Overemployed Lessons: Pros, Cons Secretly Working Multiple Remote Jobs

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.