The AI filled out his car insurance application and asked him what it could not answer
The AI filled out his car insurance application for him. Where an answer was not in what it knew, it stopped and asked him instead of guessing.
A random mix from the whole library. Shuffle for a new set.
The AI filled out his car insurance application for him. Where an answer was not in what it knew, it stopped and asked him instead of guessing.
The AI completed and filed the user's resident tax report through Korea's HomeTax system.
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.
Eleanor Konik had the AI and AI team up on dashboards for local nonprofits. The AI did the early research and dug up grant chances the groups had not seen, like a group that pays for field trips to battlefields, a free textbooks program for private schools, and creative arts projects, and the lists were put behind a password for her friends to use.
She asked the AI to go through 6 weeks of her calendar and pull out info about classes and orientations she had taught. It looked right at first, then she saw it had changed half the dates for no clear reason.
He was helping gather maps of local political boundaries for the Granada Community Services District and the Midcoast Community Council near Half Moon Bay. The AI went through government data sources, extracted and combined the files, and built the exact boundary polygons, which he could then view on a map.
The developer set a scheduled job in plain words: every weekday at 8:30, send events from all calendars plus emails needing a reply, in five lines or fewer. The first run arrived at 8:44 with an apology for the delay, covered all 16 calendars, removed duplicate events and listed private events by time only.
During a 30-day trial diary, the author shows the AI filling out a school field-trip permission slip it had found in his email — one of several family-admin tasks it handled from his accounts.
The author describes using AI to resolve a six-month-old travel medical insurance claim with Cigna. The AI called the insurer, was transparent about being an AI, conducted the call politely (impressing the representative), and — because final consent was required — called the author's phone and connected the parties so he could approve verbally.
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.
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.