Where do you often place your room for error in the house of risk? That is, how do you prefer to err when you guess on anything, for fun or when planning? Do you tend to overshoot, underestimate, alternate, something other?
Should you think more than twice about something you need to think about on more than one occasion? That depends on the type of person you are, and/or what that something is.
How often do you intentionally get yourself into things about which you don’t know much? And how have they generally turned out? Do you seriously wish you would get yourself into things about which you didn’t know much more or less often? There isn’t a right or wrong answer to any of those questions. You are who you are, although if you seriously wished you would get yourself into more things about which you didn’t know much, you might want to plan on how you’ll make that happen as it won’t likely happen on its own.