Context Rot

It's about to be the quiet week between holidays, and if you're anything like me, you're feeling the pull to audit things. The calendar. The goals. The budget. The recurring meetings that somehow multiplied when you weren't looking.

This instinct is good. Things accumulate dust, systems drift from intention, and the new year offers a natural reset point.

Most people won't think to audit their context.

I came across a concept recently that has been sitting with me: context rot.

It comes from research on AI memory systems, and the idea is simple and critically important: context doesn't stay fresh. It degrades over time. The information you captured, the assumptions you encoded, the knowledge you documented—all of it has a shelf life shorter than you think.

Context rot happens silently. There's no error message. Things still work—they just work less well than they could, in ways you don't notice because the degradation is gradual.

"Context rot happens silently. There's no error message. Things still work—they just work less well than they could, in ways you don't notice because the degradation is gradual."

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This isn't just about AI. Think about the organizational context you're carrying into 2026:

Your product strategy. The one you finalized in Q1, based on market conditions that have since shifted. The competitive landscape looks different now. Customer priorities have evolved. But the strategy doc sits unchanged in the wiki, slowly fossilizing into received wisdom.

Your roadmap assumptions. Built on customer feedback you gathered eight months ago. Those customers' problems have evolved. Some have churned. New segments have emerged. But the roadmap still reflects January's understanding of the market.

Your customer insights. The synthesis you did after last year's research. The personas. The journey maps. How much of that reflects who your customers are now versus who they were when you captured it?

Your team's mental models. The shared understanding of what's possible, what's hard, and what matters. Formed through experiences that are increasingly distant from current reality.

All of this context is rotting. Quietly. Continuously.

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Now layer AI on top.

The prompts you refined through trial and error? Built on models that have since evolved. What was optimal for Claude 3.5 isn't optimal for Claude 4.

The workflows you designed? Probably built around limitations that no longer exist, or missing capabilities that arrived after you stopped iterating.

The AI guidelines you wrote in Q2? Fossilizing into policy that nobody questions.

The deeper problem is that those AI systems are often built on your organizational context. They're ingesting your strategy docs, your customer insights, your roadmap assumptions. If that foundation is rotting, everything downstream is compromised.

Context rot compounds.

This isn't a new problem. Context has always decayed. But the cost of that decay just went up.

Before AI, a stale strategy doc was friction—annoying but survivable. The real strategy lived in people's heads, in hallway conversations, in tribal knowledge that adapted faster than any document could.

Now? AI doesn't have access to the hallway conversations. It only knows what you've given it. If the documented context is stale, that staleness gets operationalized. Compounded. Scaled.

"AI doesn't have access to the hallway conversations. It only knows what you've given it."

The maintenance work that used to be a nice-to-have is now load-bearing.

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I just published a Saturday Morning Coffee video about using AI to audit your recurring meetings before the new year (also posting to LinkedIn tomorrow). The premise is that your calendar is an operating system—it determines what information you receive, which relationships you maintain, and where you have visibility.

Your organizational context is also an operating system. It shapes every decision, every prioritization, every AI interaction. And it deserves the same periodic scrutiny.

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I'm not going to give you a checklist. It's the holidays, and you don't need homework.

But if you find yourself with a quiet hour between now and January, here's a question worth sitting with:

What context are you carrying into 2026 that's already stale?

The strategy. The roadmap. The customer understanding. The AI workflows. The assumptions about what's possible.

Some of it is still good. Some of it is rotting.

The new year is a fine time to figure out which is which.

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Happy holidays. I'll see you in January.

Break a Pencil,

Michael