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Can employees take a second job?

Distributed workforces present new challenges, like the software engineer who secretly worked two full-time jobs simultaneously. Here’s where employers should care, from’s latest Culture Builder newsletter.

The number of Americans working two jobs has been declining since the 1990s. (Photo by Elvis from Pexels)

Written by Technically Media CEO Chris Wink,’s new Culture Builder newsletter features tips on growing powerful teams and dynamic workplaces. Below is the latest edition we published. Sign up here to get the next one this Friday.

“Have you heard about the remote employee who took a second full-time job without ever telling anyone?”

That email from a tech founder caught my attention. I hadn’t heard that before and questioned how pervasive such a thing could be. The founder introduced me to a tech CEO who I interviewed last week. In the last year of widespread remote work, he reports uncovering three examples in his network of clever professionals doing just that — one was an high-performing software engineer, one was in sales and another an HR exec.

And then this week, tech writer Kat Maddox tweeted a screenshot of a Hacker News poster detailing their “10 fully remote engineering jobs.”

“The bar is so low, oversight is non-existent, and everyone is so forgiving for under-performance I can coast about 4-8 weeks before a given job fires me,” the poster wrote.

In newsrooms, two is a coincidence, three makes a trend, and one absurd-sounding viral internet comment deserves at least a deeper look.

The number of Americans working two jobs has been declining since the early 1990s. In 2017, the figure was under 5%, according to the Bureau of Labor Statistics. The last 15 months have been so disruptive it’s hard to predict if we’ve seen a change, and it’s difficult to separate the data between people working multiple shift jobs to make ends meet and professionals double-dipping when the Zoom cameras are off. But as burnt out office workers and skittish employers prepare for a new phase of remote and hybrid work, it’s worth playing out this particular and potentially challenging scenario.

Note, this is very different from employee side hustles, which can be a healthy outlet for curious and creative teammates. An exec with a coaching practice, or a teammate with a passion project might be a blessing.

The difference is motivation, transparency and productivity. If your teammate is working outside office hours, open about the work and still able to perform at your company, you don’t have a problem. Otherwise, even if it doesn’t break an employee agreement, a lack of motivation, transparency and productivity are all cause for dismissal.

So, in short, can an employee take a second job? Unless it expressly violates a signed employee contract, yes — legally speaking. But it almost surely breaks other boundaries of any at-will employment.

“Transparency is a watchword in work engagement,” said Madeline Bayliss, an IBM exec turned workplace culture advisor, in an email: “Employees need to practice it, too, for their own well-being.”

The point is that distributed workplaces will present new challenges. Have you heard or experienced this? Have you done it yourself? Anonymous or not, I’d love to hear from you:

I doubt double-dipping W2 professionals will become a widespread problem, even with more distributed work. Instead, your focus should be on making your company a more flexible and welcoming environment so your best teammates can thrive. Culture does better detective work than you ever can.

And now the links.

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