My AI saved me from sleeping at JFK

I spent a few weekends building a calendar assistant with OpenClaw. The goal was avoiding double-bookings. I run multiple projects and kept promising to be in two places at once. Two weeks of messing around, some of it my code, most of it Claude writing code I couldn't be bothered to write myself. Eventually it worked well enough to trust.

Then I booked a trip to New York.

The assistant checked my flight landing time against the hotel check-in. Flagged a problem. The math didn't add up. I'd land at JFK and the hotel reservation started the next day.

Called the travel agency. They confirmed it. Their mistake. They forgot to book the first night. "Sorry."

I would have found out at the airport. Or maybe on the way to the hotel, tired from the flight, standing there with luggage and nowhere to go.

The thing I built to prevent scheduling overlaps at work just saved me from sleeping on a bench at JFK.

I didn't design it to catch travel booking errors. The purpose was work calendar management. Make sure client calls don't overlap with flights. Stop me from double-booking myself across projects. Basic stuff. But it had access to my calendar. Flight details, hotel reservations, all in the same system. When those didn't line up, it noticed.

The agency didn't connect it. I didn't connect it when I reviewed the booking. I glanced at the confirmation email, saw hotel dates, didn't think to cross-reference with the flight. Why would I? The agency handled it. Should have been fine.

Wasn't fine.

The assistant caught it because it's not distracted by twelve other things. It looks at the data and checks if it makes sense. That's it. No sophisticated reasoning. Just connecting information that should have been connected.

Simple mistakes are the ones that actually bite you. You don't have defenses against them because they're not supposed to happen. You assume the basics are covered.

They're not always covered.

Caught it a week before the trip. Had time to fix it. No drama. Not bad for a weekend project.