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Bosses are freaked out you’re working 2 jobs—and remote work and AI have let the cat out of the bag

By
Tristan Bove
Tristan Bove
Contributing Reporter
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By
Tristan Bove
Tristan Bove
Contributing Reporter
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May 16, 2023, 2:04 PM ET
The Night Owl Trader Working late into the night, a man is seen from behind as he analyzes market trends and exchange information in his home office.
The Night Owl Trader Working late into the night, a man is seen from behind as he analyzes market trends and exchange information in his home office. Alexandr Muşuc

Technology was supposed to bring us closer together, but instead it’s fueling paranoia and mistrust—in the workplace at least.

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The age of remote work helped women, people with disabilities, and members of the LGBTQ+ community feel more included in the workplace. But bosses were never completely comfortable with employees having more flexible hours and greater independence, especially since some workers started using their new-found freedom to work multiple jobs at once. 

Corporate leaders might be starting to gain an edge in the battle to have employees back in the office a few days a week, but that doesn’t necessarily mean they’ll be able to clamp down on their workers’ “overemployment.” Rapid advances in artificial intelligence could become the next ace up employees’ sleeve in their quest to fill up their days with as many side-hustles as possible.

The commercial advent of A.I. in the form of wildly popular applications like ChatGPT is already transforming offices, and could have major implications for productivity expectations. Generative A.I. tools like ChatGPT could make workers nearly 14% more productive, an April study by MIT and Stanford researchers found, while novice and low-skilled employees were able to work 35% faster than they would have without an A.I. assistant.

The technology, in which companies are already investing billions, could rival the Internet and modern infrastructure in terms of its impact on worker productivity, billionaire hedge fund manager Paul Tudor Jones told CNBC on Monday.

“I do think the introduction of large language models [and] artificial intelligence, is going to create a productivity boom that we’ve only seen a few times in the last 75 years,” he said. “Let’s say that this large language model is going to give us a productivity boom of 1.5% over the next five years per year, which I think is possible.”

Employers are already thinking about how they can tap A.I. to improve their companies’ output. For example, James Clark, CEO of digital marketing firm Clearlink, declared in a video address last month that the company should “put out 30 to 50 times our normal production” after he realized that A.I. could accomplish in 30 minutes some content writing jobs that would normally take humans a full eight-hour workday. 

But absorbing all those productivity gains for themselves might not be an easy task for companies, as some workers are already applying their overemployment skills honed during the pandemic and taking advantage of A.I. to work multiple jobs at once, a fact that wasn’t lost on Clark.

“Some of our developers could be working for two different companies. We don’t know. We hope that’s not the case, but we don’t know,” he said during his address.

Clark may have good reason to worry, as anecdotal evidence is already emerging of workers tapping A.I. to earn more on the side. Users are using ChatGPT to write increasingly convincing cover letters to apply for multiple jobs, and last month, Vice reported it had spoken with multiple workers who were holding up to four jobs at once thanks to ChatGPT. One overemployed worker was able to increase their salary from $500,000 to $800,000 a year thanks to the technology—and working remotely. Fortune could not independently verify those reports. 

Workers refined the art of doing multiple jobs at once while working remotely during the pandemic, often earning two full-time salaries while still working a manageable 40 hours a week. The pandemic-era phenomenon of quiet quitting, when employees did the bare minimum of their job requirements, has been primarily attributed to widespread burnout, but it has also allowed some workers to get by with a mediocre performance at multiple jobs.  

But even if A.I. could be a boon to workers seeking to become overemployed, it might also widen the gap in trust between themselves and their employers, which has already been severely eroded by remote work. While workers have long insisted that they are just as productive working from home as they are in the office, if not more so, bosses like Elon Musk and even Sam Altman, CEO of ChatGPT creator OpenAI, are far from convinced.

Employers have become so uncertain about whether their workers are being productive at home that some have resorted to remote monitoring technology to keep tabs on their at-home employees. Some companies were already spying on employees before they went remote, like JPMorgan Chase, the country’s largest bank, which launched a data-collection and employee monitoring system shortly before the pandemic began that staffers referred to as “Big Brother.”

The trend caught on during the pandemic, with companies like Barclays Bank and UnitedHealth Group tracking everything from how long it took them to write an email to what they typed on their keyboards. But just as employees and bosses are seemingly reaching a compromise over remote work, a new technological development could be poised to stir up old paranoias.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
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