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The first thing to decide will be whether you are going to paint the portrait entirely from life, from photographs and some life studies, or entirely from photographs. the first option has the most old-world-master flair, but is stressful and high-pressure- I prefer doing some sketches and taking rough color notes from life, and then doing the finished work in the studio with photos and my notes. Of course, for clients from farther away who find you through the internet or something, this might not be an option. In those cases I like to get as many photographs as possible, if only to get a better "fee" for the subject.
The next step is to make some rough sketches- you probably already have an approximate size in mind, if only because of budget. Is this an intimate portrait, a person's face and expression seen larger than life? Or will you be painting their whole body and all of it's potential language and nuancing? Will you use a vertical format, or the less conventional horizontal one? What is the tone of the portrait, where will it be hung? these questions give you a starting point- a medium sized, formal portrait to be hung in the office, a small portrait of someone's child in their christening outfit that will be in some beautiful nook of the house, a large, dramatic partial nude that might be destined for the master bedroom.
Thumbnail sketches are your friend at this stage- place the head first, since it's almost certainly your focal point, and let the other necessary elements flow. Figure out what makes an interesting composition. Look back over those reference photos and sketches often! you'll probably come up with two or three ideas you like well enough to present to the client.
Another thing that is your friend if you still find it challenging to capture a likeness- carbon paper, or tracing paper. Use them, not necessarily for the final work, but to become familiar with the contours of your subjects face, everything from the way their eyes crinkle to the shape of their teeth. When I get done with a portrait I swear I know that person's face far better than my own, if only because of the intense observation that's required :)
And then you're ready to begin. At this point you're familiar with the subject, and you know which images/pose you're using for reference. Take a deep breath, and take in that blank canvas you're about to transform.
With your medium of choice- graphite, charcoal, or thinned paint- place the head, the center of interest. Begin to map
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