Subject: Let the people you know surprise you Our minds are prediction machines. This isn’t a flaw—it’s a feature. We are constantly building internal models of the world in order to anticipate what happens next. It’s how we move efficiently, how we stay safe, how we coordinate with other people. And part of getting to know someone is building a model of _them_. Their history. Their motivations. Their habits. Their thinking patterns. The way they tend to respond. When that model works well, it feels deeply rewarding—on both sides. There’s comfort in being understood, and satisfaction in understanding someone else. Predicting a preference. Anticipating a reaction. Knowing what someone will say before they say it. That feeling is real connection. The problem is that people change. Usually not in obvious ways. Not all at once. But slowly, quietly, and continuously. Experiences accumulate. Priorities shift. Old beliefs loosen. New ones form. Meanwhile, our models tend to stay frozen in time. Over time, this creates friction. Frustration. A sense that “you’re not acting like yourself” or “you should know me better by now.” Both people feel misunderstood, even though neither is acting in bad faith. Here’s the uncomfortable truth: The longer you’ve known someone, the more likely it is that your understanding of them is out of date. Familiarity increases confidence, but not necessarily accuracy. This ties into something deeper about judgment itself. The moment we decide we understand something—really understand it—we tend to stop collecting new information. The mental file gets closed. Any new data that challenges the existing picture is minimized, ignored, or explained away. Certainty feels good, but it often comes at the cost of accuracy. Instead of continuing to experience a person directly, we begin interacting primarily with our _model_ of them. That’s where surprise disappears. Sound judgment—about people, situations, even ourselves—requires tolerating ambiguity longer than feels comfortable. It means resisting the urge to finalize our conclusions too early. It means staying open to the possibility that the story isn’t finished yet. Curiosity is what keeps the model alive. Ask people you know well what they think—_now_. Ask what’s been on their mind lately. Ask how they’re reasoning through things. Ask what’s changed. Not as an interrogation. As maintenance. I’ve written more about these ideas elsewhere—about curiosity versus judgment, and about how premature certainty quietly undermines understanding: [[14. In pursuit of happiness, be curious, not judgmental.]] and about how judgment forms, solidifies, and how we can learn to hold it more carefully. This newsletter is an ongoing practice of that same posture: staying open, resisting closure, and leaving room for updates—about others, about the world, and about ourselves. Leave room for surprise.