A millennial IT support professional shares how he juggles five full-time remote jobs for nearly $800K annually, balancing work and family life despite recent layoffs in the tech industry.
A millennial IT support professional named Damien has been secretly juggling five full-time remote jobs since 2021. In April 2025, Business Insider reported on his secret career as he earned about $368,000 annually from three roles. Since then, he's added two more positions to reach a total of five, earning approximately $746,000 per year.
Damien wakes up at 4 AM and starts work around 6 AM, logging onto his jobs based on the different time zones of his employers. He typically works until around 5 PM each day, managing a 11-hour workload without feeling overwhelmed. Despite the demanding schedule, Damien has managed to support his family, buy a new car, and prepare for a future with fewer job opportunities.
In an interview, Damien shared that he almost accepted a higher-paying position in 2021 but decided against it when he realized he could maintain both roles secretly. Over time, he grew concerned about getting caught due to occasional business meetings attended by employees from his two companies. In 2022, he quit both positions and started a new role paying around $140,000 annually.
In early 2024, Damien added another full-time remote IT job with an employer less connected to his other work. By March 2026, one long-term contract had ended, but he replaced it with another position, keeping him at five full-time roles. He attributed this to the cyclical nature of IT hiring and the broader tech slowdown.
Damien said that seeing former tech colleagues post about recent layoffs on LinkedIn has made him feel guilty. "I don't want to take all the jobs that are available when there are people out there that truly need roles," he explained, emphasizing his concern for job security and fairness in a competitive industry.
Over the past three years, Business Insider has interviewed over two dozen overemployed workers who have used their extra income for various purposes. Most say the additional money outweighs the risk of burnout or professional repercussions. However, Damien's situation is unique as he feels more guilt due to recent layoffs and return-to-office mandates reducing remote role availability.
Damien shared how he landed his newest roles through direct applications, believing companies overestimate the amount of work required for each job. He noted that while generative AI tools could potentially help with IT tasks, they haven't proven effective yet because of the human interaction and problem-solving involved in his roles.
To avoid suspicion, Damien built a program to make his computers appear active while delivering high-quality work. Despite this, he still worries about getting caught but has developed strategies to minimize scrutiny.
Damien said maintaining some form of work-life balance is crucial for him. He avoids working after 5 PM and spends evenings with his family. While the extra income has allowed luxury purchases, Damien hopes to eventually generate passive income through real estate or starting a business to reduce dependence on overemployment.
In conclusion, Damien's journey from three jobs to five demonstrates how job juggling can provide financial security and flexibility for families in the tech industry. However, recent layoffs have made him more conscious of his actions, balancing personal gain with ethical considerations.
