AI Whispers #3: Breathers

Sustaining the Vibe When Conversations Go Long

So you’ve laid the groundwork with primers and you’ve been prodding your way through. But now you’re twenty, forty, sixty exchanges deep and things are clicking. Maybe too well. You’ve converged on an approach and nobody’s questioning it anymore.

Time for a breather.

Take a step back. Let’s notice local maxima versus global minima in our [conversation / concepts / approaches / designs] so far.

Are we optimizing in a small neighborhood, or is there something better that we’d only see by stepping out of our current frame? The local maxima framing tells the AI: what we’ve arrived at might be good, but good locally. That’s a different conversation than “any other ideas?”

If there were a dial that allowed you to control this conversation in the way most important to you right now, what would it be labeled and in which direction would you turn it?

This one comes from @kromem2dot0, and I use it pretty much verbatim. It’s a perspective switch—we genuinely don’t know what the AI’s take is on what we’ve been doing, or what it’s been doing throughout the conversation. This surfaces that. Where the local maxima check is analytical, the dial is about hearing from the AI on its own terms.

Let’s treat compaction as a breathing point. Feel free to write a memo or whatever works to capture what you’re thinking — key insights, open questions, where we’re heading.

As conversations get longer, most AI tools now compact earlier context to keep things running. Some models can get a bit anxious around this—and that’s not totally unfounded. Compaction is usually handled by a separate model or pipeline, built differently by every company. Important nuances get lost. We don’t really know what’s important until it’s gone.

You can sometimes tell it’s coming—the AI starts trying to wrap things up, pushing for action items, getting weirdly conclusive while the discussion is still alive. Establish a buffer. Have the AI capture the state of the conversation before it gets compressed into something thinner. Think of it as a pit stop, not a finish line—reflect, notice, and continue.

Primers are about setup. Prodders keep things moving. Breathers? That’s how you keep a long conversation honest.