Career Polygamy: The Hidden Rise in Second Jobs


oonlighting is nothing new. For decades, some workers have either opted or, due to economic conditions, been forced, to work a second job after they’ve finished a day with their primary employer. The pandemic, as it did in so many other areas of life, however, has rewritten the rules: A growing number of workers are taking on second jobs, but doing them at the same time as they work during their primary gig.

Call it Overemployment, Career Polygamy, or a high-stakes game of cat-and-mouse. But the work from home movement has helped many workers be more efficient at their job—and, ultimately, more daring.

With the distractions of office life removed, some jobs can be done in less time. And some people are using the extra hours to inflate their bank accounts. It is, of course, a morally questionable area. Advocates say they’re finally evening things out with a system that has taken advantage of them for years. Detractors, though, say neither employer is getting their money’s worth.

Take, for example, the case of Michael Redmond, an assistant principal in the D.C. Public Schools system. A long-time (and highly-praised) employee, he seemed set. In 2020, though, for 17 weeks, he also served as the principal of a Rhode Island school, officials say, reporting to one job in person while working virtually at the other. At both jobs, he earned full-time wages, and ethics filing claims. Redmond ultimately left both jobs.

While working two jobs isn’t illegal, even simultaneously, it could be a contract violation, which would get you terminated from one or both positions, like Redmond. And if you work at a job where you’re regularly exposed to confidential information, that could heighten the chances of negative consequences.

There are, as you might imagine, no hard statistics about this corporate double-dipping, since many of the people who do so make a big effort to prevent one company from finding out about the other. There are resources and support systems for those who are curious, though. The most popular of these sites is, which offers tips and community-based success stories from people who have pulled it off.

How popular? Last August, the site had under 1,000 members. By late March, it had over 16,500 members on its Discord server (and another 29,000-plus on its subreddit). The people exploring the idea range from newcomers, who are looking for support, to some (mostly tech workers) who have been working multiple jobs for years.

For many people, it’s a chance to substantially increase their income. While the workweek might be as much as 100 hours long, it can bring in as much as $600,000 per year, say some workers pulling it off. For others, who might work at a company where layoffs and being passed over for promotion are regular occurrences, it’s a good backup.

Whatever the appeal, advocates say it’s part of the new workplace reality.

“I think for most, there's no going back,” says Isaac Price, founder of “The money is life-changing, as long as they don't burn themselves out. Some go a little crazy at first, stacking on way more jobs than they can handle. Others take a more long-term view of slow and steady… planning on mini-retirements … once they've reached certain financial independence milestones.”

Double-dipping from the corporate pool takes some maneuvering. People who have done so successfully say there are a few tricks to making it work. For instance, don’t take every meeting if you don’t have to (and be sure people know when you’re in one). Think twice about what you put on sites like LinkedIn (and utilize privacy settings) and never start two jobs too close together

The big question, of course, is what will happen when companies recall workers to the office and can more closely monitor what workers are doing. Price says he could see over employment in non-tech fields come to an end, but says it’s likely not going to eliminate the practice among tech workers.

“It's free marketing functioning as intended,” he says. “In truth, if you're delivering business results … no one cares how many ‘bosses’ you're working for.”

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