If there are two choices to make, which one is the best one?
There could be two food items on a menu, one that you’ve eaten many times before and another that you’ve never tried.
You might have some free time to practice a skill you’re already good at. Should you practice that skill, or should you learn a new one?
When there are choices to make, and you have decided on one of them, how do you know that you’re headed in the right direction?
There is a neat little trick that I call the discomfort compass. Whatever it is that you’re doing, if you feel uncomfortable, then you’re on the right track. This compass helps when making certain decisions. You simply orient yourself in the direction of the uncomfortable. However, like a compass, you might notice that the direction you are following, let’s call it north, is always ahead of you (if we ignore some technicalities). That is, when you reach your destination, there’s still more to the north. Similarly, when you do something enough to the point where you feel comfortable, it might be time to pick up the compass again and follow it to the next destination. You might stagnate otherwise.
Derek Sivers said the same thing, although a bit more eloquently.