Learning to paint (or draw) well takes years of practice, and on the way it’s not uncommon to get stuck in a rut where you feel like you’re no longer improving, but you still aren’t happy with where you’re at. While some might throw in the towel here and declare that they’re just “not talented enough” there are a few relatively simple steps to break out of your box and figure out a new approach that can further develop your skills.
Before you can really make stylistic choices about your own work, you need to be able to know which assumptions you (and others) are making when you’re painting. Draw a very rough sketch of a person. You’ll probably end up with some kind of oval for a head, and a series of oblong roundish things outlining the rest of the body. Why should a head be an oval? Why not some other shape?
Picasso used square heads; cartoon characters sometimes don’t even have a real head (think Spongebob), but we still think of them as recognizably anthropomorphic. Think about all of the other things that you make unconscious, and really very arbitrary assumptions about. How do you think about trees, clouds, houses, animals, or flowers? What if it were different? What about colors? Is the sun really yellow or the sky actually blue all the time? Does it even matter how it is in real life? What If you decided to change it?
Once you’ve removed some of the constraints you didn’t know you were setting for yourself you can set new ones. One of my favorite examples is South Park. If you were on Myspace or early Facebook in the early to mid 2000s you’ll remember a south park character builder that went around at some point encouraging people to make south park avatars for themselves or their friends. This is a great example of a highly constrained medium. Everything is limited, from the shape of head and bodies, to clothing, to hair, to facial expressions. While it’s not exactly fine art and I wouldn’t necessarily constrain myself to such an extent, it’s very distinctive and recognizable while still remaining functional.
Setting Good Constraints
Once you’ve tried that you’ll notice very quickly that setting good rules isn’t as easy as it sounds. The easiest way to learn how to go about it is to borrow from other people’s work. Pick some of your favorite artists and analyze their work. Take note of what assumptions they’re making, and what stylistic choices they’ve decided to make. Then pick up your brush and paint your own version of the same painting.
The way to make it work is to add in, or change, one particular constraint that the original artist was operating under. A single rule can fundamentally alter the entire painting, or it can be almost totally unnoticeable. For example if you decided that everything had to be some sort of geometric shape, you would have a much more drastic impact than if you decided that leaves were always red.