Millennial Earns $280K Secretly Working 2 Remote Jobs After 4 Layoffs

After getting laid off four times in four years, Reed was desperate for some level of job security. So he decided to try working two full-time jobs simultaneously.

In March 2020, Reed, who’s in his 30s and based in New York, was laid off from his strategic operations job in the tech industry. It took him six months to start a new job, but layoffs struck again. His next job only lasted less than a month due to the company’s financial hardships. By December 2023, he’d lost his fourth job in just over three years.

“It was easy to get the jobs because there were jobs out there, but it was hard to keep them,” said Reed, whose identity was verified by Business Insider but who asked to use a pseudonym, citing a fear of professional repercussions. Between 2020 and 2023, more than 800,000 tech industry employees across the globe were laid off, according to TrueUp’s layoff tracker.

After the fourth layoff, Reed said he had a eureka moment.

“I was like, ‘The only way for me to combat not continuously being unemployed is to have two jobs,'” he said.

This year, Reed is on track to earn about $280,000 secretly working two full-time remote jobs, which pay about $175,000 and $150,000 respectively. With the additional income, he said he supports his partner — who has been unemployed for three years — helps his parents pay their monthly mortgage, and assists his niece and nephew with their college tuition.

“I need these two jobs to sustain my life with my partner so we can stay in our apartment and still save money, and do all those adult things that I’m responsible for financially,” he said. “I don’t really have a choice.”

Reed is among the Americans who have secretly juggled multiple remote jobs to boost their incomes. Over the past two years, BI has interviewed more than two dozen “overemployed” workers who’ve used their extra earnings to travel the world, buy weight-loss drugs, or simply pay the bills. To be sure, holding multiple jobs without employer approval could have professional repercussions and lead to burnout. However, many job jugglers have told BI that the financial benefits have generally outweighed the downsides and risks.

Return-to-office plans can thwart job jugglers

After his fourth layoff, Reed started applying for remote jobs, intending to accept two full-time offers if he could get them. In March 2024, he landed his first job. He said looking for another role — between all the applications and interviews — sometimes felt like a second job. In December 2024, he finally achieved his goal and began job juggling for the first time.

During his job search, Reed tried to prioritize employers that seemed committed to remote work, but this didn’t always go according to plan. Around early September of last year, Reed finished the interview process for a remote position at Amazon. But soon after he’d finished interviewing, Amazon announced that many corporate employees would be required to work from the office five days a week beginning in January.

When Reed received a job offer for the role, it was no longer remote: He’d be required to work full-time from the nearest office, which he said was about 30 to 40 minutes away. He decided to decline the offer and, in December, accepted a remote position with another company.

While other companies have also announced return-to-office policies, Reed feels confident his two current jobs will remain remote. To his knowledge, neither company has ever had a mandatory in-office policy.

Taking breaks and getting enough sleep can reduce the stress of job-juggling

Reed said his typical workweek is about 60 hours, but he does some of his work in the evenings and on weekends. While juggling two jobs can be very stressful at times, Reed said he’s found some ways to manage this stress.

He gets up earlier than he needs to so he can prepare for the workday ahead — but makes sure he still gets enough sleep: He said it’s easier to manage stress when he’s well-rested. Additionally, rather than switching between his two work laptops every few minutes, Reed tries to focus on one job for an extended period of time before pivoting to the other.

“I have to take breaks in the middle of the day to be able to decipher between one of the two jobs because it does get a little overwhelming,” he said.

Reed said he has an advantage that many job jugglers don’t have: He generally doesn’t have to worry about having two meetings scheduled at the same time. That’s because he usually schedules the meetings he has to attend. He said he blocks off his meeting times for one job on the other job’s calendar, which helps him reduce his chances of getting double-booked.

“It has been way more manageable than I thought it was going to be,” he said of job juggling. “If you can get into a rhythm of how it works and get organized with how you do the work, it’s totally possible to do.”

Job juggling can lead to burnout

Over the past couple of years, Reed said it’s taken him longer to land job offers. He thinks this is because many of the remote roles he’s applied for have hundreds of applicants — and that the interview process has become more extensive.

“I used to be able to do two, three interviews max and you would get an offer,” he said. “Now it’s like a hiring screen, a take-home test, a panel, you have to do a presentation — there are like six or seven steps.”

Looking ahead, Reed said he has no plans to stop job juggling. He doesn’t think it’s sustainable long-term, but with his partner still looking for work, he can’t afford to stop now.

“For now, I’m giving myself a three-to-five-year window,” he said. “Because burnout is real. It’s going to happen eventually.”

​​Do you have a story to share about secretly working multiple jobs or discovering an employee is doing so? Contact this reporter via email at jzinkula@businessinsider.com or Signal at jzinkula.29.