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Instead Of Side-Hustling, Some People Are Secretly Working Multiple Remote Jobs At The Same Time

"Overemployed is a way for us to take back control and not play this game."

Why overwork at one job when you could work just hard enough at two? That's the question that a new movement of "overemployed" workers who secretly juggle multiple remote jobs are asking, and TBH I don't entirely hate it.

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Real wage growth for most Americans has been pretty flat for decades, with the average raise at about 3%, and mass corporate layoffs have left many workers feeling understandably less loyal to their employers. Plus, with rising costs of living, even people making over $100K a year report feeling broke. 

While I strongly believe that you shouldn't *have to* work more than one full-time job, for some, that's not always doable, and others genuinely enjoy the challenge. And though juggling multiple jobs is certainly not for everyone, I can see how this arrangement would be an attractive option for a certain type of person and career.

To learn more, I emailed with Chloe and Isaac from Overemployed — a website that's chock-full of tips for folks who are interested in working two jobs at once.

They said their overemployment journey started last year. "We were looking for jobs during the pandemic and once we got one, we were joking, 'What if we don't quit?'" Chloe said.

Woman working from home
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"If we don't do well, they'll just fire us, right? One way to find out. Try it." So they did and soon discovered that they liked it. And they weren't the only ones. "We started the site to write about our experiences and then found there were other people doing the same thing." 

Isaac added, "We started this community because this has been an open secret in the tech world for a while now; just no one talks openly about it. However, with the pandemic, aka the great unplugging from the office, many have awakened to how life and work ought to be, especially with the mass layoffs that were happening through one of the worst years of humanity in 2020."

On Overemployed, you can find tips on everything from filing taxes with two jobs to advice on keeping your manager's expectations low. There's also an Overemployed Discord where members share their experiences and questions anonymously.

Two Job Tip💡- Afraid to type the wrong boss name in an email? Add custom autocorrect entries to catch it. Tina > autocorrects > Linda #twojobtips #overemployed #WFH #remotework

@TheOveremployed / Via Twitter: @TheOveremployed

There are some pretty wild success stories, like this comment: "I've hit $400k/year at times, $300k+/year a few times, and $200k+/year consistently. I do have some weeks where I work like a madman but for the most part, I work a relatively normal work week." But there are also plenty of cringeworthy fails, like this story: "First week in a company and I joined the all hands with a Gmail account from another company (luckily not on mine, but on a different name). The CEO was asking, 'Who the hell is this [some name]?' I hadn't started my camera so I silently quit the meeting and rejoined with the right account then."

So is this like an extreme form of side-hustling? Chloe said it's totally different. "We don't see it as a side hustle. We see it as a confirmed promotion or raise that we would not have gotten staying in one job."

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"If I'm putting in double the hours, I want to be paid accordingly, not a 'promise' we will get you in next promotion cycle," they continued. 

So instead of working really hard in one job, trying to get promotions and raises, the overemployed said they're taking their income into their own hands.

Woman balancing a stack of office equipment on her shoulder
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"I've experienced a time where I did great work and had all the emails to prove all my accolades. Come review time, my manager pointed to the times I was late to two meetings, few missed emails, and cited I was not manager material, and there goes my promotion. All that hard work and peer support, but what my manager 'felt' about me and biases are what is between us and a promotion," Chloe explained. "Overemployed is a way for us to take back control and not play this game."

But overemployment isn't for everyone. "It really depends on your company/boss and your specific situation. I would say sales, recruitment, or jobs that have a lot of interaction are not a great fit," Chloe said.

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And it's definitely a privilege to be in a position to secretly work two jobs in the first place. For people already juggling work and childcare, and folks who don't have computer-based jobs, this style of working is pretty inaccessible.

But for certain people, overemployment can be a workable option. "Have you had friends who tell you I only work X number of hours a week? There's not one profession we can point to, but chances are if you're at a job for a while and you have mastered the speciality and finish your tasks in a short amount of time, it will work for you."

However, like a side hustle, many employers don't love the idea of employees working other jobs and it could violate any contracts or noncompete agreements that you signed when you were hired. So people who are overemployed usually have to hide it and some go to Mrs. Doubtfire–esque lengths to do so.

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The first rule of being overemployed is literally "don't talk about being overemployed," and Chloe said that keeping multiple jobs secret is one of the hardest parts of juggling their gigs. In comment threads on the site, workers with two jobs reported using separate computers for each job to avoid slipups and make sure that they wouldn't get caught. Others have talked about their tricks for attending two Zoom meetings at the same time, which is now a stress dream that I'll never stop having. One Discord member wrote, "Earlier this week I was presenting on one job; second job was stand-up. Got to me and I couldn't talk so I'm dialed in with mute on my phone. I unmute and re-mute a couple of times. And then ask in the chat: 'Can you not hear me?' I completely avoided talking during the meeting."

Members also recommended staying off social media, especially LinkedIn, to prevent any networking overlaps between jobs.

Since overemployment has been gaining more attention, Chloe said they've seen some misconceptions, like that workers who choose this path are lazy and entitled.

Person joining a video call for work after dark
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To counter this take, Chloe said that though they might not be star players at both jobs, they are still meeting requirements and getting the work done. "We understand what our manager is looking for and we meet those expectations. 'Mediocre' has a bad connotation. Throughout life we are told to 'exceed' expectations but if we exceed expectations, we get a promise (of promotion), maybe a layoff, and maybe a raise of 7%. Why should we overwork? With two jobs, we know that if we do extra hours, we are paid accordingly."

Chloe and Isaac said that while it's super worth it for them, they don't plan to do it forever. "A whole paycheck goes to saving for financial independence," Isaac said.

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"For me, personally, my financial model shows me if I keep being overemployed over the next five years, I'd be financially independent with my current expenses growing at about 3%. My goal is to be financially worry-free, and work 20–25 hours on whatever tickles my fancy, like Overmployed and spreading the message."

Now I'm extremely curious: What do you think about overemployment? Would you want to try it? Why or why not? Share your thoughts in the comments below!

And for more stories about work and money, check out the rest of our personal finance posts