The Agent Knew I Was Going to a Wedding
It still didn't know to pack my rings. You have to teach it about yourself.
You’re reading Playbooks & Priorities, a newsletter about working, parenting, and working parenthood.
I’m a packing list person. Not everyone is, and I’ve made peace with that. But somewhere along the way I figured out that spending fifteen minutes prepping a list upfront makes the actual packing embarrassingly fast. Instead of one long, stressful session the night before a trip, you do a short thinking session early, and then execution becomes almost mindless. I hate that this is true, but alas it is.
A few weeks ago, before a trip to New York with my husband and three kids, I pulled my historical packing lists out of Todoist and handed them to ChatGPT. Then I did something that made the output actually useful: I layered in context.
I told it the kids were older than they were for the trips those lists came from — no bottles anymore, but yes cups. I told it that the adults were going to a wedding, which meant specific outfits, specific shoes, specific bag. I told it we’d have a few days of sightseeing in the city, so we needed comfortable walking shoes and layers for May in the northeast. A beach packing list from last July and a New York City spring packing list are not the same document, and the more specific you can be upfront, the less you’re fixing later.
The list it generated was genuinely good. It reminded me to pack heels.
It did not remind me to pack my metals.
The agent knew the event. It didn’t know me.
My husband and I call them our metals — our real wedding rings. Day to day, I wear silicone rings. I have four or five, bought in a pack, and when they stretch out I replace them. Different colors, sometimes stacked, I don’t think that hard about it. I never worry about losing one at the gym. I never worry about hurting my finger on a barbell. For as long as I’ve been married, I’ve been wearing my silicone rings.
But for weddings, funerals, formal events, family photos — I wear my real rings. Always. It’s just a rule I have. My husband knows it. My sister knows it. My close friends know it. It’s one of those things that lives in the ambient knowledge of the people around me.
ChatGPT knew I was going to a wedding. If I had stopped to think about it for two seconds, that would have fired a connection in my brain: wedding, formal, metals. But that connection lives in the personal logic of me — it’s not a general truth about weddings. Most people wear their real rings every day. The agent had no reason to flag it.
I showed up to the wedding in a formal gown wearing a silicone ring. The bride did not notice. I noticed, the whole night.
Generalizing is easy. Knowing you is not.
Agents are genuinely good at generalizing. Of course you need heels for a formal wedding in New York City — that’s pattern-matched from a thousand packing lists, travel guides, and style articles. The model pulled from a well of general knowledge and got it right.
What agents can’t do is know you. Your specific rules. Your personal defaults. The things everyone close to you has absorbed over years of proximity. That’s not a flaw in the technology- it’s a structural limitation. The model knows what’s generally true. It doesn’t know what’s true about you unless you tell it.
That gap is yours to close. And how you close it matters more than most people realize.
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Not all context belongs in the same place.
There are a few different tools for giving an agent context about you, and they’re not interchangeable.
Memories are for personal facts that should travel with you everywhere. Things like: I wear silicone rings day to day but always pack my metals for weddings and formal events. I CrossFit four mornings a week, but I never work out while traveling, so workout clothes stay off the packing list. My youngest is eighteen months, so we still need a stroller or at least a baby carrier. You tell it once, it applies automatically going forward, across conversations and tasks. Low maintenance, high leverage. If it’s a fact about you that a close friend would just know, it probably belongs in memory.
An agents.md file or skill is different. This is workflow-level context- the rules and instructions that govern how a specific agent or task should operate. Not “here’s who I am” but “here’s how this works.” If you’ve set up an AI agent to handle your weekly planning, the agents.md might specify that Mondays are meeting-heavy and shouldn’t get deep work blocks, or that Friday afternoon is your reflection window. That’s not a personal fact- it’s an operating procedure. It belongs in the file that governs that workflow, not floating in general memory.
The distinction matters because information in the wrong place either doesn’t travel or doesn’t apply. A personal fact buried in a task-specific skill file won’t show up when you’re doing something unrelated. A workflow rule stored only in memory might not be specific enough to actually govern behavior.
Start with one missed thing.
Think about the last time an AI got something almost right but missed something personal. That gap — the thing it didn’t know — is your first memory entry. Write it in plain language, one sentence, and add it to your model’s memory today. The metals are in my ChatGPT memory now: “I wear silicone rings day to day but always pack my real wedding rings for weddings, funerals, formal events, and family photos.” One entry. Done.
Then work outward. Think about the routines and rules that govern your week- the protected time, the scheduling quirks, the output preferences- and write those into an agents.md for whatever agent they apply to. You don’t have to do it all at once. Do it when something goes wrong. Every time an agent misses, that’s a prompt to ask: is this a memory entry or a workflow rule? Add it. Move on.
The people who get the most out of agents are the ones who’ve done this incrementally over time, treating every near-miss as a data point. It’s not a one-time setup. It’s a practice.
That’s the whole game: you teach it the things that everyone close to you already knows, and then it stops being a powerful stranger and starts behaving a little more like someone who gets you.
If you’re the kind of person who thrives with a guided worksheet. No worries, I got you. Download The Agent Context Inventory. It includes some personal examples about my calendar. Good luck!