How 4 people got away with secretly working multiple remote jobs and making over $300,000 a year — and the closest they came to getting caught

• Secretly working multiple remote jobs has helped some Americans transform their finances.
• But it isn't easy juggling multiple jobs at once and getting away with it.

Some Americans are secretly working multiple remote jobs to boost their incomes. Despite having double the meetings, duties, and coworkers, many have managed to get away with it undetected.

Avoiding detection can come with massive rewards. In recent months, Business Insider has spoken with several people who've earned as much as $500,000 annually working two or three remote jobs simultaneously. They've used the extra money to pay off their mortgages, save for their kids' college education, plan for an early retirement, and take expensive vacations.

Pulling this off isn't easy, so "overemployed" people appear to be a small share of the US workforce. Job juggling also comes with some risks. While working multiple jobs at once may not violate federal or state laws, it may breach some employment contracts and be a fireable offense if a worker is ever found out.

Business Insider asked four current and former overemployed workers how they managed to pull it off. They spoke on condition that pseudonyms would be used for fear of professional repercussions, but BI has verified their identities and earnings.

Be good, not great, at all of your jobs

Justin, an IT engineer in his 50s, earned over $300,000 in 2022 secretly working three full-time, remote IT engineer jobs. He said the extra income had helped him pay off debts, max out his 401(k), and pave the way for his dream of retiring at 65.

Over the past few years, Justin has studied all the excuses for missing meetings, not turning his computer camera on, and not being available for extra tasks. But his top piece of advice for job jugglers was to be good, not great, at all your roles.

It's important to be good at your job so your bosses don't suspect anything, he said. For some workers, this might mean focusing on just two jobs rather than three. It's important to not be "great" at a job, though, to avoid the extra responsibilities that could come with a promotion, Justin said. He added that this also resulted in his bosses expecting less of him and not overwhelming him with work.

Justin said the closest he'd ever come to getting caught was when he forgot to exit a Google meeting at one job — and quickly took a phone call related to a different job.

"My director came back on the Google meeting as the call from my other job ended," he said via email. "He could have heard my entire meeting, but he never questioned me about anything. That was a dumb mistake that I have not repeated."

Don't double-book meetings and confide in a trusted friend

Joseph, a network engineer in his late 40s, earned $344,000 in 2022 secretly working three remote jobs. He said the extra income enabled him to pay off the remaining $129,000 on his mortgage and that he hoped it would allow him to someday send his children to college debt-free.

While Joseph was laid off from two of his jobs last year and is not currently overemployed, he said his job juggling was never exposed.

To avoid suspicion, Joseph said managing his work calendars was key. On his first job's digital work calendar, he'd add any meetings or obligations he had for the other two jobs, labeling them as "private" so no one could see the descriptions. This helped him avoid double-booking and prevented him from being bothered during these periods.

Additionally, Joseph had one good friend at each of his first two jobs whom he told about his overemployed lifestyle.

"I really just needed someone on the inside to understand there might be a meeting I miss here or there," he said via email.

Joseph said the closest he came to getting caught was when one of his employers asked him if he could travel for a project.

"I told them that I have a family obligation and could not travel," he said.

Check your employers' policies on overemployment

William, a Texas-based tech worker in his 30s, earned over $500,000 across four remote roles in 2022.

His first piece of advice for job jugglers who are worried about getting caught: check if your companies have explicit policies against employees having multiple jobs.

William said both of his employers allowed workers to have multiple jobs as long as they met expectations and there were no direct conflicts of interest, such as working for a competitor. But he still kept his overemployment a secret from everyone outside his family.

"It was more of a 'don't ask, don't tell' situation as the assumption would be that it wouldn't impact your main role," he said via email.

William said it's easier to balance multiple jobs when a person has more control over their day-to-day responsibilities and schedules. He said the closest he ever came to getting caught was when one of his managers asked him to add the company to his LinkedIn profile.

To avoid listing his simultaneous jobs on LinkedIn, William said he decided to hibernate — or temporarily deactivate — his LinkedIn account.

If you're productive at your jobs, your bosses might look the other way

John, a millennial IT professional in California, was on track to earn over $300,000 in 2022 across two remote jobs. He said he'd been able to save over $150,000 since he became overemployed a few years ago and that he hoped to use these funds to buy a home someday.

John said the best way to avoid suspicion was to be very productive at both jobs, which he said came down to a combination of luck, practice, and skill. He said he only worked about 40 hours a week and that the skills he learned in one job sometimes helped him become more productive at his other job.

John said the closest he's come to getting caught was when he forgot to mute himself on a work call while he was speaking on another call for a different job.

"It was a brief call but enough for my boss to ask me about it," he said via email. "I just said it was a client."

Despite his best efforts to avoid suspicion, John said he thought one of his bosses might suspect he was double-dipping. But as long as he remains productive, he said he's hopeful this suspicion won't become a problem.

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

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 jzinkula@insider.com.