How ChatGPT Is Helping Me Sell Everything I Own

Almost every day I see another news article about advances in artificial intelligence. The A.I. Futures Project spent the last year trying to predict what the future will look like as A.I. gets more and more embedded into our daily lives. They predict that A.I. systems will surpass human-level intelligence, not in 10 years but in 3. That’s right, by 2028 A.I. will no longer need any human help with R&D, because it will be automating its own advances and building smarter and smarter versions of itself. What could possibly go wrong?

There is a point at which infusing A.I. into everything becomes absurd. I saw a news story the other day about the fact that employers are relying more and more on A.I. recruiters and application systems, while job hunters are using A.I. to strengthen their applications, even sending A.I.-generated people on virtual interviews. We now have computers interviewing other computers. In some cases companies don’t actually want human employees. I saw this billboard (pictured above) in Times Square the other day that said “STOP HIRING HUMANS.” Where does it end?

Carey sent me a YouTube video last month in which a woman asked ChatGPT to build her a business by going on Facebook Marketplace, finding free stuff, arranging a courier to pick it up, writing and posting listings for Facebook and Craigslist, negotiating with buyers and arranging for pickup. In one day she made about $300 and all she had to do was babysit ChatGPT (she called hers ChadGPT) and meet with the buyers to collect the cash.

This gave me an idea. With my current lease running out at the end of July, going locationless is starting to feel imminent and very real. The most daunting part is the idea of liquidating most of my possessions. I live with my teenage son in a fully furnished two-bedroom apartment. Maybe ChatGPT can help me sell everything?

To test out this idea, I asked ChatGPT to “help me sell my Kitchenaid stand mixer.” It asked me a bunch of questions, and in just a few seconds it generated the following listing, so compelling that when I shared it with Carey he said he wanted to buy it from me:


KitchenAid Epicurean Stand Mixer – Vintage Sunny Yellow – Excellent Condition + Attachments

$250 (or best offer) – Pickup Only

Rare vintage KitchenAid Epicurean stand mixer in a beautiful pale yellow. This model is known for its powerful motor and durability—built to last and perfect for serious home bakers or collectors.

Includes:

  • Original stainless steel mixing bowl
  • Flat paddle, wire whisk, and dough hook
  • Clear plastic pouring shield
  • Bonus: Meat grinding attachment

Gently used, in excellent working condition—no scratches or dents. This mixer has been well cared for and still runs like a dream.

Cash or Venmo accepted. First come, first served!


I have no idea how to price used furniture and appliances, so ChatGPT’s advice will be invaluable there. It even gave me the following advice, that I should “List the mixer for $250–300 to start and accept offers. If you’re in a hurry, you could drop it to $200—but with the meat grinder and good condition, you’ve got room to negotiate.”

ChatGPT offered to make different versions of this listing, a friendly, informal one for Facebook, something more concise for Craigslist, and a neighborly, reassuring one for Nextdoor with step-by-step instructions for posting on each platform. It even offered to help draft responses for people who ask “Is this still available?” or want to negotiate.

Lastly, and this is where it gets really good, it offered to make a spreadsheet to keep track of all the items I am selling. If you know me at all, you know that I LOVE a good spreadsheet. I was already leaning toward upgrading to a paid version of ChatGPT in June, and this last offer sealed the deal. As much as I complain about how A.I. is invading every part of our lives, it sure does make the prospect of selling most of my worldly possessions a lot less intimidating!


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I’m Jane.

Welcome to a life of boundless adventure! Join me as I explore new horizons, discover hidden passions, and embrace vibrant experiences. This is our time to dream bigger, live bolder, and create unforgettable memories. Ready to live a bigger life? Let’s dive in!

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