Portraits are one of the things I wanted to do most with painting; unfortunately they were the most difficult. I discovered that doing a portrait of someone I knew was almost impossible, however if I didn’t know them it was usually relatively successful. I didn’t twig on this immediately and as a result I had my share of failures. Now after 50 years I’m trying it again and it’s going relatively well.
I’m approaching portraiture differently this time. I print out an image of the subjects face at about the correct size, then tape it to my painting surface and proceed to paint the image onto the painting using the printed image as a guide. This initially strikes me as a cheat but if that’s what it takes to get a likeness then I will do what it takes. I’m using dividers to take measurements off the printout and transferring them directly to the painting surface. Once I have a likeness, or something close, I can select other areas of the painting to work on.