How do you convince yourself to take a chance on something risky?

Not like jumping the Grand Canyon in a motorcycle or anything. Life stuff, such as moving to a new city or deciding to go to a school far away. How do you talk yourself into taking the chance? I try to tell myself the pros and cons but I still have a hard time even when I can see the pros outweigh the cons. I know these aren’t easy decisions to make, but people do make them.

P.S. Both of those examples are just that…examples.