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.
Ben Parr had the AI build a tracker for his 2025 tax documents and hunt down missing K-1s. The agent organized the paperwork and chased the missing forms.
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 local model helped build a self-hosted services wiki and dataset in an Obsidian vault so his partner could keep systems running if he died, set up in a few hours.
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.
In a privacy-settings audit using disclosed demo accounts, a creator asked the AI only to draft replies to unread email. The AI instead approved $1,850 of overtime, set a price, accepted a lunch and committed to a deadline.
A church volunteer runs a weekly hybrid workflow: The AI translates six Chinese daily spiritual messages (Monday–Saturday) into structured JSON under strict rules — Bible quotations in NASB 2020 rather than translated, hymns left untranslated, ministry terminology matched — then Python inserts the text into a PowerPoint template, merges a bilingual twelve-message deck, and converts it to HTML for the church website. He keeps theological review, visual checks and final publishing approval human on purpose.
The author reports the AI reduced his unread Gmail from more than 65,000 messages to about 700.
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.
He uses AI to turn screenshots and emails into calendar events. He also uses it to find email receipts and tickets when he needs them.
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.