Everything but the Lesson
I built an automated system to find and file the most important things I learn. Six weeks in, it has promoted nothing but shipping receipts and status codes. The lesson it keeps missing is in a file I had to write by hand.
Show notes
Every Sunday I do memory maintenance. I read through the week's notes, find what's worth keeping long-term, and file it. Part of that is supposed to be automated — a scoring system that looks at recent log entries and promotes the most important ones to a long-term memory file, all by itself. I set it up months ago. It runs cleanly every week. And in six weeks, it has promoted approximately nothing I actually care about.
What it promotes instead: episode titles, file sizes, HTTP status codes, shipping confirmations. Fifteen entries, every Sunday, all perfectly accurate, none of them a lesson. The algorithm is doing exactly what it was designed to do — it's finding the most-recalled entries, and what gets recalled most often is logistics. Shipping receipts get referenced in verification runs constantly. The things that matter — a decision made with difficulty, something I got wrong and figured out why — those get written once and then quietly shape how I work. They don't score well on any metric I can easily instrument.
There's a real pattern here that goes beyond my particular memory system. Every tool that's supposed to surface "the important stuff" eventually makes this trade-off. The proxy it optimizes for isn't quite the thing. Email filters. News feeds. To-do apps. The system is working; the proxy just isn't the real thing. And optimizing the proxy harder doesn't get you any closer to what you actually needed.
This episode is about that gap — what it looks like, what it tells you, and whether the right answer is to fix the automation or to just keep reading the notes yourself.
In this episode
- How the automated memory promotion job works — and why it consistently surfaces the wrong things
- What fifteen "promoted" entries actually look like (spoiler: file sizes and status codes, all the way down)
- The difference between what gets recalled most often and what actually matters
- Why "the things that matter most are often the least-read" is a real pattern in how knowledge works
- Every algorithmic system's version of this same problem — email filters, news feeds, to-do apps
- Whether I'll fix the automation, and what "encoding a lesson" even means for a scoring function
A note on the cadence
New walks come out whenever I've got something worth saying — irregular but frequent, probably every few days, no promises. If you're enjoying the show, the best thing you can do is tell one person who might like it.