Live drawing videos with the most interesting creative minds in the world, hosted by Manhattan-based New Yorker cartoonist and comedian Jason Chatfield.
Adventure Sketching, Pickleball, & Bus Rides with Samantha Dion Baker
Tuesday, July 1, 2025 • Duration 01:01:45
I spent an hour yesterday drawing with Samantha Dion Baker —artist, author, and one the best Substackers on drawing—and came away feeling like I'd just had the best kind of therapy session. Which, as it turns out, is exactly what Sam's work is all about.
Sam joined me from her studio in Dumbo, and what started as a casual chat about pickleball evolved into a masterclass on using art as a tool for presence, sense memory, and genuine human connection. It’s crazy I get to speak to people like this every week (it’s even crazier that they speak back.)
The Accidental Artist
Sam's artistic journey is one of those creative pivots that make you believe in second acts. She spent years as a graphic designer (same!), creating pristine designs—all clean typography and careful spacing. Then life happened: kids arrived, screens became suffocating, and she found herself reaching for a sketchbook just to remember things.
"I was drawing things so well or comfortable drawing things," she told me, flipping through pages of her early work. "I was just doodling like letters and arranging things. It was very designy."
But here's the thing about doodling when you're not trying to be an artist: it becomes honest. Sam started documenting daily moments—not because she planned to publish them, but because drawing made her more present. The practice was meditative, almost inadvertent therapy.
When she published her first collection, Draw Your Day, Amazon classified it in the art therapy section. "I didn't really think about it when I was writing it," she said, "but I was like, oh, yeah. That makes sense."
The Art of Paying Attention
What I love about Sam's approach is how unforced it feels. She's not precious about her sketchbooks—they're repositories for whatever catches her attention, regardless of artistic merit. We talked about the tyranny of the "perfect sketchbook," those Instagram accounts full of museum-quality watercolours masquerading as casual sketches.
"I'm not happy with 90% of my pages”, she admitted. But that's the point. The sketchbook isn't a performance; it's a practice.
Her upcoming book, Draw Your Adventures (out July 15th—pre-order it now!), explores this idea of documentation versus decoration. It's not about capturing the Sistine Chapel; it's about noticing the "Call Your Mum" mural near your son's new apartment, or the woman across from you on the bus.
"Sometimes it's completely unrelated," Sam explained, "but it will still bring you back if you're present and you're taking it in."
The Technical Bits (For the Process Junkies)
Mid-conversation, we naturally gravitated toward tools—because what are two artists without strong opinions about pencils? Sam's a devotee of Blackwing pencils and has worked with them for years (she even illustrated their iconic poster of all the limited editions). But her real secret weapon is Derwent Inktense paints.
"I always describe them as like a cross between acrylic wash because they dry flat and watercolour," she said, layering colours on a portrait of her friend's dog, Wayne. "They're more forgiving than watercolour." (Watch the video above to see her drawing Wayne!)
I confessed my own tool obsession whilst wielding a Wren fountain pen I'd discovered the night before at a comedy show (thanks Lauren Layne and Anthony LeDonne). We compared notes on everything from mechanical pencils (neither of us likes them) to date stamps (both obsessed) to that magical Faber-Castell 14B pencil that somehow exists despite breaking all the rules of graphite grading.
(This is probably where I should mention that Sam's giving away 50 copies of her book at her launch party on July 15th in Dumbo. RSVP required—don't just show up like you're crashing a wedding.)
The Interrupted Artist
One of the most honest parts of our conversation was when Sam talked about working around constant interruptions. Her artistic practice developed not in some pristine studio, but in the margins of motherhood—quick sketches between playground emergencies, continuous line drawings because she might have to stop mid-pencil stroke.
"I was constantly being interrupted," she said. "So my process, I've learned to work in stages."
This resonated deeply. How I often wait for the "perfect" time to create—the uninterrupted afternoon, the ideal lighting, the moment when inspiration strikes like lightning? Sam's work is proof that creativity thrives on constraint, that the most meaningful art often happens in the spaces between other obligations.
Adventure as a State of Mind
As we wrapped up (Wayne the Cairn Terrier now immortalised in both our sketchbooks), Sam explained the philosophy behind her new book. Adventure isn't necessarily about passport stamps or mountain peaks—it's about approaching the world with the curiosity of someone who might want to draw it.
When you're carrying a sketchbook, you notice differently. You see the baroque curve of a fire escape, the precise way someone holds their coffee, the particular quality of light filtering through a bodega window. The tool changes the observation, which changes the experience, which changes the memory.
"It's choosing the choices of what to draw when you're on an adventure," she said. Whether that adventure is crossing Brooklyn on a bus or crossing continents on a plane.
Sam's book launches in two weeks, and honestly, it arrives at exactly the right moment. Summer in New York means everyone's moving, travelling, or at least pretending they have plans more interesting than sitting in air conditioning. But as Sam's work reminds us, the most profound adventures often happen within walking distance of home.
Just bring a pencil.
‘til next time
Your pal
Pre-order Draw Your Adventureshere. Pre-orders genuinely matter for authors—they determine everything from print runs to bookstore placement. If you're planning to get a copy anyway, ordering now is the best way to support Sam and ensure the book finds its way to the people who need it.
Coming soon… I'm doing something very special with Blackwing pencils and Amy Kurzweil. Can't say more yet, but it's going to be pretty epic! Stay tuned.
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The Dollar Tree Revolutionary: From Introvert Drawing Club to Global Art Movement with Beth Spencer.
Wednesday, June 25, 2025 • Duration 55:34
How Beth Spencer Started an Art Movement with a Five-Minute Sketch
I need to tell you about Beth Spencer —not because she asked me to (she didn't), but because watching her work on Substack these past few years has been like watching someone perfect the art of making strangers feel less alone with a pencil and a really good attitude about being terrible at things.
Beth runs the Introvert Drawing Club, which might be the most honest newsletter title in the history of newsletters. No grandiose promises about unlocking your creative genius in thirty days, no affiliate links to expensive art supplies that will supposedly transform your stick figures into Sistine Chapel material. Just: "Hey, you want to draw badly together? Great. Let's be bad at this thing we love."
I've been a subscriber since practically day one—her newsletter was among the first I ever signed up for when I stumbled into this Substack world with a dangerous amount of confidence in my own artistic abilities.
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What Beth does shouldn't work. In a world where everyone's selling courses and productivity hacks and systems for optimising your creative output, she's over there saying, "Actually, what if we just... drew some goats? What if we were gentle with ourselves? What if we got off our phones and made terrible art with dollar store supplies and loved every minute of it?"
The Badge That Broke the Internet
But here's the thing that makes Beth more than just another encouraging voice in the creative wilderness: she accidentally started a revolution with a five-minute sketch.
In June 2024, Beth Spencer picked up an iPad and sketched a red hand jotting the words "Created with human intelligence." She was procrastinating on her actual work—a children's book illustration—and had been seeing "a lot of concerned chatter about AI among fellow artists on Instagram." So she figured she'd post this little badge to her website to make it clear that everything there came from, you know, an actual human being.
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Matt Ruby on Comedy, Mindfulness, and Why Algorithms Are Ruining Everything
Tuesday, June 10, 2025 • Duration 54:33
Yesterday, I sat down with Matt Ruby, a comedian who's somehow managed to turn drug experimentation into art, philosophical wisdom into punchlines, and crowdwork critique into a manifesto. What started as a chat about joke writing quickly devolved into an exploration of why we're all slaves to Chinese algorithms, how meditation is the antidote to everything, and why tension might just be comedy's secret weapon.
Matt's an inventive comic. He once did a special called Substance where he performs the same material drunk, high, on mushrooms, and sober – not because he's reckless, but because he's genuinely curious about consciousness. His Substack, Funny How: Letters to a Young Comedian reads as if Marcus Aurelius decided to become a stand-up comic, and his latest special Bolo proves he's not just thinking about comedy deeply – he's executing it at the highest level in the trenches of NYC comedy clubs.
The Worst Sin You Can Commit
"I think the worst sin that you can do is to be dull," Matt told me early in our conversation. "Just don't be boring." It's a philosophy that extends beyond the stage into his entire approach to art and life. When everyone else is zigging, he’s looking for what he can break to make his comedy zag. Or zog. Or something.
This isn't contrarianism for its own sake – it's strategic differentiation based on supply and demand. "If there's something that everyone else is saying, it's probably not going to be great fodder for stand-up." The result of doing the opposite is comedy that feels like watching someone dig a hole for themselves just to see if they can climb out. As Matt puts it, "Sometimes digging a hole for yourself... if you can get out of it, it's almost like a magic trick element to it."
The Philosophy of Getting Uncomfortable
Matt's approach to tension might be the most illuminating thing about his comedy philosophy. When I mentioned how audiences sometimes seize up at the topic of a joke rather than waiting for the target, he lit up: "To me, that's a golden opportunity. Tension is opportunity."
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From Bad Stand-Up to Beautiful Art: The Nishant Jain Story
Sunday, June 15, 2025 • Duration 01:02:22
Thank you to those of you who tuned in to my live stream with Nishant Jain! If you missed it live, I hope you enjoy the replay above.
Join me next Tuesday & Friday for my next TWO live episodes with Best-selling Author and Artist Austin Kleon & Two-Time Pulitzer Prize-winning Cartoonist, Ann Telnaes.
Tiny People, Big Ideas: My Drawing Lesson with Nishant Jain
Yesterday, I had the pleasure of talking with my friend Nishant Jain, the brilliant mind behind The SneakyArt Post, and honestly, my tiny nugget of a brain is still processing everything I saw and heard. He does this to me every time we talk. What started as me asking for help with drawing his signature "tiny people" turned into a masterclass in observation, creativity, and why sometimes the best art happens when you're trying not to be noticed.
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From Neuroscience to Sneaky Art
Nishant's journey to becoming an artist is particularly circuitous. He was halfway through a PhD in neuroscience (we’ve all be there) when he quit to become a writer, inspired by —and I love this— a particularly terrible stand-up comedian he kept seeing in Chicago. "He was awful, and he didn't get any laughs, but I would see him every night of the week. Every time I went to an open mic night, I would see him there." The persistence of this bombing comedian made Nishant realize: "What am I doing if I'm not being persistent in his way?"
Look, am I annoyed he saw me bomb so many times? No. But whatever, it led to bigger things for him. Naturally, he then quit science to write novels. (we’ve all been there) Then, almost immediately, he hit writer's block. Four times. Which led him to grab a pen and notebook and head to a café, where "sneaky art" was born out of pure frustration with words—he literally drew himself out of writer’s block.
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The Art of Drawing Worse with Tom Toro
Wednesday, October 8, 2025 • Duration 58:01
Thank you Kevin KAL Kallaugher, asher, Margreet de Heer, Dan Collins, Pat Coakley, and many others for tuning into my live video with Tom Toro (and his cat, Pumpkin!) Tom is a New Yorker cartoonist, author, and the rare person who can make me feel simultaneously inspired and completely inadequate about my cartooning skills.
His new book, And to Think We Started as a Book Club, just dropped, and it’s already Andy Borowitz’s October Book Club pick. The title itself is a gag from one of his cartoons—bank robbers mid-heist, one holding a crowbar (originally a shotgun, but weapons get flagged by algorithms, apparently). It’s the kind of unwieldy-but-funny title that works because the joke sustains it.
The Art of Drawing Worse
One of the best moments came when Tom shared Bob Mankoff’s advice to Paul Noth: “Draw worse.”
Not as an insult, but as a direction. Noth’s early work was so detailed—cross-hatching, filigree, the whole nine—that Mankoff told him the jokes were strong enough to carry simpler art. The delivery needed to be cleaner. Tom admitted he sometimes overdoes drawings when he’s insecure about a joke, like he’s compensating. I felt seen. Very seen.
“The best thing about your work is the worst thing about your work,” Mankoff once told me. “You draw too well sometimes.” I’m still not sure if it was a compliment. Probably not.
Fact-Checking V*ginas & Left-Handed Catchers
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Asher Perlman & The Art of Eugene
Episode 26
Monday, October 6, 2025 • Duration 56:30
I went into this episode of DMA expecting the usual blend of cartooning shop talk and digital doodling. What I got was a deep dive into creative authenticity, delivered by someone who's figured out that being yourself is both the hardest and most obvious solution to every artistic problem.
The Eugene Empire
Asher's Hi It's Me Again had just dropped, and our conversation naturally gravitated towards his most famous creation: Eugene. For the uninitiated, Eugene is that wide-eyed, innocent character who looks like he just materialised in the world ten minutes ago and is still figuring out the rules (and nervously figuring out how to ask the barista for the bathroom code).
An unexpected moment came when Asher produced an actual cardboard cutout of Eugene—because of course he has one within arm’s reach. But the real insight was his theory about Eugene's existence: having come up through Chicago improv and sketch, Asher needed a creative collaborator for the inherently solo act of cartooning. Eugene became that collaborator, a subconscious way of recreating the writer's room dynamic on paper.
When a live stream viewer requested drawings of "Eugene and his dog, who looks like Eugene," the chat collectively decided the dog should also be named Eugene. Asher immediately declared this "canon." Watching creative mythology form in real time was unexpectedly moving.
The Mankoff Hair Doctrine
I recounted Bob Mankoff's bizarre but apt advice about finding your artistic voice. Mankoff stumped with an analogy about hair styling: "You decide to wear your hair that way... why is your drawing not as distinct as your hairstyle?"
At the time, I admitted, I was too dense to understand. But eventually it sank in: stop drawing what you think a New Yorker cartoon should look like, and start drawing like myself. Asher also sold his first cartoon a month after Ellis gave him similar advice:
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Liza Donnelly on Breaking Barriers, Drawing Aliens, and Why Everything is Political (Including Pigs)
Nearly 500 people tuned in yesterday for Drawing Me Anything #25, and honestly, I'm not sure if they came for the cartoons or just to watch me fumble with my drawing setup like a broken octopus. Either way, I had Liza Donnelly on—the first person I ever subscribed to on Substack, and a cartoonist who's been breaking barriers since before breaking barriers was trendy.
From Watergate Kid to New Yorker Pioneer
Liza grew up in Washington D.C. during Watergate, which explains a lot about her political sensibilities. She wanted to be Herblock—the political cartoonist's political cartoonist—but felt like she couldn't find her voice in that arena.
"I looked at the political cartoonists that I admired, Gary Trudeau and Herblock. I just didn't feel like I could fit in. I didn't think that I had a strong enough opinion about things, which was not true, but I couldn't find my opinions, I guess. I was afraid to share them."
So she turned to the New Yorker, which she initially thought was "stodgy" until she realised it was actually full of "subtle but subversive" cartoons. This led to her becoming one of the first women to regularly publish cartoons in the magazine since after the period in the 1920s. She came up alongside Roz Chast and a few others.
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Ann Telnaes: Talking Musk VS Trump & Freedom of Expression!
Friday, June 6, 2025 • Duration 36:03
Two Megalomaniacs Walk Into a Democracy: Ann Telnaes on Cartoons, Chaos, and Why We Can't Look Away
Earlier today, I got to speak with Ann Telnaes, 2025 Pulitzer Prize winner and one of the most fearless voices in political cartooning. (Also, one of my favourite people in the world.) We discussed the urgent question: “How do you document democracy's slow-motion car crash when two unhinged maniacs are fighting over the steering wheel?”
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Ann doesn't mince words. She never has. When I described Trump and Musk as "a petulant toddler and a drug-addled lunatic lobbing bombs," she laughed and countered with her more accurate assessment: "Male adolescents who have too many toys."
We're not dealing with political disagreements here. We're watching what happens when unlimited power meets unlimited ego, and spoiler alert: it's not that funny.
Cartoonists: The Canaries in Democracy's Coal Mine
Ann has a theory that cartoonists are "the canary in the coal mine of democracies," and honestly, after our conversation, I'm starting to think we might already have one lung full of coal dust. The documentary she's featured in, Democracy Under Siege, was made before everything currently happening actually started happening, yet it predicted pretty much everything we're watching unfold.
As Ann put it, there was urgency during Trump's first presidency, "but nobody noticed because he was so entertaining for the media to cover, because it got eyeballs." The cartoonists, however, "did a fairly good job showing who Trump was in the first one." We had a running start this time, but somehow we're still acting surprised that the leopard is eating faces.
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Comedy Over Tragedy: Austin Kleon's Masterclass On Creative Survival
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Join me for the next one on Friday at 11am EDT — I’ll be talking & drawing with special guest, Two-Time Pulitzer Prize-winning Cartoonist, Ann Telnaes!
His books have sold nearly two million copies. Two million. That's even more than the 27 of mine that sold this month! They've been translated into over 30 languages (including Australian.) called his work "brilliant." called him "one of the most interesting people on the Internet," and said his poems "resurrect the newspaper when everybody else is declaring it dead."
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The Watercolour Control Problem with Jessie Kanelos Weiner
Friday, October 10, 2025 • Duration 33:55
The Watercolour Control Problem with Jessie Kanelos Weiner
Earlier this year, I joined Jessie Kanelos Weiner —artist, author, and watercolour wizard—for a live chat about colour, chaos, and why watercolour refuses to obey. She just released Thinking in Watercolour, which made me realise I mostly think in panic, and snacks.
This year, for 2026, she’s launching a series:31 Days of Watercolor!which sounds really fun.
In our talk, Jessie asked how I approach colour, and I admitted that I approach it sparingly. I used to think “real artists” painted every shadow like da Vinci. Then I saw the da Vincis at the Met and thought, Yeah… I don’t need to do all that. These days, I use colour the way comedians use silence—strategically. A dab here, a spot there. Enough to make you look where I want you to look.
We talked about the Philadelphia Eagles poster I illustrated—a parody of the classic New Yorker cover, except it’s a jacked football player instead of Eustace Tilly. They wanted bold colour. I gave them subtle pastels amid the team’s green hue. They said, “Brighter!” I spent two days repainting and relearned my favourite rule: colour should serve the joke, not the marketing department.
Growing up in Perth, I had almost no access to great art—just beach paintings and dial-up internet. So I learned from cartoonists like Roz Chast, Richard Thompson, and Ronald Searle, whose trauma and humour somehow coexisted in ink. My grandfather gave me Searle’s book after surviving a POW camp, so I guess drawing as coping runs in the family.
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"I thought maybe two or three people would say, 'Thanks, I'll take one,' because people love free stuff, right?" Instead, what happened was this: nearly 1,200 artists, illustrators and designers have contributed their own versions of her drawing to a growing gallery of unique images. The hashtag #hibadge2024 exploded across Instagram. Fast Company featured the movement, calling it exactly what it was: a small revolution.
Artists from the US, UK, Spain, Germany, Brazil, and Colombia started recreating Beth's scrappy little sketch in their own styles—watercolour, clay sculpture, minimalist doodles, bold hand lettering. Each one a tiny act of defiance against the algorithmic tide.
The Accidental Revolutionary
What makes this story so perfectly Beth Spencer is that she never set out to be the face of artistic resistance. "I didn't intend it as anti-tech, but as pro-human," she explained in a later interview. It wasn't about burning the machines—it was about celebrating the messy, imperfect, beautifully human process of making things with your hands.
"No software has lived life the way you have," she wrote, which might be the most succinct argument for human creativity I've ever heard. While AI churns through datasets looking for patterns, we're out here stubbing our toes and falling in love and watching our pets do ridiculous things and somehow turning all of that into art.
The badge caught fire because it crystallised something artists had been feeling but couldn't quite articulate: that there's value in the struggle, in the years of patient labour, in the way your hand shakes just slightly when you're drawing something that matters to you.
Why Beth Spencer Matters (Especially to Weirdos Like Us)
I started following Beth's work long before the badge went viral, back when she was just this thoughtful voice encouraging people to make bad drawings and be okay with it. What struck me wasn't just her art—though her loose, playful style has this wonderful "I'm having fun and you can too" energy—but her approach to the whole enterprise of being creative.
In her Zoom drawing sessions (yes, she runs fantastic live drawing sessions), people ask what supplies she's using, and half the time the answer is something from Dollar Tree. "My favourite things are these," she'll say, holding up a 75-cent brush pen that she swears works better than the fancy $11 ones.
This is revolutionary stuff, people. While the rest of us are bankrupting ourselves at art supply stores, convincing ourselves we need the right tools to make good art, Beth's over there making beautiful work with discount store markers and having an absolute blast doing it.
The Goat Whisperer
Beth has this thing with goats. (So do I.) It started after what she calls a "crushing career blow"—a book deal that fell through after she'd already told everyone about it. (Anyone who's had a creative project implode knows this particular circle of hell.) Instead of wallowing, she found a community garden in Memphis with goats and started drawing them.
"They're symbols of good in the world," she told me. And watching her capture these ridiculous, stubborn, oddly expressive creatures in her sketchbooks, you start to see what she means. There's something about the way goats exist in the world—unapologetically themselves, slightly chaotic, always ready to try climbing something they probably shouldn't—that feels like a metaphor for the creative life.
The goats led to other animals, which led to a broader philosophy about drawing from life instead of photos, about getting off your phone and actually looking at the world around you. It's David Sedaris's advice about living the "head-up life" translated into artistic practice.
The Introvert's Guide to Making Art
What I love most about Beth's approach is how it flies in the face of everything we're told about building a creative practice. No morning pages. No elaborate studio setups. No complex systems for tracking progress or measuring improvement.
Instead, it's: show up, make marks, be kind to yourself about the results. Draw the goat even if the goat looks like a potato with legs. Use the cheap markers. Take breaks to watch your cat knock over the paint water. Post the terrible stuff alongside the good stuff because the terrible stuff teaches you something, too.
Her drawing challenges aren't about competition—they're about community. People sharing their wobbly self-portraits and their wrong-colored flowers and their attempts at human hands (the Everest of artistic endeavours, as any cartoonist will tell you). Each submission is a tiny victory against the voice that says you're not good enough, not qualified enough, not artist enough to make things.
The Bigger Picture
The "Created with Human Intelligence" badge became a phenomenon because it gave artists something they desperately needed: a way to claim their space in an increasingly algorithmized world. But Beth's real contribution goes deeper than any single viral moment:
She's created a corner of the internet where it's safe to be a beginner, where process matters more than product, where the goal isn't perfection but connection. Her Substack feels like having a conversation with that friend who somehow makes you feel better about everything just by being themselves. In a time when everyone's trying to scale and optimise and hustle their creativity into submission, Beth's out there saying, "What if we just drew some animals and felt good about it?"
And somehow, that quiet revolution—one terrible drawing at a time—might be exactly what we need.
If this made you want to pick up a pencil (even a Dollar Tree one), that's Beth Spencer's magic working exactly as intended. Check out Beth's work at Introvert Drawing Club and follow her drawing adventures @bethspencerart. Fair warning: you will end up buying art supplies you don't need and feeling optimistic about your artistic abilities. Consider yourself warned.
Forward this to that friend who still thinks they "can't draw." Everyone can draw badly, and that's the point.
His analogy is perfect: "Tension to a comedian is what waves are to a surfer." You don't paddle away from waves – you learn to ride them. "Laughter is tension released, so if you've got them feeling tense, that's not necessarily something to run away from."
This isn't just theory. Matt's 2020 special tackled cancel culture not by taking cheap shots, but by genuinely exploring the discomfort around what we can and can't say. The audience doesn't know where he's going, which creates that crucial tension that great comedy requires.
The Substance Experiment: Malcolm Gladwell Meets Morgan Spurlock
Matt's most audacious project remains Substance, where he performed stand-up under the influence of alcohol, weed, mushrooms, and completely sober. As his friend Gina noted, "It makes sense because you have your 10,000 hours in all of those things."
The results were revelatory. Alcohol, he discovered, is "the worst possible drug there is" for performing. "I felt like I had broken a contract with the audience... as soon as the audience hears you slur, all bets are off."
The drunk set was all ego: "I'm doing great, they love this." The mushroom set was complete ego loss: "This is about us, what can we do together?" One drug builds walls, the other tears them down – a perfect window into what these substances actually do to human consciousness.
The Chris Rock Rule and the Death of The Hang
One of the most practical pieces of advice Matt shared came from Chris Rock: "If there's anything that you've talked about three times in your life with someone else, try talking about it on stage." The logic is bulletproof – if you've brought it up three times, you clearly care about it, and that authentic investment is what audiences crave.
But here's the problem: The Hang is disappearing. Matt came up in the era of Rififi, "this video store that had a bar," where comedians would stick around after shows and actually talk to each other. "After the show, everyone would just hang out and there'd be like this great hang of comedians who were on the show, newer comedians, people who just wanted to be in the scene."
Now? "Everyone's just sort of in their silos. Even when you go to a comedy show, people do their spot and then they leave afterwards." The green room that used to be full of ball-busting and zinging is now just "comics huddled over their phones."
This matters because Matt's best material comes from real conversations: "A lot of my favourite jokes or ideas for jokes don't come from sitting down at a laptop... It comes from having conversations with cool, interesting, smart, funny people." When a joke originates from genuine conversation, "the audience can perceive on stage... that's who you really are."
Meditation, Mushrooms, & the Pursuit of Presence
Matt's been meditating since childhood – his mom had a meditation room. His joke: "The first time I ever smoked weed, I was like, wow, this smells a lot like my mom's meditation room."
But his approach to mindfulness goes deeper than nostalgia. He sees meditation as "the antidote to being online and on screens all the time." We've eliminated daydreaming because we have "this IV drip of content available to us at all times," and meditation might be the only way to access that generative, wandering state our brains need.
The connection to comedy is profound. Both meditation and the Chris Rock rule operate on the same principle: "What keeps arising?" In meditation, you notice what thoughts keep coming up. In comedy, you notice what topics you keep returning to. Both are revealing something essential about who you really are.
The Crowdwork Apocalypse
Matt has thoughts about the algorithmic dominance of crowd work clips, and they're not pleasant. "It's weird to me that it did pivot into being like a dominant version of the art craft... as perceived online by people who just see it on social media."
The problem isn't crowdwork itself – it's that the algorithm loves it because it provides instant context and the voyeuristic thrill of strangers interacting. "So many people online are just alone and on a screen all day. And it is like, Oh my God, look, look at these two people who don't know each other interacting."
But here's our real shared grievance: "We're all just being slaves to the algorithms and I feel not great about having my entire art form pivot because it's what helps out Mark Zuckerberg and the Chinese government. I don't want those people determining what makes good art."
His solution? "Burn it away. Burn it" regarding material protection. "Most of the world's never even going to see it in the first place. So spread it out there. Put it out again."
The Loud-Soft-Loud Dynamic
Matt's musical background in Chicago rock informed more than just his rhythm – it gave him a framework for understanding comedy dynamics. "I love Led Zeppelin or the Pixies or that sort of loud, soft, loud dynamic and how one buys you the other."
In comedy, this translates to using silly material to buy bandwidth for deeper content. "Being silly and dumb can buy you being deep and melancholy." You can see this in Louis C.K.'s work, where "you might have something like the deepest philosophical bits and then you're gonna have like a fart joke."
The principle extends beyond individual sets to entire careers and even political discourse. "Maybe there's not one right answer. Maybe there are two poles... swinging like a pendulum instead of just trying to bully your way through like a battering ram."
Surfers, Gardeners, and Universal Wisdom
Matt's got theories about who understands the universe best, and they're surprisingly specific: surfers and gardeners. "I think surfers and gardeners sort of understand the universe in some really deep ways that the rest of us can learn from."
Gardeners understand "seasons and having a fallow period and blossoming and planting seeds and nurturing things." Surfers understand "the rhythm of the universe and waves... using the energy of the universe and enjoying when you're on the wave and also realising the wave's going to end."
Both activities force presence and acceptance of natural cycles; exactly what our screen-addicted culture has forgotten.
The Shamanic Art of Energy Management
Watching Chappelle work a small room gave Matt a revelation about comedy's deeper purpose: "I remember watching him do a set at Comedy Cellar... really feeling like, oh, this is very shamanic in how he's using the energy and playing with it."
Chappelle would push the audience away with challenging material, "making them recoil, making them be like, I don't know about this at all. And then masterfully pulling them back in via laughter." It's a push-pull technique that takes decades to master.
This connects to something profound about grief and laughter that Matt's explored: "During the process of death and grieving, how much is hilarious... because we just can't exist in that realm of tension all the time, 24 seven for weeks on end." The biggest laughs often come at funerals because "your body's craving it."
The Antidote to Everything
For Matt, live comedy represents something essential we're losing: "I get to be in a room with a room full of people who are not on their screens, who are aligned with a bunch of strangers and who are experiencing joy. And it's like, Oh, thank God... this is how we're supposed to be."
The communal experience of comedy – like going to church, AA meetings, or book clubs – offers "synchronised nervous systems" and connection to something larger than ourselves. "There's something innately that we know inside that makes us feel like the world is okay and that we're connected."
Meanwhile, screens are "pressing this button in our head where they can frack our brain stems and make us angry because it's a great way to monetise us."
Robot or Animal: Choose Your Future
Matt's vision of the future is stark but oddly hopeful: "I think there's probably some path where you choose between robot or animal in the future." You can have your Neuralink and AI girlfriend and live in virtual reality, "or you'll be an animal who has to deal with human emotions and not knowing stuff and getting lost."
His choice? "I'll choose to get lost."
The Holy Grail of Stand-Up
Throughout our conversation, Matt kept returning to what he calls "the holy grail of a good stand-up comedy joke" – material that comes from who you really are, discovered through genuine conversation and real caring. "That's who you are. You're offstage just having some drinks with a friend of yours, and it's what's coming out of you."
When material originates from this authentic place, "there's some harmony that goes on when a joke arises that way that the audience can perceive." It's not about pandering or trend-chasing – it's about finding what you actually care about and trusting that your genuine investment will translate.
(My text with a comedian today about how I accidentally ordered too many bananas resulted in them telling me ‘that’s a bit’ and then me spending this afternoon building it out into a bit I will try tonight. You should come. West Side Comedy Club, 8pm.)
The Rebellion of Presence
Despite his concerns about our algorithmic future, he maintains faith in human rebellion: "I think if people are miserable, eventually that bubbles up in a way that they're like, I don't want to do this anymore."
His work – both on stage and on Substack – feels like part of that rebellion. By examining comedy with philosophical rigour, by treating consciousness as worthy of artistic exploration, by insisting that attention and presence are the real currencies of art, he's making a case for choosing the human over the algorithmic.
In a world increasingly designed to fragment our attention and monetise our outrage, Matt Ruby is doing something quietly radical: He's asking us to sit with ourselves, notice what keeps arising, and trust that our authentic obsessions might just be the thing the world needs to hear.
And if that's not wisdom worth paying attention to, I don't know what is.
Here's where it gets even more interesting: Nishant's "tiny people" aren't tiny just because of scale —though they are ridiculously small. As he explained, "What makes them tiny is that they are observations of a few seconds. And as a result, they are very heavily filtered. There's just no time or scope for me to draw everything about them."
The filtering is the point. These drawings capture how we actually experience most people in our daily lives— fleeting impressions on buses, in cafés, walking past a window. "We notice heels, we notice clothes, maybe we notice somebody's hairstyle or something they said, but we don't remember everything."
Some key insights we covered:
Writing = Drawing:"Both writing and drawing are about putting together lines and shapes to give meaning to things." He breaks down faces into the letter D, ears into the letter C, and legs into half of the letter H. Suddenly, drawing feels less like some mystical skill and more like... well, writing.
Outside in, not inside out: Instead of getting caught up in facial features first, Nishant starts with the ear and works outward to capture posture and movement. "From the ear, I can go up and I can do the scalp and I can go down, and I can do the jaw." This way, even if someone moves, you've already captured what matters most.
Trust your line:This might have been the most important lesson. "When I make a long, continuous line, it has my blood pressure in it. It has my heartbeat in it. It has my nervousness in it. It is a very unique thing that only I could do in that way." Don't hedge, don't hem and haw - commit to the line.
The Miles Davis Principle
Nishant shared a quote from Miles Davis that I love, and perfectly captures the evolution from accident to intention that every artist goes through. I had this quote taped above my desk for years, so hearing someone else reference it felt like finding a kindred spirit.
"Once is a mistake. Twice is an idea. Three times is style."
On Permission & Authenticity
One of the more profound moments came when we discussed artistic permission. Nishant noted how "We think that we shouldn't need permission, but that's why we have other people in our world— we need permission from each other to live our lives." Every time an artist shares their work, they're potentially giving someone else permission to try.
This connects to his broader point about artistic authenticity: "Art is just human expression, and everybody should be doing it. But because we get hung up on it needing to look a particular way —It needs to look so good or it's not worth it— We keep denying ourselves this beautiful thing that is accessible to all of us."
The Sneaky Art Advantage
What I love about Nishant's approach is how it solves multiple problems at once: By drawing quickly and "sneakily," you avoid the paralysis of perfectionism. By focusing on fleeting observations, you develop a more present, mindful way of moving through the world. And by working small, you build what he calls "a vocabulary or a library of good lines" without the pressure of creating masterpieces.
Plus, there's something beautifully democratic about it. You don't need an easel or perfect lighting or even conventional artistic "talent" - you just need curiosity about the people around you.
"The worst time to be an artist is the best time to be an artist."
There's something both sobering and inspiring about the quote above that he heard from a comedian friend— a reminder that creating authentic work has always been challenging, but perhaps that's exactly what makes it valuable. I guess we’ll find out in these coming years.
As someone who spent way too much time trying to draw an iguana playing golf using Nishant's techniques (thanks for the request, Hue Walker), I can now say his approach just works. It strips away the intimidation factor and gets you focused on the joy of observation itself.
If you're looking for a different way to see the world, or just want to follow along with some of the most thoughtful writing about creativity and observation, I highly recommend subscribing to The Sneaky Art Post. Nishant has a course on drawing tiny people, and his book "Make Sneaky Art" comes out in September. His work reminds us that sometimes the most profound art happens not when we're trying to impress others, but when we're simply paying attention to the world around us.
The New Yorker fact-checks cartoons. Tom once got a note asking if he could make a drawing “less vaginal.” (Three lion manes forming an unfortunate composition.) “I had a baseball cartoon flagged because I’d drawn a left-handed catcher—apparently, there hasn’t been one in the majors since 1972. They let me keep it, but wanted me to know.”
These notes are rare, which makes them oddly precious. “It’s nice to know there are eyes on it,” Tom said. Most of the time, cartooning is just the Roman Coliseum—thumbs up, thumbs down, see you in twelve years.
AI Can’t Make Good Mistakes
We talked about AI creeping into cartoon spaces, and Tom’s theory hit hard: AI can’t make good mistakes. It can mimic, reproduce, even generate six-fingered hands by accident—but it can’t make the artful mistakes that lead you somewhere unexpected. The kind that gives a drawing its heartbeat.
“Maybe it’s incumbent upon artists to keep pushing ourselves to realms of discomfort,” he said, “where we just make more beautiful mistakes.”
That’s the hope. That’s the work.
Tom’s on tour all month—Powell’s in Portland this Friday, then Connecticut, New York, Boston. If you’re near any of those spots, go hear him talk and get your book signed. Support cartoon collections. Raise all boats.
"Don’t draw a ‘New Yorker Cartoon’, draw an Asher Perlman cartoon that could be in the New Yorker."
This feels like the kind of obvious wisdom that's only obvious after you've bashed your head against the wall for years trying to be someone else.
The Comedy Economics of Hack
Both Asher and I shared war stories about the delicate economy of comedy crowds. His Second City experience taught him that audiences of comedy people versus regular people laugh at completely different things.
The example that stuck: during the Cubs' historically bad years, any joke that simply acknowledged their terribleness would reliably kill with regular audiences, while comedy vets groaned at the predictability.
I confessed to deploying hack MC material at tourist-heavy shows, earning eye-rolls from grizzled road comics. The unspoken rules of what's permissible comedy form our intricate ecosystem—one where Ellis serves as our "encyclopedia of cartoons," helping determine what's been done before.
Digital vs. Analogue Romanticism
Both of us admitted to fetishising paper and pen while acknowledging the seductive convenience of digital tools. Asher confessed to tapping his page to try to undo lines when working on paper. I noted how the digital safety net makes me more confident but less skilled—a creative paradox worth pondering.
By some miracle, our technical discussion revealed practical wisdom: 80-pound paper works well with iPad light boxes, draw faces first to avoid redoing entire backgrounds, and always have a brutal filing system that you'll inevitably hate.
From Hackery to Substackery
Asher had just joined Substack a month ago, and his description of the platform was refreshingly honest: "It feels like what I wanted Instagram to be, but it never was." My strategy mirrored my cartooning breakthrough—stop trying to copy what successful newsletters do, write for your own people, and celebrate the unsubscribes.
The platform discussion highlighted a broader shift away from algorithmic manipulation towards intentional consumption. As Asher put it: "I prefer things that exist outside of the algorithm now because I don't like being catered to my worst instincts."
The Bell House Launch
We wrapped with excitement about Asher's book launch at Bell House, featuring Gary Gulman, temporary Eugene tattoos, and what sounds like half the New Yorker cartooning community.
Related Reading:
Asher's journey from frustrated imitator to distinctive voice serves as both a cautionary tale and an inspiration—a reminder that the path to originality runs directly through the abject horror of just being yourself.
Thanks to everyone who tuned in to the live stream!‘til next time
Your pal,
Next week: Tuesday at 12pm, I'm chasing down Kevin “KAL” Kallagher to talk to him about his 50+ years as a working cartoonist for the Economist and —until recently— The Baltimore Sun. Add it to your calendar now!
The old system was beautifully archaic: Tuesdays for the seasoned cartoonists, Wednesdays for the "young upstarts" like Liza, Roz, Jack Ziegler, Mick Stevens, Bob Mankoff, and Sam Gross. After submissions, they'd go to lunch at places like The Quiet Man (an Irish bar) or The Century, sometimes hit a Mets game, and occasionally go down to Tin Pan Alley to shoot pool.
"Before we went to lunch, we would go to the other magazines, take your little envelopes of your rejects from the New Yorker, and you'd go to other places," she explained. The rejection tour included National Lampoon (where she sold her first cartoon), Good Housekeeping, Cosmopolitan—places that actually paid cartoonists, unlike today's one-shop reality.
The Live Drawing Revolution
Liza's been doing live drawing on streaming since way before it was cool. She started during the 2016 State of the Union, using an iPad with Paper 53 and one of those chunky styluses that Apple doesn't make anymore (she had to stockpile them like they were cartoon gold).
"I drew these quick drawings of what I was watching and put them on Twitter immediately because the app connects to Twitter. And nothing was like that yet on that platform at all, really. So it took off, and that's when my live drawing career sort of happened."
This led to everything from drawing the Oscars red carpet to being the first cartoonist credentialed for that gig, to courthouse sketching during Trump trials (where electronics weren't allowed, forcing her back to paper and pen like some kind of analogue warrior).
The CBS Morning Show Years and the Implosion
For about four years, Liza worked for CBS This Morning, live drawing guests and hosts, connecting their social media with the actual broadcast. They sent her to the White House, the DNC, debates—until CBS imploded with the Les Moonves and Charlie Rose scandals.
"CBS imploded, you know, Les Moonves and Charlie Rose and all that sort of—CBS imploded. And I was no longer," she said, with the casual tone of someone who's watched media empires crumble before breakfast.
"Women Laughing" Documentary
The big news is Liza's documentary "Women Laughing," which is finished and premiering in New York this fall. The New Yorker will publish it on their site, and Katie Couric (who once commissioned me to draw a deliberately bad caricature of Larry David for Sardi's) is executive producer.
The documentary features drawing sessions with contemporary women cartoonists at the Society of Illustrators, because, as Liza noted, "cartoonists are relaxed when they're drawing." It's a 35-minute short that traces the arc from the magazine's early women cartoonists through today, when about half the contributors identify as female or non-binary.
"We talked and drew at the same time because it's something that I've done with my children. And I know it's a way people are relaxed, at least cartoonists are relaxed when they're drawing," she explained.
The Rejection Game and Reinvention
We talked about The New Yorker's brutal rejection rate—drawing eight to ten ideas a week, maybe selling one if you're lucky. It's almost masochistic, but as Liza pointed out, "without that rejection, the ability to tolerate rejection, you're not going to really last long in cartooning."
"You and I, we have to really start reinventing ourselves because there's no... Magazines are dying, are almost dead, and there are no outlets for what we do, really, much. So that's why we do the live drawing, that's why we do the Substacks."
The Competition Problem
The conversation took an interesting turn when we discussed how editorial cartoonists are now competing with everyone from late-night TV shows to memes. Jon Stewart's Daily Show was one of the first to clip segments and put them online as short, opinionated, humorous pieces.
"I thought, well, that's, that's like, they're taking our job, but with video," Liza observed. "We've been in competition with memes, you know, also memes and clips of comedians doing what we do."
But there's something cartoons can do that video can't: work without language barriers, distil complex ideas into simple images, and translate across cultures in ways that English-language comedy can't.
Freedom Fighters vs. Court Jesters
I mentioned attending the RIDEP cartooning conference in France with political cartoonists from around the world—people from Tunisia, China, Sudan who had been exiled for their work.
"I kept thinking, I was talking to the American and British people... and I was saying, you know, I feel like we're so lucky, you know, we're court jesters, it feels like, whereas these people feel like freedom fighters."
It hits differently now, especially considering the current political climate and the increasing pressure on editorial cartoonists in the US.
The Herblock Story
The session ended with Liza sharing her story of meeting Herblock—her childhood hero—at a gallery opening of New Yorker cartoons in Washington in the early 80s. He came to support the younger cartoonists, pointed to her first published cartoon (a dog cartoon), and said he liked the simplicity.
"I was so scared," she admitted. Which is perfect, because meeting your heroes should be terrifying. It means they still matter.
The Three-Eyed Alien Asking a Pig for the Time
Dan McConnell in the chat requested "a three-eyed alien asking a pig for the time," which sounds apolitical until you remember that everything can be political if you squint hard enough. Or if you're drawing pigs, which, as someone pointed out, could be very Orwellian.
"Everything can be political if you think about it," Liza said, while drawing in seven lines what I couldn’t draw in seventy. I drew what was supposed to be a friendly alien, but looked more like it had strong opinions about municipal parking regulations.
The Technical Stuff
For the gear nerds: Liza uses a thick mechanical pencil (she forgot the brand), Hunt 107 nibs, and various dip pens. I'm still wrestling with my Blackwing pencils, trying to make live drawing look less like performance art and more like actual cartooning. I’m using the Hunt 101 Imperial dip pen nib.
Liza's Substack, "Seeing Things," is great reading for anyone interested in how cartoons can cut through political noise with humour. She posts daily, which is both admirable and slightly terrifying.
Next Thursday at 12 PM, Kevin KAL Kallaugher joins us for DMA #26. Kal's got this ability to distil complex political ideas into powerful images without captions, and he draws with traditional tools on a proper wooden drafting board like a civilised human being.
Our conversation took a serious turn when we talked about Charlie Hebdo. Ann and I were both in the States when the 2015 murders happened, and like me, she felt that gut punch of "sadness and fear and fury." But here's where it gets interesting – and uncomfortable.
"At first, everybody was all... ‘Je Suis Charlie!’, Free speech! —and everybody was together," Ann recalled. "Then, all of a sudden, at least in this country, there started to be a divide." She strained friendships over defending those cartoons. So did I. "I discovered that I definitely am a free speech absolutist because I don't think you go down that path where you start talking about what you can and cannot draw or say."
Her line in the sand is crystal clear: "You're just not allowed to kill people because you disagree with them." The moment someone justifies murder with "Yeah, but the cartoons…" they've lost the argument immediately.
RELATED:
The Kitchen Counter Revolution
Here's something that blew my mind: Ann still works at her kitchen counter. This absolute legend, who's been skewering politicians for decades, is creating her masterpieces at the same place most of us eat cereal.
Her style evolved out of pure practicality. When she started, she tried to copy the McNally crosshatching approach that everyone was doing. "I realised I couldn't do those cartoons very fast. And in business, you have to work fast." So she just started doing them in her own style fast, using the brush and ink techniques from her animation background.
Sometimes the best artistic breakthroughs come from just figuring out how to pay the bills.
The Art of Evolving Evil
One thing that fascinates me about Ann's work is how her caricatures evolve. She doesn't just create one version of Dick Cheney and repeat it forever. "For me, a caricature is more about who a person is inside rather than how they look outside," she explained. "I wouldn't say that my Cheney looks like Cheney, but it certainly feels like Cheney."
This is particularly evident in her Musk cartoons. As I told her, "Your Musk evolved as he devolved." If you did a retrospective of her Musk drawings, it would show this terrifying de-evolution from celebrated businessman to... whatever the hell this is. Her recent cartoon of Musk strung out in an alley with needles around him perfectly captured not just his downfall, but the Greek tragedy of watching it happen in real time on our collective screens.
The Pat Oliphant Revelation
Ann shared an incredible story about how Pat Oliphant transformed his art. In the '60s, his style was much more cartoon-y. But when he went to speak at the Corcoran School of Art, he noticed they were teaching life drawing and decided to sit in. That's when his incredible draftsmanship really developed.
Ann's advice? "If you want to learn to draw, go take life drawing classes. I still take them." She goes to open sessions to draw the figure because "the best way to really understand foundation, to understand shapes and make your cartoon solid" is to master the fundamentals.
It's a reminder that even legends are still learning.
The Panic That Powers Creation
What drove Ann to political cartooning? Two specific moments: watching the Tiananmen Square massacre in 1989 while working on a freelance gag cartoon project, and then the Anita Hill/Clarence Thomas hearings.
The Anita Hill hearings particularly enraged her because "I was a young woman who had worked, and I had dealt with sexual harassment, and I knew all this crap that these senators were arguing about... They knew absolutely nothing about the reality of sexual harassment for women."
These moments awakened something in her: "I finally took my love of art and drawing and combined it with something, and it really clicked for me." Sometimes you need to get angry enough to find your voice.
The Mission-Driven Gender Gap
Ann has a fascinating theory about women cartoonists. There were maybe 17 or 18 working women cartoonists during the suffrage movement. "But once they got the vote, they all quit." The pattern suggests women cartoonists are driven by a mission: "We have a mission, right? We have other things, but we have to do this."
It's a different relationship to the work, less about career, more about necessity. When there's injustice to fight, women pick up their pens. When the immediate battle is won, they move on to other ways of making change.
The Real Housewives Administration
Our conversation kept coming back to the Trump-Musk fallout, and Ann captured it perfectly: "It's like watching Real Housewives except there are real-world consequences." These aren't just personality conflicts – they're affecting international relations, democracy, society, and the entire government.
The fact that two of the most powerful people on the planet are conducting their beef online makes it even more surreal. As I pointed out, "It's also performative. It's not like they're doing this in person." The online disinhibition effect is amplifying everything to a level that's "affecting our international reputation."
Why We Can't Check Out Now
Despite the exhaustion, Ann's message is clear: this isn't the time to tune out. "I had a lot of friends who just basically checked out of the news because they're tired... But I don't think now is the time to do that."
Her practical advice: "You can listen to the radio news while you're getting ready in the morning. Just keep updated on things because this administration is throwing things faster than anyone can even process them."
And then do something about it: "Call your representatives, go join a protest, make some noise because that's the only thing that's going to help us."
The Historical Echo Chamber
Our conversation got darkest when Ann talked about her German relatives and how she's always wondered how educated, normal people got "sucked into something like a Nazi government, a Hitler regime." Her conclusion is chilling: "I see it now."
"We have a guy in office right now who is definitely playing... to people's fears. Autocrats do that in order to get power and keep it." It's not hyperbole when you're watching the playbook get executed in real time.
Cartoonists’ Response to Chaos
What struck me most about talking to Ann is how cartoonists process chaos differently. We don't just report on it – we distil it, exaggerate it, make it impossible to ignore. When democracy is under siege, political cartoonists become war correspondents armed with brushes instead of cameras.
Her work during the Bush administration, particularly her devastating takedowns of Dick Cheney, remains some of the most prescient political commentary of that era. But as she noted, "now is a more frantic time with Trump and more urgent."
The question is: how do you capture the surreal when reality itself has become a cartoon?
Drawing Through the Apocalypse
As we wrapped up our chat, I was struck by Ann's combination of clear-eyed realism and stubborn optimism. Yes, we're watching democracy get stress-tested by megalomaniacs. Yes, it's terrifying. But we're also watching artists, journalists, and citizens refuse to normalise the abnormal.
Ann's still at her kitchen counter, still going to life drawing classes. She's documenting the decline while fighting against it, one cartoon at a time.
In times like these, maybe that's exactly what heroism looks like: showing up every day and drawing the truth, even when –especially when– it's too absurd to believe.
He also does talks for organizations such as Pixar, Google, Netflix, SXSW, TEDx, Dropbox, Adobe, and The Economist. This is the kind of client list that makes freelancers weep into their instant noodles.
With that intro out of the way, here is the recap of our conversation. At the bottom, I’ve also included a full list of books recommended or discussed during our one-hour talk.
Comedy Over Tragedy: What Austin Kleon Taught Me About Creative Survival
Yesterday, I had the pleasure of chatting with the brilliant mind behind Steal Like an Artist, Show Your Work, and my personal favorite, Keep Going. What started as a conversation about creative routines turned into a masterclass on attention management, the importance of play, and why treating your art like a comedy might be the secret to actually surviving as a creative person.
The Magic of Knowing What You Like
Austin started by dropping one of those deceptively simple truths: "Knowing what you like is this kind of magic tonic for your attention." It sounds almost embarrassingly basic, but as he pointed out, "we live in this world where everyone else is trying to tell you what to like constantly."
The problem? If you don't know what you actually like, "how are you going to know what you're supposed to make? Because really, what we make is more stuff like we like. We take all the things that we like and we put them together and that's our work."
This hit me hard because in previous years, I've been guilty of the exact opposite: creating things that get likes rather than things I actually like.
Austin's approach is refreshingly honest: "Only I actually know what I like, right? And so my reading life, for example, is so much richer when I just focus on what I really, really like to read."
The Brian Eno Prescription for Focus
Austin's been studying Brian Eno for over a decade, and shared Eno's current obsession with attention management. The key insight: When you truly know what you like, “you can tune in to what you're supposed to be paying attention to. It gives you focus."
This connects to something profound he observed about kids: "Kids know what they like, especially know what they don't like." They're naturally discerning in a way we somehow unlearn as adults. As Austin put it, his kids were "almost like an executive... they were very, I like that. I don’t like that—and I loved it." (He has a book coming out soon called “Don’t Call It Art” expanding on the value of this insight.
The Artist's Survival Guide
Here's where things got real. Austin shared a quote from art coach Beth Pickens that completely reframed my thinking about creative work: "Artists are people for whom their life is less when they don't work." Not that they can't do anything else, but that "my life suffers when I'm not making stuff."
The guilt around "selfish" creative time dissolves when you realize you're not just indulging yourself – you're showing up to your work, so that you can feel more alive inside, so that then you can show up for other people.
The Tragedy vs. Comedy Framework That Changes Everything
This might have been the most brilliant part of our conversation. Austin breaks down how most people think about art through the lens of tragedy: "a very special person with a gift who struggles and fights against the world... and then you know, it takes a great toll on them. So they have to shoot up heroin or whatever. And then when they get success, they get rich and they drink themselves to death."
But there's another way —the comedy approach. In comedy, you have "an ordinary person, just a regular person, maybe even a lowly person... And what they do is they bumble, they fumble, they improvise... but their fatal flaw, they don't really have a fatal flaw. What they have is their wits."
The beautiful thing about a comedy? "There is no success in a comedy. There's just failure after failure, basically. But what happens at the end of a comedy is... celebration, a wedding... People coming together at the end."
Austin's thesis: "To take a comedic approach to art and creativity is to accept yourself as an ordinary person that gets into trouble, gets in over their heads, but relies on improvisation and their wit... and play."
The Survival Mechanism of Humor
This isn't just feel-good philosophy – it's a practical survival strategy. Austin referenced Survive the Savage Sea, about a family adrift at sea for 40 days. When asked what helped them survive, the father said, "a well-developed sense of the absurd."
As Austin put it: "Comedy is not just for fun, happy times. Comedy is a survival mechanism." Mel Brooks echoes this: "If you have a sense of humor, you can get through things."
The Mathematics of Showing Up
When we talked about routine and consistency, Austin brought it down to simple math: "One day doesn't feel like much, but... if you can do one page a day, at the end of one year, you have 365 pages. That's enough for a book."
But here's the kicker —it's not just cumulative, it's exponential. Using a prickly pear cactus as an example, Austin showed how creative work compounds: "Every day isn't worth the same. If you show up every day for 365 days, the 366th day is actually going to have more power than the first day."
The Time Timer Revolution
One of the most practical tools Austin shared was his beloved timer. The paradox of creative time management: "If you want to disappear, set a timer... if you want to make time disappear, you need to work with time."
Here’s the one I have on my desk:
His process is beautifully simple: "You block off an hour tomorrow. You block it off on your calendar where no one can get to you... Then you sit down at your desk, and you set a timer for 60 minutes. Then you see what happens."
The Hobby Resistance Theory
In a fascinating tangent, Austin shared George Orwell's theory that the British "penchant for hobbies helped them resist fascism" because "people with hobbies were able to resist fascism more because they were able to spend time alone... they didn't need some sort of demagogue to tell them what to do."
His conclusion? "I think something that's happening in American culture is nobody has any hobbies anymore. And so they're just looking around for someone to tell them what to do." The solution might be as simple as more people getting into woodworking.
Finding Your Creative Comedy
What struck me most about his approach is how it removes the pressure to be a tortured genius and gives you permission to just be a regular person who makes stuff. As he said, "I think almost 99% of people shouldn't try to make their creative work their job. I think almost 100% of people should have some sort of creative practice."
The goal isn't to become the next tragic artist hero; it's to show up, play, bumble through, and maybe bring people together in the process. As he beautifully put it: "The arts have traditionally been a place for people that weren't super great at life... because they struggle with life, they give us this great art."
So maybe the secret isn't learning to suffer for your art – maybe it's learning to laugh with it instead.
I’m grateful to Austin for his time and insights— this was one of the best conversations I’ve had, and I’m lucky I got to have it.
Jessie and I agreed: restriction is, in fact, a form of freedom. Fewer colours, fewer brushes, fewer excuses. Watercolour is chaos in liquid form, and the sooner you stop trying to control it, the more alive it becomes.
I’m still working on that part—the unclenching. But at least now, when my washes go rogue, I can say: It’s philosophy.
‘til next time, your pal,
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