This chapter reviews the intimate connection between belief and reality according to James, showing how one’s sense of reality is necessarily related to a subjective feeling of acquiescence. Starting with a brief discussion of the relation between imagining, willing, and believing, it covers a very basic issue in James’s psychology and philosophy: how it is that our thought comes to accept, however provisionally, a particular view of how things are and, perhaps too, of what lies behind them, whether that trans-conscious dimension of reality be articulated in scientific, religious, or other forms of interpretation. Treating belief as entailing hypotheses, the chapter discusses James’s distinction between live and dead hypotheses and how they confront us with either forced or avoidable as well as either momentous or trivial decisions. His crucial argument involves the right to believe what one is inclined to believe, so long (but only so far) as dispositive evidence to the contrary is lacking. The chapter pursues these matters through works published by James after The Principles of Psychology and introduces James’s radical empiricism and pluralism, clarifying how these philosophical commitments impacted upon his own belief in the multiplicity of ways that reality can be viewed.