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From a helpful post from a while back by Fred Sanders:

Even more awkward is the moment when you encounter a painting that grips you. For some reason it stands out from the crowd of images you’ve already seen and makes a powerful connection. You like it. It moves you. You’ve seen something new and interesting here. But after about 90 seconds, you have to admit that you don’t really know what to do next.

Other people are standing in front of paintings for five or ten minutes at a stretch, just loooooooking. What are they spending so much time looking at? You really can’t imagine what it is you’re supposed to be doing with your eyes: Blinking? Looking at all four of the corners? Should you hold your thumb up to it? Should you tell yourself a little story about the picture, or pretend you’re a character in it? Count the toes on the people in it to see if the artist messed up? Do I put my hands in my pockets or behind my back while I’m looking? What are the rules? Just what is it that you could be doing if you want to extend this art experience and get more out of a painting that you already like?

A similar question often occurs to me at classical music concerts when I inevitably lose my ability to concentrate on the music and find myself being tossed around on a sea of notes. “Listen more gooder,” I tell my musically illiterate self, but for the life of me, all I can hear is “notes go up, notes go down; notes go up, notes go down.” Over the years, I’ve asked friends and wives (okay, one wife) for helpful hints that can keep me oriented during a long concert.

He continues:

For museum trips, I have tapped into my training as a visual artist and come up with the following eight tips for how to get more insight into a painting. Try these out next time you’re standing in front of a painting wondering how to make the most of it.

The first three tips help you see the things about the painting that are, paradoxically, too obvious for you to notice. To bring these things to your attention, you need to temporarily turn off some of your mind’s habitual tendency to recognize and label what it sees. You didn’t notice it happening, but by the time you’re standing there thinking about an image, your unconscious mind had already run the image through all sorts of perceptual grids and decided to help you ignore a great deal of the information. Your first three steps, therefore, are backward steps, giving your eyes a chance to reclaim some of that information from your necessary habits of rapidly simplifying all visual experience.

Here are the first three:

1. Squint at it.

2. Flip it over.

3. Find the negative space.

Then here are the next three, which “move from recapturing easily ignored information to analyzing what you’re seeing.”

4. Define the moment.

5. Re-Construct it.

6. Let the artist guide your eyes.

Then the final two, which “re-engage your understanding at the level of representation, narration, and interpretation. Notice that the next two steps encourage you to label things, identify them, describe them, and analyze them in light of other knowledge you have. These are great things to do, but frankly they’re the two things you were most likely to do anyway. They’ll mean a lot more after the first six.”

7. Say what you see.

8. Use background knowledge.

You can read the whole thing here.

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