Editor’s note: In April 2025, Business Insider wrote about an IT support professional named “Damien,” who was secretly juggling three full-time remote jobs and on track to earn about $368,000 (Damien is a pseudonym, but Business Insider has verified his identity and employment.) Read that story here. In a recent interview, Damien shared how his overemployment situation has evolved.
When Business Insider first spoke with Damien last year, he wasn’t having much trouble secretly juggling three full-time jobs.
Since then, he’s lost one of those roles but added three others. He now works five full-time remote IT jobs that together pay about $746,000 annually, income he’s used to support his family, buy a new car, and prepare for a future with fewer jobs.
Damien said that on a typical workday, he wakes up at 4 a.m., hits the gym, and starts work around 6 a.m. — staggering when he logs on based on the three different time zones of his employers. He said he’s usually logged off from all of his jobs by around 5 p.m., and that despite the 11-hour days, the workload is usually manageable.
He would have been open to a sixth role, but Damien said that over the past few months, seeing former tech colleagues post on LinkedIn about recent layoffs has made him feel a little guilty.
“I don’t want to take all the jobs that are available when there are people out there that truly need roles,” said Damien, a millennial who lives in the Mountain West. He asked to use a pseudonym and his identity was verified by Business Insider.
Over the past three years, Business Insider has interviewed more than two dozen overemployed workers who have used their extra income to travel, pay off debt, and retire early. Most job jugglers say the extra money outweighs the risk of burnout or professional repercussions, though tech layoffs and return-to-office mandates have reduced the availability of the remote roles they rely on.
Damien shared how he landed his newest roles, how he juggles five jobs without getting caught, and his plans to eventually leave overemployment behind.
How he went from 3 jobs to 5
In 2021, Damien was making about $90,000 a year working in remote IT support, when he landed a better offer: $110,000 per year for a different remote job. He almost accepted the higher-paying position, he said, until he realized he could just do both — and keep it secret from his employers.
But over the next year, Damien grew concerned he’d get caught, after realizing employees from his two companies occasionally attended the same business meetings. In 2022, he quit both roles and started a different position paying close to $140,000 per year.
In 2024, he again added a second full-time remote IT job with an employer he believed was less connected to his other work.
In early 2025, Damien landed a third role. But he kept aggressively looking for new ones in case one of his existing roles dried up. But nothing came through quickly, which Damien attributed to the cyclical nature of IT hiring and the broader tech slowdown.
In September, after about six months of searching, Damien landed a fourth full-time role. Months later, a recruiter outreach led to a fifth. By March 2026, one long-term contract had ended, but he replaced it with another position, keeping him at five full-time roles.
Damien said job juggling has transformed his family’s finances and allowed his wife to quit her job. He said his primary motivation is creating financial security for his family and ensuring he’s never dependent on a single employer. That concern weighed more heavily on Damien last year, when he struggled to land a replacement for his third job.
“I remember thinking, ‘Wow, if I was truly jobless, I would’ve spent six months before I even heard back from someone,'” he said.
That made him feel less guilty about holding multiple jobs.
How he juggles 5 jobs and avoids suspicion
Damien, who said he’s landed most of his jobs through direct applications, believes he can juggle five jobs because his employers overestimate the amount of work his jobs require. He understands why some companies have cut roles in an effort to improve efficiency.
“Companies are probably like, ‘We have all these people that aren’t doing anything, so we need to tighten up a little bit,'” he said.
Damien said he’s explored whether generative AI tools could help him complete his IT work more efficiently, but that he hasn’t found many strong use cases so far — something he attributed to the amount of human interaction and hands-on problem-solving his roles require.
While Damien still worries about getting caught, he has ways of avoiding scrutiny. He said he built a program that makes his computers appear active — and that he delivers high-quality work.
“I just don’t give folks a reason to think that they need to be tracking me,” he said.
Read more about people who’ve juggled multiple jobs
Life after overemployment
Damien said he’s been able to maintain some form of work-life balance by avoiding work after 5 p.m. and spending time with his family in the evenings. He typically gets about six hours of sleep a night — roughly as much as his body allows anyway.
But in recent months, Damien said he’s focused more on generating passive income through real estate, building long-term wealth, and potentially starting his own business. He hopes doing so will eventually make him comfortable moving away from overemployment. He added that while the extra money has afforded him luxuries, people eventually “run out of things to buy.”
“I don’t want to work like this forever,” he said.
