The Four Things I Wish Someone Told Me Before I Started Oil Painting
The Four Things I Wish Someone Told Me Before I Started Oil Painting
Oil painting has a way of humbling you. No matter how long you've been at it, the canvas has a habit of reminding you that there's always more to learn. After years of painting coastal scenes, florals, and Western landscapes — through competition entries, plein air sessions, and countless hours in the studio — I've accumulated a handful of lessons that I wish someone had handed me on day one.
These aren't technical tricks or supply recommendations. They're the kind of foundational truths that tend to only reveal themselves after you've already done things the hard way.
1. It Doesn't Have to Look Like a Photo
When I first started painting, I was obsessed with photorealism. I wanted every edge to be seamless, every transition to be invisible. I spent an embarrassing amount of time drybrushing — dragging a nearly-dry brush across the surface to blend transitions and eliminate any visible brushwork. The goal was to make it look like I hadn't been there at all.
Below is a landscape I painted in my early days that perfectly illustrates my point. Is it a good painting for a high school sophomore? Sure. But notice how every transition is smoothed which creates almost a blurred effect that drowns the painting.
Here's what I didn't understand then: the brushstroke is the painting.
Over time, I started noticing a pattern. The paintings that got the most genuine reactions, the ones people lingered on and sold were almost never the tightly rendered ones. They were the ones I painted quickly and expressively. The ones where you could feel the energy of the session, where the process was visible in the marks. A loose, confident stroke communicating the shimmer of water or the weight of a coastal cliff can do something a perfectly blended passage simply cannot. It has life in it.
Now compare the landscape above with my more recent painting, Cowboy Study below. I probably spent anywhere from 10-20 hours on the landscape above, whereas I spent 45 minutes on the painting below. This painting sold within days of me posting it, the other sits in the closet of my childhood bedroom collecting dust.
Photorealism is a legitimate and impressive discipline. But if you're picking up a brush for the first time, give yourself permission to let it look like a painting. That's not a limitation — it's the whole point.
2. Learn to Draw
There's a reason drawing is the very first class required in every serious art program. It isn't a prerequisite you check off and move past. It's the foundation everything else is built on.
Before you ever pick up a brush, you need to be able to see — to understand spatial relationships, perspective, proportion, and negative space. Drawing trains your eye to read a scene accurately and your hand to translate what you see onto a flat surface. Without that skill, you're essentially trying to build a house without knowing how to lay a foundation.
Where this pays off most directly in oil painting is in your underpainting. When you can draw well, you can set up a strong compositional foundation quickly and confidently. Your underpainting — that initial sketch-like layer that establishes your shapes and basic values — becomes a roadmap rather than a guess. You spend less time correcting structural problems mid-painting and more time actually painting.
The artists I've admired most, regardless of their style or subject matter, can all draw. That's not a coincidence.
If you're early in your painting journey, invest real time in drawing. Fill sketchbooks. Work from life. Study perspective. It will make every hour at the easel more productive, and the improvement in your paintings will be immediate and obvious.
3. Establish Your Darks
This one was drilled into me early. Instructors said it, books reinforced it, and for years I acknowledged it and promptly ignored it in practice.
Then I started actually doing it — and the difference was hard to argue with.
Establishing your darkest values first gives you a fixed reference point for everything that follows. In oil painting, value — the relative lightness or darkness of a tone — is what creates the illusion of form and depth. When you know where your deepest shadows sit, every subsequent decision about midtones and lights becomes much cleaner. You're not guessing. You have a bottom anchor.
There's also a practical reason to work dark to light: oil paint is opaque and layerable, which means lighter, thicker paint applied over darker passages builds form naturally and convincingly. Working in the other direction — starting light and trying to push darks in later — tends to muddy everything.
Establish your darks. Commit to them. Let everything else build from there.
4. Messing Up Isn't Just OK — It's Critical
This might be the most important one.
If you're not making mistakes in your paintings, you're not experimenting. And if you're not experimenting, you're not growing. It really is that simple.
Every failed painting teaches you something a successful one can't. A color mix that goes muddy, a composition that falls apart, a session where nothing works — these aren't setbacks. They're data. They're the mechanism by which you actually improve, not just the price you pay for improving.
The artists who plateau are usually the ones who stop taking risks. They find something that works and they stay there, producing competent, safe work indefinitely. There's nothing wrong with that if consistency is the goal. But if growth is the goal — if you want your work to genuinely evolve — you have to be willing to fail regularly and visibly.
Paint the thing you're not sure you can pull off. Try the palette that intimidates you. Work larger than is comfortable. Mess it up. Learn from it. Go again.
The canvas is forgiving. Progress is made in the mess.
Start Simple, Stay Curious
Oil painting for beginners doesn't have to be overwhelming. Pick a simple subject—maybe a single piece of fruit or a basic landscape. Focus on understanding how the paint moves, how colors mix on your palette versus on the canvas, how long you have to work before things start to set up.
The American West that fills my canvases now started with pretty mediocre paintings of rocks and sage brush. Every master painter began with the same fundamentals you're learning today. The only difference between a beginner and a professional is time spent with the brush in hand.
Your first oil painting doesn't need to hang in a gallery. It just needs to teach you something about the medium that will make your second painting better. And that's enough to start.