Millennial Makes $300K Working Multiple Jobs, Catching Job Jugglers

Eric was paid to catch employees secretly working multiple jobs. Then he became one of them.

A few years ago, Eric was working in an IT role at a large company. His job responsibilities included investigating three types of “illicit employment” within the organization: workers who outsourced their job responsibilities to overseas contractors, foreign actors who infiltrated companies by posing as legitimate hires, and employees secretly juggling multiple jobs without the company’s approval.

But Eric said there wasn’t much suspicious activity to investigate, and that he was working as little as one hour each day. Then he had an idea: What if he took on a second job to boost his income?

While Eric considered it, he initially held back because he was worried about getting caught. But that changed the following year, when his employer asked him to focus more on detecting job jugglers, and he realized just how difficult they were to identify. After weighing the risks, Eric applied for and landed a remote role, bringing his combined annual income to roughly $300,000. He said he only worked a couple of hours a day across the jobs.

In addition to the financial benefits, Eric said he took the second job to gain an inside look at the “overemployed” world, one that might help him identify job jugglers. He said the firsthand experience helped him catch several employees who were ultimately fired.

But this success came with a growing problem for Eric, one that ultimately cut his job-juggling journey short. He feared the very system he was building to catch others would end up catching him, and jeopardize his career.

“It was like being the lead investigator on your own murder,” said Eric, whose identity, employment, and income were verified by Business Insider, but who asked to use a pseudonym, citing fears of professional repercussions. “It was a wild time in my life.”

Eric, a millennial based in the US, is among the Americans who have secretly juggled multiple jobs to increase their incomes. Over the past three years, BI has interviewed more than two dozen “overemployed” workers who’ve used their extra cash to travel the world, buy expensive weight-loss drugs, and pay down student debt.

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To be sure, holding multiple jobs without employer approval could have professional repercussions and lead to burnout. Additionally, tech layoffs and return-to-office mandates have created obstacles for current and aspiring job jugglers. However, many overemployed workers have told BI that the financial benefits have generally outweighed the downsides and risks.

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A spending spree and improved detection methods

Eric never planned for his job juggling to last forever. While his initial concerns about getting caught eased enough for him to accept the second role, he still worried that he’d eventually be exposed.

“I thought I could make some money real quick and get out,” he said.

But if his savings started ballooning due to his two incomes, Eric feared he’d get “emotionally attached” to the extra earnings, making it harder to walk away. His solution was to spend freely on things he’d normally avoid. He said he viewed job juggling like renting a luxurious car: fun while it lasts, but not something you do forever.

“I was ordering stuff off Amazon all the time,” he said. “It was like expendable income.”

In addition to unlocking this spending spree, working multiple jobs gave Eric firsthand insight into how people with multiple roles operated — knowledge that helped him sharpen his detection skills and catch job jugglers.

“It really wasn’t until after I had my second job that I started getting actionable outcomes from my investigations because I just knew exactly what to look for,” he said.

Eric said he used internal company activity data to look for behavioral patterns that could suggest someone was juggling multiple jobs, such as sudden swings in productivity during specific parts of the day. Some workers were highly active in the morning and quiet all afternoon, or vice versa. His thinking, based partly on his personal experience, was that job jugglers would split time between their two roles.

“I’d go back historically and see that at one point they were working all day and now they’re not,” he said. “So it just came down to behaviors.”

When an employee’s activity seemed suspicious, Eric said he’d contact their manager and ask how often the worker appeared on camera during meetings, whether they’d missed any lately, and whether their work quality had declined over time. If concerns persisted, he’d suggest the manager schedule a one-on-one video call during the worker’s usual inactive hours. If the employee repeatedly asked to delay or reschedule the call, that would raise red flags, and the case could eventually be handed off to HR.

The risk became too big to stomach

Even as Eric’s detection capabilities improved, he said he wasn’t too concerned about his own work behaviors being flagged. But that changed when he discovered that a security software program used by both of his employers could detect when multiple devices were running the software on the same home network — an indicator someone could be juggling multiple jobs.

While he wasn’t certain it would expose him, the realization made him nervous. At the same time, he was having mixed feelings about the ethics of overemployment. So, after less than a year of working two jobs, Eric decided to drop one of his roles.

“As I went further and further along, I realized I couldn’t keep this up because I was building detections that were going to catch me,” he said.

While overemployment has become more common due to the rise of remote work, Eric said he doesn’t think most companies are particularly concerned about it. His detection work occasionally comes up during job interviews, and from what he’s gathered, employers generally believe job jugglers will either drop a job after burning out or reaching a financial goal, or be let go for underperformance.

If catching overemployed workers isn’t a big priority for most companies, many job jugglers might be able to avoid detection, at least in the short term. Looking back, Eric said he sometimes wonders whether he could have kept going a little longer.

“I just felt like I was going to get caught, and I didn’t want to lose my entire career, so I had to stop,” he said. “But man, I kind of regret it sometimes. It was really good money.”