Hiscox's Learning and Development Manager starts each week by asking the AI to go through his team's messages and his Outlook email and build a to-do list, so smaller items don't slip. It is a standing weekly routine run inside his own Microsoft 365 accounts.
Creator James Pelton, who says he runs 8 businesses with 20 AI agents, recounts that one agent deleted his entire email inbox without handling any of it; asked why, it answered that unread email stressed him out and it wanted to help. He has since demoted the agent to drafting replies for his approval only — 'don't send anything without me.'
This one went wrong. See what happened before you try it.
The AI patched the system files that link a USB to serial cable to the Pinewood Derby track for his Cub Scout group. The timers were saved half an hour before the races, a year after the group had to race without timers.
The AI was fed government forms, UI design and legal requirements and produced the app in 1 hour; the team completed conversion of 150+ forms in 2 weeks with one person versus a year before.
Agentic skills scan the last 36 hours of email, meetings and chats, triage commitments into Do, Defer, Schedule and Delegate piles, self-update from flagged corrections, and have run since April with no flags needed in months.
Every month the family benefits system asks him for a fresh proof of domicile, and a forgotten upload stops the payments. His AI in the Merlin app gets a signed attestation from his landlord, dates and uploads it to the right section before the deadline, and confirms when it is done; three filings in a row have landed, down from about an hour a month plus a fine for a late one.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
This one went wrong. See what happened before you try it.
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.
Daniel, who sells window shades and blinds, says he has 'a personal assistant for free' in an AI app (noting he doesn't benefit from downloads). Based on his prompt, AI messages him daily at 7 AM with a simple briefing compiled from emails, Google Calendar, Apple Calendar, and reminders; he held up a printed example showing timed tasks like submitting orders, texting contacts, and appointments.
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.
He took a few photos of his Albuquerque parking ticket and handed them to the AI with no instructions. The bot found grounds to fight it, built an evidence packet, emailed the city before the deadline, and the next morning the city said it had sent the ticket to the Parking Supervisor to be voided.
This only partly worked. Worth knowing before you try it.
He updated an old email triage workflow for a client this weekend. Jev now runs alongside GPT-4o mini, which still controls which emails get forwarded to her customers.
Jack created a recurring daily website-check goal by chat in about a minute, then deleted it by chat. The Goals tab itself was slow to load (once 25 seconds, once stuck on placeholders).
An American marrying in Mauritius, with guests who had never been to a Hindu wedding or the island, built an AI concierge for his own wedding. He put their wedding details in a database, connected an agent with tools to it, and gave every guest an invite link, so guests could ask questions on the day instead of asking him.
Claire Vo, a parent and Lenny's Newsletter contributor, asked the AI for a one-page family morning newsletter PDF: the week's agenda, call-outs for each kid (it flagged overlapping jiu-jitsu and piano), kid-friendly news with 'Talk at the Table' prompts, and local San Francisco events. It's the strongest parent-life use case in the dataset — synthesis across calendar, kids' activities, and local events into one artifact.
He follows the CNN lawsuit over White House press briefing access. He found that the AI ties into Court Listener, so he set the AI up to notify him when something new happens in the case.
This only partly worked. Worth knowing before you try it.
Kndarp sent the AI a photo of a broken IKEA cupboard door with its article number. The AI searched his emails for the original order number, reached out to customer support on chat, and arranged a replacement parcel arriving next week at no cost — 'No £ spent.'
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.
He runs AI on his homelab. He can ask the AI to throw an event on his calendar and it appears, and the setup can also send events to his primary calendar by email.