I have always been a drawer but I started painting seriously, with oils, about two years ago. In that time I have learned a lot and wanted to create a list of things to remember while I'm working. Painting is an ambiguous process and can not be quantified into rules. Rules can be and are broken. But I like to have something to fall back on when I'm feeling stuck. This is for everyone who is interested, but it's also for myself. I'm sure I'll update this list from time to time, as it is by no means complete.
These apply specifically to my process in representational oil painting, But I'm sure some of these could be appropriate in other areas.
1: Risk over fear, always.
If you have the *good taste to know that something could be better, then go for it. Don't let fear prevent you from making something great. This is really about taking something that may be precious to you and being willing to risk destroying it. I put this first because I think it is the most important of this list. This is how we grow as artists; through risk, struggle and experimentation. It is also one of the most difficult hurdles to overcome, and pops up all the time.
*Ira Glass on Good Taste (YouTube)
2: When your stuck look to reality or go back to knowledge.
When you are working with a model, photo or reference of some sort and you find yourself stuck, just look to reality. Sometimes though you have to go back to knowledge.
You may find yourself having an anatomy issue and all you need to do is keep your eyes on the model, paint what you see not what you think. In other cases a trailing arm may have a warm light cast on it in your photo reference. However, It's making the arm pop to much in your painting; making the painting feel flat and awkward. In this case knowledge trumps reality. Make the arm recede more; make it cooler in color, darker, add some background color to it or paint it more roughly.
3: Don't be lazy.
If you see a problem or anticipate a problem, don't avoid it. Chances are it will come back to bite you and you may be making it more difficult for yourself in the end.
And more broadly, If you find yourself too tired or uninspired to paint or draw... just do it, don't think, just pick up your pencil or brush and make something. Making a painting is a challenge in more ways than the obvious. Sometimes you have to force yourself to just work despite everything you are feeling or the external forces in your life. It must be a priority. A painter works hard.
4: Trust in your process, in yourself.
This is a big one, especially if you are trying something new, taking risks. Have faith that what you are doing will work out in the end. Even if your piece ends up in the trash, at least you learned from it. As Steve Jobs famously said, "...you have to trust that the dots will somehow connect in your future". That is a wonderful piece of wisdom and rings true for painting just as much as building a ridiculously successful company. If you don't have faith in your work and your abilities you risk giving up or not even trying at all.
Sometimes you have to throw everything aside, any stresses, fears or doubts. Just exist in the moment, painting. Believe in your painting. Confidence is always an ally, even perhaps a bit of ego.
5: The painting as a whole.
My mentor calls it "knitting". Getting sucked into a small area of your painting and just focusing on it, building outwards from there. Don't depend on that too much. Your painting is an entire piece, people will look at the entire piece, not just the hand you spent an entire day on. Working piece by piece can leave your painting with a patchwork feeling. If you touch here, also touch over there. Build connections across your entire painting that speak to the composition.
This is not to say that you can not give areas certain special attention. Just be aware, do not get stuck. This leads us into number six...
6: The problem is not what you think.
You may be looking at your piece and wondering why something is not working. The answers are not always that obvious. An eye may look off because the ear is too close or the back of the head is missing. The eye itself is fine. It's the connections it shares with other elements that are off.
These are problems that sometimes require a bit of "drastic" action. Have an *educated friend look to your work, turn it upside down, look at it in the mirror, take a picture and look at it on your computer. Check your tonal levels by turning the image greyscale.
The key is to gain some perspective. Look at your painting in different way to gain different insight.
*By educated I mean someone who can give you a real critique, not just "oh i like it". Show them the painting next to another of your finished paintings so they can make comparisons.
7: Don't look back.
This one I just ran into a couple days back. I had my painting in front of me as I was eating lunch and was fairly happy with how things were going up until that point. I decided I needed to make a small change to the face and then I would move on (stop knitting!). Well i made that change and before you know it, things were all different. I couldn't help feeling that I had made things worse in some way... but there was no going back.
Just accept how things are now and think about how you can move forwards, don't try and recapture something you had in the past. It's a path that leads to a fear of messing something up that can cripple your momentum. Keep your eyes in the future.
8: Be Bold
If your painting is feeling like it doesn't have the power it needs, be willing to go too far. You can always pull back. Give yourself a splash of power to use as a guide. Put an exeptional color on an elbow or in the background and use that as a reference point to bring up everything else. In the end maybe you take that reference back down, but it's done it's job.
9: Let the painting stand.
When you feel like you're finished with a piece. Bring it home, let it stand on your kitchen wall for a week or two, or even more. Really start to look at it and let others as well. This is like beta testing. You will gain much more insight as to whether you are through with it or not.
10: Building a connection.
This one is more just an insight. I can sometimes tell straight away whether a painting will be successful or not. Even with only the first few lines put down. Maybe it's the emerging composition or just my mood, but I have made a connection with something. That connection is really important for me. Sometimes you loose a connection and sometimes you get one way later on, after you have really worked through and struggled.
Connection is something you should always listen to, It will tell you to keep going. A lack of connection, for too long may tell you to move on, but don't use it as an excuse to give in too soon.
It's hard to describe it, but you know it when you feel it. It's a rush.