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Work Daze – Side Gig on the Side

Just when you think you’ve experienced every crazy thing that can happen in the workplace, something mega-crazy shows up.

In this case, the mega-crazy showed up on The Muse website in the form of a Rachel Bitte post, “4 Questions Smart People Ask About Side Gigs (So They Don’t Lose Their Jobs.)”

If Bitte is right, there are actually people for whom one horrible job is not enough. They want to have a second horrible job, aka, a “side gig,” to fill the empty hours when they could be home, quaffing kombucha cocktails and binge-watching “Son of Zorn.”


Looking beyond masochism, there may be good reasons to have a side gig. Have you “got some big ideas for a new passion project?” Bitte asks. “Or maybe you’re saving for a big trip and looking for cash flow outside of your career. Or perhaps you’re trying to monetize a hobby you love.”

It’s difficult to argue with any of these reasons, except for monetizing a hobby you love. Extreme ironing is a magnificent sport and well worthy of Olympic status, but no one is going to pay a penny to see you iron a tea towel while riding a Harley. Except me, of course.

And here’s where Bitte comes in.

  • Are Side Hustles Even Allowed at My Company?Bitte writes, “39 percent of working Millennials have started their own gig on the side.” This suggests that employers will understand if you show “some serious drive to add more work to your plate when you could spend your evenings lounging around instead.”This may be true for industrious millennials, but I’m not sure it applies to you, someone who does their lounging in the daytime — at work. That’s why you need to check the company rules and regulations to see if “you’re in the clear legally.” This could be a real problem if you signed a “noncompete” agreement, instead of a “noncomplete” agreement. That’s the legal document that acknowledges, “I will probably not finish any project I start, so don’t bug me.”
  • How Do I Know if There’s a Conflict of Interest?This could be a problem, I suppose, but the solution Bitte suggests is much, much worse. “The simple no-mess way to avoid any potential conflicts of interest is to set up a meeting with human resources.”Completely ridiculous, right? By the end of your first day on the job you knew that the best way to stay employed was to avoid all contact with human resources.If you do see an HR professional roaming the halls, and you can’t hide under a desk fast enough, you might mention, in passing, that you are contemplating a side gig. Also mention that if the HR professional keeps their yap shut, you’ll pony up 10 percent of your side salary. You’ll probably have to negotiate up 25 percent, but it’s worth it.
  • Do I Have to Tell My Boss? My Company? HR?As long as the company doesn’t specifically ban side gigs, and assuming you’ve got HR in your pocket, there’s no legal reason to tell management that you’re going to be even less focused and effective now that you have a second job.But what happens if someone discovers you? They see a Facebook photo of you selling tacos out of a suitcase, or actually catch you hustling said tacos while at work.My advice: You might as well spill the beans. “The last thing you want,” Bitte writes, “is them blaming a recent mistake on the fact that you’re not focused.”

    Absolutely! It’s much better when management blames your mistakes on the fact that you’re lazy and really don’t care.

  • How Can I Make it Clear to My Manager That I’m Still 100 percent Into My Current Job?Even Rachel Bitte concludes that no matter how well you dot your t’s and cross your i’s, “your performance at work might be viewed under a microscope, so you need to be sure you’re on time for meetings, hitting your deadlines, and just generally firing on all cylinders.”Unfortunately, you’re rarely on time, never hit your deadlines, and when it comes to cylinders, you fire like a seized-up engine from a 1953 Hudson Hornet.But this doesn’t mean you can’t try a side gig. After all, if someone who works as little as you can hold on to one job, chances are, there’s a good chance you can hold on to two.

Bob Goldman was an advertising executive at a Fortune 500 company, but he finally wised up and opened Bob Goldman Financial Planning in Sausalito, California. He now works out of Bellingham, Washington. He offers a virtual shoulder to cry on at


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