Hindsight is often a great teacher. You can try and try to figure out the optimal actions and the best choices to make, and yet sometimes you just have to step out and experiment. You will quickly know if what you thought was a prudent idea turns out to lack the vibrancy and wisdom you thought it would.
Someone once told me, it is not what I do, but what I do next. I choose to get up dust myself off and try, try again.