4 Questions Smart People Ask About Side Gigs (So They Don’t Lose Their Jobs)


Even though you love your day job, you’ve got some big ideas for a new passion project. 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.

Whatever the case, side gigs—no matter what form they take—are becoming a smart move both financially and career-wise. And the smartest people know there are a few questions you should ask before diving in if you’re currently employed full-time.

1. Are Side Hustles Even Allowed at My Company?

In an economy where 39% of working Millennials have started their own gig on the side, smart employers understand that bans on outside projects can stifle creativity, push employees underground, and create a culture of distrust. They also know they stand to lose out on really exceptional and industrious people. After all, it takes some serious drive to add more work to your plate when you could spend your evenings lounging around instead.

But before moving ahead, you need to scan through the fine print on your contract and the company handbook to make sure you’re in the clear legally. Read carefully to make sure there isn’t a potential conflict of interest (more on this below!) or specific policies such as a non-compete clause. Look specifically for sections that discuss how long the non-compete applies, what type of work you are prohibited from doing, and whether or not the non-compete is only regional.

If you don’t, you could be setting yourself up to get fired or worse, sued. Unless your side hustle is in the exact same line of work as your day job, it probably won’t be an issue—but better to be safe than sorry.

2. How Do I Know if There’s a Conflict of Interest?

The simple, no-mess way to avoid any potential conflicts of interest is to set up a meeting with human resources or your corporate legal rep.

There’s no need to go into specifics about the clients, the size of your projects, or what they are paying you. But a quick rundown of the basic information will help you avoid some of the major pitfalls, such as poaching your company’s clients, unintentionally stealing intellectual property, or using their resources on your side gig (yes, including that work-issued laptop that you bring home to watch Netflix on).

3. Do I Have to Tell My Boss? My Company? HR?

If what you plan to do is allowed by your company, then there’s no reason why you necessarily need to disclose your side hustle. But although it isn’t legally necessary to tell folks, it’s more than likely—with social media—that one of your co-workers will find out.

If your office is one where a Facebook discovery could lead to an awkward conversation with your boss, save yourself in advance by just giving them a heads-up that you’re working on something outside the office.

Use this opportunity to explain how the skills you stand to gain from your side hustle will benefit your employer, your project team, or the company down the road. Pitching your side project this way will temper your supervisor’s fears that you’ve become disenchanted with your job and make him or her focus on the value of your entrepreneurial spirit. Who knows, they might even have some helpful advice or potential connections.

This will not only ease any anxiety you might be feeling about doing something sneaky, but will also prevent your supervisor from feeling that you were dishonest or shady with them. The last thing you want is them blaming a recent mistake on the fact you’re not focused.

4. How Can I Make it Clear to My Manager That I’m Still 100% Into My Current Job?

Depending on who you’re talking with, the term “side hustle” can come off as a dirty word. While rare nowadays, there are still those who think an employee won’t be able to give his or her best effort at a nine-to-five job while also focusing on a part-time business venture. That by having a side project, you are in some ways cheating on your employer.

The best way to put your boss at ease is to have that initial “Here’s what I’m working on conversation” and assure them of your commitment. Then, set strict boundaries for yourself and stick to them. Keep in mind that after this discussion, 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.

And know this: No supervisor, no matter how open he or she is to your project—will be pleased if they catch you working on your own business on their dime, especially if you’re not hitting all your goals at work.

It can be exhausting to put in a full day and then turn around to work on your side hustle all night. But because it can be such a rewarding way to gain valuable skills, supplement your income, or make you feel great, you should try to make it happen. Because if you do all of the above—checking to make sure you’re not doing anything unethical or illegal and talking to your boss—there’s nothing really stopping you.


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