Should You Tell Your Boss You're Side Hustling?

Should You Tell Your Boss You're Side Hustling?

by Kit Warchol
February 11, 2016


At our weekly happy hour recently, a good friend and I discussed a major crossroads in her career in the music industry. After 20 years in the business, she’d left her freelance career working for various labels to take a salaried position with a more corporate company in the industry. A wise move when you’re craving stability, right?

Except she’d quickly discovered that her previous freelance career had afforded her the flexibility to cover unexpected expenses. After a few jaw-dropping car repair bills and a rent hike, it hit her: she’d accepted too low of a salary, and she was stuck with it—at least until she found a way out.

The music industry, like many creative fields, gets a bit touchy when you choose to take on side gigs. It’s understandable given that different record labels are often pitted against each other, struggling to make what little profit they can.

But it’s also a small world where innovative personalities get a reputation, and my friend is one of them (there’s a reason why I seek out her company as often as possible). She’s the woman everyone wants when they’re considering tackling a major campaign. By the time we met for our drink on a Thursday, she’d received two requests for her help on contract projects that week alone.

As nice as some extra money sounds, if you’re happy with your full-time gig, there’s absolutely no reason to jeopardize it.

Here was a potential solution to her financial trouble: she could offset her lower paycheck with some extra income. But she was also faced with the ultimate conundrum: while officially her company hadn’t told her to turn down side work, she also had a sneaking suspicion that if she asked, they’d say “absolutely not.”

But what if she didn’t ask? She weighed the logic, drifting back and forth:

“I know plenty of men in this industry who would just do it without even thinking this much about it!”

“If they find out, though, I could just say that I didn’t know that it wasn’t allowed, but I wonder if they won’t believe me?”

“Do you think I could ask the client to not tell them? That’s weird, right?”

Let’s set aside the possibility that male colleagues could get away with the behavior, while she felt certain she couldn’t. What should we use as our guiding policy when it comes to informing your boss you’re side hustling?


You love your job. As nice as some extra money sounds, if you’re happy with your full-time gig there’s absolutely no reason to jeopardize it. Approach your boss about the offer. They’ll appreciate your candor, and chances are if they love you as much as you love them, they won’t say no. 

You get the sense they wouldn’t want you freelancing because it’s a conflict of interest. Probably best to discuss it with your boss. You can always make an argument in favor of doing it if they say “no,” but understand that if they say no, and stand their ground, you should absolutely not take the gig. {Click to Tweet}

You know it will get back to them. Potential projects typically come through your network, and many of those people you meet through work. After all, it’s how you spend most of your day.

If, say, a company client asks for your help on the side, and you suspect there’s even a remote possibility that they’ll mention it to your boss, make sure you’re the first one to out yourself. Tell your boss that you’ve been asked to take on a project and see how they react.

If they voice concern, have an argument prepared in favor of the work. Some key points to make: it won't affect your work, may actually add to the skills you can use around the office, and will ultimately build the company’s relationship with the client in question. 


You’re confident that it doesn’t affect your work, and that you won’t be working on it during your salaried hours. And hold yourself to it. It may be tempting during a slow meeting to check your emails (or texts) about a side hustle, but make it a policy to not do so. If it turns out you do need to explain your freelance work, being able to assure your boss that you’ve never and will never work on those projects on the job is essential.

You hate your job, you’re hoping that the gig may lead to a new job offer, and you’re prepared for the consequences. That might sound harsh, but as long as you’re OK with what might happen and you determined to make a change, go for it. Just know that you’re assuming a higher risk. {Click to Tweet

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Are you ready to master the side hustle? Join our next webinar, where we'll go through the whole process of turning a side gig into a full-time job. 

BTW what do you think about these policies? Are we missing some other key points to consider?