Overemployment: Reinventing moonlighting in the digital age

Data from the US Census Bureau’s Longitudinal Employer-Household Dynamics (LEHD) highlights a growing trend in the US of multiple job-holdings over the past two decades, particularly among women, who in 2018 had an average multiple job-holding rate of 9.1%. Today’s moonlighting is far from the traditional part-time job scenario. These knowledge workers have seized on the privacy provided by remote work to secretly take on two or more jobs—multiplying their paychecks without, ideally, working much more than a standard 40-hour workweek.

Overemployment, or OE as the dedicated community refers to it, is surging with activity, as evidenced by the growing popularity of platforms like overemployed.com and the r/overemployed subreddit. Overemployed.com, established by Isaac P.*, a pioneer in the OE field, serves as a gathering place for professionals seeking guidance on OE. Meanwhile, the subreddit r/overemployed has attracted over 270,000 followers, becoming a crucial outlet for sharing strategies and experiences about juggling multiple jobs.

This evolving dynamic of OE is rewriting the rules of traditional employment, highlighting the innovative and adaptive spirit of the modern workforce. Albeit culturally taboo, is OE really illegal or a fireable offense? Why do these workers risk their livelihoods for increased paychecks?

At-will and at odds: Legal facets of overemployment

So, is OE legal? If you’re asking Issac P.*, creator of overemployed.com and avid OE supporter, yes, working multiple jobs is legal. “In the US, at-will employment is the law, meaning thanks to the free market, it’s fair game for employees to cash in two full-time paychecks at once,” he explains. “The bottom line is we live in a free agent economy—it’s legal to work multiple remote jobs and sell your skills to multiple bidders.”

The US Department of Labor has no specific policy governing moonlighting for private-sector employees. In the context of at-will employment, including specifically in New York, the legality of holding multiple jobs isn’t directly addressed either. It seems the policies regarding moonlighting depend on individual employers. In other words, while federal law doesn’t prohibit moonlighting, private employers can set their own policies regarding employees working multiple jobs. Employment contracts or company policy can specifically restrict it, or if it involves a conflict of interest stipulated in the employment contract, i.e., the worker signs non-competes prohibiting the employee from working with competitors.

For Marcus Mossberger, a prominent future of work strategist for technology companies, it’s a gray area. “Of course, there are potential legal ramifications [with an] employment contract that stipulates you’re not allowed to work for a competitor … However, I think we all recognize those are really hard to enforce,” he says.

For instance, several states have enacted or modified laws that significantly restrict the use of non-compete agreements. Attorney General Rob Bonta made these clauses illegal in California in March 2022. Washington, D.C. has one of the most restrictive laws, banning non-compete agreements with minor exceptions. As of January 2022, Illinois limits non-competes based on employees’ annual salaries. Oregon and Washington State have also modified their non-compete laws, adding specific guidelines and limitations. Colorado and Nevada have enacted laws adding limitations and penalties associated with non-competes. So, there seems to be a disconnect between legal stipulations and their real-world enforcement.

“Within the first two months of 2023, I brought my employer revenue that is approximately 10 times my annual salary … I don’t think I’m robbing my employer of anything.”

Ethical conundrums and corporate realities

Termination looks to be the main risk of OE. From an employer’s perspective, explains Mossberger, this trend is often viewed with concern. Many employers rely on their employees’ total commitment and availability. “They want to get the best out of you and want you to be available when they need you,” he explains, underscoring the potential conflict. Therefore, the first pillar of OE workers is secrecy. But do these workers feel guilty?

Max R.** , a seasoned OE worker with a Ph.D. in computer science intelligence who has worked for a major tech giant, in academia, and in consultancy, doesn’t seem to lose sleep over his OE secrecy. “Within the first two months of 2023, I brought my employer revenue that is approximately 10 times my annual salary … I don’t think I’m robbing my employer of anything.” He adds, “The only non-renewable resource in your life is time. My time is my own, and how I choose to spend it is my personal affair. So, why would I spend all of it advancing someone else’s ideas and goals? If my assigned work is completed, I see no reason to devote the remaining hours of a standard 40-hour workweek to these corporate overlords.”

Jason C.** , another OE worker and a senior data analyst in the ERP data analytics space, agrees with the ethical sentiment: “I’m not anti-work or anti-capitalist, but the frank truth is that corporations are notorious for lying to their workforces about things like layoffs, stringing people along on promotions and pay increases, and engaging in dodgy legal and ethical practices. To borrow a phrase: ‘For stealing billions, you get parole; for stealing thousands, you get jail time.’ The system is unequal. They have lost the moral and ethical grounds they could [use] to justify their condemnation of people practicing OE.”

“… my brain enjoys doing multiple things and moving between various jobs and projects. I look at people who have been doing one thing for years, and to me, it looks like pure suffering.”

The hidden incentives driving overemployment

So, why would OE workers risk getting caught in a lie? Money is clearly a big factor, but it’s not about having a lavish lifestyle. If secrecy is rule number one, then frugality comes in a close second. Many in the community are adherents of FIRE, which is short for Financial Independence, Retire Early.

For Jason, the financial benefit is life-changing; he is paying down debts from previous financial mistakes. “The challenge has been to ensure that we don’t engage in ‘lifestyle creep’, meaning we don’t get dollar signs in our eyes and use the additional income to inflate our living standards. We still shop frugally, don’t eat out often, and optimize our [bills]. [Almost] every penny of the increased income goes toward debt, and once that’s gone, toward retirement. If anything, doing OE has made us more frugal,” he adds.

However, Mossberger also points out that financial gain is not the only motivator for employees who pursue multiple jobs. “Some people are doing it because they’re bored; they want to try new things,” he says. For Max, this is the case: “I have ADHD, and my brain enjoys doing multiple things and moving between various jobs and projects. I look at people who have been doing one thing for years, and to me, it looks like pure suffering.”

There’s another incentive. Unlike most Americans, those who work multiple jobs don’t have to worry about layoffs. Adam G.** , another OE enthusiast who is a strategist for a sizeable multinational energy and manufacturing company, explains why these workers hedge their bets: “[For past generations], companies took care of you. You worked there for 35 years plus and, [once retired] had pensions. Nowadays, especially in the US, [companies] can fire you for any reason. We see the tech industry ebbing and flowing. There are a lot of layoffs, which we saw with Microsoft, Amazon, and the many thousands laid off at Meta. [OE workers] are doing this to ensure they have an income at the end of the day.”

So, how are they making it happen?

Mastering time management, juggling calendars, and maintaining secrecy are all aspects of successful OE. So, how are individuals doing it without getting caught while still excelling in each role?

Remember the first rule of Fight Club? “Do not talk about Fight Club.” Well, this is the OE community’s motto: secrecy is vital. “Speaking bluntly, this type of work requires bald-faced lying to maintain secrecy,” says Jason. “This applies to your resume, interviewing, making excuses for missing meetings, etc. Ultimately though, if you’re keeping on top of your work, you shouldn’t have to be deceptive on a day-to-day basis,” he adds, “Come up with a plausible story about your work history, and stick to that. Minimize activity on social media as much as possible and discuss your decision to do this only with your most trusted confidants.”

To keep up with his workload, Jason uses “incredible amounts of caffeine.” But he also makes his time intentional with deep focus sessions to pound out the work. “That’s how I work best. Otherwise, it’s about meeting the expectations of whatever leadership demands you,” he says.

Max also prioritizes his time: “I use a color-coded Google Calendar to ensure my schedules for different jobs don’t overlap.” But this technique doesn’t always work. “When I was working with the tech giant, they [had a] culture of filling up any open time on calendars,” he explains. “For instance, if I appeared free, colleagues would schedule meetings, even at short notice … I started manually synchronizing my calendars [by] setting busy blocks. However, my time was often not respected, even when marked as busy. [In my opinion], it’s a microaggression to take [someone’s] time without consent,” he adds.

Jason strategizes his work day the night before. “I make sure my next day is conflict-free across my roles and their meetings. Thankfully, J1 and J2 are light on meetings. J3 is much more meeting-heavy, and they are earlier in the morning since I work with European teams collaboratively. I keep a list on my personal laptop of all deliverables and action items across all three jobs with a prioritization scheme and due dates. As I sit in J3’s morning meetings, I complete work for my J1 and J2 as much as possible.”

For those unfamiliar with the OE lingo, OEers rank each of their jobs by the priority they place on it. J1 is the favorite, the one they’ll tend to before the others. J2 is the backup, and J3 is the backup of the backup. This means overemployment is not supposed to last; they are backups when other jobs fail. “People need to realize that OE isn’t going to continue forever, that it is just temporary when you do it,” says Max.

Could you handle overemployment?

OE is definitely not for the Reddit r/antiwork crowd, jokes Adam. “I would recommend it to entrepreneurial folks, people who want to do more, people who are driven by an external need,” he shares.

Max recommends OE for anyone “who wants to fully embrace their ADHD.” He says, “It’s not for everyone. You need to be able to juggle multiple things at the same time. If you already have a full-time job and multiple side passion projects, then I think you have the ability to do OE.”

Jason warns newbies from trying to undertake OE: “You really need to be competent and consistent to pull this off,” he says. “No one straight out of college has the skillset nor the discretion to do their tasks independently, as many of these roles [require]. It’s better to skill up and get good than to force it to happen early in your career. No amount of money is worth sacrificing your mental health. [It’s] better to have consistent balance than to burn too hot too early,” he adds.

“They might even joke about how people like me had only one job in the past and question the security of such a lifestyle.”

Will overemployment redefine the future of work?

Mossberger thinks so. “The concept of loyalty [is] a relic of the past. The next generation has different expectations. We will see more people [with] side hustles and multiple jobs,” he says. “I think the next generation is more like, ‘Look, why do you care what hours of the day I work?’. I don’t see this distinction [between] work-life [and] personal life [in the future]; it’s just life and how [everything] meshes together,” he adds.

Mossberger also sees one full-time job as a relic of the past. “I think my kids, in a decade, will likely be juggling 3 or 4 part-time jobs simultaneously. It will be the new normal for them to work in a regular job, engage in graphic design, sell items on Etsy, and manage other side hustles. They might even joke about how people like me had only one job in the past and question the security of such a lifestyle,” he says.

Yes, employers would prefer that OE not happen. But Mossberger has an argument for them: “Employers need to adapt to this trend,” he suggests. “Allow individuals to gain what they are seeking inside of your organization.” The concept of offering internal side hustles, project work, or new pursuits within the organization is relatively new. Still, this approach could serve as a solution for employers to retain their employees’ engagement and prevent them from seeking fulfillment elsewhere.

Adam’s J1 employer actually knows he has his own business on the side. “They don’t know to what extent I am working [outside the company]. But I got their approval when I opened my consulting business,” he says. “They essentially said that as long as I don’t discuss our company’s proprietary information, I am free to pursue other opportunities,” he adds. Adam’s company isn’t based in the US, which he thinks is part of them encouraging honesty. “I feel like a lot of American companies would automatically assume that [workers] can’t possibly do their role and other businesses [at the same time],” he says.

OE’s role in shaping future careers

Because of OE, Adam is on track to pay off his student loans in a few years. Max is working on snagging a passion job in academia where he can work with the top minds in his field, but of course, he will keep some of his consultancy work on the side.

For Jason, professional growth and skill development have been two of the best-hidden benefits of OE he never anticipated. “By working at three different companies, each with their own unique sets of tasks, tools, challenges, and deadlines, I am acquiring a diverse range of skills and experiences. This variety enriches my professional expertise, which I can leverage in interviews and future job roles, effectively tripling my learning and growth opportunities,” he says.

In our new normal, employees seek variety and fulfillment in their professional lives, while employers need committed and focused team members. The future of work may well depend on how successfully this balance is achieved and adapting to the evolving needs and aspirations of the modern workforce. Let’s see if OE continues to trend with the new generation!

*Issac P. is his self-given public pseudonym

** Names changed for anonymity

Photo: Welcome to the Jungle

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