A Landscape Painter’s Guide to—Embracing Imperfection and Perfection – Easel Talk #44
There’s a paradox at the heart of painting that every serious artist eventually confronts: the pursuit of perfection will either propel you forward or paralyze you entirely. The difference hinges on a single concept, functioning perfectionism, and understanding it might be the most liberating realization of your artistic career.
I’ve always had a perfectionist streak. I like to think of myself as a functioning perfectionist, and there’s a meaningful distinction between the two. Perfectionism as an ideal is valuable. It gives you something to strive toward, a north star for your work. But if you let this ideal grip you too tightly, it becomes a prison. I learned this the hard way, watching someone I worked for waste countless hours obsessing over details that ultimately didn’t matter, mixing teal carpet colors to microscopic degrees of precision while the schedule slipped away. Time is our most valuable commodity, and it shouldn’t be squandered chasing impossible standards.
Painting demands thousands of decisions. From the moment you choose your canvas size and color cast, through every brush stroke, every shape you move, every value you adjust, the decisions never stop. If you become real perfecty about every single one of them, you’ll gradually become immobilized. The only antidote is to move forward, make your best judgment, and trust that the accumulation of good decisions will carry the work.
The Masterpiece Question
People often ask me to show them my masterpieces. I’ve done some good paintings, some really good ones, but I can’t honestly say I consider any of them to be masterpieces. And that’s intentional. Art history and future generations, not the artist, get to decide what’s masterful. When we look back at the great painters, we see hundreds of good paintings, but a few that rise above the rest. That distinction isn’t something the artist declared for themselves. It emerged over time, through the collective judgment of those who came after.
When you finish a great painting, you don’t lean back and declare yourself done. You don’t think, “Well, I’ve achieved my goal. Time to move on to something else.” No. You immediately want to do another great painting. That hunger, that constant drive toward the next work, is what gives life meaning. It’s what keeps you creating.
The Volume Principle
The most powerful argument against perfectionism comes from an unexpected source: Picasso. That man worked constantly, producing roughly 40,000 works in his lifetime, paintings, ceramics, etchings, drawings, whatever he could create. Do you think all 40,000 were masterpieces? Of course not. But he has enough masterpieces to fill books, and the point is undeniable: volume matters.
You can’t paint your way to mastery by doing two paintings a year, no matter how much you agonize over each brushstroke. That elitist mindset, “I use only the finest paints and brushes, and every stroke must be considered”, simply doesn’t work. You have to crank them out. You have to create and create and create. The cream rises to the top naturally when you’re producing at volume.
If you want to learn how to paint, make a lot of paintings. Keep them simple. Keep them quick. If they’re bad, throw them away. Don’t work on expensive materials when you’re starting out. People think they need special brushes or fancy paints to become skilled, but the actual truth is humbling: what makes you a better painter is producing a lot of work. Paint every day, and as you go, discard the bad pieces so they don’t stink up your studio and your mindset. The lessons that needed learning will be integrated as you move forward. You won’t need to remember the failures, you’ll simply be better because of them.
Living With Imperfection
Even paintings I’m quite pleased with contain elements that irritate me upon later inspection. I’m sensitive to tree shapes and how they work against the sky, and months after finishing a piece, I’ll suddenly notice an awkward angularity that I missed entirely while painting. The me who was actively creating was doing my best to interpret the reference. The me reviewing it months later, with fresh eyes and critical distance, sees things differently.
You must learn to live with imperfection in your work. That painting that bothers you? If it’s not genuinely abysmal, you have a choice: correct it or live with it. Most of the time, living with it is the right call. I once sold a painting with what I call “lollipop tree syndrome”, a straight trunk with a little round crown, exactly what you’re not supposed to do. A visitor came in, fell in love with it, and bought it on the spot. That tree is out there in the world, and while it might stink up my legacy in some cosmic sense, it clearly moved someone enough that they wanted to live with it. It brought them joy.
Painting doesn’t have to be perfect to be powerful. It doesn’t have to be flawless to move someone.
Wabi-Sabi
The Japanese have a concept called wabi-sabi. It’s the aesthetic philosophy that finds beauty in imperfection, impermanence, and incompleteness. Rather than seeking artificial perfection, which is always an ideal and never a reality, wabi-sabi values the authentic character that emerges when we embrace natural flaws.
The most famous example is cracked pottery. When a ceramic piece develops a crack, instead of being discarded, the flaw is embraced. Sometimes the crack even creates a pattern or asymmetry that adds visual interest and authenticity, making the piece more beautiful than it would have been without the imperfection. The object still functions. It still holds coffee. But now it also tells a story.
Your paintings will be like this. The imperfections aren’t failures, they’re features that tell the story of how the work was made. They’re evidence of the artist’s hand, the struggle, the process. Nothing is perfectly formed, or perhaps everything is. The perspective matters.
Functioning Perfectionism: Setting Standards That Work
You develop functioning perfectionism by learning discrimination. You need to determine which details absolutely must be addressed for the work to succeed, and which details would simply be nice if they were right, but where you have latitude. If you get the big things in the right place and manage to express yourself in an appealing manner, that’s often enough to carry the painting far beyond competence into genuine resonance.
The aspects that matter most in painting are proportion and balance of forms. I talk extensively about this in my book because it’s foundational. Big shapes with well-modulated color and a pleasing composition will please a lot of people. That composition, how the large forms work against the proportions of the canvas itself, that’s 90% of the painting. Everything else is secondary.
The details you’re certain are absolutely critical, this shadow, that highlight, the other flourish, these matter far less than you think. As a functioning perfectionist, you’ll gradually learn to work on the proportional and compositional fundamentals while releasing your grip on details that don’t serve the whole.
The more you paint, the less attached you become to individual pieces. That painting that seemed so important? It’s in the rear view mirror now. You’re focused on the next one, wanting it to be great too. This cycle is what keeps you improving.
Developing Your Eye
Your ability to perceive perfection or imperfection is deeply tied to who you are as a person. Some people have a more innate sense of aesthetics, others must cultivate it. But discernment can be developed.
The masters can bootstrap you faster than you can get there alone. My own artistic evolution accelerated dramatically when I committed to studying tonalism deeply. Studying the work of great painters, not scrolling mindlessly through thousands of images on social media, but actually engaging with the work of proven masters, this shapes your eye and your standards.
Make studies after the work of painters you admire. Don’t obsess over capturing every detail perfectly, instead focus on the experience of making the study. This is how you train your eye. Be selective. Feed yourself with high-quality work, and you’ll develop aesthetic sensibilities that naturally raise your standards and your output.
Three Questions for Your Work
When you finish a painting and you’re uncertain whether to keep it, display it, or discard it, I use three criteria:
A. Are you ashamed of it? If the answer is genuinely no, if you can look at it without shame, even if it’s not your best work, that’s a reason to keep it. If the answer is yes, you should know what to do: scrape it, paint over it, or if it’s already dry, throw it away. Don’t let bad work stink up your studio or your confidence. Early on especially, paint on inexpensive surfaces. Make paintings every day. If they’re bad, toss them without guilt. You’ll mind far less if you’re producing volume.
B. Is it saleable? Could someone else love this? Could you sell it? I have paintings that I wouldn’t call great, that I struggled with, but that I know will find a home. That painting behind me right now, I had to push through real resistance to finish it, but it’s saleable, and someone will love it. That’s enough.
C. Could it be improved in the future? Sometimes a painting isn’t quite there, but it’s not bad enough to discard. You can put it aside. Later, when you’ve developed new skills, you might revisit it, maybe with a power glaze, maybe with a complete rework. This is especially valuable when you’re starting out. Put these works in a box. Don’t let them live in your studio where you see them daily, whispering that you need to fix them. The only things you want to see regularly are works you think are genuinely great, pieces that feed your drive to create better work.
The Balance
Embrace imperfection in a perfect way. Don’t waste time on details that don’t matter. Don’t chase impossible standards you cannot achieve. But do hold yourself to a standard that pushes you forward. This balance, this middle path between careless indifference and paralyzing perfectionism, is the secret.
It’s a wonderful way to spend your life. You have something to move toward. You have a north star. And you have permission to be imperfect on your way there.
I’ve been in this studio since 2011, selling work since day one. I’m dramatically better now than when I started, not because I perfected my earliest paintings, but because I made thousands of them. I painted constantly. I threw away the bad ones. I learned from everything. And even now, even with all that accumulated knowledge, I still struggle sometimes. I still make paintings that don’t come easily. And that’s okay. If it were easy, it wouldn’t be valuable.
The paintings you make don’t have to be masterpieces to matter. They don’t have to be flawless to be beautiful. They just have to be honest, made with genuine effort, real standards, and the acceptance that imperfection is part of the work’s authentic character. That’s not a compromise.
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