War with Art

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.

• 00:00 — 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.

• Wind, Sand and Stars — Antoine de Saint-Exupéry
• Acid for the Children — Flea
• Big Magic — Elizabeth Gilbert
• Tao Te Ching
• The Shining

Thanks for listening to The War with Art, where we talk about the messy, frustrating, occasionally ridiculous business of trying to make things.

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.

• 00:00 — 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.

• Wind, Sand and Stars — Antoine de Saint-Exupéry
• Acid for the Children — Flea
• Big Magic — Elizabeth Gilbert
• Tao Te Ching
• The Shining

Thanks for listening to The War with Art, where we talk about the messy, frustrating, occasionally ridiculous business of trying to make things.

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.

• 00:00 — 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.

• Wind, Sand and Stars — Antoine de Saint-Exupéry
• Acid for the Children — Flea
• Big Magic — Elizabeth Gilbert
• Tao Te Ching
• The Shining

Thanks 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 intro

02:04 — 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 Aardehn

07:48 — 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 episode

• What it actually feels like to finish a major creative project
• The strange emptiness that can follow years of focused work
• Why finishing something can feel a little like grieving
• Learning to accept that a work is finished—even when you can still see things you'd change
• The transition from making a project to letting other people experience it
• The long journey of Aardehn: Awakening
• Returning to Fan Expo, where the Kickstarter began
• Finally getting a physical copy of the book in our hands
• Why 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.

• 00:17 — Cottage edition and setting the scene
• 01:42 — The hidden weight of creative expectations
• 07:10 — Sequels, second albums, and following successful work
• 12:42 — Kickstarter pressure and disappointing supporters
• 17:32 — Using expectations as motivation instead of fear
• 21:44 — Stop waiting for perfect—release the work
• 24:20 — 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” card

02:24 — Overthinking, instinct, and breaking creative paralysis

04:04 — Improvisation, happy accidents, and fluid drawing

06:28 — Forced momentum and creating without hesitation

07:43 — Brutal artistic critique and learning through reaction

10:16 — Risk, spontaneity, and disrupting creative comfort zones

12:16 — The Beatles, improvisation, and art as play

15:13 — Jazz, Pollock, and letting the work evolve naturally

16:30 — 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.

00:16 — Creative risk as a series of decisions

• Not one leap—multiple commitments over time
• Art as responsibility, not just pursuit

01:30 — The feeling of a “calling”

• Influence of family, taste, early signals
• Balancing ambition with humility

03:20 — Teaching as legacy

• Skill as cultural inheritance
• Atelier model vs modern theory-heavy systems

04:30 — What students actually need

• Not ideas—tools to execute them
• Technique first, expression second

06:00 — Doubt as a teacher

• Fear of not being “good enough”
• Success = students surpassing you

06:50 — Good teachers vs bad teachers

• Insecurity limits students
• Strong teachers push beyond themselves

09:45 — Career mistakes and lessons

• Working with people who don’t value you
• Learning to align with respect

11:20 — Relationship to his own work

• Sees paintings as lessons, not finished statements
• Keeps work as a record of mistakes

13:20 — Case study: a failed painting

• Art Bears the Soul to Man
• Poor planning + time pressure → overcrowded composition

17:40 — Artist vs audience perception

• Viewers liked what he didn’t
• Process vs outcome gap

19:00 — Overthinking vs instinct

• Tension between refining and overworking
• Letting the work “be the work”

Final — The core lesson

• Growth through iteration and honesty
• Patience as a fundamental skill

• Dune (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 skills
• How to draw from the past without being trapped by it
• And how to make work that feels rooted in your own place and time
• We close on the reality underneath it all:
• The gap between what you feel and what you can make
• The isolation of carrying that internally
• And the understanding that this tension never fully goes away

00:10 — 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 guarantees

John 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 seen
• Why social media often works against the kind of art he’s trying to make
• Drawing a line between promotion and becoming an “influencer”
• Finding ways to stay honest in how you present your work

The 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 define

From 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.

00:12 — 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