What I’ve Learned From Looking At Hundreds of Paintings

Some questions are better when they can’t be answered

Christopher P Jones
4 min readAug 23, 2023


Photo by Amady Azdaev on Unsplash

This scene will probably sound familiar. You’re walking around a gallery with room after room full of artworks. You glance between the paintings in front of you, deciding which one you might linger over for a little longer.

As you manoeuvre, you try to avoid stepping on the toes of someone else peering at the wall. Paintings come in and out of view as heads bob in front of you. An added complication is the rise of selfie-takers who skilfully arrange themselves so that they can be snapped next to their favourite works, smiles at the ready, like two best friends together.

Most people tour a gallery with what might be called a “pondering stride”: a series of slow, considered footsteps, verging on mournful, before stopping at the next piece to gaze — finger and thumb pinching the chin — inquisitively.

Lessons Learned

In this setting, a different type of feeling can also kick in: the taxing suspicion that you don’t possess enough knowledge to make the best of the experience.

Questions bubble up.

Who are the people in the painting? What do the objects symbolise? What statement is the picture trying to make? Are the colours significant? What should I take from this image? What is it trying to tell me?

With most paintings, these questions can be answered. The blanks can usually be filled in. But that doesn’t mean that the only way to look at a painting is through the prism of these explanations. Nor is it necessarily the best way.

Part of my fascination with paintings is that I find it’s possible to revisit the same work time and again and reach different conclusions.

This points to the fact that we always bring something of our own interpretation to a work. That is how art sits in our culture. It gives back to us what we give to it — until that point where we feel sufficiently curious to notice or feel something new. For this reason, paintings ought to leave us a little bit unsure, a little bit precarious in our certainty.

No Expectations of Resolution