Overworked remote jobs offer financial security, says Generation X

“We became less dependent on one company because we were employed by multiple companies,” said Brian, who asked to use a pseudonym for fear of professional repercussions, but his identity is known to BI. “If something went wrong, it wasn't a big loss. We just temporarily lost our paycheck.”

Over the next 15 years, side hustles provided Brian with the extra income and job security he was looking for. But it wasn't until 2020, when there was a month's overlap between his transition from one full-time job to the next, that he realized he might be able to secretly juggle two full-time jobs at once. So he decided to give it a try.

According to documents viewed by BI, Brian earned over $150,000 in several remote jobs last year. He said the extra income helped him pay off his credit card debt and allowed his family to travel for up to six weeks at a time while he worked remotely. He says he now has two full-time and four part-time jobs and lives in the U.S. only for part of the year because he travels internationally so frequently.

Managing all of those jobs can be stressful—Brian said there have been many “hundred-plus-hour weeks” in recent years. But he said the long hours are worth it: Last year, he was laid off from one of his jobs, but he was well prepared for it.

“The biggest impact for us was knowing that our family’s future is not dependent on the success of a job or business,” Brian said.

Brian is one of the “overemployed” Americans who have secretly taken on multiple remote jobs to increase their income and job security – BI interviewed over two dozen of these job jugglers. These people have earned up to $1 million a year in their jobs and used their extra income to pay off student loans, save for retirement and afford expensive vacations.

While some companies are OK with their employees doing extra work on the side, doing so without permission can have consequences. In addition, competition for remote positions, the need to return to the office, and burnout have led some job jugglers to question whether overemployment is sustainable.

Brian shared his “secret recipe” for avoiding burnout and his top tips for overworked workers.

The “secret recipe” for avoiding burnout as a job juggler

Working two full-time jobs at once can be financially lucrative, but it can also be mentally exhausting. To stay motivated, Brian, who is in his 40s, has a “secret recipe” to avoid burnout: He juggles two full-time jobs for only part of the year.

“If we feel like we are running out of time for family or leisure, we should reevaluate our situation and choose to continue in the full-time position that is most likely to maintain our lifestyle until the next over-employed opportunity arises,” he said.

While it may seem risky to leave a remote job and hope to find a new one later—especially since competition for remote positions has become so fierce—Brian said he's gotten pretty good at finding remote positions. He reported being contacted regularly by recruiters and said he recently interviewed for three full-time remote positions in the same week.

Additionally, Brian said that applying and interviewing regularly helped him stay up to date with hiring trends and learn about roles that he could return to later if he wanted to take on more work. He said that during his over-employment, he took on a mix of permanent and contract roles.

Appreciating time management and staggering working hours can help overemployed people

Brian says he keeps his overemployment a secret from his full-time employers. He has some advice for current and aspiring job jugglers to avoid suspicion.

First, it is helpful to find workplaces where employers do not require employees to keep their cameras on during meetings.

Second, from a time management perspective, it is helpful to have jobs with staggered working hours – perhaps because the companies are based in different locations. This reduces the overlap in working hours between jobs, he said.

Finally, Brian recommends doing whatever you can to improve your time management skills.

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

Brian says he plans to continue juggling multiple jobs for the foreseeable future and is considering taking on a third full-time job for a while to further increase his income and job security. For him to consider just one job, Brian says it would have to be work-from-home and pay at least $250,000 a year.

One job is not enough for him at the moment. He simply cannot trust that his employment will last.

“Most jobs today come with an inherent risk of longevity,” he said. “That ranges from the elimination of a position to major personnel changes within the department or company.”

Are you working multiple remote jobs at once and are you willing to discuss details about your salary and schedule? If so, contact this reporter at [email protected].