Advice on a Haircut?

I'm so back an forth with what I want to do with my hair, but here lately I have been wanting to make it really short. My hair is at the shortest part shoulder length. It was shorter, but it grew. And not I want to go even short than I have ever done before. I'm just so scared if it won't look good on me or I won't like it. Of course, I do this every time, and it ends up looking amazing on me.

Here's what my hair is now:



And this is what I want to do with my hair:

It won't show up

I'm not going blonde, or at least not right now. I've done that twice now. What do you guys think? Should I go for it?