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Turning a Hobby into a Side Business… Will My Boss Find Out?

We need to clarify what your goal would be if you started a side hustle


I work in a finance role in a company I’ve been with for close to a decade. In my free time, I enjoy varied hobbies like building things around the house, outfitting friends’ cars with accessories, and making artisanal cheeses. My wife and friends have been suggesting I turn one of these into a side business, but I’m reluctant, mainly because I’m afraid my boss might find out, and he wouldn’t like it. Is there any way around that?

~ Hobbyist


IT sounds like your biggest concern about turning one of your hobbies into a business on the side is upsetting your boss — which makes sense, since right now, he’s the one paying your salary. So let’s begin by exploring why something like this may upset a boss. There are only two reasons I can think of:

  1. You’ll have less time and energy to focus on your job.
  2. Your boss may worry you plan to leave your job (which in turn puts your job at risk).

Before we answer your question, we need to clarify what your goal would be if you started a side hustle, so we can verify whether or not those concerns are valid.

The two obvious reasons to start a business are either: a) to eventually replace your job and salary; or b) to get paid for things you’re already doing for free.

Based on the way you asked your question, I’m going to assume that it’s b) — you’re planning on staying at your current job long term, and just want to make a hobby more official and profitable than it is right now.

If that’s the case, your boss probably has nothing to worry about. It seems like you have enough free time to engage in multiple hobbies outside of work (though choosing to turn one of them into a business will probably force you to focus on that one area). If you’re careful and responsible, you can easily ensure that this doesn’t affect your job performance.

At this point you’d want to speak openly with your boss, so that he knows all of this. I’d suggest scheduling a time to “have coffee“ with your boss, and sharing what you’re up to with him directly. You might say something like:

“Hey, you know how I’m really into cheeses? So I actually opened an Instagram page with pictures of my work. It’s something I started charging for, since I find myself doing this every weekend, and figured my time is worth something. But I wanted to make sure you know that it’s very much a hobby, and my focus during the week is 110 percent my job, as it’s always been.”

Now you don’t have to worry that your boss might see an ad of yours, come across your social media page, or hear coworkers speculating about your intentions — he’s already in the know, and he’s heard it directly from the source.

Smart business owners recognize that they don’t own their staff’s time outside of work, and when employees engage in hobbies (even profitable ones!), they often come back to work energized and recharged, actually increasing on-the-job productivity.

Note of caution: Don’t spend time at work talking about your side business, or selling your services to coworkers. Do find ways your outside interests can benefit your workplace, like offering to bring in a cheese platter to a company event or doing the handy work around the office.

What if your goal actually is to have your side business eventually replace your day job? I’d still suggest you start out with the same attitude, ensuring that it doesn’t detract from your role in the company in any way. Often when people try turning a hobby into a business, the fun part disappears, and you find that all you’ve done is created another job for yourself. Once you’ve done it for a while, you’ll know whether or not it’s really a good idea.

How to navigate that conversation with your boss is another question — I’ll be waiting to hear from you when you get there!


Shaina Keren is a career consultant who helps people discover and create careers that fit their best talents, interests, and life goals. She also advises businesses on hiring and keeping “the right people in the right seat,” in a win-win approach to growing businesses and careers.


(Originally featured in Mishpacha, Issue 903)

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