In my life and in the lives of people I’ve worked with, these are some signs you’ve hit the limit of useful information you can gather: You are able to argue credibly for and against the options you’re considering from all angles. You’re stretching for insight by asking people for advice who are more than one step removed from the problem or who don’t have experience solving problems of this sort. You feel like you need to learn more, but you’ve stopped learning new things, and are instead in a constant loop reviewing the same information (or same arguments) over and over.