Are you a risk-taker? Are you a type of person who jumps headfirst into the next available opportunity or do you take time reasoning about your choices? I have always considered myself a rational thinker, I like weighing my facts, I like considering both sides of the story, and I like having facts to support my decision. Don't get me wrong - I have made some impulsive decisions; however, even those 'impulsive' decisions are typically backed up by a good collection of facts and goals.
I know we are all prone to questioning every decision, thinking and re-thinking what the 'right' path may be in any given situation. My advise would be - take risks. Don't always opt out for the safe option, as this will only leave you with more questions, regrets and what-ifs. Don't be afraid to make mistakes or to end up disappointed with your choice, as any undesirable outcome will only serve you good, helping you eliminate the things you don't like/need in your life. Think about it, how else would you know what those undesirable things are if not by taking your chances?