A millennial IT worker, known as "Damien," has taken overemployment to the next level, secretly juggling five full-time remote jobs that collectively pay about $746,000 annually. Despite the tech layoffs that have hit the industry, Damien's story reveals how some workers are capitalizing on remote work inefficiencies.
From 3 to 5 Jobs
Damien started his overemployment journey in 2021, earning $90,000 from one remote IT support job. After landing a better offer for $110,000, he decided to do both secretly. Over time, he quit those roles and later built up to three jobs by early 2025. After a six-month search, he added a fourth in September 2025 and a fifth by early 2026, replacing a contract that ended.
The Daily Grind
Damien wakes up at 4 a.m., hits the gym, and starts work around 6 a.m., staggering logins across three time zones. He logs off by 5 p.m., working about 11-hour days. He says the workload is manageable because his employers overestimate the time needed for his tasks.
Avoiding Suspicion
To avoid getting caught, Damien built a program that makes his computers appear active. He also delivers high-quality work, saying, "I just don't give folks a reason to think that they need to be tracking me." He hasn't found generative AI useful for his IT roles due to the human interaction required.
Guilt and Future Plans
Despite the financial success, Damien feels some guilt seeing former colleagues post about layoffs on LinkedIn. "I don't want to take all the jobs that are available when there are people out there that truly need roles," he says. He's now focusing on passive income through real estate and hopes to eventually leave overemployment behind, noting that people "run out of things to buy."
Key Takeaways
- Overemployment can significantly boost income but comes with risks of burnout and professional repercussions.
- Tech layoffs and return-to-office mandates are reducing the availability of remote roles for job jugglers.
- Damien's story highlights the inefficiencies in remote work that some workers exploit.
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