From tiny postage stamp portraits to the big black and white image of my friend, Freddie Stendahl, I’ve drawn at least 1500 portraits over my career. Drawing a detailed portrait can be a powerful and unusual experience, especially when it is of a close friend. When I’m choosing what angle or lighting to use for the drawing, I need to leave thinking behind and rely purely on feeling. Reasoning always lets me down. Once I start rendering, I only become aware of the light and dark pattern, and textures before me. I often forget who I’m drawing or even that I’m drawing a person. At some point, the magic occurs, and the pattern becomes a likeness that has a bit of heart to it. After the drawing is complete, I feel a higher level of closeness with that person, but I doubt they feel the same.

Thinking is not often your friend. One of the two worst things (and they’re very similar) you can think about while making portraits is, “Uh-oh, this isn’t coming out well.” That self-judgement kills the project before it begins. And almost as bad is, “Hey, this is starting to really come out great.” When you hear this, you no longer have the awareness you need.