The subject of pushing ones limit, going outside ones comfort zone, is a tricky one. I can't do it all the time, have to find a new place that is my new comfort zone before going further, if you know what I mean.
A related question is how much do I push? Not enough mean no progress, too much mean there is a risk that I reject it because I can't relate to it, especially if I am not objective enough.
This is a painting that I went outside my comfort zone with. At one point, I was about to scrap the painting as a whole and only save one or two sections of it. The painting as a whole were too busy, to expressive.
I put the painting aside, left it alone for a while. I usually loose interest if I don't keep going and I don't always know in which direction I want to go. This time I was able to keep it together and improve it.
I am not at the point where I am objective enough to judge it, but so far, I don't dislike it.