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

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.