The Question AI Can’t Answer for You

August 31, 2026 - 12:18

A recent 12-hour travel ordeal turned into an unexpected lesson about the limits of artificial intelligence. What started as a simple booking mistake became a frustrating chain of missed connections, canceled trains, and rebooked flights that no algorithm could untangle. The assistant on my phone kept suggesting the same logical solutions, but it couldn't understand the human factors: the tired child, the closed ticket counter, the driver who refused to wait more than five minutes.

We are told that AI will handle the drudgery, the scheduling, the routine decisions. And it does, most of the time. But the moment a situation stops being routine, the machine falls apart. It cannot read the tiredness in a stranger's voice, cannot weigh the cost of a missed dinner against the benefit of a cheaper fare, cannot know when to break a rule because the rule no longer applies.

The real question is not whether AI can answer questions. It can, and it will get better. The question is whether we are willing to accept that some answers require lived experience, judgment, and a messy, irrational sense of priority. That 12-hour trip taught me to keep the human in the loop, not as a backup, but as the one who decides what the loop is for.