War with Art

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.

Timestamps00:17 — 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.

Timestamps00:16 — 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
Referenced in this episodeDune (visual composition reference)
Russian historical painting (czar coronation imagery)
Classical atelier / apprenticeship model (concept)