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

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 innovation
• Following rules vs breaking them
• When technique becomes a cage
• Why your weaknesses might actually become your voice

Eric 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.

Timestamps

00:09 — 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.

Timestamps

00:10 — A “random show” and why we’re trying it

01:27 — Done vs perfect (and why it never goes away)

02:19 — Deadlines, pressure, and forcing the release

03:44 — Why “perfect” is the wrong word

04:42 — Litmus tests: how do you know when something’s done?

06:21 — Being tired vs being finished

07:45 — The emotional slog near the finish line

10:48 — Live service vs print: the pressure of permanence

13:00 — Producers, editors, and creative unlocks

16:05 — Collaboration as an unlock, not a compromise

20:09 — Creative soulmates and shared momentum

25:00 — Trust, feedback, and getting closer to “good enough”

28:31 — Inviting audience topics + closing thoughts

In this episode of The War with Art, we pull another card from Brian Eno and Peter Schmidt’s Oblique Strategies deck and get a prompt that hits uncomfortably close: “Bridges — build — burn.”

From modular synth patches you create and then tear down, to monks spending days on intricate work only to wipe it clean, we talk about why building and burning is baked into the creative process. Sometimes you have to strip a piece back to its core idea. Sometimes you have to scare yourself a little. And sometimes you have to let go of what you’ve already built... even when sunk cost is screaming at you to keep it.

The guys also explore the deeper version: making something can be a bridge between who you are now and who you become after you’ve finished — and once you cross, you don’t really get to go back.

If you’ve got your own interpretation of the card, drop a comment as we’d love to hear it.

“Maybe you need to burn the bridge in order to make it not easy — and then rebuild something new.”

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Timestamps:

• 01:10 — What *Oblique Strategies* is (and why we’re using it)
• 02:40 — The card: “Bridges — build — burn”
• 03:50 — Burning as a creative tool: risk, conflict, and scaring yourself
• 06:10 — Modular synths: build the patch, then tear it down
• 07:15 — The monks: the work matters more than the artifact
• 12:05 — The deeper take: building a bridge to a new version of yourself
• 16:45 — Audience, tone, and the bridges you build (or burn) with words
• 19:10 — “Diet vanilla” and using the cards to push the work further

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Referenced in this episode:

• Oblique Strategies — Brian Eno & Peter Schmidt
• Sand Mandala: Sacred Art of Tibet (Thames & Hudson) — on the creation and ritual destruction of sand mandalas
• Sunk cost fallacy” (concept)

In this episode of The War with Art, we talk about the inner critic — that voice that shows up right when the work starts to matter.

Eric, George, and Sheldon dig into what it actually says and why it can sometimes be useful, but also how easily it can tip into full imposter syndrome. We also get into the difference between "done" and "perfect," why art is something you surrender rather than perfect, and that strange thing that happens when you've listened to your own work so many times that you can't tell if it's genuinely bad or if you're just sick of hearing it.

If you’ve got your own way of dealing with the inner critic, drop a comment — we’d love to hear it.

“If it were easy to make, there’d be no point in making it.”

Timestamps:

• 02:30 — What the inner critic actually says
• 04:30 — “Done vs perfect”
• 09:00 — When criticism turns into imposter syndrome
• 11:30 — The AI temptation
• 20:00 — Outnumbering the inner critic through collaboration

Referenced in this episode:

• Dilla Time by Dan Charnas
• Ratatouille — the critic archetype
• Theodore Roosevelt’s “Man in the Arena” (speech)

Pulling a random card from The Deck of Oblique Strategies, the guys discuss...

The guys talk about what they've learned over the past few months.

Thinking about the future means reflecting on past mistakes. What would you do differently? The WWA explores.