Fashion Inspiration: Undercuts

I like to stay up on the latest fashion statements - clothing and beyond. A hair trend that I haven't been able to stop thinking about lately? Undercuts. Like this one:

I've actually been obsessed with undercuts for a while. Ever since Anya Ayoung-Chee was on Project Runway in 2011, I've dreamed about having an undercut like hers:

I always tell myself that I'm too old. I can't do it because of my career. I don't know what other people will think. But because I've been so inspired by all of the cute undercuts I've seen recently, I actually think that an undercut is something I want to try!

We only live once, right? Stop dreaming, start doing? No risk, no reward? It will grow back? Fuck it? What other sayings can I tell myself about the benefits of taking a risk before I do it? 

I need a little hand holding and encouragement on this one. So if you have an undercut and love it, tell me I'm making the right choice!  If you've taken a haircut risk in the past and it paid off, tell me!