I was pretty sure I had taste. I knew what good looked like. I knew Richard Thompson1 could draw a fencepost with three lines and make it feel like the whole emotional weight of suburbia hinged on that fencepost. I knew a Roz Chast squiggle could hold more neurosis than a whole year of tele-therapy. I knew what worked.

And then I tried to do it myself.

Spoiler: it did not work. At all. The punchlines were obvious. The drawings were stiff. Everyone’s arms looked like soggy churros. I once drew a hand that looked like an undercooked prawn trying to dial a phone. I knew it was bad—and worse, I knew why.

It’s what Ira Glass famously calls “The Taste Gap.” (He didn’t trademark it, but he probably should’ve.) It’s that weird, humiliating limbo between what you love and what you’re currently capable of making without weeping into your cup noodles.

Here’s the thing nobody tells you: The better your taste is, the more painful the gap feels.

It’s like having the palate of a Michelin inspector, but the only thing you know how to make is singed toast and runny scrambled eggs. And yet you keep making those eggs. Over and over. Because one day, maybe, you’ll finally Bourdain something that doesn’t taste like pure regret on toast.

Most people quit in the middle of the gap.

Which makes sense. It’s dark in there. There’s a lot of echo. And the only way out is through volume. You have to make an unreasonable amount of stuff.2 Embarrassing amounts. The creative equivalent of lifting weights in a Planet Fitness parking lot while wearing Crocs. (I’ve seen it. I’ve lived it.)

But every now and then, after years of crumpled pages and flopped sets and jokes that landed with the grace of a cinder block to the face, you’ll crap out something that feels… right?

It won’t be perfect. But it will match your taste. And you’ll think: “Oh. I’m getting closer.” And that’s enough.

At least until tomorrow, when you make something new and the gap yawns open again like a sinkhole in your soul. But that’s just the process.

Anyway.

‘til next time!
Your pal,

PS. If anyone wants a cartoon of an undercooked prawn trying to dial a rotary phone, my inbox is open.

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Hey, friends!

Before I start: I just wanted to finally let you know that I’m so excited to have the best-selling author of two of my favourite books of all time on Draw Me Anything. The special guest is none other than — Author of “Daily Rituals” and the excellent substack .

You may have heard an I talking about Mason’s excellent books on our episode this week. If you missed that one, you can see the replay here. I’ll be speaking with Mason on Substack Live on Tuesday, 17th June @ 1pm EDT. Add it to your calendar now!

Okay, on with the show…

Five years ago, I was sprawled on my couch at 3am, completely absorbed in Mason Currey's Daily Rituals: How Artists Work—scribbling marginalia like some deranged graduate student. When I finally looked up from the last page, the streetlights outside were flickering, and the sun was rising over the city. Tell me the last time you had an experience like that with a book?

On my second reading, I went through and highlighted something I found as a very interesting correlation across 400 years of the greatest writers, artists, poets, composers and other creative minds detailed in the book.

The people I’ve excerpted below are from just the first book, and they aren’t just a random collection of artists and thinkers; they’re some of the most influential minds who ever lived.1 Everyone from Stephen King, to Albert Einstein, Ernest Hemingway, Charles Darwin, Beethoven, Mozart, Truman Capote, Toni Morrison, Maya Angelou, George Orwell, Voltaire, Benjamin Franklin, Jean-Paul Sartre, Murakami, Yeats, Stravinsky, Charles Dickens, David Foster Wallace, Jung, Arthur Miller, and dozens of others.

I've always had this delusional notion that real artists chain themselves to their desks for 8-10 hours daily, grinding through to-do lists with mad hustle! (Yes, I actually used that phrase unironically.) It's completely unnatural—like trying to force creativity through a meat grinder. Thankfully, other artists have also figured out this approach is bullshit. The pattern that emerges from actually successful people is much simpler.

So, there are a few variations on the theme, but the very distinct pattern is this:

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I squeezed tightly into 's packed book launch for Glass Century at a bookstore on the Lower East Side.

I didn’t realise it would be so full, so I stood awkwardly at the back of the room with a plastic cup of wine, pretending I knew anything about being a writer. Barkan’s insights on fiction writing from that night have been rattling around in my head ever since. As someone who thinks deeply about writing, he offered some refreshingly honest takes on what makes novels work—especially when it comes to grounding big stories in specific details.

I’m going to geek out about writing for a minute, I hope that’s okay. It’s a new world to me, so I’m still finding my feet. I’m assuming if you’re reading this, you like reading, and you like New York. And don’t worry— I’m not going to review the book. It’s great. I’m on the last chapter, and I don’t want it to end. There are far more qualified people to dissect this novel than me. You’ll probably find them lurking around Substack.

I have to confess, I was never a big reader growing up— not really. My literary diet consisted chiefly of Spider-Man comics and MAD Magazine. I didn’t come to the enjoyment of reading until around 2007, when I discovered Christopher Hitchens and David Sedaris. From there, the whole literary chasm opened up and I fell in. I think reading is one of the best things anyone can do to get better at just being a human; getting to inhabit the mind of other people for a time, and live a zillion different potential lives within one lifetime. It’s like a cheat code to the human brain (and empathy).

"You can read a 19th-century book and get an excellent sense of the day-to-day life of that period," Barkan observed at the launch. "You can find out what things cost, you can find out political dynamics." He lamented how contemporary novels often feel "intentionally made" rather than lived-in, missing those crucial particulars that anchor readers in time and place.

"There are so many ways to get at New York," Barkan said, while being interviewed by , "which is what I love about it."

The same could be said for his approach to fiction—multiple entry points, all grounded in the specifics that make stories feel real rather than simply ‘constructed.’

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Today, I did something different on "Draw Me Anything" — I pitted my human sketching skills against the mighty ChatGPT 4o. Me versus the machine that has apparently digested the work (and employment opportunities) of every human artist who ever picked up a pencil or stylus.

Would twenty-odd years of professional cartooning stand a chance against an algorithm that's supposedly going to replace us all?

The challenge was simple: I took your drawing requests and raced against ChatGPT to complete them. For each prompt, I punched the exact same request into ChatGPT, then we both drew simultaneously. Dog poop, vintage jukeboxes, dragons, human flies, pencils on romantic dates — we covered quite the artistic spectrum.

I don't want to spoil the results, but I kept finding myself finishing drawings while staring at ChatGPT's little "still generating" animation. Turns out there might be some life in this old dog yet…

As I mentioned during the stream, I've been thinking a lot about what calls "aliveness" in creative work. There's something uniquely human about art made by, well... humans. Even when AI produces technically impressive results, there's often a deadness to it once you know it's machine-made.

The full video of this AI vs. artist showdown is available for paid subscribers above. If you're curious to see whether I beat the robot (and by how much), or just want to watch me frantically draw a horse riding a bike while playing a French horn, consider upgrading to a paid subscription.

Speaking of future episodes, I've got some fantastic Substack Lives lined up:

• , recent Pulitzer Prize-winning cartoonist

• from (Add to calendar)

• from

• (who I'll be joining on his Substack live next Tuesday at noon)
  …and more!

Thanks to everyone who tuned in and submitted ‘prompts’. I'm not even tired.

‘til next time,
Your pal,

The future is knocking, and it's not tapping gently.

A note by from today got me animated yet again about the brazen gaslighting leaders are doing when it communicates to staff about AI and what it is doing to their jobs.

“The story always sounds the same: Technology will change everything. Adapt or perish. Yet adaptation mysteriously always means producing more for less, with an ever-smaller slice of the pie.”

I’d highly recommend you read the full note below, then the insufferable CEO memo from Fiverr CEO Micha Kaufman.

The Future of Jobs, The Future of Art.

The latest Future of Jobs Report from the World Economic Forum (WEF) is out, which might as well have been titled "Have You Considered a Career in Food Delivery?"

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I was reading it on my phone at Grind Café on West 43rd as one of three baristas with an arts degree handed me some latte art so perfect it made me question my entire career. The irony wasn't lost on me— I was simultaneously admiring human artistry while reading about its imminent obsolescence.

OpenAI's Sam Altman —a man whose casual tweets or vocal-fry utterances can send entire industries into an existential spiral— recently announced that AI will soon "…do what only very talented humans can do today." He dropped this with the nonchalance of someone mentioning a slight chance of rain on Wednesday. He went on to explain that creative fields will be the first to fall, with cognitive and physical labor following behind — a sort of digital Hunger Games where the artists are sent to die first. How thoughtful.

"Soon, AI tools will do what only very talented humans can do today. (I expect this to go mostly in the counter-intuitive order--creative fields first, cognitive labour next, and physical labour last.) Great for society; not always great for individual jobs."

"When anyone can create amazing art, there will be incredible upside for humanity, but downside for most individual artists,"

…he tweeted, presumably while a team of human designers crafted his slides for his next TED Talk about how wonderful the future will be. So there you have it. Both business leaders and the AI industry itself agree:

‘AI is coming for your jobs, and no one is safe.’

That said, it's not all digital doom and gloom. The WEF report also suggests that while traditional artistic roles may decline, the broader design field shows promising growth in other areas: UI and UX design ranks as the eighth fastest-growing job category, which is essentially saying, "Don't worry about losing your job designing billboards — you can always design the interface that helps the AI design billboards."

Something I've been saying for years is that design and illustration aren't really about being able to "use Photoshop" — it's about applying creative thinking to real-world problems. And according to the report, that's something humans still excel at. For now.

Employers consistently rated AI's ability to replicate creative thinking as "very low" or "low," with creative thinking ranking fourth among skills expected to grow in importance by 2030. This suggests that while AI may automate certain technical aspects of creative work, actual human creativity remains difficult to replace. I'll drink to that — and I did, finishing my now-lukewarm latte with a smug sense of temporary job security.

This optimism comes with an asterisk the size of the Empire State Building:

While employers believe AI has limited capacity to replicate creative thinking, they express more confidence in AI's ability to perform design and user experience tasks. In other words, while clients might still need your brain, they might not need your hands. Great news for my carpal tunnel syndrome, terrible news for my landlord.

So what's an artist to do in this brave new world of artificial "creativity"?

Here's my back-of-the-napkin survival guide, written from the trenches:

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Thinking in Watercolor with Jessie Kanelos-Weiner

I had the pleasure of hosting watercolor extraordinaire, on today's Draw Me Anything! We dove deep into her fantastic book "Thinking in Watercolor," which I've been devouring since it came out.

Unlike traditional watercolor books with rigid techniques, Jessie's approach is refreshingly forgiving and experimental. She shared that she wrote it for "the younger version of herself who liked drawing but didn't know what to draw" - someone with time but not necessarily resources or training.

As a self-taught artist living in Paris, Jessie believes watercolor helped her discover herself after moving to a new country. We compared our watercolor setups (my Windsor & Newton kit versus her Kuretake Japanese watercolors) and discussed essential techniques.

Some key watercolor tips from our session:

• Use H pencils (4H or 6H) for preliminary sketches - watercolor makes regular pencil marks permanent

• Watercolor pencils make great sketch tools that blend with your washes

• Always identify your light source to add dimension

• When stuck, change your physical position (stand up, work larger, flip the paper)

• Patience is crucial - "it's literally watching paint dry"

• Make test swatches before committing to your good paper

• For quick-drying emergencies: radiators, hairdryers, or sunshine (but never put your watercolors in the oven!)

Jessie also shared a brilliant Paris art supply store roundup!

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There's something uniquely torturous about illustrating jazz. It's like being asked to draw what water sounds like, or sketch the taste of a Wednesday.

Early in the pandemic, I found myself hunched over my drawing board, locked in my East Village apartment with a commission that felt both thrilling and completely terrifying – my first jazz album cover. The musician, Seattle-based Ryan Burns, had been using his quarantine time with suspiciously productive energy, recording sessions remotely with his bandmates from their individual isolation chambers. The album title, "Postponed Parade," was so painfully apt it made my molars ache.

To Ryan's eternal credit, he not only insisted on paying properly (a radical concept in the arts), but gave me complete artistic freedom. "Just listen to the music and do your thing," he said, which every artist knows is simultaneously the best and most paralyzing instruction possible.

I’m lucky enough to live next door to Birdland— one of New York’s most iconic jazz clubs. I get to see a lot of live jazz each week. (For my money, though, nothing beats Mezzrow or Smalls… except maybe Ornithology) But I digress… My favourite jazz album art of all time is for Dave Brubeck, and happens to have been drawn by one of my favourite people in the world: Arnold Roth. Arnie signed my Brubeck album covers for Sophie and me many years ago, and they’ve proudly hung in every apartment I’ve lived in New York, if for no other reason than to remind me ‘how it’s done.’

I slid my headphones on, cranked up the volume, poured a hefty glass of whiskey, and sank into that peculiar purgatory where creativity and self-doubt engage in mortal combat. After three hours, and what felt like sixteen midlife crises, I managed to produce something that didn't make me want to fake my own death and start over in New Zealand.

What emerged was a drawing that captured the energy of five musicians playing together while being forcibly apart – a visual representation of the strange, disconnected-yet-connected reality we'd all been living in. The design had a certain chaotic harmony to it, much like my apartment after what I call a "cleaning."

Ryan Burns wanders onto Chicago stages like a midwestern shaman who accidentally grabbed a banjo instead of a staff. His music emerges from some unholy matrimony between John Prine's storytelling and Fleet Foxes' harmonies—if those harmonies had spent a winter in a Chicago apartment with broken heat.

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I’ve visited two life-altering projection art exhibitions recently—one at Mercer Labs here in Lower Manhattan that’s absolutely worth the trek downtown, and an even more mind-blowing installation in Tokyo called Borderless by a group called Teamlab.

Picture the villain in that Spider-Man film where drones use projectors to create entire immersive worlds out of nothing, and you’ve basically got Borderless. The Japanese, unsurprisingly, have mastered the art of making you question whether you accidentally ingested something hallucinogenic on your way through the door.

The technology today is staggering. Artists paint with light the way Michelangelo carved marble, except no one’s getting carpal tunnel from a chisel. I wandered through digital waterfalls that responded to my movements, thinking about how twelve years ago, when I was still in Melbourne, projectors were basically glorified slide machines with the ambition of a government employee on a Friday afternoon.

Back in 2011, while New York was still a distant dream involving roaches larger than the rodents in my apartment building, I accidentally became the “projection designer” for an experimental theater production in Melbourne. A generous title, considering my qualifications consisted of “can draw things” and “knows how to Google technical problems without crying.”

The Kin Collective, as they called themselves, was a troupe of eight alarmingly talented actors from various backgrounds—basically the Avengers, but of acting. I was their Jarvis: a disembodied voice backstage, trying to make technology behave while superheroes performed in front.

My task was deceptively simple:

Design a set for their debut show, Glimpse, without actually building anything physical.

Instead, I’d digitally draw and animate environments that would be projected behind the performers as they moved through vignettes developed using improvisation techniques from New York acting coach Larry Moss. (In Australia, casually name-dropping a New York coach gives you theatrical diplomatic immunity.)

Pitching the idea to the venue went about as well as you’d expect when saying, “We want to replace scenery with light.”

“So… no set?” the venue manager asked, looking at me like I’d proposed performing in the nude while juggling live ferrets.

“No, there’s a set,” I said. “It’s just… theoretical.”

The technical challenges began immediately. If performers stepped into the projector’s path, they’d suddenly have someone’s living room projected onto their faces—disorienting for everyone, unless you’re doing a show about human furniture (which, to be fair, is probably happening somewhere in Bushwick right now).

We spent days testing projectors and lenses, trying to find the maximum keystone angle (adjusting the tilt of the projector to avoid image distortion—a term I definitely didn’t panic-Google at midnight). Lighting designer Chris Chaney had the impossible job of blending stage lighting with projections so there were no harsh edges. It was like convincing cats and dogs to form a basketball team, but somehow he pulled it off. And I definitely didn’t just finish watching Air Bud before writing this...

My design philosophy was minimal: “Just because you can doesn’t mean you should.” This stood in stark contrast to many digital artists today, whose mantra seems to be, “If the audience isn’t having a seizure, you haven’t used enough effects.”

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Don’t forget, you can now order my book online from www.realdogowner.com

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Thank you to , , , , , and many others for tuning into my live video with ! Join me for my next live video in the app next Thursday May 1st, at 3pm US EDT. Click here to add it to your calendar.

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Drawing Dogs & Talking Shop with Claire Powell

I recently had the absolute pleasure of live-streaming with the brilliant UK illustrator, , where we nerded out about art tools, techniques, and our shared love of dogs for nearly two hours!

We dove inky-hands-first into the world of traditional drawing tools – Claire's impressive collection of dip pen nibs (stored in an old Quality Street chocolate tin!), her experiments with reed pens, and my obsession with fountain pens and bronze nibs made by Dan Berry. We bonded over our mutual admiration for master illustrators like Ronald Searle, Gerald Scarfe, and Ralph Steadman, discussing how these influences shaped our styles.

Claire shared her journey from digital illustration back to traditional media, revealing that finding the right medium was key to developing her distinctive style:

"I think you find your medium, and then you will find your style."

We swapped stories about drawing under pressure – Claire's experience in TV graphics and my newspaper deadline days – and how that adrenaline rush can actually improve your work by making you less precious about perfection.

The conversation took fun detours into dogs in British countryside pubs, the challenge of capturing canine energy in drawings, and Claire's quest for the perfect dog breed for her lifestyle.

As we sketched away on camera, Claire revealed her surprising evening plans: watching snooker championships (the most British thing ever). I surprised her with a drawing from my book featuring a dog on a snooker table – the perfect parting gift

Our book "You're Not a Real Dog Owner Until…" launches Tuesday, and Claire's got a copy making its slow way across the Atlantic. If you enjoyed this episode, please be sure to share it with someone you think might enjoy it.
I really appreciate your support!

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Your pal,

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Here is a small selection of the drawings from today’s session…

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As you might have heard me bleating about ceaselessly, my writing partner and I have a book coming out next week. It’s a nerve-wracking process, flinging a book into the world— so many things have to go right at the same time to give it any chance of success; and even then, a tariff, a news story on launch day, or a shipping issue could upend the entire enterprise.

We’re lucky so far, however! The book has been getting great early reviews and is now the #1 New Release for Comic Strips and Graphic Novels on Amazon!

When we’re collaborating, we have to kind of block out all of these things while we’re coming up with the thing to keep our spirits high and dive head-first into the process of writing and drawing the thing. So, today, I’m going to peel back the curtain (my studio doesn’t have a curtain, but you get it) on the most important parts of the process behind creating a book from scratch.

Before we kick off: If you like this kind of thing, you can subscribe to our podcast called “Is There Something In This?” which is our writers’ meeting for coming up with jokes and cartoons for the New Yorker. You can listen wherever you get your podcasts, or click here.

Research

The first part of the process involves looking at every other dog book we can find and making sure we don’t replicate what’s already been done, as well as learn from the incredible cartoonists who have done work with dogs before. I dove head-first into the incredible George Booth’s back catalogue, as well as the creator of the Mutts comic strip, Patrick McDonnell. They both have an incredible ability to capture the spirit of dogs in a way I don’t think anyone else can. (That said, I have also studied the work of Nick Galifianakis, Peter DeSéve, and to see how they capture dogs, and somehow imbue them with human qualities without it feeling too hamfisted.)

I make countless studies and sketches to get a sense of the level of abstractness in the cartoons- I want the dog breeds to be recognizable, but also feel like they have a unique look.

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We have about 110 gags to draw, so the ideas have to match the style of the drawing— they need to be silly, but grounded in truth. The entire premise of the book sprouted from a stand-up bit I’d been doing about New Yorkers and was developed into a series. Here’s a short clip detailing the backstory:

Keeping Track of the Jokes and Avoiding Replication

Scott and I have our own process for coming up with these, which involves using the app “Miro,” which is kind of an infinite whiteboard with sticky notes (we did our first book using actual sticky notes, and it got… a bit messy.) Using Miro means we can work from anywhere. Including New York bars that let you bring laptops.

We draw on the experiences we’ve had as dog-owners over the years, we talk to friends, family members, strangers waiting for the bus, other people picking up poop on the street in the morning— anyone who can give us insights into how common these premises are understood to be. This is where Scott shines in the process—his ability to vacuum up slices of life, vet premises, and stress-test the veracity of the scenarios is unrivalled. He’s a monster.

RELATED READING:
If you’re a creative worker and haven’t had the opportunity to collaborate with someone, I highly recommend it. It took me over a decade to start working with someone else, and I can’t tell you what a difference it makes.

The Order of Things

We throw a zillion jokes into a Google spreadsheet before transferring our final selection to Miro, separating them into themes/chapters to see how the order and flow feel. Our editor goes through each one, making notes and edits, moving things around, and showing us how the sausage is really made.

Cast of Characters

We did a bit of ‘world building’ and created families that would own the dogs, as well as ensuring we weren’t continually portraying the same kinds of people. These characters live in the “Parent” and “Dog-Owner” variants of our book series, and will no doubt make reappearances in future titles. It helps to have this bible to refer to, and to make sure we break up their appearances in the book so we don’t have 4 pages together with the same people.

Pencils

This part also requires us to get together and —similar to our New Yorker cartoon process— match scenarios with each joke that aren’t just ‘see-say’ (ie. The cartoon doesn’t always necessarily have to depict the exact joke; it can be its own related scenario that has jokes of its own embedded, including chicken fat*

(*Coined by MAD Magazine: Little background gags that you have to seek out by exploring the image carefully.)

I use a mechanical pencil wrapped in gauze and tape so my hand doesn’t fall off. Also, a pacer pencil I bought at CVS. I start with light blue, then build up with red lead for clearer lines.

I wanted to make sure there was a clear and consistent rule across the book about anthropomorphizing the dogs: we didn’t want them standing on two legs, doing human things; we very much wanted them to be grounded in the reality of the real world, but just heightened for cartoony effect.

Example Idea: Dogs on Beds

One of the more common ideas that kept coming up was that, despite people saying they trained their dog to sleep in their own bed, many owners confessed that they actually let their dog sleep on their bed— and often at the expense of their own comfort. Depending on the dog, they contort their bodies to ensure they don’t wake their precious pup.

We attacked this idea from a few different angles and established our ‘no-anthropomorphizing’ rule from here. You can see we started with the dog in pajamas, in bed reading “Eat, Play, Love,” but it was too absurd. We wanted to pare it back a bit to just show the reality of the joke, which, in itself, was a punchline.

Once we get the word economy and order lined up, we lay out all the book pages in a separate section of the Miro board, along with the pencilled out drawings that accompany each joke.

Inks

Once the pencils are done, we move to the final inks, then colours. I used a flat for the first time in my career with these books, and I feel like an idiot for only just thinking of it now. Nahia Mouhica was a lifesaver in doing the flats for the book before I went in and added shadows, wash, and highlights.

Keeping track of the pages is done in both Miro and manually, on my drawing board with a big printout of every page. It’s intimidating to look at, but it keeps you panicked enough to sit down and get it done.

To keep from becoming a hunchback, I would often ink on a lap desk in the living room, with Morris sitting nearby for quality control and farts.

This joke ended up being the first one in the book, so we made sure it had a nice contrast with the rest of the jokes that followed:

Next time, I’ll delve a little more into the process of book-making, but I thought you might like this little peek at what goes into every page of making a book like this. We’re really proud of how it turned out, and would love you to buy a copy for the dog-lover in your life. It drops one week from today!

‘til then, Your pal,

Pre-Order Your Copy Today!

Drawing the New York Literary Elite: An Artist Interloper at an Upper East Side Soirée

The invitation arrived via Paperless Post—the modern equivalent of a wax-sealed envelope delivered by footman. "P…

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Every morning, I take the dog out for a walk for an hour or so. No earbuds, phone off, just a book under my arm, a pencil in my pocket and a poop-bag in my hand.

Some of the best creative ideas I’ve e…

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There's a particular sweet spot in the art of cartooning…

That perfect moment when your reader's eyes widen, and they let out an involuntary snort. I once saw it happen in real time while sitting on t…

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Seven years ago, I wrote a version of this post for Medium, and it went a bit insane. ‘Viral’ doesn’t really cover it. Many similar articles have popped up in its place in the years since, but here is one of my most-requested tips from people asking, “How do you fit it all in and still find time to draw for yourself?”

The reason I’m sharing it with you today is that the most essential part of being an artist truly is finding time to draw for yourself. It’s so easy to shove it off to the side ‘until conditions are perfect’, but the truth is: If you’re ever going to get around to making the art YOU want to make (and reading these posts!), you’re going to have to have a disciplined system, and stick to it.

Preface:

Being a freelance cartoonist sounds like a fun job. But I’ve learned over the past 20 years that if you want to pay the rent and create art for yourself, it means you’re going to need a system. Paying the rent with your art also means taking on a lot of work that often has a deadline, which you need to balance with your personal art-making time— and if, like me, you have inattentive ADHD with chronic time blindness, you’re going to need two things:

1. A clock somewhere in your eyeline from your workspace.

2. A calendar.

The clock can be your phone in ‘nightstand’ mode, or a physical clock on the wall, or a tablet— but it needs to be clearly visible. The calendar can be a physical calendar or a digital one, but it, too needs to be visible. Keep it on your screen as much as you can.

Tip: If you use a Mac, then you’re working, use an app called “MeetingBar” which shows ou the thing you should be working on right now in your taskbar along the top of the screen.

So, how does the system work?

On a given week, I do a daily cartoon, regular New Yorker cartoons, I do stand-up comedy shows all over the city, write two Substacks, draw caricature commissions, illustrations for the Waking Up app, do live drawing at events around the city, take care of my Frenchie, and somehow find time somewhere in there to exercise, sleep, and attempt a date. If it sounds like a lot of work, it is.

The short answer is: Realistic attention management.

The longer answer is: I have a system that works around my brain and subverts any tendencies to procrastinate — especially during periods of extreme willpower depletion.

One of the biggest productivity revelations I had in the last 20 years while working freelance and trying to juggle a million different projects was to work directly from a calendar, not a To-Do list.

To-Do Lists VS. Calendars

I worked from a To-Do list for a long time, using a page each day to cross items off. It felt good to run a line through things as I got them done, but sadly, I never really got as many done in a day as I should — or could have.

Some tasks take longer than others, but all tasks look the same in a list. Seeing them in a calendar gives you a more realistic idea of how long tasks will take to get done.

I’m not anti-list.1 If you need to write down all of the things you need to do in a list to get them out of your head (especially before sleep on a Sunday night), then, by all means, do so. But once they’re down on that list, start plugging them into your calendar to give you an actual idea of how much time you have to do them.

Knowing you have assigned these tasks a time and date to be completed, you will be freed from the anxiety those unfinished tasks create in your mind. This nagging anxiety is known as The Zeigarnik Effect.

The Zeigarnik effect is a psychological phenomenon describing a tendency to remember interrupted or incomplete tasks or events more easily than tasks that have been completed.

If you’re anything like me, you probably fall into the ‘dreamer’ category of time psychology. The dreamers are the ones who have a poor ability to predict how long something will actually take, show up late to things, miss deadlines and generally end up having all their work snowball into Friday afternoon. (See: Parkinson’s Law.)

I’ve had an ongoing, futile feud with the inexorability of time since I was very young, and it continues to this day. The following measures go some way to subverting my perception problems.

This is a basic look at my template day, which is variable but a starting point to help me plan:

Trick #1: Copy & Paste.

To remedy my old dreamer tendencies, I now make a habit of ensuring that on completion of a task, I adjust the calendar event to reflect the ‘actual’ time it took. ie. I may have allowed 30 minutes, but it took an hour. I may have thought it would take an hour, but it took 45 minutes.

I then copy and paste those similar or identical tasks that I’ve completed before when I’m scheduling for the week ahead. I usually do this on Sunday night. It gives me a realistic idea of how much time I actually have to get everything done versus looking at a blank calendar. (Note: I’ve tried working from the freedom of a blank calendar… don’t do it. It’s not pretty.)

If you have repeating tasks each week, as I do, you’ll be able to copy and paste the entire series of repeating tasks that accurately reflect the time it takes to do them. For instance, I used to have to write comic strips, ink and colour them, I had to sit and draw up my batch for the New Yorker each week, Record an episode of the ITSIT podcast, and, lastly, I knew I would always have to go into the New Yorker from 11am — 12:30pm every Tuesday to pitch my batch. These things are repeating items on my calendar, and I blocked out the exact time it took each time (including travel time if needed).

IMPORTANT:

1. For tasks you’re doing for the first time (or larger tasks broken into smaller tasks), allow for Parkinson’s Law: ie. figure out how long you think it will take, then double it. It’s much better to have slack than to try and borrow time from other tasks.

2. If you have a task that takes place away from your office/studio/home, create a block called “Travel” and put it on either side of the event:

   

   Why not just add the travel time to the event block itself, you ask? Sometimes, it helps to know when an event ‘actually’ starts, so if it’s at 7pm and your time block says 6pm because you planned for an hour of travel, you lose the information on when it actually kicks off. So, it should look something like this:

   

   

   Trick #2: Colour code your calendar.

   To give you a clearer idea of the kind of work you will be doing in a day, it can help to colour code the kind of work that needs doing. You get a clear, concise 10,000ft zoom-out view of exactly what kind of work you’ll be expecting to get done.

   

   For instance, some work I do needs me to be on my laptop, some need me to be in my studio with my drawing equipment, and some things don’t work and need their own calendar, like going to the gym, stretching or a medical appointment.

Trick #3: Know how long to block distractions.

I use the Focusme app on my phone to block websites I know I habitually go to when I’m procrastinating, and SelfControl.app for the Mac to similarly block websites and social media on my laptop until the job at hand is completed. These are timer-based apps, and I know from the calendar how long to set each one.

Trick #4: Bundle similar jobs or ‘mindsets’.

If you know you’ve got a bunch of admin (emails, invoicing, QuickBooks, blog posts etc.) and you know it’ll be basically the same mindset and toolset for all of them, block those tasks together. If they don’t require the same amount of energy as, say, the really big project you have to start, leave them for later in the day when your energy is a bit lower.

If you need to move to a different desk for drawing than you use for writing emails, then bundle your drawing desk activities together, and bundle your emails desk activities together. I even have different colour-coded calendars for the two kinds of tasks, to make it easier.

Tip: If they’re high-priority tasks, shift them to earlier in the day so you give them your full attention. Your energy and willpower wain throughout the day, so be sure to get your M.I.T. done first thing before anything else.

Also, be aware of your own individual habits and energy patterns. If you’re more focused and creative in the morning, schedule your creative tasks for then. If you’re more productive in the afternoon or the late evening, switch to then. Obviously, deadlines sometimes rob you of the luxury of scheduling things for your optimum times, but do this when you have the opportunity to.

If there are certain days of the week that you know you’ll be more available to get certain kinds of things done, schedule all your admin tasks for that day or all your creative things for that day.

For example: I do all my Admin on Mondays when I’m most focused and I’ve just had a relaxing Sunday. I do my best creative work on Tuesdays, so I block that out for drawing and other creative work. On Wednesdays, I return to the desk and do invoicing, bookkeeping, answering snoozed emails, etc.

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Drawing is Thinking.

Today, I want to get back to basics— As you can see in the video above, today we’re going to look at the joy of pencils. It is one of the oldest tools in the drawing toolkit but easily one of the most dynamic and customizable.

Dave Gray, Founder of XPLANE and co-author of Gamestorming, describes sketching as “a conversation with yourself.” I always liked that idea— that when you’re actively letting an idea take shape in front of you, you’re no longer just noodling with amorphous shapes and ideas; you’re making decisions and negotiating with the page. It’s very much a conversation.

The pencil is a magnificent tool, capable of bringing any idea to life. Yes, I do know the story that “NASA Spent Millions to Develop a Pen that Would Write in Space, whereas the Soviet Cosmonauts Used a Pencil” — it is, alas, a myth, albeit a pretty fun one. I like it because it makes the simplicity of the tool the hero. It does one thing, and it does it well.

You can learn a lot by watching other artists sketch or studying their pencil roughs.

I remember seeing Peter DeSève sketching out a character from Ice Age in pencil and just watching the fluidity of his elbow and wrist and how he built these things out of nothing by finding relationships between shapes— adding and removing volume, finding balance in the composition in real-time. it was like watching a magic trick. At the exhibition of his work at the Philippe Labaune Gallery in New York, they showed some of the pencils of his New Yorker covers and character designs, all of which were utterly mesmerizing. I spent half a day in there poring over these explorations on paper and vellum. I much prefer seeing peoples’ pencils than their finished art. (See below).

Page before Pixels?

One thing I’ve always stressed to beginner artists is the skill of working things out on a page in pencil before you jump to digital. Yes, digital pencils are useful when you’re working out compositions, shifting layers and working with an Art Director or client in iterating an idea, but the initial stage of getting the page from your mind into the world is best done at the drawing board— a skill only developed by doing repeatedly, using whichever version of a pencil you’re comfortable with.

Mechanical, Traditional, and everything in between.

I use different kinds of pencils for different kinds of projects. I have different leads for roughing out compositions that I might be inking over (ie. using non-photo blue) or for when I’m building an idea up in stages and levels, so I can differentiate the different areas of the composition. For this, I use a mechanical pencil (you can see the specific kinds of mechanical pencils I use here.)

Am I against doing digital pencils?

Absolutely not. In fact, sometimes, it’s one of the best ways to work out an idea. I’ve included my digital pencils for both Photoshop and Procreate in your premium subscriber bundle folder. Let me know what you think of them. (or upgrade to access the folder.)

I sometimes layer differently-coloured pencil layers in Photoshop or Procreate to figure things out on the screen the same way I do on the page. It depends entirely on the project, the workflow, the rounds of feedback and the amount of people involved in the Process.

Above is a rough digital pencil composition for a page from my upcoming book about dogs. I switched out the tennis player a few times, as well as the dog— I had different kinds of breeds of dog to see which would be the funniest for this gag. (We landed on Jack Russell in the end.)

However, the other thing about working things out on paper as opposed to a digital screen, is the tactile sense of putting your hand and mind to work in sync. There’s a very distinct feeling you get when working with tangible tools as opposed to a stylus on a screen— they’re not ‘better or worse’ they’re just different.

My preference is to work it out using real-world tools whenever I can. Sometimes, I even produce the finished art in pencil if the assignment allows. I love the work of Harry Bliss in the New Yorker, which really reproduces that pencil texture nicely in print.

Flight of the Blackwing

I’ve been drawing with these for two weeks, and I think I’m in love. The leads are the perfect softness, the balance of the pencil is just right, and the eraser is more precise than anything else I’ve got lying around. I have no idea how long this affair will last, but at the moment, things are going well, and I’m hoping this box of their new Matte Greens lasts me for the rest of the year.

(Full Disclosure: They haven’t paid me to plug their products. However, they recently gifted me this box at an event in NYC. Even so, I would have bought these eventually.)

There’s also something about exploring the design of other artists and how they use pencils that can be a really helpful way to expand your visual vocabulary. They may use the tools in a way you wouldn’t have thought of, or created an effect by holding the pencil a certain way. Above, I was playing with some ideas on getting the expressive motion of dogs through the —admittedly inimitable— George Booth’s book “About Dogs”. I think he might have been the best artist to capture dogs using any tool, let alone pencils. (Related: Read Roz Chast’s recent post for the New Yorker on Booth’s cartoons here.)

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I do end up scanning pencils in* to bring them to photoshop to ink when I’m looking to produce something replicable and consistent— for a book or a comic strip that needs to have consistent line-weights. *Sometimes I just take a photo with my phone which is usually enough.

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The above cartoon for Air Mail appeared out of thick air while I was stalking the then-vacant streets of the Flatiron District. Here’s my process for the cartoon from conception ( ooer ) to completion. ( oo-er! )

August 7, 2020
New York, NY

Phase 3: Eat outside.

When outdoor dining was allowed as part of the Phase 3 pandemic reopening of New York, some neighbourhoods were filled with empty chairs being glared at by waiters slumped in their doorway, tapping an anxious pencil against their order pad. Many were still fearful that dining out was just too big a risk.

Others, like the recent Gen-Z accumulation in my neighbourhood, lept gleefully from their walk-ups and filled the sidewalks. Occasionally, they were a little too comfortable returning to the sidewalks and were given a stern talking-to by Governor Cuomo. (I’m looking at you, St Marks Place).

The neighbourhoods like Flatiron, Kipps Bay, Gramercy, Murray Hill and similar were a little more timid. But eventually, people were lured to the curbside tables and chairs with the notion that they were helping financially-stricken small businesses stay afloat, if just for the summer.

I had become friends with several of our local small business owners who own restaurants in the area like Plado, Book Club Bar, Post, Cornerstone Café1 and Root & Bone.2 One of the drawbacks of this new normal was dining alongside a phenomenon that New Yorkers just tolerate as a part of life on a daily basis:

Mountains of hot trash, thrice weekly.

Where I was raised in suburban Western Australia, we had ‘Bin Day’ once a week. It was my job to wheel the bins out to the end of the driveway and have the garbage trucks come by with their hilarious metal arm and do their thing. You could often find me sprinting down the driveway barefoot with two wheelie bins in tow, screaming “WaaAAAAAaait!” because I’d forgotten to put them out the night before.

In New York, “Bin Day” is every second day. The sheer volume of waste that is accumulated on a daily basis in Manhattan alone is astonishing, but you don’t even notice the bags on the sidewalk after a while…unless it’s Summer.

Then the term ‘hot Chinatown garbage’ rings a pungent bell with anyone who’s had the privilege of stepping through puddles of stinky bin water in July. This unmistakable fish waft can interrupt the best of dining experiences; hence the spark of an idea that struck me as I passed these restaurants.

My older sister is a wine expert, and despite her best efforts, has yet to teach me good etiquette.

She visited New York right before the pandemic, dining in various restaurants around the five boroughs and was probably one of the only people I’d trust with that little ritual the waiter plays when opening a $14 bottle of Sauvignon Blanc from New Zealand. The other 99.9% of people—myself included— are really just playing a small pantomime of “I definitely know what I’m doing.” to impress whomever they’re sharing a table with.

It always strikes me as such a funny, bullshit ritual. I think I’ve seen a grand total of one bottle sent back to the kitchen in my whole life, and that was because the wine was ‘corked’. (Which is ironically only discoverable once it is uncorked.)

I wanted to draw this little ritual in that restaurant setting above.

The setting is a lone couple on a date, the waiter playing out the little wine ritual, and the guy really getting into the ‘impress my dining partner’ performance, with a gigantic pile of wet, hot, fly-ridden summer trash behind him.

I’ve been drawing up little New York scenes for myself lately and figured I’d give this one the same treatment with a bit less detail. I jumped on the Wacom tablet with a number of photo references and sketched out the scene in three or four thumbnails.

One of the iterations was with the woman in the foreground with her back to us, on the left of frame, the man smelling the wine in focus in the centre, with the waiter to his left, and the stack of garbage to his right in the background.

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"The end of a melody is not its goal."

~ Philosopher & writer Friedrich Nietzsche on enjoying the process.1

A lot of you wrote to me after reading my essay on using AI in your creative process— then again after I lamented the lazy use of AI Art Generators for a major brand campaign that has littered the New York Subway. It’s a topic that animates the creative community in a lot of different directions, and it’s only getting more animated with new models popping up every week.

One thing that struck me was that throughout all of it, there is a thread that keeps returning again and again, and it is the reason I started this newsletter:
The thing that brings people back to the value of something is the work that went into it—the friction between conception and completion— not the quality of the output. The reason you’ll pay $4000 for a hand-crafted piece of bespoke wooden furniture over a $200 mass-produced robotic pre-fab IKEA table is because it’s unique. It’s something that took artisanship and skill to make.

Am I saying mass-produced furniture lacks value? No. But when creation becomes automated, the human intentionality - the care and attention in crafting each unique piece - gets stripped from the process. Even if the automated version achieves technical perfection, it misses the inherent value of human craftsmanship.

Bill Ahrens, one of the only people on the planet who can hand-pinstripe a car, is a great example of why you might pay more for a car he’s decorated over something that was done using a machine. Does it make sense? Probably not. But it’s the difference between humans creating unique things in the world and robots mass-producing things in a factory.

The ever-intrepid wrote today about the use of DeepSeek, China’s market-rattling new LLM, which seems to be as good, if not better, than the US LLM offerings including ChatGPT and Claude. By the end of the deep dive (which I highly recommend you read), she arrives here:

After hearing the hype, I decided to test DeepSeek myself, dumping in notes for a post I’m writing on chatbots and oral culture. My expectations were low: LLM outputs tend to carry an unmistakable robotic sheen. But for the first time ever, I watched an AI generate readable—even rhythmic and engaging—prose from my pile of fragments.

I was stunned.
For a few hours, I wondered if I should put my own sweat into the essay at all. Then, as if a sign from the gods, Rayne fisher-quann’s latest essay hit my inbox. AI might feel magical in its frictionlessness, but (human) writing—like walking—is valuable because of the friction:

Sometimes it’s tiring or slow, sometimes it’s boring or pointless [...] When you choose to walk, you choose not to pursue immediate gratification or even comfort but simply to expand the number of things that might happen to you. Walking invests in the potentiality of your experience with almost no promise of tangible reward at all, which is something like being alive.

The scenic route! The love of the game! Of course, I remembered, recalling one of my own old posts:

That’s the human difference—not the final output, but the spark of creation. The fact that you start bad and get good later, the work of figuring out where you’re going while still on the way there.

I know I may sound like a broken record when I write here, but it’s because in a world that is adopting these ever-more intelligent AI tools, we can’t forget the reason we do the things we do in the first place.

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Happy Friday!

If you’ve been banking up things to read for the weekend, have I got some links for you! The following are some insights from both myself and the very helpful from her guest post for Sub…

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It’s the only time I do it, thank Christ. The s…

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One windy weekend in 2022, I was wandering around the Billy Ireland Cartoon Library & Museum in Columbus with fellow cartoonist Maria Scrivan. We were fresh off the behind-the-scenes tour of the archives, shamelessly drooling over the original artwork on display by Charles Schulz. The wide-ranging exhibition celebrated what would have been “Sparky”’s 100th birthday. A photo of his pristine, minimalist studio caught my eye, and I noted to Maria how clean it looked. “Oof. He makes my studio look like something out of an episode of Hoarders.”

My creative process looks less like a workflow and more like a crime scene.

I barricade myself in the studio, turn off my phone, and my studio transforms from "moderately organized workspace" to "what if a tornado hit an art supply store?" I disappear into the work like a monk with ADHD and access to too many pens. Only when I've wrestled the thing into submission and the project is complete do I restore order. I emerge, blinking into the sunlight like a cave dweller, because the line between "creative genius" and "actual madness" is apparently just basic housekeeping.

This is what my studio looked like while I was working on a recent piece for the New Yorker…

Immediately after I emailed the Cartoon Editor with the finished artwork, I packed up my studio, and it once again looked like this. Bordering on Dexter-level forensic cleaning.

As I hunched over and continued to gawk at Sparky’s studio in awe, Maria said,

“My studio is a total mess while I’m working: It looks like a bomb hit it. But whenever I finish a project, I absolutely have to pack everything away as a sort of ritual, to exorcise the work from my brain.”

I stopped in my tracks…

This is the third time in a month I have independently heard the exact same thing from other professional cartoonists: Tom Richmond, the brilliant illustrator and caricaturist behind many of the movie parodies in MAD, had just told me the exact same thing when we were at that year’s National Cartoonists Society Reuben Awards in Kansas City.

It was almost identical:
He sits down to work on a project and allows himself to kind of explode pens, brushes, ink, paper, and scraps of reference images all over his space, and it looks like a disaster zone after a hurricane.

By the way, this is a man for whom I have an all-consuming case of studio envy. He is the most organized cartoonist I know, so it surprised me to learn that he allowed himself to create a mess to bury himself in the zone.

Then, when he sends off the final art to the Editor/Art Director, he takes his time in a personal ritual he’s had for years, where he goes around the studio and packs everything away, puts trash in the bin, stores his pens, ink, brushes — whatever he used in the process of creation — in their places. Then — and ONLY then — can he move on to the next thing in his day.

The other cartoonist I had a conversation with was Garry Trudeau, the cartoonist behind Doonesbury for the past 55 years. He’d shared a photo of his studio, post-clean-up. I said I was so envious of his pristine setup because my studio at the time looked like the entire room sneezed.

He said,

“I’ve long had this odd, celebratory habit — right after I make a deadline, I pick up my studio, ready it for the next one.”

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This week, many cartoonists have stood in solidarity with

Ann Telnaes

after her resignation in protest after the Washington Post refused to run a cartoon depicting the slew of…

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I hate to start the New Year off with a gripe, but I really do have to draw attention —pun very much regrettable— to the scumbags who are in charge of the campaign art for the sneaker company Skechers. A company that, in 2022, reported annual revenue exceeding $7 billion. Billion. With a B.

They’ve decided to decorate our commute with AI-generated advertisements that look like they were excreted by a sentient Roomba having a stroke.

Now, companies and agencies are free to do whatever the hell they want. Nobody is under any obligation to hire real artists if there are cheaper alternatives available. The free market is what it is— if there are cost savings to be made, bean counters will find them. But not even waiting until the technology is good enough to produce a decent image that would otherwise have paid the rent of a working illustrator for 3 months is just gross. Not only does it repel people who would otherwise consider buying your product (just look at the comments in my post below), but it undermines the reputation of your brand.

You want people to associate you with low-quality, half-assed imagery that A.) Looks like shit, and B.) Doesn’t even depict the shoes you’re trying to sell? Are you high? (Don’t answer that.) It’s terrible PR and sloppy marketing using a lazy advertising agency.

The process of making something good usually involves more than just one person prompting an AI generator and making minimal tweaks before shipping it to be printed on hundreds of billboards around the New York subway.

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If it were an attempt to ‘get folks talking on social’ or ‘be controversial’, it doesn’t really work... It’s received a profoundly negative reaction, and it makes the brand look like they don’t even care about the product, let alone the potential customer.

Again, the process of a professional making something by hand, be it with analogue or digital tools, (or a hybrid of both) yields something humans can feel. Even someone walking past this image with no experience in illustration can tell something is artificial and ‘off’ with this art. (And yes, it is art, whether you like it or not.)

Lastly, I don’t really know what the message is…?

It’s two oddly proportioned women walking in opposite directions in what looks like a vaguely Parisian street, wearing anything but the product that is being advertised. There are hallucinated flags for imaginary countries and ghoulish onlookers with no particular expressions. And is that meant to be a pile of laundry or a small child standing nearby? I guess we’ll never know.

It all just feels like a giant troll. But to what end? If we’re going to just start churning out AI slop for major ad campaigns to save a bit of cash, there’s no telling where the basement is on using this hot garbage.

Ok, I don’t want to be a total Doomer…

The fine folks over at Creative Boom just released their 2025 illustration trends, and wouldn't you know it - actual human artistry is making a comeback.

// 3. To see the 'hand of the artist.'

In response to lifeless AI-generated work and CGI, illustration agents are more attuned than ever to pieces that aren't just hand drawn or handmade but that demonstrate the hand of the artist in the sense that the voice or visual language discussed in point one is integral to the work. Sarah Beetson represents the global agency IllustrationX and its artists in Australia and is the company's talent scout. For her, it's not about ditching digital processes but bringing them together with physical world creativity.

"I always look for work that has elements done by hand, especially as style trends can run so obviously along digital lines," says Sarah. "For example, for a few years, there has been a very obvious trend with Procreate-made work using similar colour palettes, brushes and techniques. Something sketched or coloured using real materials by the artist in part of the process can certainly have a uniqueness about it and often outlasts trends."

Evidence of the artist's hand will bring viewers closer to the work emotionally. "Analogue techniques and styles that nod to craft always captivate and invite the viewer to linger; pairing this with glimpses of behind-the-scenes material will really capture commissioners' attention and place real value on the work created, the thrill of which you do not get from AI," adds Sam at Brilliant Artists.

For what it’s worth, I’ve had some anecdotal evidence of people recoiling from the uncanny valley feeling from art that looks like an AI generator made it and reaching out to commission a human who ‘can still make things by hand with pen and ink.’

This is in no way a reliable indicator of a larger trend. It is, however, alleviating the panic attack my accountant had when looking at the income I made before and after AI Art Generators became so prevalent. (It’s …stark.)

Even if the art is created digitally on a tablet, at the very least, the client/Art Directors I’ve worked with have enjoyed dealing with a human instead of incessantly altering prompts to try and get the exact result they want. (They have relayed such frustrations transparently. I tried not to grit my teeth.)

My advice? Next time, hire real sketchers.

Want your brand to look like it wasn't conceived by a malfunctioning toaster? Hire human artists. We still exist, and bonus: we can actually draw hands that don't look like props from a horror movie.

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When I launched Process Junkie, I had one goal: to figure out why creative people do what they do and share my own insights and advice on the creative process.

The existential spiral started with How …

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I often get asked about the process of submitting cartoons to the New Yorker. So, I thought I might write it out for you to enjoy here.

There’s a very slim chance you may have already read my 3-part account of my first time submitting cartoons to the New Yorker, eventually resulting in my first sale in 2017. (Part 1, Part 2, Part 3) Part of this process is in there, but the part I’ll cover today is the very beginning of the process right through to the very end.

When I first wrote this process out below, it was 2020, and the New Yorker was still admitting people into the building to meet with the Cartoon Editor every Tuesday. I would go in person to sit with the editor and get real-time feedback. These days, there is no longer any in-person review of batches, and cartoonists don’t go to the magazine in person, but the bones of my process are largely unchanged. I’ll write more about this in the footnotes.

With that out of the way, here is my very specific 10-step process for submitting cartoons to the New Yorker, originally published in January 2020:

1. The ideas stage.

This is arguably the most important stage of the entire process. (Apart from the part where you get to pay your rent on time.) The ideas stage is an elusive, bizarre process whereby you somehow generate a number of ideas that might make a good cartoon, seemingly out of thin air.

The truth is, much like finding your soulmate, they don’t appear when you’re looking for them. They pop up in the moment between swiping your Metcard and getting to the bottom of the stairs as the F-train is arriving. (And you’d better have a notepad ready when it falls outta your head.) More often, they pop into your head somewhere between the moment you’re washing your hair and rinsing out the conditioner. So, you’d better have some Aquanotes ready when that joke about a praying mantis at a singles bar bubbles up.

I write tags/captions, concepts, draw compositions, facial expressions— whatever the idea needs to get it going and scribble it down with wrinkly fingers. My shower wall often looks like this in the morning.

2. The idea-development stage.

This stage varies wildly from cartoonist to cartoonist. I personally like to work on my ideas throughout the week alone, and then if there’s anything I can’t figure out on my own, I bring it to my writing partner, Scott, for a writers’ meeting. He always has great ideas, too, so we mull them over and try and punch them up before pitching them.

We used to just meet at a pub and do this on a Monday night, but one day, Scott had the bright idea of turning the meeting into a podcast. I told him it was a terrible idea. “Nobody wants to listen to the ins and outs of two idiots dissecting the frog for an hour every week. It’s a visual medium!”

I was wrong. Very, very wrong, in fact. The podcast now has thousands of listeners. Needless to say, we walk out of the podcast with a batch of ideas to pitch to the editor and agonise over for the ensuing week.

LISTEN TO THE PODCAST HERE

Once I have the ideas in sort of ‘pitchable’ form, I go back and agonise over the wording, the punctuation, the execution and, of course, the drawing.

3. The ‘agonising and crying into your drink’ stage

Once I’ve essentially muddled through a few different executions, I sit at my desk with pencil and coffee scotch, and try to draw up the batch of ideas. It can be excruciating when something isn’t flying off the page, jiving, hitting the mark , working.

4. The pencils stage.

The pencils are done using a regular old pacer-style click pencil that you can pick up at your local CVS (or steal from a co-worker). I’ll often erase a facial expression to get it just right, or sketch out a few poses on a separate sheet of paper to try and get the right position.

Sidenote: Someone whose work I really admire for pose is Will McPhail. He McSucceeds to nail every single pose in his cartoons to illustrate the expressions perfectly.

This particular idea is one Scott pitched on the podcast — in fact if I recall, it was Scott’s OSPOTW* for that week. (*Outback Steakhouse Pick-of-the-week®, in which, if the idea gets sold and runs, I have to take Scott to Outback Steakhouse for a steak and martini dinner, to my chagrin. (I fucking hate Outback Steakhouse.)

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5. The inking stage.

Once the pencils have left me with only a patch of hair on the left side of my scalp, I move on to the ‘inking’ stage.

There are two kinds of inking stages in the life of a cartoon— one is for the ‘rough’ that is pitched to the magazine. And the other is for the ‘final’ or ‘finishes’. The rough is the basic idea of the cartoon, drawn to the execution level that makes it clear what the cartoon would look like. Once in a while, it’s worth just submitting a finish to give as clear an idea as possible. This isn’t always practical, but most cartoons I’ve sold to the New Yorker were from submitting finished gags.

For the inks on this one, I used a Uniball vision fine, along with a Japanese Kuretake Fude Brush Pen in Retail Package, Fudegokochi, Fine Point (LS4-10S). For the chess pieces, I used a super-fine brush pen I found in an art shop in Paris (ooer) called Magasin Sennelier. I have no idea what it’s called.

Depending on the cartoon, I may use a lightbox (pictured above) for the inking stage. For this one I did a combination of re-penciling from a lightbox of the first pencils (oof) and inking over the lightbox the regular way. This mini LED USB-powered lightbox was from the devil Amazon.

6. The erasing pencils, scanning & clean-up stage

Once the inks are pretty much done, I let them dry properly before erasing pencil lines and adding any final details. For this particular one, I wanted to mimic a chess game my friend Ethan and I had just played in Madison Square Park that afternoon, where he whipped the pants off me in under 10 minutes. I changed just a few of the pieces just to screw with him when he sees it in print.

I scan the piece using one of two methods, depending on the level of detail in the cartoon. If it’s pretty basic, I use “Adobe Scan” on my smartphone. If it’s a bit more detailed like this one, I use my glass flatbed scanner unit on my printer and upload it to Photoshop for…

7: Wash and Finishes stage

Depending on the cartoon (and the amount of time I have to turn it in) I will either use a hand-made watercolour wash (below) or a digital wash in Photoshop, using a Wacom tablet. I have pretty much replicated my ‘by hand’ tools in my Photoshop brush presets, which helps keep things looking consistent. (Note: Premium subscribers have access to these brushes when they upgrade to paid)

Stage 7 Addendum: Digital Finishes

For this one, I used the Cintiq Pro 16” (my review here) to do the final washes and touch-ups on the cartoon at 600dpi, while watching Seinfeld in the corner to calm my shaky nerves. Also pictured: Me wearing a glove that stops me sweating all over the screen.

Here are the various stages the cartoon goes through once scanned in:

I add the caption last, which saves me from agonizing over it too much while I’m drawing. I already agonised in Stage 3. Stage 6 is too late for that malarkey.

Then it’s time to print it out, email a PDF of the batch to the cartoon editor, call an Uber and crawl down the FDR to pitch the cartoon in person.

Some days if I’m organised, I take the subway down to the World Trade Center stop and walk through the Oculus to calm my nerves… then I come to remember it’s a shopping mall and my anxiety returns.

The New Yorker moved from 4 Times Square downtown to the new World Trade Center in 2015, along with Vogue, Vanity Fair, Wired, and a slew of other Condé Nast mastheads. It’s certainly more pointy.

8. The Pitching to the Cartoon Editor stage

I check in with security at the desk, then get a pass to zip through 38 floors in record time whilst trying to pretend to be comfortable that the numbers are on the outside of the elevator.

This is also the only other time we get to bump into other New Yorker cartoonists and trade anxieties and air our kvechables. We don’t have permanent passes, so we often have to wait at the glass doors for someone to walk past and let us in before we can get to the sign-in list. Sometimes it can take a while. Sometimes smart people like Sofia Warren (above) call someone’s extension which I should totally learn how to do.

We then round the corner to the cartoon department and put our names on the sign-up list. This one is from the last day of the previous cartoon editor. It’s a veritable who’s who of who’s here.

The Cartoon Editor sees cartoonists in the order of the list.

While we wait our turn, the cartoonists sit in the makeshift Cartoon Lounge (whatever board room is free) and talk shop, or avoid eye contact. I make a habit of going and getting coffee to see what books might be available in the kitchen… also, to wake me up before I have to speak to humans.

I always dip into the side office and pick up that week’s issue, flip to the contents page and see if anything of mine ran in that issue (yes, that is how we find out - at the same time as you do) and, if not, enjoy what else made it into those elusive 16 slots for cartoons.

One morning I flipped open to see my name in print, pitching a terrible joke to Gus Van Sant (name drop complete) and making a general tit of myself. Nothing unusual, really.

While I wait, I like to re-order my batch in the vain hope that it’ll make some kind of difference whether I’ll sell something this week. I try to make it like a W-shape, like a comedy set: open strong, dip a bit, hit them in the middle with something big, then dip right before the big closer. I have absolutely no evidence that this does anything at all, but I insist on doing it every week.

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