The biggest problem is making the leap of faith. Everyone is scared to do it because in the military, things are done for you. Reference the article below. I'm not calling you a female, but the last paragraph of that article says it all.
Female veterans struggle in jobs market - USATODAY.com
"In the military you get taken care of in so many ways that you forget how to do things for yourself," Fazio says. "What I needed most was someone to help me learn to live a normal life again."