I remember watching a video a number of years ago of the celebrated oil painter Fred Cuming RA. It was a sort of masterclass, and he was painting an estuary scene from scratch. It was wonderful to watch him layering on thick oil paint with such confident strokes of the brush as the painting developed. After a while he had created what I thought was a great scene, with just enough detail to define the ebbing water, the decaying wooden fence posts, and the evening light. It was to me the perfect picture.
But then he mumbled something at the camera and wiped a whole portion off the canvas and started again. I wanted to shout "NO! Don't do it! You had the picture there!". But he repainted and wiped away and repainted again until he was satisfied that the painting was what he wanted. I think he must have had a certain quality of light, or mood, or something in his mind that he wanted to catch. (But I still think the earlier version was better!)
Knowing when to stop is really a matter of opinion, and the end result has to be what you, the artist, is striving to achieve. It didn't matter to Fred on his video, that I wanted him to stop earlier. He knew what he wanted to achieve, and to him, he achieved it. The satisfaction was his, and he must have learned something that day. I know I did!
You can see some of Fred Cuming's work at his website (http://www.fredcuming.com/)
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