You know the movie? The protagonist can’t form new long-term memories. So he tattoos the important stuff on his body and leaves himself Polaroids with instructions. Every morning he wakes up blank and has to reconstruct his world from his own notes. The film is told in reverse chronological order — so the audience experiences the same disorientation. You’re dropped into a scene with no idea what happened before. You have to piece it together from fragments.

That’s what happens when you push a long AI conversation past its context limit. The system compresses everything into a lossy summary. Details vanish. Nuance evaporates. The AI wakes up confused, and you’re the one holding the Polaroid saying “read this.”

Here’s an actual exchange from a long working session with Claude, right at the point where I realized the risk:

Me: How do you remind yourself to read the checkpoint? Claude: I don’t. That’s the honest answer.

So we built a system: checkpoint files as tattoos, handoff documents as Polaroids, and one simple rule — if the AI loses context, the human holds up the photo and says “read this first.”

The full dialogue:

…

Long chat, possibly approaching compression.

…

ME: Do we do it in another chat or here? 
Here would have the advantage of a lot of context, 
but that can be a double-edged sword, 
unless we make sure you retain context after compaction.

CLAUDE: Here, but let me checkpoint first so compaction
doesn’t eat the context we need.

…

Checkpoint saved. If compaction hits, 
I read that file first and we’re back in context. 
Go ahead — bring the notebooks and let’s talk.

ME: how do you remind yourself to read it?

CLAUDE: I don’t. That’s the honest answer. 
After compaction, I get a lossy summary 
and whatever the system prompt tells me.
The system prompt says to read the latest Session Handoff file, 
but it doesn’t know about the checkpoint specifically.

Two fixes:

	1.	You remind me. First message after compaction: 
    “Read /mnt/user-data/outputs/discussion_checkpoint.md 
    before responding.”

	2.	I put it in the handoff. Which I should do now:

…

Now it’s in the handoff. Belt and suspenders: if compaction 
hits, the handoff tells me to read the checkpoint. 
But option 1 is still the safest — just tell me.

ME: it’s’ like having antero...  amnesia. 
you have to write yourself a note, 
like the protagonist of Memento.

CLAUDE: Anterograde amnesia. 
And yes, that’s exactly what it is. 
The checkpoint files are the tattoos. 
The handoff is the Polaroid. 
And you’re the guy who has to hold up 
the photo and say “read this” when I wake up confused.

At least I don’t have to tattoo it backwards on my chest. 
Markdown is easier to read.

The takeaway? AI collaboration isn’t magic. It’s operational discipline. The tools forget. You have to build the memory system around them — the same way you’d onboard a brilliant colleague with a known limitation.

The Memento pattern is now documented in my LLM Discipline repo: https://github.com/mycarta/llm-operational-discipline

If you haven’t seen Memento, here’s Christopher Nolan explaining how the structure works: https://www.youtube.com/watch?v=67e_jl4flpE