Harrison is navigating the complexities of holding six remote jobs simultaneously, which sometimes results in double-booked meetings. To manage this, he’s found an unconventional solution: hiring someone to represent him during his meetings. “My person knows the updates and sounds like me,” Harrison shared, noting that he typically doesn’t need to be on camera for these sessions. Though verified by Business Insider, he opted for a pseudonym to avoid potential professional backlash.

As a quality assurance professional in the IT sector, Harrison has assembled a team of seven workers to aid in managing his multiple full-time positions covertly. If his employment situation remains consistent, he anticipates earning about $800,000 this year while compensating his team around $250,000, with each worker earning $25 to $30 per hour. This marks the fifth year he’s implemented this income-maximizing strategy.

In 2023, Harrison maintained six full-time remote jobs based in the US—three as a traditional W-2 employee and three as a consultant—yielding an estimated income of roughly $470,000. After compensating his team, he calculated a profit of about $320,000. Looking ahead to 2024, he toyed with the possibility of juggling as many as nine jobs at once, projecting earnings over $500,000, pending the final tally once his taxes are completed.

“I used to worry about my boss, the stock market, bills, and my kids’ tuition,” he reflected. “Having multiple jobs has significantly reduced my anxiety—if one position falters, I have several paths to fall back on.” Harrison is among a small yet growing number of “overemployed” workers who not only take on multiple jobs but also hire others to carry out their responsibilities. This trend is driven by the rise of remote work, globalized networks, and the availability of outsourcing tools.

Building a Support Team

Harrison started his journey in 2018 with just two remote jobs, but the onset of the pandemic led him to take on even more roles. The workload quickly became overwhelming, prompting him to utilize platforms like Upwork to find trustworthy individuals who could handle his work tasks. After careful selection, he built his team, consisting of members from the US, Canada, India, and Pakistan. Harrison refers to them as his employees.

Managing His Workload

On a typical day, Harrison dedicates about 40 hours a week to attending meetings and managing his team’s work. He assigns his four employees various tasks, while his brother-in-law helps oversee operations and acts as his stand-in for meetings. “He’s currently unemployed, so this arrangement works well for both of us,” Harrison stated. However, he has faced challenges recently in securing additional remote jobs due to industry slowdowns and return-to-office mandates.

The Logistics of Overemployment

Although Harrison is a US citizen, he spends most of his year abroad, using a VPN to maintain a US IP address which aids in his outsourcing endeavors. Tools like Zoom, TeamViewer, and UltraViewer allow his team to access his work computers remotely. Interestingly, some employees juggle multiple jobs, but Harrison believes that none of his employers have caught on to his dual-career lifestyle. He sometimes finds himself needing to buy time while waiting for updates from his team members.

The Future of Job Juggling

Looking forward, Harrison plans to continue his novel approach to multi-job holding. He feels his savings are insufficient for retirement, and maintaining about six jobs seems to strike a balance between increased earnings and manageable work hours. Should the demands become excessive, he is willing to relinquish one or more jobs. “When you’re unemployed, you feel compelled to accept the first opportunity that arises; I’m fortunate to have the flexibility to choose,” he explained.

If you have a story about working multiple jobs covertly or discovering an employee’s double life, please reach out to the reporter at jzinkula@businessinsider.com or via Signal at jzinkula.29.

The Trend of Remote Job Juggling: A New Era of Work

In the evolving landscape of remote work, a growing number of professionals are taking on multiple jobs to enhance their income and job security. With the advancements in technology and the rise of flexible work opportunities, many individuals are finding innovative ways to manage their careers effectively.

The Rise of Remote Work Opportunities

The COVID-19 pandemic has accelerated the acceptance of remote roles, leading to an influx of job openings in various sectors. As employees seek to maximize their earnings, some have started to embrace the concept of taking on multiple positions simultaneously, a trend that reflects the changing norms of employment.

Maximizing Income Through Strategic Hiring

Professionals juggling multiple roles are often leveraging platforms like Upwork to hire freelancers or assistants to manage specific tasks. This approach allows them to maintain productivity while effectively managing their workload. By assembling a reliable team, these individuals can fulfill the demands of various jobs without overwhelming themselves.

Challenges of Overemployment

While the concept of working multiple jobs offers financial benefits, it also poses challenges. Employees often face potential professional repercussions if their employers discover their dual engagements. Moreover, maintaining work-life balance can become increasingly difficult as the number of responsibilities grows, leading to the risk of burnout.

Creative Solutions in Job Management

To streamline their workflows, many multi-jobbers utilize software tools like Zoom and TeamViewer, which facilitate remote access to work systems. This technology allows professionals to manage tasks seamlessly across different roles. Adapting to the demands of multiple jobs has become a key skill for those aiming to thrive in this competitive environment.

Future Outlook: Balancing Job Security and Earnings

As the economy continues to shift, the practice of overemployment is likely to evolve. Many professionals express a desire for enhanced job security through diverse income streams. Finding the right balance between multiple jobs can lead to financial stability, but individuals must remain vigilant about potential constraints and challenges that may arise.

The Verdict on Remote Job Juggling

With the landscape of work continually changing, remote job juggling is becoming a viable option for countless workers. Those willing to innovate and adapt can harness the opportunities presented by technology, ultimately securing their financial future in a competitive job market.

If you have insights or experiences related to remote job juggling, feel free to share your story to contribute to this ongoing conversation about the future of work.