The Bane of my Existence

Work...I know we all have to do it, but I swear, when I was a little kid, I had such a different vision of what it would be like. It was very glamorous when I envisioned what my life would look like today, and it was SOOOO different in my wild dreams. I wish we could continue dreaming like we did when we were young. The world had so many options. In my mind, I could do absolutely anything. I even pictured myself playing at Wimbledon against Venus Williams. When did it become okay to be complacent and just go along with the machine of society...working every day, doing the same thing every day, and just living the mundane life with no excitement...?
I wish I had the guts to make some really risky decisions. How does one go about learning how to take risks when we have responsibilities that we have to care for...? I have bills, rent, car payment, student loan payments, etc., etc., etc.
In my wildest dreams today, I wish I could just pick up and move to an exciting place where everything is new and nothing is the same. I'm sure in some ways, familiarity is a great thing, but familiarity is what keeps me from moving forward and growing and learning more about myself and the world. I want to be scared and power forward anyway to push through to the other side of great.
Does anyone know how to do this? I'm unsure and I sure could use something new in my life, albeit scary.