I was watching a video from Dan Applebaum and his response to the question "Should I do this?" caught my attention. The interesting part is how he explains that although the question seems like a reasonable one to ask ourselves, it actually reveals little flaw in our human psyche.
So, instead of asking "Should I do this?"
Ask, "If I do not do this, will I regret it?"
The thinking behind this is that you get to eliminate the "wrong" choices from the onset by choosing to measure losses against the cost instead of benefits against the cost.
This is important because we're tapping into a flaw of human psychology, we hate losses more than gains.