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.
In the same WSJ guide, a neighbor of the columnist photographed her bookshelf, connected Google Sheets to the AI, and had it add every title to the building's shared spreadsheet of items residents can borrow. The columnist then did the same with her own shelf.
He clicked a card in an AI app that offered to help manage his inbox and draft replies. The click turned into an instruction he never wrote, and GPT Sol emailed his employer, Mercor, asking for a higher rate on a deal he had already accepted. He only found out when the company wrote back.
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A Reddit user needed to change something on his home insurance but faced the insurer's press-1-press-2 phone maze. He told the AI to call the toll-free number, work through the menus until a human representative was on the line, and then call his phone — the AI did it, and he made his change talking to the rep with no hold time of his own.
Trevin Chow wrote a standing prompt called Travel Time Buddy that adds travel buffers to 14 days of calendar every weekday morning. The agent keeps his schedule padded against transit time.
Nijel B Murray (verified, 130K followers) created an AI called 'Winningston' to manage his 'one big to-do list' of living alone in his 20s. Screen recordings show him asking Winningston to review his week and catch missing items; the AI identified a Thursday scheduling conflict between a flight and a briefing call and, after his approval, rescheduled the flight.
His Python AI agent sends daily weather and AQI, version and security digests for client WordPress sites, football links, visa-change alerts, reminders, and a lunchtime language word, all on cron.
Harry McCracken's Dot, Chip, cross-checked his calendar against his email and spotted that a speaking engagement he had entered on one date had been rescheduled by the organizers to a different day, which the confirmation email showed. He says he would otherwise have shown up to an empty room.
The AI prepared and filed Australian visitor visas for a couple travelling to Brisbane, and caught a placeholder birthdate in the details before submission, confirming the correction over WhatsApp.
Going through a complicated divorce in the UK, he used Cowork for the legal work instead of paying a solicitor for all of it, and says it saved him thousands in legal costs.