A Gen Xer who makes $150,000 secretly working multiple remote jobs says 100-hour weeks are worth it to ensure his family is financially secure

A Gen Xer (not pictured) says secretly working multiple remote jobs has boosted his income and job security.

In 2004, Brian decided that he didn’t want his family to be reliant on one source of income.

He’d heard about too many people who had lost their jobs seemingly out of nowhere, and he wanted to do whatever he could to protect himself from that situation, he told B-17. So he started looking for part-time remote jobs in addition to his full-time remote role in the IT industry.

“We started being less dependent on one company by being employed by more than one company,” said Brian, who asked to use a pseudonym because of fears of professional repercussions, though his identity is known to B-17. “If something went wrong, then no big loss. We just temporarily lost a paycheck.”

Over the next 15 years, working side jobs gave Brian the additional income and job security he was looking for. But it wasn’t until about 2020, when there was one month of overlap in his transition from one full-time job to another, that he realized he might be able to secretly juggle two full-time jobs simultaneously. So he decided to give it a shot.

Last year, Brian earned more than $150,000 across multiple remote jobs, according to documents viewed by B-17. He said the extra income had helped him pay down credit-card debt and allowed his family to take trips for up to six weeks at a time while he worked remotely. He now has two full-time and four part-time jobs and lives in the US for only part of the year because he travels internationally so frequently, he said.

Managing all these jobs can be stressful — Brian said there had been many “hundred-plus-hour weeks” over the past few years. But he said the long hours were worth it: Last year, he was laid off from one of his jobs, but he was well prepared for it.

“The biggest impact has been the confidence that our family’s future is not tied to the success of any one job or any one company,” Brian said.

Brian is among the “overemployed” Americans who have secretly worked multiple remote gigs to increase their incomes and job security — B-17 has interviewed more than two dozen of these job jugglers. These people have made as much as $1 million annually across their jobs and used their extra income to pay off student debt, save for retirement, and afford expensive vacations.

While some companies may be OK with their employees doing extra work on the side, doing so without approval could have consequences. Additionally, competition for remote roles, return-to-office mandates, and burnout have led some job jugglers to question whether overemployment is sustainable.

Brian shared his “secret sauce” for avoiding burnout and his top tips for overemployed workers.

The ‘secret sauce’ to avoiding burnout as a job juggler

Working two full-time jobs at once can be financially lucrative but also mentally taxing. Brian, who’s in his 40s, said he had a “secret sauce” to stay motivated and avoid burnout: He juggles two full-time roles for only a portion of the year.

“When it starts to feel like a drain on family time or fun time, that simply means we evaluate our situation and I choose to continue with the full-time role that has the best potential to maintain our lifestyle until the next overemployed opportunity shows up,” he said.

While it may seem risky to drop a remote job and count on finding a new one later — especially when remote roles have become so competitive — Brian said he’d become quite good at finding remote roles. He described regularly hearing from recruiters and said he recently interviewed for three full-time remote positions in the same week.

Additionally, Brian said applying and interviewing regularly for jobs had helped him stay up to date on hiring trends and learn about roles that he could circle back to later when he wanted to take on more work. He said he’d taken on a mix of salaried and contract roles throughout his overemployed experience.

Valuing time management and staggering working hours can help the overemployed

Brian said he’d kept his overemployment a secret from his full-time employers. He has a few pieces of advice for current and aspiring job jugglers when it comes to avoiding suspicion.

First, he says it’s helpful to find jobs in which employers don’t require workers to have their cameras on during meetings.

Second, from a time-management perspective, he says it’s helpful to have jobs with staggered working hours — perhaps because the companies are based in different locations. He said this reduced the amount of overlap in working hours across jobs.

Last, Brian recommends doing whatever is possible to improve time-management skills.

“Build a 24-hour calendar that allows you to strictly block off the most important part of your day,” he said.

Going forward, Brian said he planned to continue job juggling for the foreseeable future and was considering taking on a third full-time gig for a while to boost his income and job security even further. For him to consider working just one job, he said, it would have to be remote and pay at least $250,000 annually.

For now, one job isn’t enough. He just wouldn’t be able to trust that his employment would last.

“Most roles today come with an inherent longevity risk,” he said. “That includes everything from a role being eliminated all the way to the department or the company being subjected to major staffing changes.”