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I was over-employed and worked other jobs on top of my full-time one. To achieve the American dream, you have to beat the system.

Isabelle Aron   

I was over-employed and worked other jobs on top of my full-time one. To achieve the American dream, you have to beat the system.
  • Kendall McGill began picking up contract work after she started working from home.
  • McGill was open about it, but after a past employer reacted negatively, she's more covert.

This as-told-to essay is based on a transcribed conversation with Kendall McGill, a 30-year-old project manager who worked multiple jobs in secret. Business Insider has 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 way more time without the long meetings or distractions that came with working in the office. I decided to spend my extra time doing more work.

I've been a project manager for six years. It's a lot of coordination. In 2021, I decided to try working two jobs simultaneously. I didn't research 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 games company called Hunt A Killer when I got a contract with Apple. I was super excited about it because everybody knows Apple.

At first, I wasn't concerned about what my other company would think. But I soon realized I had underestimated how seriously they would take it. I updated my LinkedIn and people at Hunt A Killer started saying: "What's going on? She posted that she is working another job. Did she leave? 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 sound like I was stealing company time, which I wasn't. There are 168 hours in a week, so if I wanted to work 80 hours, I could.

I was doing all the work assigned to me, but they felt like they weren't getting enough bang for their buck, so they started giving me more work.

After that, I realized that if I did this again, I needed to keep it a secret and lay low. After the Apple contract ended in July 2022, I left my full-time job at Hunt A Killer in September 2022 as well.

I job-hop often and always look out for new contract work

I had another full-time job and a contract lined up at companies where nobody knew me. I typically job-hop after a year or when the contract ends.

I've been working this way on and off since 2022. I try not to go more than six months without a part-time job on the side. I've done project-management jobs in tech, 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 of a commitment and feels more risky. I've been at my current job for 11 months. I'm enjoying it, so I'll probably stay longer.

3 jobs at once 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 usually from 7 a.m. to 7 p.m.

I live on the East Coast but one of my jobs is often on the West Coast. I don't always have jobs on opposite coasts, but it's my preferred way of working. I can wake up early and do my East Coast work. By 2 p.m., I'd start doing my West Coast job until around 7 or 8 p.m. It could get a bit overwhelming — I was exhausted most of the time.

Generally, I work 12 hours a day and have a job on each coast

I usually check if I'm legally allowed to work another job before taking it on now. For example, I wouldn't work for two competing companies at once — that's a legal disaster waiting to happen.

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

Meetings for different jobs have rarely overlapped, but it has happened. I'd have to juggle muting, volumes, and cameras. I didn't usually have to speak in both, so it worked out.

I take breaks and a quick walk each day but generally eat lunch at my desk. Once my meetings are over, I return to the East Coast job and do emails and other desk work. Then, I do the same for the West Coast job.

I work each job in chunks rather than both at once — I don't want to confuse things. I have separate laptops and I'll close or put the laptop I'm not working on over to the side.

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

When applying for jobs, in-person meetings, micromanagement, or mandatory hours are red flags. If you're on a salary, you can fly under the radar as long as you're getting your work done.

People don't know when I'm working as long as I attend meetings. They just know that it's done. Apart from that job at Hunt A Killer where they found out, no one has ever complained.

I file regular W-2 taxes and my filing status has never changed. I don't register my jobs differently. I was initially nervous about the legality of it all, but if my bosses don't have any reason to look into it, they probably won't.

I have multiple résumés highlighting different skills and jobs rather than listing all my jobs simultaneously. If it ever does come up, I make it seem like the dates overlap less than they did. I've only been asked about overlap once in an interview, and I didn't get that job.

I'm happy working like this to maintain my lifestyle

I'm happy working like this. I don't have a super-busy social life. I'm more introverted. My friends and family know I work multiple jobs.

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

That goal of buying a house kept me motivated. It would have taken me years to do that without working multiple jobs.

We've been sold this American dream, but how can you achieve it with inflation, a pandemic, layoffs, and all these other things? The only way is to beat the system, find a loophole, and get around it.

I don't feel secure having one job in the current landscape with AI and layoffs. The companies will do what's best for them, so I have to do what's best for me.


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