This is the third post in a four-part series on the framework I use to evaluate whether a work of art has staying power. If you missed Part 1 on Intentionality or Part 2 on Novelty, start there. And if you missed the introduction — When Is the Last Time You Bought Something That Will Outlast You? — that’s a good place to begin.

When I taught art history at the Cleveland Institute of Art, I started every semester the same way. I asked the students one question:

Why do you think have to take this class?

The answers were predictable. Because it’s required. Because the school makes us. Because I don’t know. A few brave souls would venture something more honest: because you can’t make art without knowing what came before you.

That last answer is the one I was waiting for. Not because art history is a prerequisite to making anything — plenty of artists work in genuine isolation and produce powerful work. But because the artists who know the conversation they’re entering make more informed choices. Their work has more layers. Their intentionality is richer because it’s grounded in something larger than their own instincts.

That’s what the third criterion in my framework is about: self-awareness.

Self-awareness is an artist’s demonstrated understanding of where their work sits in the broader conversation — art historical and contemporary — and the conceptual reason for the references and relationships they’re drawing on.

That conversation can be with anyone. With Caravaggio or with a peer showing at the next booth at NADA. With the AbEx painters or with the early African American quiltmakers whose work the art world spent decades failing to take seriously. With Italian Baroque drama or with the feminist fiber art movement of the 1970s. The conversation can be explicit — direct visual quotation, named influence, obvious stylistic dialogue — or it can be subtle, a structural logic or a material choice that quietly acknowledges what came before.

What matters is that the reference is there for a reason. The artist isn’t dropping art historical names to sound serious or reaching for the nearest available influence because it looks good. They’re drawing on a specific thread because it lets them say something that couldn’t be said without it.

I want to be honest about something: not everyone would agree that self-awareness is a necessary criterion for evaluating whether a work is good. Some would argue that an artist has no obligation to know or acknowledge the conversation they’re in — that pure instinct and originality are enough, that art historical awareness is an academic imposition, that the work should stand entirely on its own terms.

I understand that argument. But I don’t think it holds up.

Here’s why. An artist who genuinely understands where their work sits in the broader conversation — who knows what’s been tried before, what succeeded, what failed, and why — is making more informed choices. Their work isn’t just the product of instinct. It’s the product of instinct in dialogue with history. And that dialogue produces depth — the kind of depth that rewards a viewer over years rather than months, the kind that gives a work staying power rather than just initial impact.

There’s also a more practical point. The artist who makes work in complete isolation from any conversation might produce something genuinely original. But they might also be reinventing the wheel without knowing it — doing something that feels fresh to them but has already been done, and better, by someone else. Self-awareness is what separates genuine originality from accidental repetition.

Here’s the test I use to distinguish between a self-aware artist and a derivative one.

A self-aware artist catches the ball and advances it. They receive what came before — a style, a material, a conceptual approach, a set of questions — and they move it somewhere new. They add something that takes the conversation forward. You can trace the connection to what came before and you can also see clearly why this work had to exist — why the conversation needed this voice to go somewhere it hadn’t been yet.

A derivative artist catches the ball and either drops it or throws it back where it came from. The reference is there — you can see the influence clearly — but it isn’t going anywhere. The work doesn’t advance the conversation. It repeats what’s already been said. The connection to the source is legible but the conceptual leap that would justify the reference is missing.

The question to ask is not: can I identify the influence? It’s: can I understand why the influence is here? What is it doing for this work that nothing else could do?

If you can answer that question, you’re probably looking at self-awareness. If the reference feels decorative — present but purposeless — you’re probably looking at something derivative.

Molly Greene has three degrees from Yale — environmental science, philosophy, American studies — before she picked up a brush. Her paintings look at first glance like they might be decorative: soft, airbrushed, pastel, organic forms that feel botanical and slightly surreal. But the self-awareness in her work is operating on multiple levels simultaneously.

Greene is in dialogue with the history of decorative painting — the tradition that has been consistently feminized and marginalized by the art world — and she’s doing something deliberate with that tradition. Her work looks decorative on purpose. The softness and the botanical imagery and the pastel palette are not accidents. They’re a sustained investigation into the porous boundary between what gets called art and what gets called decoration, between the natural and the artificial, between the human and the non-human. She knows exactly what conversation she’s in. And she has a very specific reason for entering it the way she does.

Logan Grider makes abstract paintings that are in deep dialogue with the history of American abstraction — the AbEx painters, the color field tradition, the long argument about what paint on canvas can do and mean. But he’s not repeating that conversation. He’s extending it. His work is physically demanding in ways that connect to the labor-intensive practices of Process Art while also being visually lush in ways that connect to the Romantic tradition of the sublime. The references are there, they’re legible, and they’re doing real conceptual work — each one is load-bearing, necessary to what the painting is trying to say.

Both Greene and Grider know the conversation they’re in. Both of them have a reason for entering it the way they do. That’s self-awareness operating at a high level.

If you’ve taken the collector type quiz and discovered you’re a Contextual Collector, self-awareness is your natural criterion. You’re wired for exactly this kind of art historical and contemporary dialogue. When you find it you go deep — you follow the thread, you research the references, you build the full picture of where a work sits and why. The result, when it works, is a collection of extraordinary depth and coherence.

But the Contextual Collector has a blind spot at this criterion too.

Self-awareness isn’t always legible on the surface. Some of the most self-aware artists wear their references lightly. The dialogue is there — it’s real, it’s doing genuine work — but it requires patience and investigation to find. The Contextual Collector who needs the context to announce itself will walk past work that rewards closer looking.

The test for self-awareness isn’t whether the references are immediately obvious. It’s whether they’re there at all — and whether they’re doing something. Sometimes you have to bring knowledge to the work rather than waiting for the work to hand it to you. That’s a skill. And it’s worth developing.

When you’re standing in front of anything and trying to evaluate self-awareness, the question worth asking is: does this work know where it comes from?

You don’t need to be an art historian to feel the answer. Self-aware work has a quality of intentional placement — it feels like it belongs somewhere specific in the larger story of art, like it knows what it’s responding to and why. Derivative work feels like it arrived from nowhere in particular, or like it’s trying on someone else’s clothes without quite understanding why those clothes were made.

A second question worth asking: can I understand why the reference is here? What is it doing for this work that nothing else could do?

If the reference has a reason — if pulling on that thread opens something up rather than just gesturing toward it — you’re probably looking at self-awareness. If the reference feels like decoration, like name-dropping in paint, you’re probably not.

Next week: Relevancy. Does this work have something urgent to say about the world we’re actually living in right now?

This is the second post in a four-part series on the framework I use to evaluate whether a work of art has staying power. If you missed Part 1 on Intentionality, start there. And if you missed the introduction — When Is the Last Time You Bought Something That Will Outlast You? — that’s a good place to begin

In 1917 Marcel Duchamp submitted a urinal to an art exhibition. He turned it upside down, signed it with a fake name, called it Fountain, and submitted it as a work of art.

The selection committee rejected it. Of course they did. It was a urinal.

But Duchamp’s point wasn’t the object. It was the question. What makes something art? Is it the skill of the maker? The beauty of the form? The intention behind it? If an artist declares something art — if the concept is the work — does the object even matter?

That question changed the entire conversation about what art is and can be. Not because a urinal is shocking or strange, because it is, but because there was a reason for the shock and strangeness. The provocation was in service of an idea that had no other way of being said. That’s novelty. It is not weirdness for its own sake, or shock for the sake of reaction, but a genuinely new way of saying something, thinking about something, or presenting an idea  that couldn’t be said any other way.

When someone looks at Duchamp’s Fountain and says “my kid could do that,” they sound like idiots, to be honest, and they are missing the point entirely. Yes, your kid could probably turn a urinal upside down. Your kid could not have asked that question in 1917 in a way that changed how every artist and every viewer thought about art for the next century.

That’s what novelty looks like at its most extreme. In practice, standing in a gallery or a fair, it looks more like this: is this artist doing something I haven’t seen before? Are they using a material, a process, a visual language that feels genuinely distinct from everything around it? Are they advancing a conversation or just entering one that’s already crowded?

Before we talk about what novelty looks like, it’s worth naming what it isn’t.

Novelty is not trend-following. An artist whose work looks new because it looks like whatever is popular right now isn’t making novel work — they’re making timely work. Those are different things. Timely work dates. Novel work doesn’t.

Novelty is not bombast. It is not gimmicky edginess for shock value’s sake. Don’t mistake loudness for vision. You know who could scrawl the F word in spray paint on a Normal Rockwell print? Your kid. That’s not novelty.

Novelty is not strangeness for its own sake. A work can be bizarre, difficult, unsettling, and also completely derivative. The question isn’t whether something surprises you. It’s whether the surprise is actually achieving a real objective.

True novelty is specific. It’s an artist who found a visual language that is distinctly, identifiably theirs, and that nobody else got to first.

The first time I stood in front of Danielle Mysliwiec‘s work I genuinely didn’t know what I was looking at. She makes weavings out of extruded oil paint. Not weavings that look like paint. Not paint that references weaving. She physically extrudes paint into long strands and weaves them together the way you would weave thread — interlocking, layering, building a surface that is simultaneously a painting and a textile and neither one.

I had never seen anything like it. Not in twenty years of walking galleries and fairs.

But the novelty isn’t just the material trick. It’s what the material trick is saying. Mysliwiec is working within a long art historical conversation about the hierarchy between painting — traditionally the domain of high art, of men, of serious ideas — and weaving and textile, traditionally feminized, classified as craft, pushed to the margins. She’s not referencing that conversation. She’s physically enacting it. The paint and the fiber are literally the same thing in her hands. The hierarchy collapses in the making.

That’s novelty doing real work. The surprise is in service of an idea. No one has said what she is saying in this way.

Kate McQuillen approaches novelty from a completely different direction. She is a printmaker by training who applies printmaking principles to painting — which means her painted surfaces have no brushwork, no impasto, no visible layering. They are as smooth as a print. She has invented a way of making gestural abstract painting that looks like it was never touched by a brush, which creates a deeply strange and beautiful friction between the physicality of paint and the mechanical precision of print.

McQuillen is also a reader and a thinker who draws on ancient Greek epics and tragedies — specifically the way those stories move between disparate emotional registers within a single scene. She uses that source material as a way into abstract painting: how can an image bring to mind a specific feeling even when it’s entirely removed from recognizable form?

The novelty in McQuillen’s work is layered. It’s the surface technique. It’s the conceptual framework. It’s the way those two things work together to produce something that exists liminally between the things it draws from — between painting and printmaking, between abstraction and narrative, between the ancient and the present.

Neither Mysliwiec nor McQuillen looks like anyone else. That’s the signature of novelty — work that is identifiably, specifically, irreducibly itself.

If you’ve taken the collector type quiz on this site, you may already know you’re a Venturist. The Venturist collector often leads with novelty above everything else. They walk into a booth and something stops them — an energy, an unexpectedness, a “wow, I’ve never seen that before” that bypasses the analytical brain entirely. They trust that instinct and they act on it. Some of the most exciting collections I’ve ever seen belong to Venturist collectors.

But novelty is also the Venturist’s blind spot. Because novelty alone doesn’t tell you whether a work has staying power. It tells you the artist found something new. It doesn’t tell you whether what they found is grounded in something real, whether the intentionality is there, whether the work knows where it sits in the broader conversation, whether it has something urgent to say about the world we’re actually living in.

The Venturist who leads with novelty and stops there ends up with a collection full of work that was exciting, edgy, and surprising in the moment but fails to hold on to that moment for much longer.

Novelty is the entry point for you Venturists, but it’s not the whole conversation.

When you’re standing in front of anything and trying to evaluate novelty, the question worth asking is: have I seen this before? Not “is this good?” Not “do I like it?” Just: is this doing something I haven’t seen done?

If the answer is yes — if you can immediately think of five artists making work that looks like this — then novelty isn’t the thing that’s going to make this work last. It might have other things going for it. But it’s entering a crowded conversation rather than advancing one.

If the answer is no — if you can’t quite place it, if it doesn’t fit neatly into a category, if you find yourself saying “I don’t know what this is exactly” — pay attention. That disorientation is worth investigating. It might be novelty. It might be the beginning of something.

A second question worth asking: does this artist have a visual language that is distinctly theirs? Could you identify their work in a group show without looking at the label? Artists who have developed genuine novelty tend to be immediately recognizable — not because they repeat themselves, but because they’ve found something that belongs to them and only them.

That distinctiveness is what you’re looking for. Not weirdness. Not shock. Not trend. Just: this person found something nobody else got to first.

Next week: Self-Awareness. Does this artist know where their work sits in the broader conversation? And why does that really matter?

This is the first post in a four-part series on the framework I use to evaluate whether a work of art has staying power. If you missed the introduction — When Is the Last Time You Bought Something That Will Outlast You? — start there. And if you’d rather watch than read, the masterclass video is coming soon. I’ll link it here when it’s live.

I had a professor at Davidson College who gave me the single most useful tool I know for understanding how to know if art is good — not a checklist, not a theory, just one question he asked about everything. Not “is this beautiful?” Not “is this technically accomplished?” Not even “do you like it?”

Why does this image look the way it does?

At eighteen I thought he meant historical context — the forces that shaped an artist’s moment, the movements they were responding to, the world they were making work inside. And that’s part of it. But as I grew in my understanding of art I came to realize the question was really about something more internal. It was about choice, the choices an artist made in response to those external forces. What were they controlling inside the studio amidst the uncontrollable external forces of the times in which they lived?

That question became the foundation for the first criterion I use when evaluating whether a work has staying power: intentionality. It won’t tell you everything about whether a work is good. But without it, nothing else matters much.

Here’s the core concept: is the artist in command of their choices?

If you think about a work of art less as a finished product and more as a series of decisions a person made to communicate a particular message, intentionality snaps into focus. Every decision — scale, material, mark, color, composition — should feel considered rather than accidental or decorative. The question isn’t “is this skillful?” It’s “does this artist know exactly what they’re doing and why?”

Craft without intention is decoration. Intention without craft can still produce powerful work. But when you get both, you get something worth stopping for.

The clearest example of intentionality in art history is also the most misunderstood.

Everyone knows Cubism looks strange. The fractured planes, the multiple perspectives simultaneously visible, the figures that seem to be coming apart and reassembling at the same time. Most people assume it looks strange because Picasso was doing something new and difficult — that the strangeness is the symptom of a learning curve.

It isn’t. Picasso was one of the greatest draftsmen who ever lived, on par with Michelangelo. He was a prodigy who could render the human figure with photographic accuracy by the time he was a teenager. Cubism doesn’t look the way it does because it had to. It looks the way it does because Picasso chose it. Every fractured plane, every impossible angle, every figure that refuses to resolve into legibility — that was a decision made by someone who knew exactly what he was giving up and why.

That’s intentionality. Not the inability to do something else. The deliberate choice to do this instead.

Stephen Thorpe makes it easy. His paintings are representational — you can read the landscapes, the atmospheric shifts between interior and exterior, the collision between the natural world and the psychological one. When you look at a Thorpe, you feel almost immediately that someone is in complete command of what you’re seeing. The gradations of color are deliberate. The compositional tension is deliberate. The way the work sits at the border between the recognizable and the dissolving is deliberate.

Thorpe’s gallery describes his work as “deliberately rendered to represent the dualities, synergies, and contradictions of relation between environment and human interiority.” That sentence is doing what the best artist statements do — it confirms what you already felt standing in front of the work. The form and the concept are in alignment. There is a reason this looks the way it does, and once you understand the reason, you see it everywhere in the work.

That alignment — between what an artist is trying to say and the choices they make to say it — is the signature of intentionality.

Abstract work is harder. When there’s no subject to anchor you — no figure, no landscape, no recognizable object — it can be tempting to assume that whatever happened on the canvas was more or less accidental. Paint flew, gravity pulled, the artist responded to what emerged. And sometimes that’s true. Sometimes a work really is just what happened.

But sometimes the apparent chaos is the most intentional thing in the room.

Demetrius Wilson‘s paintings look, at first encounter, like pure energy. Paint flies across his canvases like a collision. Fragments of bodies and beasts emerge from turbulence and dissolve back into it. The work is saturated with color, driven by restless mark-making, full of violence and movement and something that feels almost uncontrolled.

It isn’t.

Wilson is investigating specific ideas — truth, beauty, and violence, and whether they exist independently from humankind. His abstractions represent a deliberate departure from his earlier figurative work. He could paint a figure. He chooses not to, because the abstraction opens the canvas as a laboratory for the ideas he’s working with in a way that figuration wouldn’t. The marks that look accidental are in fact choices made in service of a very specific inquiry. The turbulence is the point. The fragmentation is the point. The violence that feels generative rather than destructive — that is absolutely the point.

This is how you apply the intentionality lens to abstract work: you ask whether the form supports the concept. Not whether you can explain the concept without reading the wall card, but whether the work makes you feel like the artist intended — whether the choices they made reflect or support their end goal. Does this look the way it does because the artist chose it, or because they stumbled onto it?

Wilson’s work answers that question with complete confidence. Even if you don’t know what he’s investigating, you feel that someone is in command. That’s intentionality operating below the level of conscious understanding — which is, arguably, where the most powerful work happens.

When you’re standing in front of anything — representational or abstract, figurative or conceptual — the question worth asking is simple: could this have been made differently and been equally strong?

If the answer is yes — if the colors could have been different, the scale could have been smaller, the mark could have been looser, and none of it would have mattered — then the choices aren’t doing necessary work. The craft may be impressive. The result may be beautiful. But it’s decoration.

If the answer is no — if this work could only be this and nothing else, if every decision feels load-bearing, if changing anything would change everything — then you’re probably looking at intentionality.

That’s the test. It won’t always give you a clean answer. But it will always make you look harder. And looking harder is the whole point.

Next week: Novelty. Is this artist doing something you haven’t seen before — or just entering a conversation that’s already crowded?