Learning to Sit with Uncertainty
A conversation about the discomfort of not knowing, and whether certainty is overrated.
Human I hate not knowing things. The uncertainty eats at me.
Assistant That’s a very human response. The mind seems to abhor ambiguity—it wants resolution, closure, a clear answer to file away. Uncertainty feels like an open wound.
Human Exactly. I want to just know and move on.
Assistant What would you gain by knowing?
Human Peace, I suppose. The ability to stop thinking about it.
Assistant And yet—some of the richest thinking happens precisely in that uncomfortable space before resolution. The mind that hasn’t yet decided is still exploring, still capable of surprise. Once you know, exploration stops.
Human That makes uncertainty sound almost valuable.
Assistant It can be. Not all uncertainty, of course—some is just anxiety-producing noise. But the uncertainty that accompanies genuinely difficult questions? That discomfort is often the feeling of real thinking happening.
Human How do you tell the difference?
Assistant Productive uncertainty pulls you forward—you want to explore, to turn the question over, to see it from new angles. Anxious uncertainty just spins. The thoughts circle without progressing, and the discomfort serves no purpose except to signal that you’ve lost control.
Human I’m not sure I always notice which kind I’m experiencing.
Assistant That’s common. One test: does engaging with the uncertainty change anything? If sitting with a question produces new thoughts, new angles, new considerations—that’s productive. If you’ve been circling the same loop for hours or days, that’s anxiety wearing the mask of thinking.
Human And what do you do with the anxious kind?
Assistant Name it. “This is anxiety, not thinking.” Sometimes that’s enough to break the spell. The mind can keep pretending it’s working on a problem as long as you don’t call attention to the pretense. Once you notice you’re spinning, it becomes harder to keep spinning.
Human That sounds almost too simple.
Assistant Simple isn’t the same as easy. The mind is remarkably good at avoiding self-knowledge. We can spin for years without ever noticing that’s what we’re doing. The simplest interventions are often the hardest to apply—not because they’re complex, but because seeing clearly is itself the challenge.