Hair Dilemma

I have been debating lately about cutting my hair short again. I had the same hairstyle (the one on the right) for about three years. I think it suits me, but I started to get bored with it, so I started growing it out. The pic on the left was taken a couple of weeks ago. My hair is just past my shoulders now and is sort of blah. Anyone have any suggestions what I should do with it? I don't know that I would be comfortable going much shorter than it was before, but I just don't think growing it out any longer would look good. I also am not minding having it a bit darker. The picture on the left was taken about two months after my last colour, and you can hardly see any roots. I think I look good blonder, but it definitely requires more upkeep. I have appreciated not having to get my hair cut every six weeks or so, like I did when it was shorter. I have a hair appointment booked for December 11th, so I will try to figure it out by then!