One Chat, One Job

There's a chat at the top of your sidebar called "stuff", and it has been open since March. It began as a question about a spreadsheet. Then it took in the email to the landlord, the holiday, the thing with your sister, and the spreadsheet again.

You keep going back to it, because it sits at the top and it feels as if it knows you.

It doesn't. Picture the chat as a desk.

Every time you send a message, the AI reads the whole desk before it replies, every page from your first question to your last. But the desk is a fixed size.

When the pile gets too tall, the oldest pages slide off the back, and the AI fills the gaps with guesses without telling you. The desk's technical name is the context window, which just means how much of the chat the AI can hold at once. I've explained it here if you want the detail.

A short chat never piles that high. "Stuff" got there weeks ago, and its answers have been getting worse ever since.

Size is only half the trouble. The pages are also about different things, and the AI reads them all as one job. Put the holiday on top of the spreadsheet, and the holiday answers come back tasting of spreadsheet, though nobody knows why.

You can't find anything in it, either. A chat called "Landlord email, October" is one you can open next March and reread. A chat called "stuff" is one you scroll for ten minutes and give up on.

The fix is a habit so small it feels like nothing. Keep one chat per job, and start a new chat when the job changes, which is different from the subject wandering a little.

"Help me plan the week" and "help me reply to Dave" are two jobs, even if Dave is in the week. To tell them apart, use the title. If you can't give the chat a name that fits everything in it, it should be two chats.

Once the chat has its name, take as many messages as the job needs. Twenty messages about one thing is fine, but the forty-message chat about six things is the one that goes wrong.

When the job is done, leave. Watch out for the words "while I've got you", because that's how "stuff" was born.

Starting a new chat doesn't have to mean explaining yourself again. Some things every chat should know. Who you are, your house rules, and the files you keep going back to all belong in a Project.

A Project lays those things on every new desk before you sit down, so you never need to keep one chat alive just to avoid typing them again. Project or Skill? helps you work out which of the two you need.

When a job outgrows its desk

Sometimes the job itself grows, and the plan becomes a project or the email becomes a negotiation. You can feel the answers getting vaguer. Don't push on. Ask the chat to pack up its own desk instead.

We're moving to a fresh chat. Write a handover under 200 words. Include the goal, the decisions we've made, what's done, what's left, and any rules I gave you.

Read the handover before you trust it, because the chat that wrote it is the one that's starting to drift. Fix what's wrong and add what's missing.

After that, open a new chat, paste the handover in, and carry on at a clean desk.

Some chats you'll want again next week. For those, add two lines at the bottom, such as "stopped here, next step is X", and the pile turns into a file.

Not every long chat needs closing. You might not know yet what the job is, and the chat is where you're working it out, so let it run.

Once the job becomes clear, name it and give it a chat of its own. Some jobs are also long by nature. Letting it interview you is meant to be one chat, because each question builds on your last answer.

A chat that's thirty messages in and still giving sharp answers can stay open, too, since one chat per job is there to stop drift. The long-chat page has a simple warning sign that tells you when drift has started.

The cost is a longer sidebar. But most tools let you search it, and a chat with a real title turns up, which a chat called "stuff" never did.

Expect the habit to take about two weeks to stick. In week one you'll catch yourself typing "also, while I've got you", and when you do, stop and open a new chat. By week two you won't notice.

What you get back is control of the job. You name the job, you decide when it's done, and the AI gets one clear thing at a time. That's the only way the AI was ever going to do its best work.

Before bed tonight, ask "stuff" for its handover. Then close it.