Today we feature a delightful conversation with Ben Orlin, author of Math with Bad Drawings: Illuminating the Ideas That Shape Our Reality, Change Is the Only Constant: The Wisdom of Calculus in a Madcap World, and, as of April 2022, Math Games with Bad Drawings: 75 1/4 Simple, Challenging, Go-Anywhere Games—And Why They Matter. Ben grew up in Massachusetts, attended Yale as an undergraduate, and, as he puts it, has taught mathematics to every age between 12 and 18. He finds teaching an appealing career and is particularly interested in obstacles that keep people away from mathematics and how students experience failure in the discipline. In this conversation, you will hear about Ben’s teaching experiences in America and England, about how he started his wildly successful blog “math with bad drawings,” about his rhythm for writing, and about how he protects his sleep.