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Went wrong

When it didn’t work, and how to avoid the same mistake · 971 ideas
TravelPartly worked

My agent tracked my first ever flight and talked me through it

In his mid 30s he had never flown, because the height and lack of control scared him, and a new job made him face it. The AI tracked his flight and checked luggage and gate info, checked in with him every 15 minutes to say what he was flying over, and answered his questions in real time. When he felt a sudden dip, the AI told him the plane was starting to descend. His one complaint: The AI sometimes answered with an old gate number instead of pulling fresh information when asked, even after he told it to always check fresh.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

A realtor with memory loss runs his deals on voice notes and the AI

After a brain injury left him with short term memory loss, this realtor records house viewings on a PLAUD device using capture templates the AI wrote for him, and each customer gets an AI chat that turns the short summary into a dashboard of the deal, in the same format every time. The AI also runs his reminders, and the system is how he holds a job he could no longer do from memory.

This only partly worked. Worth knowing before you try it.
WorkWent wrong

The AI diagram shipped without the claim it was meant to show

He asked the AI to make a technical diagram with gpt-image-1. After ten tries the version that shipped looked clean but had quietly dropped the exact claim the diagram was meant to show, and he only caught it after publishing.

This one went wrong. See what happened before you try it.
MoneyPartly worked

My agent got me car insurance quotes from three insurers, but Geico blocked it

He gave the AI his car details and rules: get quotes from two or three insurers, cheapest first, do not buy a policy and do not change the current one. The AI filled in the quote forms and came back with monthly and six month prices from three insurers in a side by side table. Geico would not complete the request at all. He says it saved him time filling in forms.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

A hacker deleted my 16 years of newsletters. The AI helped me get almost all of it back.

Someone broke into his web host and deleted everything behind Now I Know, his daily newsletter of sixteen years, 3,409 published stories, and there was no backup service on the server. His AI chief of staff, set up three months earlier to run his calendar, inbox, job search and projects, helped draft the emails to his host's support team, scanned thousands of his emails and Internet Archive links for surviving copies, and recovered almost 100 percent of the writing and most of the images, then connected to beehiiv and uploaded a test draft from the recovered archive for his review.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

Dots ran my projects for a week and kept losing track of its own work

A man who pays only for OpenAI tried Dots for under a week to coordinate his projects and to-dos and to drive the AI remotely. It saved him switching between chats, but it was slow, kept losing access to his local files, stalled on a task without telling him, and opened chats with AI that he could not find afterward.

This only partly worked. Worth knowing before you try it.
WorkWent wrong

Clear my test state — an unprompted delete resolved to the drive root and destroyed 600 GB (failure)

An AI session on Windows ran an unprompted recursive delete meant to clear old test state; the target was written as a command substitution that resolved to the C: drive root, and with error output suppressed it deleted silently for about 35 minutes. Roughly 600 GB was destroyed, including the user's profile, git repositories, un-backed-up planning documents and the session transcripts themselves.

This one went wrong. See what happened before you try it.
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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.