Jen Allen, 35, a real estate agent from Delaware, found herself in financial trouble after a "traumatic birth" that left her newborn daughter in the neonatal intensive care unit. The situation piled on many medical bills and forced her to take unpaid leave from work. Between the inability to work and the enormous medical expenses, Jen soon found herself with $23,000 in debt.
With no idea where to even begin tackling the debt, Jen decided to turn to ChatGPT for help. She explained that she already used ChatGPT daily for her business—marketing, management, pretty much everything—so when she finally decided to deal with the debt, it made sense to include ChatGPT in that conversation too. She said ChatGPT already knew everything about her, which made it easier to talk about her debt and find ways to get out of it.
In May, she sent the following message to the AI chat system: She said she was in debt to a credit card company, she didn’t know how much she owed, but she needed to do something about it and didn’t know where to start.
The program helped her "create a debt repayment tracker in Google Sheets" to determine the total amount she would need to pay back. Then, she "built a 30-day challenge" to pay off her debt. That meant that every day for a month, the chat would give her a new task to complete—from canceling unnecessary subscriptions to selling unused items on Facebook Marketplace.
Jen noted that some of the ideas were pretty wild, but they were fun. She said some of them actually made her money immediately and kept her accountable every day.
One of the most effective things ChatGPT got her to do was "search her state’s websites for unclaimed money." According to Missouri’s treasury program, "unclaimed property includes money from bank accounts, stocks, bonds, and contents of abandoned safe deposit boxes."
The chat also created a "meal plan" for Jen so she could cook at home and reduce eating-out costs. It encouraged her to call her credit card company to ask if they could lower her interest rate. In addition, she sold old photos she had taken to Shutterstock.
Not only that, the chat introduced her to easy side hustles she had no idea existed. These included encouraging her to sign up for a program called User Testing, which pays people to try new products, as well as a company called Rover, which pays people to walk or care for pets. It even made her look for spare change around her house—including in the couch cushions—and she eventually found about NIS 185 (USD 50) in coins.
Another strange but effective tip it gave was to sell her junk mail to a company called Small Business Knowledge Center. On its website, the business declares that it will give you "points" redeemable for gift cards, in exchange for your junk mail, such as insurance and financial materials including insurance, annuities, accidental death, auto, critical illness, dental, disability, group/individual health, investments, life (VUL, term, etc.), long-term care, P&C, worksite marketing, etc.
The company explained that "types of materials can include arm’s-length brochures, product booklets, updates, sales kits, direct mail franchises, program guides, sales packages, CD/software courses, new product announcements, sales contests or promotions, etc. Our clients use this information for competitive intelligence and product development."
Other suggestions from the chat included switching mobile phone providers to a cheaper service, signing up for "cashback apps," searching for old gift cards she might have forgotten about, and redeeming any reward points she may have accumulated.
Most importantly, Jen said ChatGPT helped change her mindset about debt by offering encouraging and positive messages throughout the journey and made her feel like it was possible.
She explained that she went from “What am I going to do?” to “I can pay this off and I can do it fast.” She added that ChatGPT didn’t do the work for her, but she was able to use it not just as the best support buddy, but also for ideas she had never thought of.
In the end, she paid off about $12,000 out of her $23,000 debt. She documented the entire effort on her TikTok account, where her videos went viral and racked up hundreds of thousands of views.
She hopes that sharing her story will help others reduce their debt as well. She summed it up by saying she didn’t expect to go viral—she was just trying to stay accountable—but she thought the reason people connected with it was because it felt accessible. She said many of the comments were from others saying they were in debt too, and that it motivated them to make an extra payment or even take debt payoff more seriously.