High-Income Workers Juggle Multiple Full-Time Jobs Using AI Tools

Workers are increasingly earning six-figure and even seven-figure incomes by secretly holding multiple full-time jobs, all while adhering to a standard 40-hour workweek. This practice, known as overemployment, has gained traction with the rise of remote work, which makes it easier for employees to juggle roles across multiple organizations without direct oversight. Some professionals, particularly in high-demand fields like software engineering and healthcare technology, are working up to five jobs simultaneously and earning more than $1 million annually. These workers rely on AI-powered tools to automate tasks such as email drafting, note-taking, and deliverable preparation, allowing them to maintain productivity across roles without significantly extending their work hours [1].

The trend emerged on social media after a Silicon Valley software engineer was discovered working for multiple startups at once, prompting other companies to investigate whether their own employees were engaging in similar behavior. Many of those in the know describe the practice as less of an ethical dilemma and more of a strategic advantage. One anonymous worker told Fortune, “If you’ve worked in corporate America, it is a lot of fluff and not a lot of substance,” highlighting the perceived inefficiencies in traditional work structures that make overemployment feasible. Another worker, holding two healthcare technology roles and earning close to $250,000 annually, argued that employers hire for expertise rather than hours, and expressed no concern over taking jobs from others in a struggling job market [1].

While the practice is legal in many cases, it raises ethical questions and concerns among industry experts. Lewis Maleh, CEO of executive recruitment agency Bentley Lewis, warned that such behavior, though not illegal, could have long-term professional consequences if discovered. He emphasized that full-time employment typically implies exclusivity and that dual employment could undermine trust. Meanwhile, sociologist Jerry Jacobs of the University of Pennsylvania suggested the trend is more of a temporary experiment than a sustainable norm. As employers become more adept at monitoring remote work productivity, the window for overemployment may shrink [1].

The phenomenon has sparked debate about the future of work and labor ethics. Some view it as a natural outcome of the high demand for specialized skills in sectors like healthcare technology, where companies compete aggressively for talent. Others see it as a potential labor market distortion that could lead to burnout or unfair competition. Regardless of perspective, the practice highlights the evolving nature of employment in the digital age, where flexibility and technological tools enable workers to push the boundaries of traditional work arrangements [1].

Source: [1] Workers are making over $1 million by secretly holding down multiple gigs—and they're doing it all within the 40-hour workweek (https://fortune.com/2025/08/03/workers-holding-multiple-full-time-jobs-secretly-remote-work-40-hour-week-overemployment-high-income/)