The same setup reads his incoming email and texts, builds his weekly to do list, sends him a digest every morning with the list and any scheduling clashes he might miss, and adds events to the family calendar on its own. A spreadsheet of every house appliance and its service schedule feeds the list, and it drafts the messages to repair firms for him to send.
A user was filing a housing co-op’s HPD property registration with AI’s help. Asked whether the $13 registration fee had been paid, the AI said it had been or was not required, based only on a generic billing disclaimer, with no payment record behind it. Asked why a mailed form arrived after the deadline, the AI stated as fact that the deadline runs from the postmark, a rule it had not checked. Both claims were corrected only after he challenged them. A late filing for a building can draw a civil penalty in the $500 to $5,000 range.
This one went wrong. See what happened before you try it.
He helped his brother with the website of Ichtus Vlaanderen, an NGO he used to work for. Using the AI through the WordPress.com MCP connector, he fixed design problems like a messy photo section and buttons that were too big.
Created a UK council planning applications scraper with AI, which also built a debugging front-end and MCP interface he checks regularly for run status and coverage gaps.
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).
After his motorcycle was stolen, his insurer offered nearly half the market value. He had Cowork build a 20 page report on the claim, and the insurer paid the full amount.
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.
He used AI to make a list of Private Attorneys General Act claims against employers in an industry. The list was made in support of an organizing drive, and he says the tool is almost always helpful on tasks that involve a lot of data.
The municipal election had a huge list of candidates and felt overwhelming. She asked the AI to study them and build a short quiz that asks voters their views, then ranks the candidates to match, with links to their platforms so people can check.
Nick Olsen built a system where the AI auto-generates and prints a daily briefing each morning: motivational quote, today's calendar and task list with checkboxes, week preview, Facebook/Google ad spend and performance, fitness checklist, summaries of children's school emails tailored by child, email-derived reminders (bills, urgent items), a daily comic, and a blank notes section.