Ethan Mollick writes that the AI noticed an airline credit of his was about to expire and, when he asked, contacted American Airlines to request an extension — an example of agents catching deadlines their owners miss.
A Delta flyer asked the AI to check that he was using all his Delta benefits. The AI could not get past the robot check screen on delta.com, even when he took over the browser and clicked it himself. Every login try was blocked.
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While Dan Shipper's Dot displayed research for changing his flight out of San Francisco, it warned the new option might overlap with his head of video's Wednesday morning recording. The recording was not on Shipper's calendar — the Dot had read an unseen Slack discussion, clocked the proposed schedule and alerted him at the moment it mattered; the rest of the column is paywalled.
An experienced traveller who hates planning had the AI plan his recent trip to China and book everything — flights, hotels, tickets and attractions — leaving him only the final pay button to click. Before travelling he ran the finished itinerary past a fresh session told to find errors, and it caught one: he was scheduled to be at the wrong train station.
Vibe-built a Wikipodcast app with a Wikipedia dump, Gemma search and summarization, and TTS; actually used it on a Rhine bike trip to listen to local history.
In the same Vergecast clip, a host describes the AI connected to his Google Calendar: seeing a media dinner party in his evening, the AI advised taking a city bike instead of the subway because it would be faster, and pinged him at 9:20 to leave in time for a 9:30 arrival. The hosts frame it as the AI being proactive to the point of feeling directive.
Chelsea Yamase documented the AI re-planning her Sardinia trip after a rental-car breakdown: re-routing through the mountains, choosing a boutique hotel near a boat launch, and booking restaurants via WhatsApp in Italian. The AI also monitored flights and deliveries and emailed about customs.
A presenter showed his AI 'Finch' planning a full Santorini trip for Oct 12–19 for him and his wife while his phone was face-down — returning flights, hotel, and rental car at a best-value total of $6,695, with AI asking for approval before booking.
In a clip from David Senra's interview with Meta's Alexandr Wang (shared on Instagram by someone), Senra recounts a billion-dollar-company founder friend who left his ID on a plane and told the AI he didn't want to be involved in the recovery process at all. The AI arranged a courier, coordinated with building security, went to the office, retrieved the ID, and got it back to him.