A Gen Xer is secretly working three remote jobs and earning over $300,000 per year.He said his overemployment has made it possible for him to retire by age 65.He shared the top strategies he’s used to avoid suspicion.
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In 2021, Justin, an IT engineer in his 50s, received the news he’d been dreading: his company had issued a return-to-office mandate.
He wasn’t ready to give up the fully remote life, he told Business Insider, so he spent the next few months looking for a new job. Eventually, he landed two remote offers, and while he briefly considered trying to work both jobs at once, he ultimately concluded it was an “impossible dream.”
But when he started his new role that summer — and his workflow was extremely slow — he realized he might have been mistaken. One day, a co-worker confided in him that they secretly worked a second remote job.
“He told me, ‘You have to look out for yourself — always be hustling,'” Justin said. “That day, I polished my resume and started looking for a second job.”
But Justin didn’t just stop at two. In the fall of 2021, said he landed — and accepted — five remote roles in a roughly one-month span. Two years later, Justin only has three jobs, but he’s fully embraced the “overemployed” lifestyle.
Last year, he earned over $300,000 secretly working three full-time, remote IT engineer jobs, according to documents viewed by Business Insider. In addition to providing him with an unusual level of job security, he said the extra income has helped him pay off debts, max out his 401(k), and turned his dream of retiring at age 65 into a potential reality. Justin, whose identity is known to BI but has been withheld due to his fear of professional repercussions, is among a niche group of white-collar workers secretly holding multiple jobs — and getting away with it.
Working two jobs at once doesn’t violate federal or state laws, but it could breach some employment contracts and be a fireable offense if a worker is ever found out. Helping workers like Justin avoid detection are some 300,000 members of the “overemployed” community on Discord and Reddit, as Business Insider previously reported.
Justin shared what effect overemployment has had on his finances and his top strategies for getting away with it.
It’s important to be good, not great, at all of your jobs
It took Justin some time to figure out how to thrive as an overemployed worker.
He said he worked four remote jobs simultaneously for seven months until one of them, a contract role, was terminated. While he earned well over six figures during this seven-month span, he said losing the fourth job was almost a relief — because his work life was becoming unsustainable.
“The money was phenomenal,” he said, “but it felt like almost every day was a challenge.”
Justin said that secretly juggling three full-time jobs, each of which pays over six figures annually, has been “fairly easy.” He said his typical workday is from 7:30 a.m. to 5:00 p.m., but that he’s usually only busy about five hours per day.
Over the last two years, Justin has studied all the excuses for missing meetings, not turning his computer camera on, and not being available for extra work tasks. But his top piece of advice for overemployed workers is to be good, not great, at all of your jobs.
It’s important to be good at one’s job so your bosses don’t suspect anything, he said. For some workers, this might mean focusing on just two jobs rather than three.
“Always be available, respond promptly, and do good work,” he said. “Keep deadlines, and if you can’t, communicate that ahead of time.”
It’s important to not be “great” at one’s job to avoid the extra responsibilities that could come with a promotion, Justin said, adding that this also results in his bosses expecting less of him and not overwhelming him with work.
“I’ve had managers at two of my jobs ask me if I need help or additional resources,” he said. “I thank them for their concern, say everything is under control, but I promise to let them know if I need help.”
Use what you’ve learned at one job to become more productive at the others
Justin said he’s figured out how to avoid meeting conflicts and join multiple meetings simultaneously when necessary. His biggest obstacles are impromptu calls from his bosses that he can’t plan for. When group meetings that include his bosses are double-booked, he said they’re sometimes a blessing in disguise — as he knows he won’t receive a surprise call from them.
In some ways, Justin said working multiple jobs that are similar has made him more productive at each of them — and that this has been a big time saver.
“If a new issue happens at job one, it’s almost a guarantee that job two or job three will see that same issue at some point in the future,” he said. “And when they do, I can cut that research time down from a week or more to under an hour typically.”
When Justin began his overemployment two years ago, he enjoyed spending his extra income on things like home renovations. But eventually, he realized that if he put a lot of his money toward savings, he’d have a chance to retire much earlier — and more comfortably — than he had thought possible.
Justin said his focus on saving has made retiring at or before the age of 65 an “achievable goal.” In the meantime, he said his favorite thing about overemployment is the job security it provides.
“It’s always a concern that companies can dump people at any time,” he said. “Having three jobs, if I got laid off at one tomorrow, I wouldn’t really skip a beat.”
Are you working multiple remote jobs at the same time and willing to provide details about your pay and schedule? If so, reach out to this reporter at [email protected].
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