Sofonisba Anguissola, Self-Portrait, 1556

When people want what they want, and they want it badly enough, they will have it. Even the most tight knit systems have loopholes, and even the tallest gates have a way around. Intellect, creativity, and strategic thinking are often the keys to success in spotting the loophole, and capitalizing on it. While writers use objects and people to symbolize a larger idea or meaning, artists have the added luxury of creating larger- scale twists.

In the portrait above, Sofonisba Anguissola paints…herself. But women could not paint themselves. Portraits of women (especially by women) were taboo, and religious works took the front seat of artistic pursuits. Here, Anguissola finds the loophole. “Not allowed to paint a portrait of myself? It’s not, you see? It’s a religious scene (where the woman painted is obviously me), I just happened to expand the scale so you can see me creating this sacred work.” The creativity and skill in artists combine in works to dodge social bullets, technical struggles, and stick the eye of the needle through every loophole.