A Gen Xer who made over $300,000 secretly working 3 jobs at the same time says overemployment allowed his partner to stop working and paid for a $20,000 cruise

• A Florida Gen Xer made over $300,000 secretly working three jobs in the tech industry.
• The extra income allowed his partner to quit their job and helped pay for a $20,000 cruise.   
• He shared four pieces of advice for current and future overemployed workers. 

After being laid off from his tech job in 2019, Robert wanted two things: job stability and multiple sources of income.

Over the course of his career, the Florida Gen Xer had lost eight jobs due to a combination of layoffs, business closures, acquisitions, and contracts not being renewed, he told Business Insider via email.

By 2021, he'd found a remote job that he said paid $180,000 a year and had a part-time gig that was bringing in an additional $2,000 a month. But when his workflow at his main job slowed, he began to fear that a layoff could be coming.

He went looking for other remote jobs and landed one that paid $190,000 a year. But before he resigned from his current role, he remembered hearing about a former coworker who was making nearly $400,000 secretly working two jobs.

So he decided to try to juggle both roles at the same time.

For six weeks, Robert said he was getting two semimonthly paychecks on the same day that he said totaled over $10,000 after taxes and deductions.

When the anticipated layoff from his first job came, his income was cut in half, but he said he'd learned a valuable lesson.

"Having another income still there only reinforced the idea that having a backup job was the best way to keep from being jobless in tech," said Robert, whose identity is known to BI but has been withheld due to his fear of professional repercussions.

In 2023, Robert earned roughly $335,000 across four remote jobs, according to documents viewed by BI, and he said working three jobs at once — which he did for about half the year — only required about 50 hours of total work a week.

Robert said the extra income from job juggling allowed his partner to quit their job, helped him pay down his car loan and credit card debt, and made it possible for him to take several expensive vacations — including a roughly $20,000 cruise that he said had more crew than passengers.

Overemployment has also provided Robert with the improved job security he was looking for. The tech industry layoffs of the past year have made him value having a backup plan as much as ever.

Robert is among a niche group of overemployed workers — many in the tech and IT industries — secretly holding multiple remote jobs and earning well over six figures a year. While some bosses may be OK with employees taking on extra work, being caught doing so without approval could be a fireable offense.

How to make overemployment a reality

After Robert's first six weeks of overemployment came to an end, he said he sent out "hundreds" of resumes in the hopes of finding a second job. A month or two later, he was deciding between two offers when he had an idea.

"Three jobs never really crossed my mind, but I thought I would try both and select the best one," he said. "When I realized I could do all three, I decided to keep them."

For nearly five months in 2022, he said he was working three jobs that he said paid him over $30,000 a month after taxes and deductions. Eventually one of the jobs, a contract role, came to an end. He then worked two jobs for a while until he found a third job again in 2023.

Over the past year, Robert has worked between two and three jobs — he currently has two roles but is interviewing for a third. If all goes well, he said he'll land the third job, juggle three roles for the first half of this year, and then drop his least favorite role. His goal is to earn $420,000 this year across his jobs.

Robert said his tentative plan is to continue being overemployed until he has $1 million in savings and retirement accounts and no debt. He hopes to accomplish this in the next few years and then focus on just one job for 10 to 15 years before retiring.

"I am far from rich but in decent shape financially," he said.

4 pieces of advice for current and future overemployed workers

Robert has several pieces of advice for current and aspiring overemployed workers.

First, he said it's good to have a primary job that one enjoys and has opportunities for career growth. But the priorities should change for any additional role.

"Your second and third jobs should be a combination of something that you can do easily, something that is not overbearing with the workload, and something that is fun," he said. "If you have two or more jobs with a high workload or are very boring, then you will get burned out."

Second, Robert said overemployed workers need to be prepared to juggle multiple meetings at once. He said this has been the most difficult part of job juggling, and that blocking off time on his calendars hasn't been a full-proof solution.

"You have to be real good at muting and lowering volumes so you stay engaged and not embarrass yourself," he said.

Robert's third piece of advice was to be smart about handling LinkedIn and résumés. He said LinkedIn profiles should list "Company" or "Company Confidential" as one's current position — and that listing all previous jobs on a résumé could raise suspicion.

Lastly, Robert said the overemployed should never stop interviewing so they have options if one job doesn't work out.

Robert said his overemployment journey likely wouldn't have happened if the pandemic hadn't led more companies to adopt remote working arrangements.

When he worked remotely for the first time in March 2020, Robert found himself with a lot of time on his hands and started thinking about ways he could grow his income.

"When COVID made working remotely more common, new possibilities opened up," he said.

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.