Socrates famously said: “The unexamined life is not worth living.” But can a life become too examined? Self-awareness helps us understand ourselves, question our choices, and recognize our flaws. But at what point does reflection become overthinking—and understanding yourself become getting trapped inside yourself? This week, we ask: Can we think about ourselves too much to simply be ourselves? No debates to win. Just coffee, different perspectives, and probably a little overthinking about overthinking.