How to figure out what to paint

A lot of students are concerned with “getting better” at “art”. But what does that really mean? I’ve found in nearly a decade of experience in teaching art to college aged students that generally it is assumed that getting better means improving one’s technical abilities. Many times they want to learn how to make something look a certain way and often gloss over the conceptual aspects of the work. But this route can be deceiving, because once you become proficient at a certain style, you’ll find yourself wondering what it is that you are going to paint. With people going into entertainment design or illustration this is simplified because they are more or less told what to paint, and the client has chosen them because they are proficient in a style they find acceptable.  But what about those artists who are given complete freedom to pursue any avenue they wish, how do they come up with new and fresh ideas?

A lot of study has gone into how to teach creativity to students. While I believe it is well intentioned it has also created a crisis in art schools all across the world. A split occurred between two camps in the 60s as new media and conceptual art began to come to the forefront. On one side there were teachers who didn’t want to stifle their students creativity by making them fit into some sort of dogmatic and technical prison. They believe that students should endlessly experiment on their own and find solutions to complex problems. Their own solutions, because if the teacher told them how to do something, then the work isn’t truly theirs, it’s mostly the teachers. The problem with this was that the work could easily be aesthetically ugly since the student didn’t have a strong enough foundation in things like paint application and color theory. On the other side there were the old school teachers; the formalists. They believed that certain compositions could be better than others, that certain color combinations are more pleasing, and that drawing and painting could be taught in a step by step manner. It’s important to remember I’m talking about Fine Art departments here. Graphic Design and Illustration departments had little trouble with defining what was good or correct, but with Fine Art it was more problematic. And rightfully so, nearly a century after Duchamp put a urinal into a gallery and called it Art, we’re still wrestling with how best to categorize and position certain art as being better than other art.  And this has everything to do with the paralysis that young and some experienced artists feel when they begin a new work/painting. The question still looms. If I learn to paint exactly how I want to paint, then what should I paint?

One concept that is important to familiarize yourself with is called “Divergent Thinking”.   Divergent thinking is the ability to bring two seemingly disparate concepts together and it’s at the heart of what we call creativity. One thing that’s interesting about divergent thinking is that we’re all born with it. It actually degrades over time. I’m not joking, in a test designed to gauge how good someone is at divergent thinking 5 year olds actually outperform 15 year olds. As we become more self conscious, we become less adventurous, and less creative. The evil “inner critic voice” pipes up, and says that something looks bad, or that something is ridiculous, or “that’s not a good idea!” .  And this is the first thing which you need to engage and it brings us to the first of many steps designed to enhance your creativity and help you figure out what to paint!

1: Be Fearless.

Fake it until you make it is a common idiom of our time, but if there’s one place where it truly fits it’s in helping artists become who they truly wish to be. This could mean fending off all sorts of evil demons and anxieties. You could make art which is confronting some trauma which you have experienced, or you could just be making still lifes in your kitchen and you’re scared as hell to show your work publicly. Either way you need to get over it, be fearless, and take the task head on.

2. The five whys.

Ask yourself why, then ask yourself why again, and again, and again. This should help you identify exactly why it is you want to make art, and help you create a schedule to achieve your goals.  Avoid saying things like “nice” and “I like” when answering these questions. It can be more difficult than you think but I’ve seen it be extremely helpful in the long run.

Why do you want to paint?

Because I want to create something beautiful.


Because the world can be ugly.


Because people don’t respect nature.


Because they want to make money.


Because some need to feed their families, and others are just greedy.

So you see what just happened there? We went very quickly to the heart of what this imaginary artist wanted to talk about in their work.  Suddenly ideas about wealth and privilege and nature should start overflowing from your brain. Which brings us to the next step.

Mind Mapping:

Now that you’ve got your creative juices flowing it’s time to record those ideas before they fade away.  And the way to do this, is with what’s called a mind map. Start with your central idea and put it in the center and then go wild making as many connections as you can to it. Lets continue with the previous theme and see what we can come up with.

mind map

Again, all of these ideas should just flow as fast as possible. Overthinking will kill it, just get as much as you can down as fast as you can and you’ll be surprised at all the possible connections. A glimpse at the mind-map above gives us an enormous amount of possibilities for paintings about the dichotomy of nature and money. You could paint deer doing cocaine with strippers. Or a salmon jumping over a strip mall. How about some stock market graphs made from moss? Or a totem pole full of executives? The list goes on, and on, and on and the possibilities are endless. The thing that’s important to remember is that you have to be playful at this stage. Channel your inner five year old and be goofy, don’t be afraid to be nonsensical  and you should be able to surprise yourself with some ideas you didn’t know you had in you!

Cheap and fast test paintings/drawings:

Once you’ve got an idea that you like. Say, a totem pole of executives. It’s time to make some tests. One mistake a lot of young artists make is to think they are going to make one perfect drawing on their nice and shiny new canvas. Screw that! You need to make a ton of small and cheap tests first. Start with making some small thumbnail sketches, just play with composition and how you want things to fit into your shape/size of canvas at first. Then gather some source material if you need to. Go to the woods near your house and take pictures of moss. Collect images of totem poles around the world. Get pictures of bank executives. Look at how currencies are designed and their format etc. etc. After you’ve got a big collection of source materials start sketching your composition in a more finished manner. These sketches can take the form of value studies, and some color studies.

Transfer your tests to your canvas:

Once you’ve got your sketching and source materials gathered and sorted it’s time to transfer these onto your canvas. This can be done by using the grid method which I outlined in a previous lesson, or even with a projector. At this point your conceptual work and planning is finished, and we’re back to the issue of technique and paint application!



This post was written by Jer

Educator and creator of I look forward to watching your progress!