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Ilaria,
I'd like to hear what exactly bothers you about the painting. Is is only the likeness? I think it's a remarkable painting, especially the paint handling and expressiveness in the face. Of course I have no way of seeing the problems with likeness, but it could be a subtle thing as you well know. In my opinion the background could use more spatial depth and less pattern.
I have lots of those "misfits" hanging on satisfied clients' walls. The problem is, I think, that we are our own worst critics. We're painting to solve problems, and we are excruciatingly aware when we have not solved a problem. On a few occasions I've asked the client if I could start over. Only once has a client ever doubted my ability because I took a long time to get the right pose or made a false start. I don't think we should be the least hesitant about telling the client we want to work more on a portrait or start over. We are artists, not machines.
The thing that disturbs me most is when the client can't see the beauty or total transcendence of a certain pose, and insists on another kind of portrait. I'm doing a commission right now with this problem. I'll put my all into it, but I'll always be thinking of what it could have been if the client had given me the artistic freedom to follow my vision.
It's also very frustrating to be in your position, to be given the freedom, and a great subject, and not be able to get the very thing you are aiming for. In your case I would encourage you not to give up. You might be in a period of artistic growth right now. Sometimes these things happen more fequently during those times. I like the idea of taking a photo and trying to pinpoint the likeness problem, and of doing something radical with the part that displeases you. It has so much potential.Good luck with this, Ilaria!
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