the finance guys take over the skyline, it’s easy to feel like the creative friction of the city is dying. But then you cram 130 writers into a red-lit room in the East Village, and the friction is back. You get to meet these names from your inbox in person. It makes such a massive difference to look someone in the eye, shake their hand, and realise they are just as neurotic and obsessed with their process as you are.

And the readings were phenomenal. One by one, after Ross introduced the evening under a precariously dangling mirror ball, writers stepped up to the microphone and read passages of their work. There’s something vulnerable and completely captivating about hearing an author read their own words out loud in a room full of their peers. You could feel the collective attention of the room holding on to every sentence as their shaky hands shuffled the pages under the spotlight where a punk band usually plays.

Of course, because this is the New York literary scene, the night was not without its underlying, highly entertaining dramatic subtext…

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I was sitting at my drawing table this morning, staring at a very stubborn ink smudge on my fingernail (I think it might be paint? But it could be ink. I don’t know.) I’d just spent two hours wrestling with my pen nib, trying to draw a person falling butt-first into a toilet. My neck hurt, my coffee had gone cold, and my brain felt like day-old oatmeal.

In moments like that, the frictionless, sterile world of Artificial Intelligence can look awfully appealing. You could just type, “person falling butt-first into a toilet, cinematic lighting, 4k,” and an algorithm spits out a masterpiece in four seconds. No ink smudges. No carpal tunnel. No existential dread or anxiety attacks.

But then I opened the news*, and I felt a deep, warm wave of schadenfreude wash over me.

(*Let’s be honest. I opened Instagram and doomscrolled until I saw a news article.)

The Supreme Court of the United States just officially declined to review a petition regarding the copyright eligibility of AI-generated artwork.

By refusing to intervene, the country’s highest judicial court signalled an implicit consensus with lower courts, effectively cementing the rule that artificial intelligence cannot be legally recognised as an author.

In short, AI art cannot be copyrighted. Zero. Zilch. It belongs to the public.

To understand why this is so massive, we have to look at the bedrock of American copyright law. The U.S. Copyright Office has consistently maintained that human authorship is an absolute, non-negotiable prerequisite for intellectual property protection. They will literally refuse to register a claim if a human being with an ink-stained fingernail didn’t create the work.

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This isn’t actually a new fight. It dates back to the late nineteenth century. I know this because I spent time researching this instead of finishing that picture of the person on the toilet. (I’ll get back to it, I promise.)

In 1884, the Supreme Court heard the landmark case of Burrow-Giles Lithographic Co. v. Sarony. Back then, sceptics of the newly invented camera argued that a photograph was just a mechanical reproduction of physical reality and lacked any creative intervention. But the Court ruled that photographs were copyrightable because the photographer made choices regarding lighting, posing, and costume, which constituted the necessary “original intellectual conceptions of the author”.

For the last year, tech bros have been arguing that typing a prompt into a large language model is the modern equivalent of clicking a camera shutter. The courts have firmly answered: No. No, it isn’t.

The judicial consensus is that formulating a text prompt is actually akin to giving instructions to a commissioned artist, rather than exercising the direct, granular control required for true authorship. You aren’t the painter; you’re just the guy yelling at the painter.

This whole legal showdown was largely forced by a technologist named Dr Stephen Thaler. He deliberately tried to register a two-dimensional artwork titled “A Recent Entrance to Paradise,” explicitly listing his AI system, the “Creativity Machine,” as the sole author. (Woof, Stephen.) When the Copyright Office repeatedly denied the application, he sued. The federal district court unequivocally affirmed the denial, declaring that while copyright law adapts to new technologies, the fundamental requirement of human creativity remains immutable.

So. The courts have conclusively determined that non-human entities-whether they’re advanced neural networks or animals (like in the famous “Monkey Selfie” dispute- Google it)- lack the legal standing recognised by the Copyright Act.

The economic ramifications of this are bonkers.

Think about all those massive corporate entities that fired their art directors and illustrators to use generative AI for their marketing, brand identity, and product design. Because the raw outputs of platforms like Midjourney, DALL-E, NanoBanana, and Stability AI cannot be copyrighted, they immediately enter the public domain upon generation… eep!

That means they cannot be exclusively owned, licensed, or protected from unauthorised reproduction. If a corporation uses a purely AI-generated logo, they possess absolutely no legal mechanism to prevent a competitor from using the exact same image.

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The irony is thick enough to spread on toast. The companies that tried to cut costs by removing the human from the creative process have just legally stripped their own assets of all financial value.

But this isn’t the end of the story; it’s just the end of chapter one. The legal frontier is now shifting from treating AI as a “creator” to treating it as a “tool”. (Or calling the person using it “A complete tool.”) The Copyright Office has indicated that if a human significantly modifies an AI-generated image or arranges it in a sufficiently creative manner, those specific human contributions can be copyrighted.

This means future litigation is going to obsessively focus on quantifying the exact volume of human “sweat of the brow” and “creative spark” required to reclaim legal ownership over algorithmic generation. Creators are now going to have to submit detailed disclosures, essentially providing a granular accounting of which pixels were generated by a machine and which were manipulated by a human hand.

It all comes back to the wobble. The friction. The ink smudges. Remember me talking about that last week? (Take a look below)

The machine can generate a flawless, antiseptic image in seconds, but the law has decided that without the struggle- without the deeply flawed, neurotic, caffeinated and unshowered human being holding the pen- it simply has no intrinsic legal value. The friction is the only thing that matters. (God forbid.)

I looked down at Morris, who was currently farting in his sleep on a sketchpad I dropped on the floor. He didn’t care about the Supreme Court. He didn’t care about intellectual property. He just wanted to be a dog. And fart.

I picked up my pen, farted, dipped it back into the ink, and went back to work drawing someone falling butt-first into a toilet. The ship might be sinking, and the tech billionaires might be trying to automate our souls, but at least the law still recognises that my messy, imperfect crosshatching belongs to me.

Read more of my writing on this here:

I want to hear from you on this one.

How are we feeling about this? Does this Supreme Court decision give you a sense of relief, or does this incoming nightmare of having to legally prove exactly which pixels you manipulated sound exhausting? Is the tech industry probably just going to find a new loophole?

Let’s talk it out in the comments. I’ll be down there reading them, right after I wash this paint off my fingernails.. (it was paint.)

‘til next time!
Your pal,