A millennial who made over $300,000 secretly working 2 remote jobs says he’ll do whatever he can to ensure he never has to commute to work again

  • A US millennial made over $100,000 last year secretly working multiple remote jobs. 
  • But hiring slowdowns and return-to-office mandates have made it harder for him to find new roles. 
  • He said he’ll do whatever he can to avoid commuting to an office for work. 

Charles is willing to go above and beyond to make extra money — except go into an office.

Back in 2019, the tri-state area-based consumer product professional had a friend who needed some help with some freelance work.

Charles took on the side gig, figuring he could use the extra income to save up for a Tesla. Since his main job was remote, he said pulling off the side gig wasn’t difficult.

After doing this for about two years, the work ended, but Charles had grown used to the extra income — so he decided to look for other remote opportunities. It was fortunate timing for Charles, as the pandemic had forced many companies to pivot to remote work. He said he had little trouble finding work-from-home positions.

“There were times when I was just sitting around with nothing to do at my main job for weeks,” said Charles, whose identity is known to BI, but he asked to use a pseudonym due to his fear of professional repercussions. “So I’m either going to stay productive by finding other remote work or just wasting time and leaving money on the table. Why wouldn’t I take on more responsibilities if I can manage them?”

Charles, who is in his 30s, is among the Americans secretly working multiple jobs to boost their incomes. Over the past year, Business Insider has interviewed roughly 20 job jugglers, many of whom are in the IT and tech industries, who’ve used the extra money to pay off debt, save for retirement, and afford weight-loss drugs. While some employers may be okay with their workers having a second job, doing so without employer approval could have repercussions.

Over the last few years, Charles has worked a mix of remote full-time and contract jobs simultaneously while keeping his overemployment a secret from his employers. Job juggling helped him earn over $300,000 in 2021, over $200,000 in 2022, and over $100,000 in 2023, according to documents viewed by Business Insider. Charles said this money made it possible for him to pay off debts, make home improvements, buy a rental property, invest in a personal business venture, and purchase a new car.

But over the past year, he said the job market for the types of roles he’s interested in has “dried up.” That’s because some companies in his industry have scaled back hiring, while others are mainly recruiting for in-person or hybrid roles. It’s left him clinging to his two remaining remote jobs, which have allowed him to not only bring in extra income — but avoid the dreaded work commute.

“Why would I leave the good job that I have where I’m 100% remote still and I don’t have to go into the city?” he said. “I’d be getting up at 6:00 a.m. in the morning and not getting home until 6:00 or 7:00 p.m. if I’m lucky. No thanks.”

Charles added that commuting to work could cost him several hundred dollars a month.

While juggling multiple full-time jobs can be very lucrative, fierce competition for remote gigs has made this unattainable for many workers. For example, the share of US fully remote job postings on LinkedIn fell from over 20% in April 2022 to about 10% in December 2023. Hiring slowdowns in industries like tech — where remote work and over employment are more common — and shifts to hybrid working arrangements have both played a role in this decline.

But despite this dropoff, job seekers’ demand for remote roles remains strong — LinkedIn said fully remote jobs accounted for nearly half of all applications in December.

Charles said he understands why some companies have shifted to a hybrid model — he presumes it’s to keep closer tabs on workers — but he said he’ll do everything he can to avoid a commute.

To prevent his employers from suspecting his job juggling, Charles said he uses separate laptops, phones, and calendars for each job. He said he’s typically able to complete his tasks for both jobs without having to put in extra hours.

“If I am in a meeting with one job that doesn’t require me to speak up, I will be doing work on the other laptop for the other job,” he said.

If an employer were to discover his overemployment, he said he wouldn’t simply give it up.

“I do my work from home, and people are happy with what I do,” he said. “If a company wants to come after me for extra earned income because of some anti-overemployment policy, I’ll fight it.”

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