A Gen Xer who secretly works 3 full-time remote jobs and makes $344,000 paid off his mortgage and is saving to send his kids to college debt-free

• A 48-year-old began working three full-time remote jobs last year.
• He said doubling his income had helped him pay his mortgage and save for his children's education.
• His work life can be stressful, but he said he'd figured out how to avoid suspicion.

Joseph, a 48-year-old network engineer from Texas, never set out to work three full-time remote jobs at the same time. 

But last year, he earned a combined $344,000 doing just that, according to documents viewed by Insider. While the stress is starting to take a toll on him, he said the extra income had made a huge difference for his family and that he planned to keep it up as long as he could. In August, for instance, the extra income helped him pay off the remaining $129,000 on his mortgage, according to a document viewed by Insider. 

In early 2020, when Joseph had one job, which paid $117,500 a year, he accepted a new remote role in the IT field with a $120,000 salary. But before he was out the door, he said a colleague convinced him to stay and try to work both jobs at once.

Joseph said he was doing only four to five hours a week of "actual work" in his position at the time, which made him think this was feasible. And if it became too much, he knew he could always quit one of the jobs.

"I hadn't really heard anyone doing this before," he told Insider. "My colleague mentioned it and I gave it a shot."

He said he started working the second job that May, which initially required 30 to 40 hours of additional work a week. Roughly six months later, his new company announced a strategic shift that Joseph feared would put his role in jeopardy. He began looking for a new opportunity.

But by the time he accepted a third job, in February 2022, a full-time IT position that paid $120,000 a year, the workflow of his second job shifted from 30 to 40 hours a week to roughly five to eight.

So he decided to try and juggle all three jobs at once.

"Job two got so easy and was still 100% remote, so I kept it while I got job three," he said, adding: "I hung in there because the pay was good and I wasn't really doing anything."

Today, Joseph said, he typically works roughly 40 hours a week across his three jobs, in addition to a few hours two to three evenings a week. He worked at the third job until September, when he accepted what he called a "new job three." He started in October, earning $125,000 a year in the new role.

Every time he took a new job, he fully intended to dedicate all his time to that role and leave the others behind, Joseph said, but "it just seemed to work out that I could do both or all three." 

Joseph's real name is known to Insider but has been withheld for his fear of professional repercussions. He's one of many Americans who have taken on additional work partly because of high inflation. He's also among a smaller group of white-collar workers secretly holding multiple full-time remote jobs to, in many cases, double their salaries. 

But the window to pull this off may be closing, as many companies are calling remote employees back to the office and listing fewer fully remote positions. Others, particularly those in the tech industry, have laid off workers in remote roles.

And as knowledge of this phenomenon grows, some members of the overemployment community are worried they'll eventually be found out. While holding two jobs at once doesn't violate federal or state laws, it could breach some employment contracts and get people fired. It's already happened to some workers.

He worried about the morality of it, but the financial freedom was worth it

At first, Joseph said, his wife was not a fan of him working multiple jobs and thought it was morally wrong. But he persisted and said his wife was now OK with him deciding how long he would continue this lifestyle.

This is partly because this lifestyle has given him, his wife, and their two children financial freedom. 

"We were able to pay off our house, the cars, and pay cash for a car for my son," he said. "I really just want to be comfortable in our financial future.

"I still live on a single paycheck. I never let myself think I have more money to spend on toys or trips. But it's nice to be able to say, 'Hey, let's go to Disney,' on a whim or buy a new dishwasher or dryer without even thinking about it."

Despite these benefits, Joseph said he felt "a little burned out," and that he's not sure how long he could continue working all three jobs. But he said a few things were keeping him going. 

First, he doesn't want his children to have to deal with student-loan debt. 

"I mainly do it so I can pay cash for my two kids' college education," he said. "I see how my college degree has helped me, and I want them to at least have the same opportunities I did."

Additionally, he wants to preserve the extra job security he's built.

"With the current economic climate and possible recession coming, I wouldn't be surprised if I was laid off from at least two of them," he said.

At the second job, where he saw his workload reduced after the company's acquisition, he said he expected to be laid off sometime over the next year. 

How to juggle meetings and obligations for 3 jobs

While Joseph worries from time to time about getting caught, he said, he thinks IT is one of the easier fields to be overemployed in.

"In the IT world, we never really work a full 40 hours a week," he said.

If he does ever get caught, he said, he's confident he'll be able to land on his feet and find other work. But he works hard to ensure this doesn't happen — and pointed to a few ways he avoids suspicion.

On his first job's digital work calendar, for instance, he adds any meetings or obligations he has for the other two jobs, labeling them as "private" so no one can see what they pertain to. This helps him avoid double-booking and prevents him from being bothered during these periods. 

"If you keep your Outlook calendar up to date, you should never have a conflict," he said. "But occasionally I do. I just have multiple headsets on with multiple meetings, and, of course, the camera is always off." 

Additionally, he said, he has one good friend at each of his first two jobs whom he's told about his overemployment lifestyle.

"They are fine with it, and I trust them not to tell anyone else," he said. "I really just needed someone on the inside to understand there might be a meeting I miss here or there."

Joseph said he rarely felt bad about keeping the other jobs a secret from his employers. If someone on his team was ever laid off — presumably from their only job — he said he would struggle with some feelings of guilt. 

"I am salary-based, so it doesn't really matter if I work 15 hours a week or 40 hours a week," he said. "If I do the job that they hire me for, then I have earned my pay."

Moving forward, Joseph said that he may quit the first two jobs to focus on the third, his "real passion." It challenges him more, is more in his area of expertise, and offers the potential for more career growth than his other two roles, he said. 

Despite the stress of juggling the three jobs, he said he's not in a rush to give them up.

"Occasionally I wonder what I would do if I only had one job," he said. "What would I do with all the time on my hands?"

Are you working multiple remote jobs at the same time and willing to discuss details about your pay and schedule? If so, reach out to this reporter at jzinkula@insider.com.

This story was originally published in May 2023.