Overemployment is not an entirely new phenomenon. It’s been an “open secret” in the tech industry for years, says an overemployed worker in his late 30s in the US Bay Area who goes by ‘Isaac’ in the overemployment community. He’s been working two jobs for years, and says he makes more than $600,000 doing it.

In April 2021, Isaac launched Overemployed, a website with articles about how to navigate holding down multiple remote jobs. (The number one rule? Don’t talk about holding down multiple remote jobs.) He says that for the past 20 years, some workers have exploited pockets in the tech industry that were remote-friendly long before the pandemic. But now, as more workers across fields all over the world have been given the opportunity to work from home, anecdotal evidence suggests more people are exploring the overemployment lifestyle.

Isaac says users of his site live all over the world and “run the gamut” of ages, from those 60-plus to people in their 20s, just starting out (who may even “double intern” and hold two remote internships). But he says most users tend to be in the 35-to-40 age range, who “have a lot of experience already and are a little jaded by the corporate world”.

Generally, both before the pandemic and during it, Isaac says it’s rare to hear of anybody getting caught; usually it’s a matter of the individual being sloppy in keeping the two jobs separate, although he’s heard of an instance in which spyware caught a programmer running a script he wasn’t supposed to be running on his primary job’s computer – that person got fired.

Isaac maintains overemployment doesn’t necessarily mean working extra-long days – workers can put in 30 hours a week at their primary job, for example, and then use the time that would’ve otherwise been filled by non-mandatory meetings or cyberloafing for their second job.

Of course, overemployment is legally tricky: whether it’s possible depends on what kind of contract a worker signed when they were hired at their primary job, and if they’re breaking any non-compete agreements. And unsurprisingly, it’s extremely controversial, or even seen as unethical; contractual obligations aside, workers are essentially lying (by omission or otherwise) to their ‘main’ employer. News outlets have called this kind of ‘business bigamy’ dishonest and wrong when readers have written in asking for advice as to whether they should ‘out’ overemployed colleagues at work.

But for those who can make the arrangement work – both legally and logistically – Isaac argues overemployed workers stand to gain a lot.

‘A moment of reckoning’

Unsurprisingly, Isaac says one reason workers take on a second, secret full-time job is to diversify sources of cash flow and make money in more efficient ways. But he believes money isn’t the entire driver.

Catherine Chandler-Crichlow, executive director for career management at Ivey Business School at Western University in Ontario, Canada, agrees, saying the framing of overemployed workers “surreptitiously trying to make more money” isn’t necessarily correct. “As we have been forced to work from home, people have probably started looking at, ‘where can my skill set be truly optimised?, ‘What are some of the things that I have a real passion for – and how might I use those skills differently?’,” she says.

Chandler-Crichlow, who specialises in studying human capital – the skills, expertise and knowledge workers bring to their jobs – says that this concept is especially germane to the discussion of overemployment. For example, there may be someone who has a primary job of being a financial analyst, but they also enjoy something else, like coding or writing. The current widespread remote working situation allows that analyst to find a job coding or writing, and to put those skills to use.

“I now become the master of what I would like to do and where I would like to spend my time,” says Chandler-Crichlow. She says that for workers in lower socio-economic groups, holding down multiple jobs is a means of survival. But what’s different here is that “professionals who could be described as highly skilled are taking greater ownership of their careers”.

Erin Hatton, associate professor of sociology who studies work and labour at the University at Buffalo in New York, US, agrees. “Maybe [workers are] trying new things. I think this is a moment of reckoning with the world of work, and thinking about what role work plays in our lives,” says Hatton. Overemployment can “free people to maybe try on other jobs for size; maybe take on extra work that may not pay well, but may be more meaningful to them.”

So, it’s no coincidence that more people are trying this out in recent months. “I think the pandemic may have pushed people to do more of that deep thought and what it is they’re spending their lives doing, and deciding I could probably do more with my life,” says Chandler-Crichlow. By pursuing overemployment more workers seem to be saying to themselves, she says: “’Yes, I want to really utilise the skills and capabilities I have. And if someone wants to pay me – I’ll do it.’”

Railing against employers

The fact that people are turning to overemployment also signals important systemic workplace issues.

For a long time, many workers have felt like their jobs are unfulfilling or meaningless – leading to problems like burnout and boreout – and that they’re constantly chasing success within a system that gives managers a disproportionate amount of power within the working relationship. That may be one of the reasons overemployment has become more popular, experts say.

So if managers don’t realise workers are doing this, are they bad managers? “My sense is that they simply do not have systems in place to surveil workers in this way,” says Hatton. “For many lower wage workers, both remote and non-remote, there is plenty of surveillance that effectively disallows this kind of double dipping. Think call centre workers who work remotely but technology monitors the number of calls they take. But for workers who [are] typically in the worksite and are not already punitively surveilled in this way, they just don’t have a system in place to monitor and enforce this.”

“How employers respond to this could also vary across of a spectrum of no support at one end,” says Chandler-Crichow, to companies somewhat giving their blessing, “as long as it does not impact your responsibilities at their organisations.”

From Isaac’s perspective as an overemployed worker, and based on the activity on his website, one of the reasons people take on secret second jobs is because they feel disillusioned with the realities of corporate life. Some workers believe secret overemployment helps them break free of employers that haven’t given them that promotion or pay rise they’ve been chasing for years.

“There’s a sense that our bosses own us a little bit, and I see this as an interesting pushback against that normative sense of ownership,” says Hatton. “It’s expected that we really owe them everything. That we’re theirs. But when push comes to shove, they can fire us tomorrow for no reason at all. This is taking back a little bit of that sense of power.”

When Isaac's company was rolling out redundancies during the pandemic, he survived, but emerged with new resolve – he wouldn’t be one of many faceless employees. “You treat me like a number, I’m going to treat you like a number,” he says. So, armed with two separate laptops, he works two separate jobs, plus a part-time gig. He says he’s never been found out or had any close calls.

What happens next?

Overemployment may be ticking up, but those who go for the secret second job are still in the minority – and the move still carries a lot of risk.

Plus, as the increase in overemployment is relatively new, there’s a lot both workers and employers alike don’t yet know. For instance, it’s unclear how companies will respond if they feel vulnerable, or if they realise an employee is breaching the terms of a non-compete contract. Perhaps managers will more closely monitor employees’ social media activity to find something incriminating, or might install software on company machines to detect anything fishy.

For now, though, some workers will embrace overemployment – as long as one of their supervisors doesn’t catch them.