While powerful in its simplicity and important to computation, the boolean can be limiting in applications. In this talk, briefly explore the history of boolean logic in computation and look at how booleans can become misused in programming languages. Explore examples where booleans obscure the meaning of code, make code harder to maintain, and hinder usability for teammates and users. Learn how to harness custom types and higher-order functions to write clearer code. More importantly, learn how to place empathy and usability at the forefront of the APIs and UIs you build.