A millennial made $280K working 3 remote jobs — until the job market turned against him: 'It was great until it wasn't'

• A millennial began secretly working multiple remote jobs to pay down debt.
• He earned more than $280,000 in 2022 across three full-time recruiting roles.
• Layoffs and a hiring slowdown forced him to give up overemployment and change careers.

Michael struggled to pay down debt until he turned to an unconventional strategy: secretly working multiple full-time jobs at once.

In 2020, Michael was working remotely as a technical recruiter, and his job wasn't very demanding. He wished he could do something more productive with his time.

"The only thing I could think about was: if I could get another job, I could save that whole salary," said Michael, who is in his 30s and lives in California. His asked to use a pseudonym and his identity was verified by Business Insider.

Two years later, Michael was earning more than $280,000 by juggling three full-time remote recruiting jobs, using the income to pay down his student loan and credit card debt and grow his savings. He said the setup was unsustainable but worth it.

"It was extremely significant while it lasted," he said.

Over the past three years, Business Insider has interviewed more than two dozen overemployed workers who have used their extra income to travel, pay off debt, buy weight-loss drugs, and retire early.

Most of them say the extra money outweighs the risk of burnout or professional repercussions — though tech layoffs and return-to-office mandates have limited the remote roles job jugglers rely on.

Michael shared how he managed to juggle three jobs, and why the arrangement eventually fell apart.

Joining the ranks of the overemployed

In 2021, Michael stumbled upon the "overemployed" community on Reddit, where users share stories and advice about working multiple jobs simultaneously.

The more he learned, the more attractive it seemed. His current recruiting job wasn't demanding, hiring was starting to boom across the US economy — which meant more demand for recruiters — and many roles were remote due to the pandemic, which made job juggling easier.

But he didn't want to rush it. Michael had recently started a new full-time remote role, doing internal recruiting in the e-commerce industry. He wanted to make sure he felt settled before taking on a whole new job.

By early 2022, he'd grown used to the workload. He also suspected that the window to capitalize on the overemployment trend was closing, in part due to economic concerns that hiring might slow down.

"I was like, okay, 'It's time for job number two,'" he said.

That June, Michael started a second technical recruiter position, in the finance industry. Like his original job, his new position wasn't very demanding. While the company was hiring, many open roles already had preferred candidates, leaving him with relatively little to do.

Michael said that on a typical day, he'd work his original job from roughly 6 a.m. to 10 a.m., take a break, then focus on his second job for about two hours — about six hours of work a day.

"After that I was done," he said. "I wasn't even working a full 40 hours a week."

Going from two jobs to three

Once working two jobs felt comfortable, Michael decided to go for three.

By September 2022, he'd landed a third technical recruiter position at a consulting firm. Michael soon found that his new role was the most demanding, so he restructured his workday.

He began waking up at 5 a.m. to work his original role for about four hours. After a break, he'd bounce between his other two jobs from roughly 10 a.m. to 1 p.m. After lunch, he'd finish off any outstanding tasks.

Despite juggling three full-time jobs, Michael said he still typically didn't work 40 hours a week. But by late 2022, the hiring boom that had made his overemployment possible began to fade.

The end of overemployment

In the fall of 2022, recession fears were on the rise, and the Federal Reserve had started raising interest rates to combat inflation — leading some employers to scrap or delay hiring plans.

"Hiring managers that I was working with were basically saying, 'If we don't get these positions hired soon, the budget goes away,'" he said.

By the end of October, most of the positions Michael had been trying to fill were closed without a hire — something he said played out across all three of his jobs over a few-week period.

He suspected that his diminishing workload could put his jobs at risk, and he was proven correct. Michael said that after being laid off from his original job in late 2022, he was laid off from his remaining roles over the following months as the job market cooled. Over the next two years, he managed to find some new positions but, in 2024, he faced a stretch of several months without any work — which he attributed to a slowdown in hiring for recruiting roles.

Michael said his job search took a significant toll on his finances and forced him to temporarily rely on others for housing.

"I had to couch surf," he said. "My whole life changed."

Moving on

Over time, Michael began to question whether he could still make a living in recruiting. It was difficult to find and retain work, and available roles paid significantly less than he'd come to expect.

Eventually, Michael pivoted to the insurance sector, which he thought offered him a better chance at a stable, sustainable income.

Looking back, Michael said he wishes he never had to pursue overemployment in the first place — that one job would have been enough to reach his financial goals. But he said he doesn't regret job juggling, even if it didn't last.

"It was great until it wasn't," he said.