Should You Tell Your Boss About Your Side Hustle? Pros/Cons

When it comes to sharing your side hustle with your boss, is honesty always the best policy?

In this post, we’ll explore whether or not you should clue your boss in about your side hustle projects.

With side hustles becoming more and more common, this is much less taboo than it once was. Many companies, like Hubspot, even actively encourage their employees to start businesses on the side.

Why People Don’t Want to Tell Their Boss About Their Side Hustle

1. Fear of Retribution

Many side hustlers fear that telling their boss would be career suicide. They’ll start to doubt your commitment to your day job!

You know your company culture best, but this was definitely a “thing” at my old workplace, where people would start to get passed up for promotions if they were deemed less dedicated to the cause.

2. Fear of Judgment

Another common fear is having your boss pass judgment on your financial situation, especially if you’re in a white collar work environment.

“Are you so bad with money you need a side hustle?” the questioning might go. And even if it’s left unsaid, the perception might be there.

That’s unfortunately the conclusion that many employers will jump to, regardless of the fact that money is just one of many reasons why someone would start a side hustle.

3. Fear of Failure

If you share about your side hustle too early, and it doesn’t work out, will that make you look like a failure in front of your coworkers?

All of these are valid concerns.

Benefits of Telling Your Workplace About Your Side Hustle

While there are certainly some perceived risks of telling your boss about your side hustle, there may be some interesting benefits as well.

1. Leverage

The knowledge that your 9-5 is no longer your only source of income gives you a bit more leverage when it comes to workplace negotiations.

Does your boss really value your work? They might need to extend a higher salary or more flexible working hours to help keep you motivated.

2. Referrals

One surprising benefit of telling my boss about my side business was he started talking about it when we were out with customers. It was a little embarrassing because the website didn’t look that great and didn’t work amazingly well, but it became a topic of conversation.

And if your side hustle is in a non-competitive industry, your boss is just one more potential referral source for new clients. For example, my wife does photography work on the side from her engineering day job. Over time, she’s built up a reputation and has taken pictures for lots of her co-workers and their families.

3. Respect

Finally, one benefit a lot of side hustlers experience is a newfound respect from their peers and managers. The percentage of people who want to start a business someday is much higher than the percentage of people who actually do, so there’s a level of admiration for those who take the leap.

You might start to hear comments like “Good for you,” or “I had a business idea when I was your age, but never took action on it.”

On top of that, seeing the whole financial picture of a business from the CEO chair of your side hustle will probably make you a better employee at your day job. At least it did for me … until I quit.

When You Should Come Clean

If It’s Required

In certain industries, disclosing outside financial interests is a requirement. This is most common in defense, legal, and government jobs.

(Most agencies in the Federal government will have an Outside Employment and Activities page, like this one from the Department of Justice, that spells out what you can and can’t do outside of work.)

When in doubt, check with your HR department.

If Your Side Hustle is Public-Facing

If there’s a chance your boss will discover your side hustle on their own, by Googling you or otherwise, I think it makes sense to be upfront about it. After all, you want to take ownership of the conversation instead of them making assumptions about what they find online.

It could be as simple as:

I’ve had a couple friends reach out for graphic design help, so I’m going to add that to my LinkedIn.

If There Could Be Any Perceived Conflict of Interest

Now of course you’re not going to start a business in direct competition to your employer, but losing clients is a legitimate concern many bosses have.

If your side hustle is in the same industry, make sure to explain how you’re separating your business from your day job, and honoring any non-compete contracts you may have signed.

When You Probably Don’t Need to Tell Your Boss

If Your Side Hustle is in a Completely Different Field

For example, I worked for a giant auto manufacturer, and my side hustle was selling shoes online. There was no way the two roles could have been considered competitors.

If You’re Tapping Into Gig Economy Apps

With the rise of the gig economy and money making apps, you probably don’t need to tell work that you’re moonlighting as an Instacart shopper or Airbnb host.

If Your Side Hustle is Super Common

Your employer probably doesn’t need to know if you’re selling stuff on eBay or investing in real estate. Even though these side hustles do take time, they’re not really a perceived “threat” because they’re so commonplace.

If You’re Just Getting Started

I don’t think there’s much sense in telling your boss about every little side project — and frankly, they probably don’t care — until you start to see some traction.

They don’t need to know every detail of how you spend your off hours. Whether you were building a bird feeder for your backyard as a hobby or building a website for your new side hustle, it doesn’t really matter.

No employer owns you 24 hours a day.

General Rules for Side Hustling and Workplace Success

Don’t Use Company Resources for Your Private Gain

That means no using your workplace-issued laptop or phone for your side hustle. When I was traveling for work in my old job, I’d carry my work laptop and my personal laptop so I could work on my business when I got to the hotel.

Don’t Use Company Time to Build Your Business

Whether you’re hourly or salaried, consider your work hours 100% dedicated to your employer. Hopefully you’re left with another 16 hours in the day (and all day on the weekends) to put toward your side hustle efforts.

Don’t Steal Clients

Your reputation is worth more than the potential legal ramifications here.

Your Turn: Does Your Boss Know About Your Side Hustle?

Let us know in the comments below and share why you have (or haven’t) told your boss about your side hustle. Then, join Side Hustle Nation to start growing your business even faster!

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