Or, How I Taught a Robot to Do My Chores While I Sleep

Lately I’ve been waking up to work I don’t remember doing. I haven’t taken up sleepwalking to my desk — something else has been up working while I slept.

For the past few months I’ve been running a small AI agent that clocks in around midnight. I named it Hemingway, after the writer who supposedly stopped each day mid-sentence so he’d always know where to begin the next morning. Its job description is roughly the same: while I sleep, look through my life and find something useful to pick up.

What it actually does

On a schedule, it wakes up and reads the boring exhaust of my week — my task list, my calendar, my saved-for-later bookmarks, the projects I keep meaning to finish. Then it picks something it can move forward on its own. Draft the blog post I’ve been avoiding. Price out flights for an upcoming trip. Read the twelve articles I bookmarked and never opened, and tell me which two were actually worth it. It writes the results up, leaves them waiting for me, and goes back to sleep.

It’s built on Claude Code, the same family of tools I used to drag this blog out of Tumblr last year. That project was about owning my data. This one is about the little nagging tasks that quietly eat a week — the ones too small to schedule and too persistent to forget.

The part nobody mentions

The mornings it gets things wrong are the interesting ones. Some days it picks the wrong task entirely, or hands me something confidently mediocre that goes straight in the bin. Left unsupervised, it will happily research a dinner reservation for a dinner that isn’t happening. So it doesn’t get the last word — I do. Every morning starts with a quick read-through: keep this, kill that, redirect the rest. The point was never to hand everything to the robot. It’s a decent night shift plus a human who still reads the output over coffee.

The strange part, coming from someone who builds conversational AI for a living, is how quickly it stops feeling strange. I spend my days trying to make machines useful over the phone; at night, I just wanted one to give me my Sunday nights back.

A confession

Which brings me to the pot. The Iron Blogger rules are simple — post once a week, or contribute to the group’s beer-and-charity fund. I’m traveling this week, and I was, frankly, on track to owe money.

So I didn’t write this post. Not exactly. I described the idea, went to bed, and let the night shift take the first pass. I cleaned it up over coffee the next morning — but the bones of it showed up while I was asleep.

Don’t tell the group.