Is there a conscious (or subconscious) process you explore when evaluating your options and how they may impact your desired outcome? Ex. You write down pro's & con's for a potential decision.

This is a personal question. Therefore, only you would be able to accurately analyze how it is that you evaluate options when making a decision. However, there are some common strategies that people follow when such a problem arises.

One example of such a strategy would be making a pros and cons list. This allows the person to better understand the problems and benefits of each approach. Another strategy would be working your way backwards. This involves thinking of the desired outcome first, and then retracing the steps that might lead you in that direction. A third example involves talking to people who have faced similar challenges and asking them for advice.