‘Overemployed’ Hustlers Exploit ChatGPT To Take On Even More Full-Time Jobs

"ChatGPT does like 80 percent of my job," said one worker. Another is holding the line at four robot-performed jobs. "Five would be overkill," he said.
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Credit: Getty stock photo)

About a year ago, Ben found out that one of his friends had quietly started to work multiple jobs at the same time. The idea had become popular during the COVID-19 pandemic, when working from home became normalized, making the scheme easier to pull off. A community of multi-job hustlers, in fact, had come together online, referring to themselves as the “overemployed.” 

The idea excited Ben, who lives in Toronto and asked that Motherboard not use his real name, but he didn’t think it was possible for someone like him to pull it off. He helps financial technology companies market new products; the job involves creating reports, storyboards, and presentations, all of which involve writing. There was “no way,” he said, that he could have done his job two times over on his own. 


Then, last year, he started to hear more and more about ChatGPT, an artificial intelligence chatbot developed by the research lab OpenAI. Soon enough, he was trying to figure out how to use it to do his job faster and more efficiently, and what had been a time-consuming job became much easier. ("Not a little bit more easy,” he said, “like, way easier.") That alone didn’t make him unique in the marketing world. Everyone he knew was using ChatGPT at work, he said. But he started to wonder whether he could pull off a second job. Then, this year, he took the plunge, a decision he attributes to his new favorite online robot toy. 

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“That's the only reason I got my job this year,” Ben said of OpenAI's tool. “ChatGPT does like 80 percent of my job if I’m being honest.” He even used it to generate cover letters to apply for jobs.

Over the last few months, the exploding popularity of ChatGPT and similar products has led to growing concerns about AI’s potential effects on the international job market—specifically, the percentage of jobs that could be automated away, replaced by a well-oiled army of chatbots. But for a small cohort of fast-thinking and occasionally devious go-getters, AI technology has turned into an opportunity not to be feared but exploited, with their employers apparently none the wiser. 


The people Motherboard spoke with for this article requested anonymity to avoid losing their jobs. For clarity, Motherboard in some cases assigned people aliases in order to differentiate them, though we verified each of their identities. Some, like Ben, were drawn into the overemployed community as a result of ChatGPT. Others who were already working multiple jobs have used recent advancements in AI to turbocharge their situation, like one Ohio-based technology worker who upped his number of jobs from two to four after he started to integrate ChatGPT into his work process. “I think five would probably just be overkill,” he said. 

‘The Best Assistant Ever’

Throughout the overemployed community, there is a quiet arms race to figure out just how much of the corporate workday can be automated away using an assortment of AI tools, some of which predate ChatGPT. The possibility of increasing their income, or at least easing the burden of holding down multiple jobs, has led to an explosion of experimentation.

When one of Ben’s bosses, for example, now asks him to create a story for an upcoming product release, he will explain the context and provide a template to ChatGPT, which then creates an outline for him and helps fill out the sections. The AI chatbot knows Ben’s title and the parameters of his duties and has become even better at understanding the context since the launch of GPT-4, the latest edition, he said. “I can just tell it to create a story,” said Ben, “and it just does it for me, based off the context that I gave it.” Ben still needs to verify the information—”sometimes it gets stuff wrong, which is totally normal,” he said—but the adjustments are relatively “minor” and easy to fix. 


Occasionally, he even asks ChatGPT to craft responses to Slack messages from his manager. In such cases, he requests that ChatGPT write the message in all lowercase, so that it appears more organic to the boss.  Another overemployed worker also told me they have started using ChatGPT to transcribe Zoom meetings so they can be largely ignored in the moment and referenced later.

Charles, who has worked as a software engineer and product manager and solutions architect, including at a FAANG company, had been all-in on overemployment since 2020—while he currently works two jobs, he worked four at the height of the pandemic—but said that AI tools have made juggling the positions much easier. 

At the FAANG company, he was able to outsource written tasks to AI tools, like writing a memo to defend and justify a business decision. In such a case, he’d input the relevant facts and parameters into an AI chatbot, which would cohesively lay them out more quickly than he ever could. Additionally, he’d use it to lay out directions for engineers (“It allows you to take, basically, a sentence and expand it out into a paragraph”); and create a “foundation” when coding. The ChatGPT-created code “oftentimes” would work perfectly, he said, but the errors could be identified and resolved easily enough, he said. 


One member of the overemployed, who, unusually, works three financial reporting jobs, said he’s found ChatGPT useful in the creation of macros in Excel. “I can create macros, but it takes me an hour, two hours, plus, to write the code, test it, make sure everything's working,” he said. By comparison, with ChatGPT, he can provide the parameters and it’ll “spit something out” that he can update and tweak to his specifications. The process can allow him to cram what is traditionally a “two-week long process” into a few hours.  (He says he avoids providing ChatGPT with confidential information.)

Daniel, a staff engineer on the East Coast who works one director-level position and another as a senior dev (one job is on Pacific time and one is in the United Kingdom), similarly said that ChatGPT’s code can leave something to be desired, but said it’s been useful when it comes to writing emails. “Most people in tech probably aren't as good at writing things as most other people,” Daniel said. He included himself in that critique of his own industry, but said it’s no longer a problem, as he can plug the key points into ChatGPT and ask the AI assistant to rewrite it “in a more professional way,” he said. “It's really good for stuff like that.”


Excitement for the potential of ChatGPT isn’t limited to the technology and financial spheres of the overemployed community. Marshall, a university lecturer in the United Kingdom who secretly runs a digital marketing agency and tech startup on the side, has become a ChatGPT fanatic since its release. (During class, he often has students run through exercises, during which time he is often able to open up his laptop and work on his side hustles.) “It’s the best assistant ever,” he told me excitedly.

Marshall has come to see himself as the idea man, and ChatGPT as the labor. “I'm quite a conceptualizing person. So I'm quite happy for my brain to do that. But the first draft of anything almost always goes through GPT,” he said.  Already, the chatbot has helped him generate business plans, internal system documents, blog posts, and Excel spreadsheets. He estimated that ChatGPT can often pull off 80 percent of the legwork, leaving him to handle the final 20 percent.  

The tool has even helped him win a grant from the U.K. government (the application was “50-50 me and ChatGPT,” he said) and complete coursework for a master’s degree necessary to receive a university teaching qualification he was too busy to handle by himself while working three jobs.

The members of the overemployed community know that what they’re doing is frowned on by corporate leaders. But that doesn’t mean they think what they are doing is amoral. “I never could mentally comprehend why it was so taboo for me to work two salaried positions,” said the Ohio-based technology worker. “There's plenty of people I've known in my personal life who have worked at Walmart from 4 a.m. to 2 p.m., and then gone and worked another job.” The financial professional similarly said he started working multiple jobs because he doesn't trust that working as hard as he can at a single job will be “rewarded with more pay,” just “more work.” By taking on more jobs, he can do more work but also “get paid for it,” he said. 


‘One Loom Operator As Opposed to 100 Weavers’

More than a member of the overemployed community, Charles, the FAANG alumni, considers himself part of the FIRE movement—short for “Financial Independence, Retire Early” Not yet 30, he is already making $500,000 working two jobs and worth around $3 million, claims he backed up to Motherboard with documentation. But he hopes to increase his compensation to $800,000 by tacking on a third position, and reach a net worth of $10 million by 35.

Even though he is already using ChatGPT to work multiple jobs, Charles still is trying to figure out ways to make his dream even easier to obtain. When we spoke he said he’s already been “able to outsource” coding tasks to a third party in the past, and that he has been hard at work trying to develop a way to have someone else mimic both his voice and image on a computer screen. Once he can do so, he said, he hopes to offshore his job to someone in India who can “do my job for me.” 

In such moments, it can feel like the AI-infused overemployed community is taking advantage of a brief moment in time, when the tools that can be used to automate a job are much better understood by the workforce than the bosses with hiring and firing ability. One person, who works multiple jobs in information technology, spoke openly about the tension that created: People can more easily hold down multiple jobs today; but, should the bosses realize just how much their jobs can be handled by robots, they could be at risk of their jobs being automated away. As a result, he said, there’s good reason to keep quiet about what they’ve discovered.

Most of the overemployed workers themselves maintain that their jobs require a baseline level of expertise, even with ChatGPT. Still, some members of the overemployed community feel they have peered into the future, and not liked everything they’ve seen.

One such person is Ryan, who works multiple jobs in data analytics and marketing in a large Midwestern city. Over the last year, he has watched in astonishment as ChatGPT figured out a way to automate an ever-growing percentage of his job, including writing ad copy and blog posts. The feat can feel exciting, and it has temporarily made his job easier.  “I can crank out a blog post in, you know, 45 minutes now, as opposed to three hours. It's insane,” he said. 

But Ryan does worry. At times, he said, he could not help but feel that the entrance of ChatGPT into the marketing sector felt like the insertion of the modern loom into the textile industry. 

“It's gonna be one loom operator, as opposed to, you know, 100 weavers,” he said.