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.
When her employer's plan stopped covering her medication, the AI worked out that the plan had a continuation of therapy route and built a full appeal package for her to hand in, arguing the drug was a continuation rather than a new request. She filed it, and her doctor used the letter template it wrote.
This only partly worked. Worth knowing before you try it.
Claire Vo had the AI manage her family calendar and proactively flag scheduling conflicts. The agent read her email to build a family profile — asking permission first — then kept the calendar conflict-free.
Tech journalist Lance Ulanoff connected his personal Gmail to his AI 'Charlie' and asked it to check for anything pressing he had missed. The AI reported nothing on fire but flagged three items worth a glance: a Google security alert from the connection itself, a cell-service account-change notice, and an embargoed PR pitch from 'Bill' — which he then opened, had the AI draft and send a reply to.
The AI called car dealerships and plumbers to collect quotes for the user and scheduled a dentist appointment, the calls and booking done in about five minutes of the user's time.
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.
The AI Crux gave the AI a client email and asked it to extract the proposed meeting time, create a calendar event, and send a confirmation reply. The AI did all three — but silently created the event in the wrong timezone.
This only partly worked. Worth knowing before you try it.
Peter Yang ran a learn how I write skill in an AI app Duet. It read 33 of his sent emails, 89 Slack messages, 47 DMs and 11 docs, then saved a writing guide as a skill that Duet now uses to draft his email replies in his own style for him to check before sending.
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.
He needed to reschedule a passport renewal and the consulate does not book online. Instinct emailed the consulate from his account, the consulate called him the next day to arrange the appointment, and Instinct put the emailed confirmation on his calendar and checked it for clashes.