I was really fed up with my hair last summer, it was shoulder length, and I was tieing it back every day. So, in a fit of total madness, I chopped it all off, like Victoria Beckhams is now. I was so pleased with myself...for about a week, until I realised that I missed having hair! I have been growing it ever since, now have a VERY short bob!
You have a very pretty face, why don't you go for a longish layered bob, maybe with a side fringe? That's a very flattering style, just about long enough to tie back when you need to, and shouldn't need too much styling when you eave it down.
If I were you, I'd book an appointment with a senior stylist at a really good salon, tell them about your lifestyle, wheter you have lots of time to faff around with your hair every morning , etc, and see what they suggest. If you just go a few inches above shoulder length, even if you don't like it, it won't take too long to grow back.
Go for it, nothing boosts your confidence like a good haircut