This article develops a formal approach to evaluating freedom in interactive settings based on the literatures on preference for flexibility and measurement of diversity. The approach posits that the value of freedom has an instrumental component - grounded in preferences - and an intrinsic component. The philosophical justification of the approach is considered and potential conflicts between freedom and efficiency are explored. On a technical level, the article extends the notion of a diversity measure to menus of lotteries, which is what is needed to evaluate freedom when many agents seek flexibility simultaneously.