I Hired an AI to Do My Chores. Now I Maintain the AI.

AI agents promise to automate away the tediousness of modern life—the overbilled rental cars, the iCloud storage alerts, the changing of leaked passwords. Jack Cheng, Every’s senior editor, put that promise to the test. But instead of his AI agent maintaining his digital life, he ended up maintaining his AI agent. From there Jack explores Stewart Brand’s philosophy of “nested maintenance,” COBOL Cowboys, and civic technologists watching Claude Code attempt to modernize government benefits systems. Read on for an account of what it means to hand our most tedious obligations to machines—and what we only come to understand about broken systems by struggling with them ourselves.—Kate Lee

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I set up OpenClaw in hopes that it would automate away the petty bureaucracy of modern life.

Maybe a Claw could keep my iCloud storage account from constantly hitting its cap, or go through my over 1,000 different online accounts and change all the passwords that were leaked by hackers onto the dark web. Maybe, I thought, it could even help my family sort out a medical bill we got from an unexpected hospital visit while traveling before we switched from our old health insurance to our current one.

It’s not the first time I’ve tried to tackle this problem. Since 2023, I’ve been hosting what I call a “Digital Mending Circle.” With a small group on Zoom, I tend to the maintenance tasks that accrue around a digital existence. Instead of darning socks or patching jeans, we update personal bios, organize photos, file expense reports, or even just catch up on email.

These activities can feel surprisingly daunting, given how trivial they are in the grander scheme. They involve re-familiarizing yourself with systems you only use occasionally (where’s that page in my WordPress admin panel again?) or facing clean-ups—the 571 items on your desktop, the gigabytes of blurry and duplicate photos across multiple apps—that will just need re-tidying months later. Maybe that’s why we so often neglect them.

Now, generalist AI tools like Claude Cowork and specialist tools like Sparkle, Every’s AI file organizer, can do many of these tasks for you—and swiftly. They’re chores that Claws, or whatever forms personal AI agents take in the future, could do for you without your ongoing input.

So I’ve been pondering this question: What does maintenance look like when you have AI running your digital life?

The maintenance of everything

“Maintenance is absolutely necessary and maintenance is optional,” says Whole Earth Catalog and Long Now Foundation founder Stewart Brand in Maintenance: Of Everything, Part One. Optional because we can put it off in the moment, necessary because putting it off for too long can lead to disaster.

We learn, in the book, of boats whose maintainability resulted in very different outcomes for three sailors competing to first circumnavigate the globe. We discover how maintenance attitudes in militaries can sway entire wars. Good and poor maintenance can both have profound consequences.

Maintenance is virtuous. But it’s also rarely seen as heroic. If it were, maybe we wouldn’t be so bad at it. Various explanations exist for why we deprioritize maintenance, ranging from cultural values (we prize new invention over care for the existing), psychology and economics (we discount what isn’t immediately gratifying), and social class (we associate many maintenance jobs with minimum-wage work done by marginalized workers).