A California Gen Xer who made over $1 million secretly working 2 remote jobs said it allowed him to travel the world, max out his 401(k), and send his kids to private school

• A California-based Gen Xer began secretly working two remote tech jobs in 2020.
• He made over $1 million in 2022, which allowed him to travel and send his kids to private school.
• He shared his top pieces of advice for overemployed workers.

Dave's "overemployed" journey began by accident.

In 2020, he was frustrated with his boss at his remote, software enterprise sales job, so he started applying for positions elsewhere, the Californian, who is in his 40s, told Business Insider via email.

He eventually landed a remote job in the same industry, but before he handed in his two-week notice, Dave had an idea: His new job started in November, but he had some restricted stock units at his current job that were scheduled to vest in January. He figured he could juggle two jobs for a couple of months, let his stock vest, and then quit.

But then he had another change of plans.

"When January arrived, I realized I was being successful at both jobs, and there was no need for me to quit," said Dave, whose identity is known to BI, but he asked to use a pseudonym due to his fear of professional repercussions. "I decided to try a few more months, and time simply passed and it became part of my routine."

In 2022, Dave earned over $1 million across his two remote jobs, including sales commissions, according to documents viewed by Business Insider. Last year, he took home more than $800,000 — roughly $200,000 at one job and $600,000 at another.

The extra income has changed his life. Dave said he's traveled across Latin America and Europe without worrying about his budget and sent his children to private school. And he said he only works about 40 hours a week between the two jobs.

"Double 401(k), double salary, double commissions, double benefits," he said. "I do not understand why more people are not doing this."

Over the past year, Business Insider has interviewed more than a dozen job jugglers who've used their six-figure incomes to pay off debt, save for retirement, and afford expensive vacations and weight-loss drugs. While some employers may be OK with their workers having a second job, doing this without approval could have repercussions if a worker is caught.

While job juggling can transform one's finances, intense competition for remote roles has made it unattainable for many people. What's more, many overemployed people work in the tech and IT industries, where men make up the majority of the employees. Additionally, return-to-office mandates and burnout have forced some of the overemployed to return to the traditional, one-job work life.

How to secretly work multiple remote jobs

Dave was unfamiliar with the online overemployed community when he started working two jobs at once, but he said he'd always wanted to have multiple income streams — he just never thought it was possible in the corporate world.

Dave said he hasn't had too much trouble managing both jobs, but that he has several pieces of advice for current and aspiring job jugglers.

First, always have a "main job," he said.

"This is the one you have on your main LinkedIn," he added. "You can talk to your friends and family about this job. It is the job that you have to seek promotions."

Second, always view one job as a side hustle.

"This is the one that you can switch at any time for another 'job 2,'" he said. "Do the minimal work, don't get fired, and collect cash every two weeks."

Dave said he's always on the lookout for a role to replace his secondary job, in case his current one doesn't work out or he finds a better opportunity elsewhere. He said he left his initial "job 2" in 2021 and started his new one in 2022, resulting in a brief gap in his overemployment.

Third, have two LinkedIn accounts. Dave said the account for the second job shouldn't have a picture and only list minimal information. To protect himself, he recommended trying to block all the employees who work at one's second employer from viewing one's main LinkedIn profile, though this is very cumbersome, he said.

He said this approach allows him to have an online record of employment with both companies without his overemployment being exposed. A former job juggler previously told BI that his boss became suspicious when he didn't have his job listed anywhere on LinkedIn.

Dave added that conversing with sales prospects on LinkedIn is an important part of his jobs, and that in these interactions, it's helpful for it to be clear which company he works for. This would be difficult without two accounts.

However, I am open to ideas to better manage that.

Fourth, Dave said it's wise for job jugglers to have two phones because "you will make a mistake" if you try to use the same phone for both roles. He also recommended having separate work computers, in part for the same reason.

Additionally, Dave recommended managing both work calendars to avoid double-booking meetings, taking advantage of both companies' 401(k) plans, connecting with a CPA for tax advice, planning your work for each week in advance, and not working for two companies that compete with each other.

Last, he said people shouldn't feel bad about secretly working multiple jobs.

"Your company will fire you when they do not need you," he said. "It is just business."

Looking ahead, Dave said he's not too concerned about his companies making him return to the office. If they did, he said he'd probably start looking for new remote roles.

In the meantime, he has no plans to stop job juggling.

"People need to take care of themselves," he said. "Companies won't do it for you."

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].