As a behavioral ecologist, I was marked by the complex decisions organisms make and in trying to understand this process, I turned my attention to how cognition evolves. Borrowing from skills I developed to understand the evolution of social signals in birds, I have sought to understand microevolutionary processes on cognitive capacities in wild birds. I will retrace highlights from some of my behavioral work and then shift to my more recent efforts on understanding how selection acts on cognition in wild birds from genes to context dependent cognition. I will also spend some time thinking a bit about how anthropogenic change impacts cognition and key issues I think need to be addressed to understand the impacts of selection on cognition.