The AI flagged all 7 of 7 calendar double-bookings before they happened
Across the same two-week inbox-and-calendar test, the AI proactively flagged every one of the author's seven calendar double-bookings before the meetings occurred.
A random mix from the whole library. Shuffle for a new set.
Life admin
Email, calendars, forms and paperwork · 213 ideasHis agents write to companies asking them to delete his data, and most never reply
Built AI agents that ask companies to delete their data; most companies never answered (case and outcome stated in the post title itself).
This only partly worked. Worth knowing before you try it.
A 20 page report the AI wrote got his stolen motorcycle claim paid in full
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.
Turn my bookshelf photo into our building's borrow list
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.
Sweep my inbox for anything pressing I have missed
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.
Generated a beautiful one-page family morning newsletter PDF: weekly agenda, kids' call-outs
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.
His email bot misspelled its own urgent tag and buried a week of urgent mail
An economist set up an email bot to bring him any message tagged #handcarry right away. The bot misspelled the tag as #hancarry in its own memory file, made a new folder, and filed a week of urgent emails deep in it where he never saw them.
This one went wrong. See what happened before you try it.
Uploaded his resume and target roles; the AI auto-applied to 50 jobs while
A young man in sunglasses sitting in his car tested the AI by uploading his resume and target job roles, then instructed it to apply to jobs while he went to lunch. Screen recordings showed multiple browser tasks running and a notification confirming an application submitted to 'ioTech Solutions.' The AI asked for information once for the first application, then reused it — resulting in 50 applications submitted while he was idle.
Let the AI answer business DMs for 19 days — 6 appointments booked
A French creator connected the AI to his Instagram and Facebook messages for a 19-day test (via Blotato and the AI): the agent sent 6,746 messages, opened 2,606 conversations, recovered 491 emails, sent 43 appointment links and booked 6 appointments.
Managed her family calendar and proactively flagged scheduling conflicts
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.
Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.