How a Millennial Earned $500k Annually by Juggling Three Remote Jobs

Charles thought that secretly working multiple jobs would protect him from layoffs. He was wrong.

Between 2021 and 2023, Charles earned as much as $300,000 annually by juggling multiple full-time jobs in product and tech. The extra income helped him pay down debt, renovate his home, buy a rental property, and purchase a new car.

When he got laid off from one of his jobs last August, he took comfort in still having a roughly $150,000 salary from his remaining role. But landing a new job proved harder than he expected. Then, in September, he got more bad news: he’d been laid off again. In just two months, he’d gone from two jobs to zero.

Over the next six months, Charles said he applied to hundreds of jobs but couldn’t land any. He had to rely on his wife’s income and tap into much of the savings he’d built up through job juggling in recent years.

“All that extra money I made kind of went away,” said Charles, whose identity was verified by Business Insider but who asked to use a pseudonym, citing fears of professional repercussions. He’s in his 30s and lives in the Northeast. “I’d never seen the job market that bad, and I was genuinely concerned for my financial future.”

But just as suddenly as he’d lost his jobs, his luck changed. A few months ago, he landed a full-time contract role through a personal connection — one that paid about $150,000 annually. Roughly a month later, after a recruiter reached out to him, Charles landed a second gig — a full-time contract role that paid about $175,000 annually. That same month, a different recruiter contacted him, leading to a third role, a full-time salaried position that paid about $185,000 a year.

And just like that, he was on track to earn more than $500,000 annually across his three jobs — more than he’d ever made in his years of job juggling. However, he would soon learn that landing the roles wasn’t the end of his professional challenge.

Charles is among the Americans who have secretly juggled multiple remote 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.

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, most job jugglers have told BI that the financial benefits have generally outweighed the downsides and risks and that they’re doing whatever they can to maintain their over-employed status.

Juggling three jobs was lucrative — but not sustainable

Earning more than $30,000 a month across his three jobs was a financial boon for Charles, but he knew he couldn’t keep it up.

The hours weren’t the issue. Charles said he only worked roughly 40 hours each week, and that the companies operated in different time zones, which limited the number of hours he had to work all three jobs simultaneously. He said he used separate laptops and calendars to keep his roles siloed — and often worked on one job while sitting silently in a meeting for another.

The bigger problem came when the manager at his full-time role began pushing him to work from the office, a shift that would require a roughly two-hour commute each way. Charles said the recruiter had told him during the interview process that working remotely wouldn’t be an issue, which made the change of tune particularly frustrating.

“I’m not wasting four hours of my time so I can sit in a meeting for two hours when I can just hop on Zoom,” he said.

While the commute alone wasn’t appealing, the larger concern was that working in an office would make job juggling nearly impossible. To make matters worse, Charles said the job wasn’t turning out to be a good fit.

He considered dropping the job, but said he was hesitant to let it go because it was his only full-time role. He worried that if the economy took a downturn, his two contract roles would be cut first, making the full-time position his most stable option.

After considering his options, Charles decided to resign. He said his goal is for at least one of his contract roles to eventually convert into a full-time position. In the meantime, he’s looking for other opportunities that offer the flexibility, stability, and pay he’s come to value. He’s also hoping the income from his two remaining jobs will help him restore the savings he depleted over the past year.

“For me, it’s about building my savings back up and then putting that money away for a nest egg,” he said. “That’s kind of the priority until I get to a point where I’m comfortable where I’m at financially.”