Secretly working multiple full-time remote jobs may sound like a nightmare — but Americans looking to make their financial dreams come true willingly hustle for it.
Over the past two years, Business Insider has interviewed more than two dozen “overemployed” workers, many of whom work in tech roles. They tend to work long hours but say the extra earnings are worth it to pay off student debt, save for an early retirement, and afford expensive vacations and weight-loss drugs. Many started working multiple jobs during the pandemic, when remote job openings soared.
One example is Sarah, who’s on track to earn about $300,000 this year by secretly working two remote IT jobs. Over the last few years, Sarah said the extra income from job juggling has helped her save more than $100,000 in her 401(k)s, pay off $17,000 in credit card debt, and furnish her home.
Sarah, who’s in her 50s and lives in the Southeast, said working 12-hour days is worth it for the job security. This security came in handy when she was laid off from one of her jobs last year. She’s since found a new second gig.
“I want to ride this out until I retire,” Sarah previously told BI. Business Insider verified her identity, but she asked to use a pseudonym, citing fears of professional repercussions. BI spoke to one boss who caught an employee secretly working another job and fired him. Job juggling could breach some employment contracts and be a fireable offense.
Overemployed workers like Sarah told BI how they’ve landed extra roles, juggled the workload, and stayed under the radar. Some said they rely on tactics like blocking off calendars, using separate devices, minimizing meetings, and sticking to flexible roles with low oversight.
While job juggling could have professional repercussions or lead to burnout, and some readers have questioned the ethics of this working arrangement, many workers have told BI they don’t feel guilty about their job juggling — and that the financial benefits generally outweigh the downsides and risks.
In recent years, some have struggled to land new remote gigs, due in part to hiring slowdowns and return-to-office mandates. Most said they plan to continue pursuing overemployment as long as they can.
Read the stories ahead to learn how some Americans have managed the workload, risks, and stress of working multiple jobs — and transformed their finances.
Meet the Americans secretly working multiple remote jobs to afford early retirement — and making up to $300K
5 people who made up to $470,000 secretly juggling multiple jobs explain the best roles for making it work
A Gen Xer making $300,000 secretly working 2 remote roles says the 12-hour days are worth the job security
Beating the system or cheating it? I set out to learn the ethics of secretly working multiple remote jobs.
4 tax-reduction tips from 6-figure earners secretly juggling multiple jobs
A millennial making $368,000 secretly working 3 remote jobs says he has no loyalty to his employers: ‘They can let you go at any point’
A millennial making $280,000 secretly working 2 remote jobs says it’s important to get in a rhythm: ‘Burnout is real’
A Gen Xer’s plan to earn $800K this year across 6 remote jobs: Hiring people to be him
Secretly juggling 2 remote jobs brought a Gen X mom $300K. Now RTO looms.
A Gen Xer made $280,000 secretly working 2 remote jobs in the medical field. He said he gave up on ‘climbing the corporate ladder.’
Fears of a return-to-office mandate prompted a millennial to secretly get a second remote job
Secretly working 2 remote jobs helped a millennial pay off his student debt. He shares why he plans to stay overemployed despite the risk of burnout.
Paying off student-loan debt and traveling the world: How the overemployed use their extra earnings
I caught my employee secretly working a second remote job. Here’s why I decided to fire them — and why I think overemployment is sometimes unethical.
A man who made $250k secretly working multiple jobs shares why the challenge was fun and helped his career
A millennial woman who made nearly $250k secretly working 2 jobs says it helped her enter a relationship for the ‘right reasons’ — not financial security
A Gen Xer who makes $150,000 secretly working multiple remote jobs says 100-hour weeks are worth it to ensure his family is financially secure
A California millennial shares how he made nearly $200K secretly working multiple jobs. He said he only worked 20 hours a week.
The golden age of overemployment is over. Job jugglers are preparing for life with only one income.
A millennial making $350,000 a year through overemployment says he only worked 50 hours a week
A millennial worked 2 remote jobs so he could retire at 50 but said overemployment isn’t worth the stress
A Wisconsin mom of 3 who made $250,000 secretly working 2 remote jobs said it allowed her husband to leave a stressful job and become a stay-at-home dad
A Florida Gen Xer who earned over $300,000 secretly working multiple remote jobs shares why he’s ‘far from rich’
A California Gen Xer who made over $1 million secretly working 2 remote jobs said it allowed him to travel the world, max out his 401(k), and send his kids to private school
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