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ChatGPT advises man against quitting his job for ‘awful’ business idea: ‘Blunt and unfiltered’

A man shared screenshots of his conversation with ChatGPT where the AI strongly advised against quitting his job to pursue an ill-conceived business idea.

Published on: May 23, 2025, 14:12:06 IST
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In a Reddit post, a user shared his conversation with ChatGPT, revealing how the AI tried to talk her out of quitting the job to pursue what he himself called an “awful business plan.”

The AI also advised him to do damage control, even drafting a follow-up apology to help him undo the impulsive resignation. (Reddit/Pexel)
The AI also advised him to do damage control, even drafting a follow-up apology to help him undo the impulsive resignation. (Reddit/Pexel)

The screenshots, captioned “I told ChatGPT I was going to quit my job to pursue an awful business plan,” show the user pitching his idea using a quirky metaphor: “You know how some people have lids that don’t have jars that fit them? What if we looked for people with jars that fit those lids. I think this would be very lucrative.”

ChatGPT responded supportively but cautiously, calling it “a fascinating metaphor” and “kind of brilliant in a poetic way,” before clarifying: “You’re talking about a real problem…”

However, the tone changed dramatically when the user typed, “I’m going to quit my job to persue this.” The AI, in a serious and direct response, said:

“Simon, do not quit your job to pursue this idea. At least, not yet.”

In a follow-up screenshot, the user admitted, “I just sent an email resignation to my boss,” prompting the AI to jump into damage control mode. It asked her to stop and check whether the email was final, adding that if there was any ambiguity, he could still roll it back.

The AI even provided a draft of a follow-up message:

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“I acted impulsively earlier today… I sincerely apologize for the suddenness.”

Take a look at the post:

The screenshots quickly caught fire online, with many flocking to the comments to praise ChatGPT’s level-headed guidance.

A user wrote, “It pivoting to damage control had me rolling, I didn’t expect it”

Another quipped, “Honestly surprising, given that this is 4o, I expected it to be like “what a great idea, you are such a visionary, future generations will read about you in history books!”

Also read: ‘I never said that I was Gupta’: Man lashes out at woman who misidentified him as Piyush Gupta on LinkedIn

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