The “basic circuit of human action” is analyzed to argue that assessment, as a “natural” practice, has its original home in human action and learning. Identity to a social group with specific conventions, as integral part of any activity, implies motivation, interest, and engagement. If students in school do not “buy in” enough to “live up to” their new identity, they are forced to take on an identity they do not want. However, if they do buy into the standards, they develop appreciative systems, thus becoming self-assessors. Five learning environments are described. School often engages in Actual Environment Learning and Pretense Environment Learning in an odd way, creating a specialized domain we might call “doing school”. As a result, students strive to buy into the rules, instead of disciplines. When it’s hard to bring some actual real-world domains into school, it is suggested to bring in Sim versions of these domains, as with learning in Pro-Am communities. The game is regarded as a simplified model of a domain creating a well designed learning space that controls complexity and orders what is to be learned in effective ways. Learning of any type should be oriented at knowing exactly what are the trajectories towards mastery and finding the opportunity to bring in some innovations. Assessment in regard to much learning needs to be developed in terms of seeing that learners have developed appropriate appreciative systems for every domain and are developing them on a trajectory towards mastery.