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Doreen,
I started off painting people I knew. My first portrait was of the child of friends and I made it very clear that it wasn't going to be for sale for the forseeable future, since I was trying to build up a body of work, and also found it difficult to let a painting go unless I knew from the beginning that itwould be a commission which I couldn't keep. Then I painted a woman friend, and after that the daughter of my secretary. In each case, I had them sign a release and also gave them a copy of the picture (good photocopies once they became available).
I carried photos of my work in a small album, and got my first commission by showing a friend a portrait of another mutual acquaintance (a game warden) about whom we were talking. He was really struck by it, and asked if I could do a portrait of his wife, and I was on my way. Because I seemed to be painting people who were fairly well known in our area, it helped when I pulled out my mini-portfolio because others could recognize them readily and see that the likeness and spirit were true to the subjects. Once you have a portfolio and/or website and/or a name for portraiture in your area, it will be easier for you to approach people to paint them or their child, just as Michael described. At that point they'll be flattered rather than wary. Good luck!
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