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.
Harry McCracken's Dot, Chip, cross-checked his calendar against his email and spotted that a speaking engagement he had entered on one date had been rescheduled by the organizers to a different day, which the confirmation email showed. He says he would otherwise have shown up to an empty room.
His morning agent reads his email and builds a prioritized to do list with time blocks for the day. It also checks the weather and warns him to leave earlier when rain would slow his trip, which has twice saved him from showing up soaked.
The AI’s tools produced printable booth artifacts for a nonprofit he advises; in about 30 minutes he had a professional PDF uploaded to FedEx Kinkos for printing.
The AI prepared and filed Australian visitor visas for a couple travelling to Brisbane, and caught a placeholder birthdate in the details before submission, confirming the correction over WhatsApp.
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.
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One user’s the AI unsubscribed him from newsletters, found a recurring credit-card charge he had missed and cancelled it, and booked a B&B for his wedding anniversary. Three different errands, one agent, all completed.
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.
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.