I seem to have a hard time working on more than one painting at once. I can work on more than one of a different media, and will sometimes have watercolors on the go as well as an oil painting, but I can’t seem to paint more than one oil painting at a time. I get so obsessed with this one work that I have to see it through to the end. I play the same album on loop for the duration of most pieces (I feel sorry for the neighbors!). I can’t change to new brushes in the middle of a work and I lose it if something interrupts me while i’m working. I’m a very obsessive painter.
every time I try to put a piece aside to sit on while I work out what’s needed, or to dry, or to work on a deadline, I get stuck. Like something pulled between two equal forces I cannot move forward or back. And then I stop and feel lost and blocked.
My studio is being set up so that I can have a few easels running at once. I love this idea, I can see it so clearly. But I worry that my obsessive tendencies may prevent me from working as I should. I need to have multiple pieces happening. I need to be able to work on more paintings, to produce salable works while I paint the exhibition pieces. To just let things dry once in a while! I need to get past my obsessiveness and move on.
Jennie's Palette 
I find the problem is the emotion often involved in a particular work can be hard to shift when working on another. Perhaps the different mediums give you the mental break away to help that emotional shift?
I know when i was recording music i often had similar issues where i had to work on one track until perfection before i could work on another.
I think you have nailed the issue on the head there 🙂 I pour a lot of emotion into my painting, especially the ochre nudes. Shifting media allows me to keep a nice buzz going, but to relax a bit and not get too overwhelmed. Wen I try to shift artworks within the same medium I lose it, and both pieces suffer.
I tend to be obsessive but I find my day job takes the edge of my obsessiveness and makes me more accommodating. I can have several stories going on at once and sometimes I abandon them for long periods of time before returning to them. I find this helps me because by the time I get back to the story I have a fresh outlook of what I want it to be. But of course this is writing, with painting it may be different.
I think this is the way a lot of artists work, I read about their methods a lot. They will have a few on the go and turn one to the wall for a while to work on another. Many swear by the method and I really wish I could do it! I am holding myself back by only working on one piece at once, but I guess it’s whatever works!
As far as I can tell that is the primary rule in the care and feeding of all types of artists, they all have their systems, they do what works, don’t mess with it! 😉
But yes, I am seriously so obsessive that I obsess about obsessing.
So I do mess with it 😛