A millennial making over $300,000 annually secretly working two remote jobs says homeownership still feels out of reach

• A millennial is secretly working two remote jobs and earning over $300,00 per year.
• He said his overemployment has helped him save over $150,000, but that homeownership still feels out of reach.
• He shared how he's balanced both jobs and tried to avoid suspicion.

John, a millennial IT professional based in California, never intended to secretly work two remote jobs at the same time.

He had a friend who was "double dipping," he told Business Insider, but he said it always sounded like too much work. Then, in 2021, when a former boss asked if he was looking for a new job, John reconsidered.

"I thought about my current workload, and I thought about what my new workload would be, and I figured I'd give it a shot," he said. "I'd save the extra money to buy a house, or go on a vacation, and fill up my retirement accounts for the aim of perhaps retiring early."

Two years later, John is still secretly working two remote jobs. He's on track to earn over $300,000 this year, according to documents viewed by Business Insider, and he said he's been able to save over $150,000 since he became "overemployed." John, 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 may not 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 John avoid detection are some 300,000 members of the "overemployed" community on Discord and Reddit.

John shared why overemployment hasn't made him feel rich and his top strategies for getting away with it.

"Homeownership still feels far away"

Doubling his salary hasn't impacted his standard of living all that much, John said. He still drives the same car, flies economy, and stays at 2-to-3-star hotels. While some of this is by choice — he tries to save and invest as much as he can — John said one expense still feels a bit daunting: homeownership.

"I wish I could say it made me rich, and don't get me wrong, I'm certainly not hurting for money," he said of overemployment. "But homeownership still feels far away."

John said the average cost of a home with his desired size and location is around $800,000. If he were to buy a home, he said the down payment would use up most of his savings, and that to meet his mortgage payments, he'd feel obligated to keep working two jobs for the foreseeable future.

Additionally, he said the large upfront housing expense would make it harder for him to support his loved ones financially. He said he's been helping his mother out and paying some of a sibling's healthcare bills.

"I'm able to help family members out without worrying about how I'm going to take care of my own," he said.

How to work two jobs at once

John said a combination of luck and practice has helped him balance both jobs.

For example, his teams' daily meetings luckily don't overlap. But, he's practiced working on one job while in a meeting for the other one.

Additionally, the skills he learns in one job sometimes help him become more productive at his other job, he said.

While he wouldn't say he's the "best" at his job, John is typically able to complete tasks ahead of schedule. This is among the reasons that, despite his two jobs, he said he only works around 40 hours a week.

Despite his best efforts to avoid suspicion, John said he thinks one of his bosses knows he's double-dipping.

"He either chooses not to mention it or simply doesn't care as long as I get my work done," he said.

Looking ahead, John plans on continuing double-dipping for the foreseeable future. Getting laid off, perhaps more so than getting caught, could be the biggest risk to his overemployment, he said. This became clear when he was laid off from one job last year — he started a new role one month later.

While taking on a third job would boost his job security, John has largely ruled out this option. That's because he said he'd already tried it twice over the last two years, only to soon realize that it wouldn't be sustainable.

"It became clear that I simply didn't have the bandwidth to focus on three things at once," he said.

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].