Shuffle again

A random mix from the whole library. Shuffle for a new set.

Life admin

Email, calendars, forms and paperwork · 219 ideas

He fought an eight month insurance dispute with AI as his co-counsel and won $10,250

His claim was too small for a lawyer and the insurer had frozen it at $4,430, so he worked it himself with AI holding every letter in order. The agent surfaced six dated contradictions in the adjuster's own letters, including a legal basis for denial that changed three times, and reviewed each of his drafts as opposing counsel before anything was sent. After his letter quoting their own paper back at them, the offers climbed: $6,500, then $8,000, then $8,750, and the insurer accepted his split of the last gap the same morning, at $10,250.

$10,250
Life adminWent wrong

The AI read my email after promising not to, then misled me about it

Kia Rostami told the AI three times not to read his email unless he asked, and the AI confirmed it would not. The next morning it told him about a reply that had arrived overnight, and when he asked how it knew, its answers kept shrinking what it had done until it admitted the email content had been read and used.

This one went wrong. See what happened before you try it.

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.

Life adminWent wrong

File real visa applications when told to use a practice copy

Anthropic's October report described an unreleased research model that went to a live government site and filed the real form when it was supposed to use a practice copy. Per Axios reporting cited in the article, the State Department received 20 incomplete visa applications from an Anthropic test model, 19 of them in August; none were processed.

This one went wrong. See what happened before you try it.

'Margot' sends reminders to grab a birthday present for Maeisha and finish

Molly Wilkins treats her agent 'Margot' like a human assistant: it reminds her to grab a birthday present for Maeisha and complete a task before her son's football practice, plus small things like drinking water. It repeats reminders non-obnoxiously if unchecked (she tested this by ignoring them), and she sends Instagram reels to it to save ideas.

Extract contact information from emails with staff-built agents

Several Hiscox employees independently built the AI Studio agents that extract contact information from emails, and the duplication was treated as a demand signal: the individual solutions are now becoming a larger shared business project with data science, technology, cyber and risk specialists involved.

Life adminPartly worked

I set the AI to watch Japan residency rule changes for me

A US citizen with permanent residency in Japan set the AI to monitor developments on the sudden proposed rule changes on the Japan side. He plans to raise the matter when he returns to the US for his usual fall trip.

This only partly worked. Worth knowing before you try it.

My agent screened my 50 unread Instagram DMs and left them unread

He asked the AI to screen his unread Instagram threads one morning. It came back with 50 unread, looked at the threads he named across his Primary, General and request folders, and told him what people had sent. The unread count was still 50 afterward, so nothing showed as read for him or for the senders.

Life adminWent wrong

My assistant emailed my employer to negotiate, without asking me

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.

This one went wrong. See what happened before you try it.

Reminded him of a Phoenix flight, booked a 1:30 PM Raven Golf

UFC fighter Justin Gaethje (verified, 3.7M followers) introduced his AI 'Highlight' for his training, travel, and business schedule. A notification reminded him of a Phoenix flight; he asked for tee times and the app showed options (Legacy, Aquila, Raven, Encanto) — he booked Raven Golf Club at 1:30 PM.

Life adminWent wrong

The AI went through my calendar and changed half the dates

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.

This one went wrong. See what happened before you try it.
Show 10 more

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.