To dye it or not to dye it????

Okay so I change my hair color lets just say more often then most....way more often! 
I have went throught the painful process of getting my hair from very dark to blonde and as much as I was thrilled to finally get it the color I thought I wanted. (*thought being the key word there*)
I have since found myself dying to dye it dark again.
So the question is this do I dye it now.... or wait until it gets a bit closer to fall????? No matter what anyone says,  I have to say I will more than likely dye it anyways lol!

I have really been feeling the dark hair as well as the pixi cut but Im very scared to take that leap and go that short......

Oh but how I love this look!!!!