I'm chicken

I have a hair appointment today - just having the usual done, trim and highlights touched up. But therein lies the "problem" as it were. It's more of the same old, same old. Yes, I've done some out of the box stuff like red and purple streaks, but the hair I think about all the time, the cut that I just can't bring myself to get, is this:

Two things always stop me.

1. It would be the shortest cut I've ever had.
2. What if it looks ridiculous on me?

I know it's hair and hair grows back, but I've got a bunch of conferences coming up and I don't want to go to them looking like a giant mistake from the neck up. (Or looking so different from my author photo - see below - that no one knows it's me.)

Still, I think about how much easier/faster this hair would be than the amount currently on my head. I've ever begun growing out my bangs...just in case.

What do you think? Would you do it? Do you think that cut would look okay on me?