If we want our intellectual lives to go as well as possible, should we be "delegating" as many information-gobbling tasks to our gadgets as we can? If not, then how much cognitive outsourcing is too much and, relatedly, what kinds of considerations are relevant to determining this? In this article, J. Adam Carter submits that one particular dimension of intellectual flourishing that will be helpful for the purpose of exploring such questions is that of intellectual autonomy, in particular what he describes as the value of one's freedom to achieve. Several related conclusions are drawn and then applied to recent discussions in the philosophy of education concerning education's epistemic aims.