The Productivity Trap

What happens when the drive to create something great becomes the very thing that stops you from making anything at all?In this random-show episode of The War with Art, we talk about the post-TennoCon crash, the pressure to always be productive, and what happens when optimizing creativity starts to kill the joy of creating.From reading physical books and rediscovering old musical tastes to experimenting with the opposite of our usual habits, we explore the value of curiosity, rest, and making things simply for the fun of it.Maybe getting unstuck doesn't mean working harder. Maybe it means making mistakes, following unexpected interests, and remembering how to play.In This Episode00:00 — The post-TennoCon comedown and the creative void that follows a big project.03:30 — Books, dreams, and giving your brain room to wander.06:00 — The surprising satisfaction of making things away from a computer.09:00 — Curiosity, wonder, and trusting the creative process.12:00 — The Shining and the dangers of all work and no play.14:30 — An experiment in doing the opposite of your usual habits.19:00 — When productivity becomes the enemy of creativity.22:00 — Why mistakes and detours aren't necessarily wasted time.24:00 — Remembering how to play without worrying about the outcome.Books and Ideas MentionedWind, Sand and Stars — Antoine de Saint-ExupéryAcid for the Children — FleaBig Magic — Elizabeth GilbertTao Te ChingThe ShiningThanks for listening to The War with Art, where we talk about the messy, frustrating, occasionally ridiculous business of trying to make things.

George, Eric, and Sheldon draw another prompt from Brian Eno and Peter Schmidt’s iconic Oblique Strategies deck. This episode’s pull delivers a simple yet provocative constraint: "Use an unacceptable color."From out-of-key "blue notes" in jazz and microtonal progressive rock to structural leaps in Dostoevsky’s The Brothers Karamazov, we explore how breaking established rules creates lasting friction. We dive into visual art history with Hans Holbein’s 1533 painting The Ambassadors—and its jarring 3D anamorphic skull—while sharing personal anecdotes on using deliberate oddities to unstick graphic novels, music production, and newsletters.The conversation closes on a reassuring truth: leaning into "unacceptable" creative choices isn't just a trick to surprise an audience—it's often the precise spark required to entertain yourself and jumpstart stalled momentum.Timestamps 00:24 — Wilderness edition in Kincardine and Oblique Strategies intro02:04 — Pulling the card: "Use an unacceptable color" 02:46 — Breaking key signatures: Out-of-bounds notes in music 05:54 — Graphic novels and structural contrast in Aardehn07:48 — Mold-breakers and unexpected choral shifts 08:54 — Dostoevsky, Moby Dick, and jarring tonal shifts in literature 11:45 — Visual contrast and the anamorphic skull in The Ambassadors 13:28 — Blue notes, microtonal guitars, and playing between the frets 18:24 — Secret themes and using weird constraints to unstick writing 20:38 — How absurd prompts kickstart creative momentum

A small victory in the War with Art. In this episodeWhat it actually feels like to finish a major creative projectThe strange emptiness that can follow years of focused workWhy finishing something can feel a little like grievingLearning to accept that a work is finished—even when you can still see things you'd changeThe transition from making a project to letting other people experience itThe long journey of Aardehn: AwakeningReturning to Fan Expo, where the Kickstarter beganFinally getting a physical copy of the book in our handsWhy it's important to celebrate the wins, even in an endless War with Art And, of course, Sheldon and Eric want to give a huge thanks to everyone who's been listening, backed, and following along on the journey.

Creative work always comes with expectations—but whose expectations are they?Recorded from a cottage on the shores of Lake Huron, we unpack the pressure of following up previous work, the fear of disappointing an audience, and the challenge of finally releasing something you've spent years creating.From music albums and novels to Kickstarter campaigns, we explore how expectations can motivate us—or quietly keep us from finishing at all. The conversation ends with a simple reminder: your next project only exists if you let this one go.Timestamps00:17 — Cottage edition and setting the scene01:42 — The hidden weight of creative expectations07:10 — Sequels, second albums, and following successful work12:42 — Kickstarter pressure and disappointing supporters17:32 — Using expectations as motivation instead of fear21:44 — Stop waiting for perfect—release the work24:20 — Turning expectations into a creative advantage

In this episode, we pull another card from Brian Eno and Peter Schmidt’s legendary Oblique Strategies deck — this time landing on the deceptively simple prompt:“Do something sudden.”Joined by painter Eric J. Drummond, the conversation turns into an exploration of improvisation, instinct, risk, and the strange balance between structure and spontaneity in creative work.We talk about the paralysis that comes from overthinking, why artists sometimes need to force movement before they fully understand where they’re going, and how “suddenness” can break creative stagnation.Eric reflects on the tension between the rigid technical training he teaches students and the fluid, intuitive process he actually uses in his own drawing and painting practice. From gesture drawing to improvisational mark-making, the discussion explores how mistakes, accidents, and risk often become the doorway to something alive.Timestamps:00:08 — Introduction to Oblique Strategies and the “Do something sudden” card02:24 — Overthinking, instinct, and breaking creative paralysis04:04 — Improvisation, happy accidents, and fluid drawing06:28 — Forced momentum and creating without hesitation07:43 — Brutal artistic critique and learning through reaction10:16 — Risk, spontaneity, and disrupting creative comfort zones12:16 — The Beatles, improvisation, and art as play15:13 — Jazz, Pollock, and letting the work evolve naturally16:30 — Characters, paintings, and works “taking on a life of their own”18:17 — Horror, artistic limits, beauty vs violence, and the role of improvisation

In this bonus episode with painter Eric J. Drummond, the conversation narrows in on something fundamental: what it actually means to take responsibility for a creative life.We start with risk—not as a single leap, but as a series of decisions that compound over time. From pursuing art as a career to building something bigger like a school, Eric frames the path not as optional, but as something closer to a calling—one shaped by influence, instinct, and a willingness to listen.From there, the discussion moves into teaching and legacy. Eric talks about skill as a form of cultural inheritance—something that has to be passed on—and why modern art education often misses the mark by focusing too heavily on theory over execution. What he’s after instead is an atelier-style model: learning by doing, building peers, and ultimately creating artists who surpass their teachers.We also get into the reality of doubt—especially as a teacher. When are you “good enough” to teach? How do you avoid becoming the kind of teacher who limits students instead of pushing them forward? For Eric, the answer isn’t perfection—it’s honesty, experience, and a commitment to the student over the ego.The second half turns toward failure and self-critique. Eric shares a recent painting he believes didn’t work—not because of a lack of skill, but because of poor planning and impatience. It becomes a case study in scale, composition, and the cost of rushing the process. And yet, the audience responded positively—highlighting the gap between how artists see their work and how others experience it.Throughout, there’s a consistent thread: the tension between internal standards and external validation, and the long process of learning how to live with both.This is a bonus episode following the three-part series.Timestamps00:16 — Creative risk as a series of decisionsNot one leap—multiple commitments over timeArt as responsibility, not just pursuit01:30 — The feeling of a “calling”Influence of family, taste, early signalsBalancing ambition with humility03:20 — Teaching as legacySkill as cultural inheritanceAtelier model vs modern theory-heavy systems04:30 — What students actually needNot ideas—tools to execute themTechnique first, expression second06:00 — Doubt as a teacherFear of not being “good enough”Success = students surpassing you06:50 — Good teachers vs bad teachersInsecurity limits studentsStrong teachers push beyond themselves09:45 — Career mistakes and lessonsWorking with people who don’t value youLearning to align with respect11:20 — Relationship to his own workSees paintings as lessons, not finished statementsKeeps work as a record of mistakes13:20 — Case study: a failed paintingArt Bears the Soul to ManPoor planning + time pressure → overcrowded composition17:40 — Artist vs audience perceptionViewers liked what he didn’tProcess vs outcome gap19:00 — Overthinking vs instinctTension between refining and overworkingLetting the work “be the work”Final — The core lessonGrowth through iteration and honestyPatience as a fundamental skillReferenced in this episodeDune (visual composition reference)Russian historical painting (czar coronation imagery)Classical atelier / apprenticeship model (concept)

Part 3 of our conversation with Eric J. Drummond begins in a place most artists avoid talking about directly: not inspiration — but blockage. After finishing a major piece, Eric finds himself stuck. The ideas are there — murals, allegories, portraits — but they won’t translate. They exist as a kind of “fog,” just out of reach.What follows is a clear look at how work actually resumes:Study leads to a new direction.Portrait evolves mid-process.One idea hands off to the next.The process isn’t linear — it’s iterative and reactive.From there, the conversation shifts into portraiture and memory. Not just capturing how someone looks, but whether the work feels like them. Eric shares the experience of painting his grandfather from memory — and the moment it was recognized as true through a single detail. That opens into a broader set of ideas:Art as a way of preserving something intangible — presence, gesture, memory — and carrying it forward.The final stretch turns to the bigger tension:How to build something meaningful with your skillsHow to draw from the past without being trapped by itAnd how to make work that feels rooted in your own place and timeWe close on the reality underneath it all:The gap between what you feel and what you can makeThe isolation of carrying that internallyAnd the understanding that this tension never fully goes awayTimestamps00:10 — Part 3 begins 00:20 — Creative block and the “fog” of ideas 02:14 — Too many directions, no clear start 04:00 — Starting small: studies and momentum 05:21 — The process as a relay, not a plan 07:23 — Returning to ideas with new clarity 10:31 — Why likeness isn’t enough in portraiture 11:45 — The gap between feeling and ability 12:51 — The moment a portrait feels true 15:00 — Art as memory across time 16:33 — Working with history in a modern context 18:03 — Taste, exposure, and composition 20:28 — Moving toward something distinctly Canadian 22:20 — Once you have skill — what do you make? 24:28 — The loneliness of being an artist 25:28 — Risk, uncertainty, and no guaranteesReferenced in this episodeJohn Singer Sargent El Jaleo The Last Judgment Moby-Dick Dracula The Lord of the Rings

In Part 2 of our conversation with painter Eric J. Drummond, the focus shifts from discipline and craft to something harder: the tension between the work and the world around it.We get into what it actually means to spend months on a single painting and how that patience is something Eric had to grow into, not something he started with. From there, the conversation moves into the realities of commissioned work: negotiating with clients, balancing truth with expectation, and knowing when a piece is finished versus when it simply has to be delivered.Eric shares the three core questions behind every portrait: how you see yourself, how others see you, and how you want to be seen. And how those tensions shape the final work.From there, things widen out:The trap of “exposure” and paying to be seenWhy social media often works against the kind of art he’s trying to makeDrawing a line between promotion and becoming an “influencer”Finding ways to stay honest in how you present your workThe conversation also explores how to make work you don’t naturally gravitate toward — and how to find meaning inside it anyway. From Tolkien’s landscapes to the idea of environment as a living participant, we talk about how artists create connection even when the subject doesn’t initially resonate.In the second half, the discussion turns philosophical:Can you create something truly transcendent in a secular world?What makes a piece of art feel real beyond what’s physically there?The idea of creating one “true” work — and why artists chase something they can’t fully defineFrom Michelangelo’s Creation of Adam to the balance between simplicity and complexity, Eric breaks down what it means to “catch lightning in a bottle” and why great work leaves space for the audience to complete it.We close on the modern tension: algorithms, AI, commodification, and whether all of it might actually push truly human work to stand out even more.This is Part 2 of a three-part conversation.Timestamps00:12 — Part 2 begins 00:22 — Taking months to complete a painting 01:37 — Commission work vs personal work 02:29 — Working with clients and creative compromise 03:26 — The three questions behind every portrait 04:09 — Adjusting the work vs staying true to it 05:12 — “I’m getting paid to paint” — perspective and trade-offs 05:34 — The trap of “exposure” and pay-to-play 06:31 — Art vs product: where does value come from? 07:20 — Social media vs real artwork 08:02 — Promotion vs becoming an influencer 09:11 — Creative energy vs marketing fatigue 10:44 — Sharing context vs performing online 11:16 — Making work you don’t love (and finding a way in) 11:37 — Tolkien and making environments feel alive 13:45 — Lyrics, language, and meaning 14:10 — Words as carriers of meaning 15:45 — Can art be transcendent without something higher? 17:26 — Ego, humility, and answering to something beyond yourself 18:18 — The idea of one “true” painting 18:40 — Michelangelo and The Creation of Adam 21:11 — What makes something feel “real” 22:25 — Perfection vs balance in art 24:59 — Leaving room for the audience 26:03 — “Make art for artists” — and why that fails 27:54 — Systems that reward safe, formulaic work 29:11 — Opting out vs playing the game 29:33 — AI, oversaturation, and human work 30:48 — Live performance and authenticity 31:12 — Could AI actually help art? 33:07 — Focusing on what you can control 34:35 — Hope, quality, and what endures

In this episode of The War with Art, we welcome painter Eric J. Drummond — a figurative artist trained in classical realism at the Florence Academy of Art.Eric builds his work slowly and deliberately, committed to beauty, discipline, and craft in a culture that often rewards speed and noise. He also happens to be the teacher of our own co-host, Eric Vedder — which makes this conversation personal as well as philosophical.We talk about what it actually looks like to begin a day in the studio — the rituals, the warmups, the sharpening of pencils and clearing of distractions — and why starting is often the hardest part of any creative practice.From there, the conversation moves into deeper territory:The tension between tradition and innovationFollowing rules vs breaking themWhen technique becomes a cageWhy your weaknesses might actually become your voiceEric reflects on his time studying in Florence, the insecurity of leaving that world behind, and a pivotal piece of advice he received: your weaknesses will become your strengths.We explore what that means across disciplines — painting, music, writing — and why the very flaws you try to correct may be the thing that makes your work singular.This is Part 1 of a three-part conversation.Stay tuned for Part 2.Timestamps00:09 — Introducing Eric J. Drummond 02:05 — What starting a studio day really looks like 03:09 — The hardest part: beginning 04:25 — Blocking in, bravery, and not getting precious 06:11 — Writing equivalents and creative rituals 08:54 — The sacred side of routine and warming up 12:28 — Discipline, the gym, and incremental growth 14:59 — Classical realism and the tension of rules 17:08 — “Your weaknesses will become your strengths” 18:43 — Flaws as style: Tolkien, Pontormo, and vulnerability 21:53 — Control, improvisation, and creative fear 25:23 — Tradition vs pushing the needle forward 27:04 — Moving beyond imitation

In this episode of The War with Art, we try something new: a random show.After wrapping another recording, the conversation kept going — bouncing between ideas about deadlines, perfection, collaboration, and the strange emotional slog that shows up near the finish line of creative work. So we hit record and followed the thread.Eric, George, and Sheldon unpack why “done is better than perfect” keeps resurfacing across art history, why exhaustion isn’t a useful metric for finishing, and how deadlines, editors, producers, and collaborators can act as creative unlocks rather than constraints.We talk about the difference between feedback that’s cheap and feedback that has skin in the game, why collaboration can push work past your own internal ceiling, and how letting someone else into the process can move a project closer to its truest version — not just its fastest ending.This is a loose, honest conversation about finishing things, trusting the right people, and carrying the work across the finish line even when you’re tired of looking at it.If you’ve got a topic you’d like us to pull next — or a question you’re wrestling with in your own creative practice — let us know.Timestamps00:10 — A “random show” and why we’re trying it01:27 — Done vs perfect (and why it never goes away)02:19 — Deadlines, pressure, and forcing the release03:44 — Why “perfect” is the wrong word04:42 — Litmus tests: how do you know when something’s done?06:21 — Being tired vs being finished07:45 — The emotional slog near the finish line10:48 — Live service vs print: the pressure of permanence13:00 — Producers, editors, and creative unlocks16:05 — Collaboration as an unlock, not a compromise20:09 — Creative soulmates and shared momentum25:00 — Trust, feedback, and getting closer to “good enough”28:31 — Inviting audience topics + closing thoughts