“Overemployment” Is A Sign Of The Times

Two jobs are better than one?

Erik Bassett


We’ve all heard about, known, or even been (I won’t tell!) full-time employees running a side hustle on company time.

I’ll stop short of recommending that practice, especially since many contracts explicitly prohibit it, but you have to admit there’s a certainly rationality about it.

And I recently learned of some workers taking this to a whole new level.

Forget writing a blog or pitching graphic design clients on your downtime; these fully-remote folks are holding down a second job.

Enter the “overemployed” movement.

Its goal, quoting the eponymous website, is to “work two remote jobs, earn extra income, and achieve financial freedom.”

Photo by Good Faces on Unsplash

How in the world is that possible?

Say you’ve always had significant chunks of downtime at work. Now, your job has become permanently remote, so there’s no water-cooler chat and fewer meetings about meetings to fill in the gaps.

You could take it easy and enjoy the flexibility. You could fritter away the time checking scores or scrolling social media. Or, circumstances permitting, you could double up on income by doubling up on jobs in the same workday.

To some extent, the stars need to align for this to succeed. It also doesn’t hurt to have exceptional communication skills, time-management techniques, and ability to compartmentalize and set aside problems.

But if your field and your personality are both conducive to it, then…why not?

I’m mean, I’m not saying it’s *not* right…

On the one hand, it’s easy to criticize those who take arguable ethical shortcuts to move closer to financial independence. Even if there’s no lying or conflicts of interest involved — and there better not be — it’s still a gray area that requires a carefully curated LinkedIn profile and extreme caution when providing references.

Then again, is double-dipping in your free time any less noble than traditional but unprofitable time-wasters like solitaire and good old-fashioned water cool chit-chat? And while we’re on the topic, is it any more defensible for employees to lay off loyal employees rather spontaneously, often while collecting public funds and rewarding CEO performance?

Perhaps what’s good for the goose is good for the gander.

This part doesn’t sit right

Thinking back to when I bussed tables and stocked clothing-store shelves—each for a whopping nine bucks an hour—two jobs would have meant twice the hours, end of story.

Even in those days, I was fortunate to get by with only one crappy job, and only temporarily at that. Some colleagues had two already, and still couldn’t make ends meet. And therein lies the deeper issue:

Those who most urgently need to double up on income are least able to do so.

I’m not suggesting that attempting “overemployment” is some sort of human right. I’m merely pointing out the irony that the sort of jobs that facilitate it are generally ones that already more than cover one’s needs. The whole movement has a high-tech bent simply because those are the (coincidentally well-paying) jobs that are most conducive to it.

And that, I submit, is what feels off about this whole endeavor.

When even generally well-to-do folks are so financially anxious that they want doubled income more than doubled free time…and those who’re struggling have no more free time to sacrifice…something’s amiss.

Solutions? Beats me. I can barely even articulate the problem.

Is this a good thing?

In principle, I’m all for beating a rigged system at its own game.

Whether our economy is a rigged system is another question, but I think most would agree it favors large, well-connected corporate players. Perhaps a feature, perhaps a bug, perhaps a little of both.

But if you’re contemplating an “overemployed” arrangement, here’s one question to ask first: what next? Financial independence is desirable but it seldom solves our deepest problems. It’s too easy to let “the hustle” (be it literal hustles or this doubly-employed variety) displace introspection and postpone our exploration of fundamental purpose.

Likewise, it’s essential to know when enough is enough. In the absence of clear, healthy goals that serve a purpose, doubled earning power may evolve into doubled golden handcuffs.