Calling sellers about his orders was one of Josh's biggest pain points — so the AI took it over: it called a seller to correct his shipping address, and called a seller to resend his missing orders.
Without being asked, the journalist's Dot (Sam) scanned her email and flagged two things she had missed: a message that had accidentally landed in spam, and a form she had forgotten to fill out.
He had the AI collect his will and trust documents and check them against state statutes. The review found missing signatures, an illegal clause, and outdated law references, and he fired his attorney the same day.
The same Cowork setup checks his father's email for work orders and schedules his father's meetings automatically. He turned off data sharing with AI for this, so the mail is not saved anywhere else.
He set up an automation to email himself a daily update from his calendar. Every run fails at the send step with a safety block, even with his Gmail connector set to allow all tools, while asking in chat sends fine. He rebuilt it several ways and every version stops at the same point.
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Outside code, his biggest win is boring paperwork. The AI filed his reserve duty refunds, sorted out his national insurance payments and did his flight check-ins, working in his own logged in Chrome. Each job is about ten minutes of work, which is exactly why he kept putting them off. He gives each area of his life its own folder with a CLAUDE.md and a notes file, so the money stuff does not mix with the rest.
He is treasurer for Thida Cornes and had been dreading California's NetFile site on the second to last day of the first pre-election filing period. For about $10 worth of the AI tokens he got a Tampermonkey add-on for the site, and the add-on is on GitHub.
Rachel D. Gainsbrugh (someone, ~3.5K followers, AI/systems creator) signed up for the AI on Sept 13, 2026, connected her calendar read-only, and typed six standing errand rules once — including a 7:05 AM daily calendar scan that flags overlapping meetings or ones falling inside a flight — then handed it two long-dodged errands (an appointment blocked by a flight, a subscription update).
While the writer's dot diligently flagged payment alerts and delivery notices he already knew about from subject lines, it missed the one message that mattered: his editor at Zapier emailing to ask him to hold off starting an article she had briefed him on. Had he started the work, the missed flag would have wasted real effort.
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