Does every rose have its thorn? Figuring out whether to make a side project into a full-time gig can be tricky

My mom loves to knit. She makes baby sweaters for the church fair, keeps our whole family in hats and scarves through the winter, and even knows how to make complicated patterns like cables and multicolor pieces. One day I asked her whether she had ever thought of selling some of the things she makes on Etsy or even opening up an Amazon storefront. She just laughed. “If I had to do it, it wouldn’t be fun anymore,” she said.

Wise words.

We hear a lot these days about passion and work. The idea is that if you combine what you love to do with what you do to make money, you will find nirvana, instantly joining the ranks of those who don’t feel like they are working and yet are making a great living.

A few months ago I was having coffee with a friend who runs a software company that makes an electronic lab notebook—an essential tool for the biotech industry. He divides his time between Kendall Square in Cambridge (where there are several hundred biotech companies within a square-mile radius) and his office in Framingham. He makes a great living and is good at what he does, but he always has a side hustle: a passion project that is what he would love to be doing but that doesn’t (yet) make enough money to replace his full-time work.

We got to talking about side projects—the things we do for fun that could also make money but that we mainly do because we want to, not because we have to. In the course of our conversation, we both realized several important realities about the nature of passion projects.

We Like to Work

Some people dream of accumulating enough money to be able to sit back and not work anymore. There’s nothing wrong with that, but it’s not what everyone wants to do. Most of the entrepreneurs I talk to wake up every morning with more ideas than they could possibly pursue. They love the process of turning those ideas into businesses and only wish they had more hours in the day. I don’t necessarily want to work 24/7—I do love my family time and my time off, and I do actually have hobbies—but I do enjoy working. I like solving problems, and I get excited about having a new and interesting challenge.

A Side Hustle May Not Work Out

If I have a full-time job and then something I’m building up on the side, it gives me flexibility to build up my book of business without the stress of having it be make or break. Sometimes I have what I think is an amazing business idea but then when I dig into it and start to try to sell it, I find out that it’s not really as viable as I thought it would be. If I had quit my job to pursue it before validating the idea, I’d be up the creek.

Sometimes It Does Work Out

On the other hand, sometimes a side gig turns out to be a great idea and rapidly escalates into a full-time endeavor. Sometimes that’s great news, because then you can quit your day job and focus on what you love to do full time. This does mean you’ll probably have a period of time where you’re trying to juggle both things, and that can present challenges too.

Sometimes You Hate It

One of the funny things that sometimes happens when your side project is a success is that you discover you don’t want to do it all the time. Something that was fun to do on the side might be a chore if it’s your actual day-to-day grind. You may also discover that managing a business that’s doing something fun is not nearly as fun as just doing that thing by itself. For example, I know people who have started surfing instruction programs because they love to surf, and then they learn that they have to spend all day managing the business and have no time to catch a wave.

Finding that elusive combination of work that you love and that also pays the bills is harder than it looks. One of the best ways to learn whether you really want to do something as a job is to try it out on the side first. That way you can discover whether, like my mom and her knitting, it’s something you’d rather keep as a hobby or whether you really would like to turn it into your full-time job.