Daniel is making more money than ever juggling two full-time jobs — but pulling it off has never been harder.
He’s on track to earn roughly $330,000 this year, but a growing list of workplace obstacles is creating headaches and threatening his overemployment setup. Daniel, who is in his 40s and lives in Texas, is one of several workers who asked to use a pseudonym, and Business Insider verified their identities.
Daniel said he used to average 40 to 50 hours a week across his roles, but is now regularly approaching 60 hours per week. Both of his jobs used to be fully remote, but now one requires a couple of office days each month. One employer had layoffs in the past year, and is now asking workers to manually log how they spend their time.
Still, Daniel said the additional income — which has helped him buy multiple rental properties and cover his child’s college tuition — keeps him going.
“I can’t even imagine going back to just a single job,” Daniel said. “I’ve gotten used to the income.”
Over the past three years, Business Insider has interviewed more than two dozen overemployed workers who have used their extra income to buy homes, travel the world, and retire early. But in recent years, holding two jobs in secret has become considerably more difficult amid return-to-office mandates, a tougher job market, and new employee-monitoring measures.
Despite this shifting landscape, interviews with overemployed workers suggest many have adapted rather than abandoned the practice. Some have embraced AI tools to work more efficiently, while others have found ways to navigate return-to-office pressures.
The challenges facing overemployed workers mirror many of the workplace pressures facing Americans more broadly. But for job jugglers, the rewards of successfully navigating those challenges are often far greater.
Read more about workers who have juggled multiple jobs
The strategies keeping overemployment alive
When one of Daniel’s employers started requiring occasional in-office work he adapted by bringing his second work laptop to the office and carefully squeezing in work for his other employer when time allowed.
The arrangement works largely because his second job isn’t very busy — and because he’s not overly worried about getting caught. Daniel said his primary employer is aware he has outside work but seems to care more about the quality of his performance than how he spends every minute of his day.
Meanwhile, that primary job has become considerably busier over the past year. Daniel said AI-powered medical tools have helped offset some of that added workload.
AI has also helped George work more efficiently. He said he uses tools like Claude and Copilot constantly. George started a second remote IT job in 2022, viewing the role as a backup in case his employer mandated a return to the office. When the return-to-office mandate never came, he decided to keep both jobs.
For job jugglers like Reed, who lost four jobs in three years and began juggling multiple roles as a job-security strategy in 2024, avoiding employer detection is critical. He said one of his employers has ramped up oversight of employee activity. Even so, he said he hasn’t heard any concerns from managers and tries to stay active and responsive throughout the workday to avoid drawing suspicion.
But avoiding detection doesn’t make workers immune to layoffs. Daniel said he’s working hard to maintain a reputation as a strong performer, taking on additional responsibilities in one role and positioning himself for a potential promotion.
“I’m actually making an effort to outperform,” he said.
The divergent paths of the overemployed
Not every overemployed worker has been able to successfully adapt to growing workplace pressures.
Kelly was earning nearly $300,000 across two full-time remote jobs when one employer asked her to relocate from Arizona to Texas as part of a broader return-to-office push. She delayed the move for as long as she could, but ultimately resigned last fall, cutting her income roughly in half.
Since leaving the role, Kelly has focused on building a business to help replace some of the income she used to support her children as a single mother.
“I still need more money,” she said. “I’m back to the drawing board.”
Others are looking for ways to preserve the flexibility they gained from overemployment, even after giving up the practice.
Lisa used to earn about $250,000 juggling two jobs, but return-to-office pressure and burnout eventually pushed her to take one hybrid role. When her employer later announced a five-day office mandate, Lisa negotiated an informal arrangement that allowed her to work remotely when needed, typically spending only a few days a week in the office.
Still, some job jugglers aren’t just staying afloat — they’re thinking bigger.
Job juggling helped Adam pay off more than $100,000 in student debt in about two years, and he’s earning more than $200,000 across two remote jobs. Rather than scaling back, Adam said he’s looking for new ways to increase his income. With little room for a third job, he’s considering other options, including day trading.
“I had a dream that I was making $500,000 a year,” he said. “That would be nice to have — invest for a few years, and retire earlier.”
But no matter how successfully job jugglers adapt to layoffs, office mandates, and increased scrutiny, many still confront the same hidden threat that can bring even the most carefully managed arrangements to an end: burnout.
“It seems like every day I’m living just to see the next day,” Daniel said. “I think I need a vacation or something, but it’s doable.”
Do you have a story to share about how you’re navigating a career crossroads? If so, please reach out to the reporter via email at jzinkula@businessinsider.com, or via Signal at jzinkula.29.
