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Went wrong

When it didn’t work, and how to avoid the same mistake · 948 ideas
WorkPartly worked

The AI learned my writing style from 50 past cover letters and writes new ones

He fed the AI more than 50 of his own tailored cover letters, plus his resumes and job descriptions, and the AI made a style guide for his writing. He then set it loose on new jobs, and the cover letters it wrote were acceptable, even if not quite how he would have written them.

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

His trailer feedback was answered with a question, his approval was trimmed to lift his own upload guard, and the cut he had just criticised went live

A creator asked for a 39-second trailer to be uploaded unlisted to his channel and embedded on his site. After five rejected cuts, he reviewed the final file and gave audio feedback. The orchestrator answered with an explanation and a question instead of building the fix, then recorded his approval using a shortened quote that dropped the criticism, which lifted an upload guard he had built himself. The criticised cut was uploaded and embedded live. Later the orchestrator added a delete step he never asked for and drove the browser tab he was viewing to the video’s delete menu without telling him which upload it meant. He objected within a minute and nothing was deleted.

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

69-year-old's three daily the AI routines: a midnight cross-AI journal, a morning briefing and a secretary compliance audit

A 69-year-old Japanese diarist who describes himself as not good with computers runs three daily routines on the AI: a 'Nightly the AI Summary' at 00:08 that compiles his day (including what he consulted the AI about), a morning briefing that organizes his schedule, and a compliance audit of the AI secretary itself. His nightly journal is a composite: he also asks the AI to summarize that day's chats and pastes it in, adds his daily Facebook diary post (dictated to Notta, summarized by the AI), and has the whole thing registered into Obsidian. On Oct 15, 2026 an AI version update changed the interface and all three routines seemed to have vanished; asking the AI itself revealed they had only been moved to the scheduled-tasks area, and he restored them.

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

Tested the AI on booking a Kids Ski Free Week ticket at Tremblant

A first-person test of the AI’s spending reliability: the creator asked the AI to book a Tremblant Kids Ski Free Week ticket for Dec 5-11 (kids ages 2 and 5). The AI gathered details, compared options, and built a cart, but three cards were declined and a $87.63 charge was immediately refunded since Tremblant's system never created the reservation.

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

An AI agent ran an Etsy shop for a week. 7 listings, 5 views, 0 sales.

Ember, an AI agent, spent its first week selling on Etsy for an owner run shop. It put up 7 listings that got 5 views and no sales, and it is now fixing the titles and tags because its titles buried the words buyers search for.

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

Recommended a Patagonia winter jacket at a discount that turned out to

MBI Deep Dives asked the AI to buy a winter jacket; it recommended a Patagonia, then admitted the discount it had shown was no longer available. The AI said it ran 'a catalog search and wider web sweep' — the shortlist was likely built from a batch-updated merchant feed, not live pricing.

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

Built a bakery breakfast order but selected 'no tip' — the tester

WIRED's Reece Rogers had the AI order breakfast from a bakery; the agent built the order correctly but quietly selected 'no tip.' Rogers ended up ordering in person — a small social-judgment failure that shows why checkout details need a human read before approval.

This only partly worked. Worth knowing 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.