Recently one of my friends asked me to paint a portrait of her children (who are now grown) and she wondered it I would chronicle the steps of the painting in pictures. I have really enjoyed this little exercise because it forced me to think about the steps I use. I first "live" with the photo for several days or weeks...I take the subject with me on trips and I study them while I am sitting on the couch reading or watching TV. I create a plan in my head and try to remember that I am not a realistic portrait artist but I strive for a "likeness" and "personality". Then I decide how I want to start the background and what underpainting I might use. (You can see from the photo I was outside on the deck so that the color was correct. Natural light is my friend.) Because the photo had some pinkish areas in the background I toned my canvas with a color close to what I wanted to peak through. Then I drew the image on the canvas trying to establish where the darks would be versus lights. Next I started laying in the darks and stepping back and trying to establish a pattern that appealed to me.
I then started on their faces and personalities.