“I “overwork” each and every oil painting I do. I call it done, then work another 20 hours on say, a few edges or some blended area. I think I know when it’ll be right, and certainly know it’s not right “enough”, so I continue, mostly dabbling until it falls or not into place. I struggle very, very, hard with my work, but I’m not satisfied by far with almost all of my work. Can you give me advice on this? I’ve heard ‘don’t fiddle’, but is hard work, experimenting continuously such a bad thing?”
I believe that experimentation and hard work are both key essentials to being an artist; you won’t go anywhere artistically without rigorously using both in your work process. However, both experimentation and hard work need to be intelligently applied in order for your paintings to positively benefit.
From what you’re describing, it sounds like you’re employing hard work and experimentation very late in the process of making a painting. For many reasons, this approach to painting can sometimes be more detrimental than helpful. Experimentation is critical to the creative process, but it tends to be at the height of its effectiveness in the early stages of a work, when one is brainstorming and trying out all different kinds of ideas. It is frequently counterproductive to be experimenting and making major last minute changes in the final stages when most of the painting is already finished.
One major issue that all artists have to contend with is when to stop working on a piece and to call it “finished”. The problem with the process of painting (as well as many other visual art media) is that you can always do more. There’s no concrete signal in the process of painting that something is officially “done”. We have to make that decision for ourselves, and that decision is frequently incredibly nerve wracking for many of us.
I know that I myself always struggle with this because I personally want my work to appear spontaneous and gestural. There is such a fine line between a drawing looking fresh and refined versus looking simply incomplete. I stop working on a piece when I notice that I’m nit picking the work, when I’m not making any major changes anymore and I’m just sitting there needlessly scrutinizing tiny details. When too much time is spent fussing about minute areas of a painting, the painting loses it’s original character and begins to look tired and labored. Hard work is important, but not if it’s misdirected and making things worse in the painting.
One of the best examples of a painter who really knew when to stop working on a painting is John Singer Sargent. He was so good at selecting which areas to fully render and which areas could be left looking more “unfinished”. This gave his paintings a freshness that was incredibly active and lively, as if the paint was still wet. In this painting above, there is a comparative tightness and refined quality to the face, while the rest of the piece is painted very loosely. Had Sargent fully rendered every part of the painting to the degree that the face was rendered, this painting would have been overworked.
One of the classic problems I see with beginning students is works that simply look unfinished. So when I work with students at RISD in my Freshman Drawing class, I ask them to go too far, to intentionally overwork a piece to the point that it “dies” in the process. The reason I encourage this kind of approach with my freshman students is because it’s important to have the experience of having pushed a piece too far in order to figure out where to stop. Then with their next work, they’re able to pull back a little to bring the work to the stage they want it to be at. This is a good exercise which provides students the skills to be able to gauge when to stop in a piece. You won’t know how far to go unless you’ve gone too far.
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Clara Lieu 
Thanks Clara so much for answering my question. It’s been 4 years now and i still do it alot. I have spent nearly 15 hours once on a small eye, mostly using a toothpick. That was about a year or two ago (no more toothpicks though).
Most recent one was nothing more than a dark blending into a light over a very large area (background suggesting water, completely out of focus). I did not feel comfortable about how much light or how much dark there was..20 hours of work. Luckily, I’m ok with it now. But not happy that i struggled that long on it just the same.
I have to let this out…i’ve been working about 10 hours the past 3 days on a background that is nothing more than a blend of paint with no structural elements at all in it. My patience is killing me. I love painting, but it just seems to go from super to the worse, and i can’t accept creeping up to an average, then stopping.