How to tell when your painting is finished? - "Shore" WIP1-3

Ever find you're not sure when to 'stop' with a painting? Do you find you tend to overwork your paintings, and that they're taking forever to finish? Do your paintings lack a focal point because everything is too detailed?

I have a terrible habit of working on paintings for too long, overworking them, not knowing when to stop, and not knowing when they're finished. I usually assume that when the whole page or canvas is covered in minute detail and I can't fit any more detail in, that the painting must be done.

I decided recently that I need to add more spontaneity or looseness into my paintings. Some of my favourite paintings by other artists are those where you can still see the pastel or brush strokes, and the paper underneath. Pastel paintings in particular lend themselves well to a loose style because they're so easy to blend and fade, but also because the strokes can be laid softly so as to see the paper underneath (especially with sanded papers).

One component to my aim of loosening up my style is to prevent my paintings feeling overworked by stopping when they're actually finished. But how on earth am I supposed to tell when to stop? I decided to test out this idea with a painting of a pacific golden plover (see work in progress shots 1-3).

Obviously, determining when the painting is finished, and when it transitions into being 'overworked' is a very subjective thing, and tends to be particular to an individual artist... some artists have a very loose style and prefer less detailed work, whilst others like a lot of detail. The problem occurs when you as an artist prefer less detailed work, but you just can't seem to stop there! You have to lay the next few (or few hundred) strokes! Adding detail to paintings sometimes feels like a bit of an addiction to me - you know it is bad for you (or your painting), but you just... can't... stop! You get too wrapped up in the minute and instant gratification of laying pretty colours, or creating pretty patterns! Yes, I am fascinated by colour and pattern!

Retrospectively, most artists have some idea whether they should have stopped their painting earlier or not (especially if they take regular work in progress photos to track the development of a piece) - unfortunately, by the end of the process it is often too late, and there is no undo button with most traditional visual art media. Determining when a painting is finished is especially difficult if you have a tendency to find fault with your own work (which most artists do - this is part of the learning process, and essentially a good thing). You see the faults, and keep wanting to fix them, even though you may not know how, so end up overworking the area instead.

So, how do you know when to stop painting?

Have a frame or mat nearby mounted or propped upright on an easel or a wall. Every now and then place your painting in the frame to test it out as a 'finished piece'. The benefit of the mat or frame is that it removes distracting 'messy edges' and allows you to judge the piece itself.
Step back from the painting and view it in its entirety - this is especially important if you work on a flat or semi-horizontal surface, because sitting to paint generally pigeon-holes you into looking at one small part of the painting at once (because you can't get far enough away to view the whole).
Turn the painting on its side, or upside down, or even look at it in the mirror. When you've been gazing on the same subject for a very long time, that subject can become stale to your eyes, whether or not it is still beautiful to most everyone else who views it. This feeling of staleness can make you feel that the painting is not 'good enough' to be finished, when in fact it is. These techniques can also point out if the painting is imbalanced in various ways (that you can't appreciate from the perspective you've been painting from).
When you start to feel that the painting is stale, put it away for a while (a day, a week, a month etc), then come back to look at it. Often with fresh eyes you will be a better judge of whether the work is finished or not.
If you start making strokes that you're not happy with, then it may be time to stop. Sometimes I get to the point in my paintings where I feel that in the last few minutes, every additional stroke I put down didn't feel right, or 'stuffed' the painting. More than likely they didn't completely ruin it, but this might be a good sign that it is time to stop.
If you start working with finer and finer equipment (finer brushes, pens or pastel pencils etc), you might be lured into overworking the detail in a piece.
If you find yourself fiddling with small sections of the piece, then you might be overworking them.
If you lose the inspiration to continue with a painting, it might be time to stop (even if you still feel it isn't finished). Creative endeavours require a certain degree of passion, and paintings without passion feel flat and lifeless.
Assess the 'artistic' elements of the work including composition, contrast, focal point, detail and the story that the painting tells. Often many of these elements must be determined during the planning process of the painting, but some things can be tweaked as you progress. Sometimes entire paintings can need to be changed because your original mental image for the painting doesn't work in practise.
Avoid the need for perfect photo-realism by putting any photographic reference material away when you assess your work (preferrably after a short break from looking at it). If the painting stands on its own, then it is often done.
Ask for constructive feedback from an artist or mentor whom you trust to give you honest but gentle feedback. They may have different ideas to you, but quite often they have a good sense of what makes a finished painting, and when you've gone too far.
Avoid addictive distractions such as listening to audiobooks while you paint - unfortunately, I'm not sure I can completely give this one up!
Work out if your painting sends the message you intended at the start - does it achieve what you wanted it to? Try to view the painting objectively and compare it with your original mental vision for the work. Be aware, however, that sometimes that vision will change through the painting process, and it helps to be open to new ideas.

At the beginning of my pacific golden plover painting (WIP 1), I knew the painting wasn't finished yet because it didn't have a focal point to draw the eye in.

A little further on (WIP 2), although the focal point was there in the bird, the composition wasn't finished because the bird was 'floating' on the page - it didn't feel like it belonged there, despite the very general blocking in of colour in the background.

Later on, however, I decided that the painting was finished (WIP 3), after I'd added rough details to the sandy mud-flat, because the bird (the focal point) was still more detailed than the background, and although there was some interest in the background (and the bird now felt as though it belonged there), I could still see pastel strokes and the coloured pastel paper through the strokes on the edges of the work.