During a recent masterclass I attended on critical thinking, as part of a virtual internship for third-year quantitative students, one of the interns asked this question in the chat: “What is the difference between thinking critically and overthinking?” As someone who identifies personally as an overthinker, I thought it would be interesting to explore how we think about these two ways of thinking. What do we really mean by them, and how do they impact us as we navigate a world that is increasingly driven by (mis)information, data, and knowledge work?