Over Employed Remote Worker on How She Juggled Multiple Jobs

• Project manager Kendall McGill began contract work after starting to work from home.
• McGill was open about double-dipping, but after her former employer’s backlash, she’s being more secretive.
• She worked a remote job on the East Coast and another on the West Coast to balance her work hours.

This essay as told is based on a transcribed conversation from Kendall McGill, a 30-year-old project manager who worked several jobs in secret. Business Insider verified their employment and financial claims. The conversation has been edited for length and clarity.

During the pandemic, I worked from home for the first time. I suddenly had a lot more time without the long meetings and distractions of working in the office. I decided to use my extra time to work more.

I have been a project manager for six years. This requires a lot of coordination. In 2021, I decided to try working two jobs simultaneously. I didn’t think about whether I was allowed to do it – I didn’t think it was a big deal.

I underestimated how seriously my employer would take my second job

I had a full-time job at a gaming company called Hunt A Killer when I got a deal with Apple. I was very excited because everyone knows Apple.

At first, I didn’t care what my other company would think. But I quickly realized that I had underestimated how seriously they would take this. I updated my LinkedIn and people at my current company started saying, “What’s going on? She posted that she had another job. Has she left? Is she leaving?

My manager approached me and wanted to know what was going on. It was an awkward conversation. I thought I was going to get fired. They made it seem like I was stealing the company’s time, which was not the case. There are 168 hours in a week, so if I wanted to work 80 hours, I could.

I did all the work assigned to me, but they felt like I wasn’t getting what they paid for, so they started giving me more work.

After that, I realized that if I did it again, I would have to keep it a secret and keep a low profile. After the end of the Apple contract in July 2022, I also left my full-time job at Hunt A Killer in September 2022.

I change positions often and am always looking for new contracts

I had another full-time job and contract at companies where no one knew me. Generally, I change positions after a year or at the end of the contract.

I have been working this way since 2022, intermittently. I try not to go more than six months without at least a part-time job on the side. I’ve performed project management tasks in technology, healthcare, and retail for companies like Apple, Hunt A Killer, and Rakuten.

I’ve never had two full-time permanent jobs at once – I think it’s too much commitment and seems riskier. I have been in my current job for 11 months. I enjoy it, so I’ll probably stay longer.

3 jobs at a time was my limit

I once worked three jobs at once for about three months. I had a full-time job and two contracts, one full-time and one part-time. I worked between 70 and 80 hours a week and my workday was generally 7 a.m. to 7 p.m.

I live on the East Coast and one of my jobs is often on the West Coast. I don’t always have jobs on opposite coasts, but it’s my favorite way to work. I would wake up early and do my work on the East Coast. Around 2 p.m., I would start doing my work on the West Coast until about 7 or 8 p.m. It was a bit overwhelming – I was exhausted all the time.

I usually work 12 hour days and have a job on each coast

I usually check to see if I’m legally allowed to take another job before accepting it now. For example, I wouldn’t work for two competing companies at the same time: that’s a legal disaster waiting to happen.

I generally work between 10 and 12 hours a day. I wake up at 5 a.m., work out and eat breakfast. I usually have all my meetings for work between 8am and 11am. If a job is on the West Coast, I have meetings for those jobs around lunchtime.

Meetings for different jobs rarely overlapped, but they did happen. I would have to juggle mute, volumes and cameras. Usually I didn’t need to speak in both, so it worked.

I take breaks and go for a quick walk, but I usually eat lunch at my desk. After my meetings are over, I return to work on the East Coast and take care of email and other office work. Then I do the same thing for West Coast work.

I work each job in chunks rather than both at once – I don’t want to confuse things. I have separate laptops and whichever one I’m not working on, I’ll close it or put it aside.

Red flags for me are in-person meetings or mandatory hours

When applying for a job, in-person meetings, micromanagement, or mandatory hours are red flags. If you are an employee, you can go unnoticed as long as you do your job.

People don’t know when I’m working as long as I attend meetings. They just know it’s done. Aside from that first job where they discovered it, no one ever complained.

I file regular W-2 taxes and my filing status has never changed. I don’t record my jobs any differently. At first I was nervous about the legalities. But if my bosses have no reason to look into it, they probably won’t.

I have multiple resumes highlighting different skills and jobs rather than listing all of my jobs at once. If this ever happens, I make it seem like the dates overlap less than before. The one time I was asked about overlap in an interview, I didn’t get the job.

I’m happy to work like this to maintain my lifestyle

I’m happy to work like this. I don’t have a very busy social life. I’m more introverted. I have a reputation among friends and family for working multiple jobs.

I don’t think I would be able to have the lifestyle I want without doing this. I bought a house in 2022 after saving $30,000 in four months while working three jobs.

This goal of buying a house motivated me. It would have taken me years to do this without multitasking.

We’ve been sold this American dream, but how do we get there with inflation, the pandemic, layoffs and all these other things? The only way is to defeat the system, find a loophole and work around it.

I don’t feel safe having a single job in today’s landscape with AI and layoffs. Companies will do what’s best for them, so I have to do what’s best for me.